Andrew Wilkinson

Why MLMs are an F-tier business: they sell the next sucker, not a service

Andrew Wilkinson ranks MLMs at the bottom of his business tier list because revenue comes from recruiting new people rather than selling a product. Only the founder and first couple of layers profit before the structure collapses.

“It's a fundamentally unsustainable business that breaks. I mean, the problem with an MLM is it's reliant on recruiting other people and it doesn't actually make money based on selling services. It's— it basically makes money by finding the next sucker. And if the person that starts the MLM finds a lot of suckers, they can make a lot of money. Yeah. And the first couple layers can make a ton of money, but then it always explodes or they get indicted or something like that.”

The worst thing that can happen to an agency is winning a giant client

Wilkinson explains why agencies are feast-or-famine: a single big client like Walmart can lead you to hire 30 people, then a new PM cuts your budget and you're stuck laying everyone off. Stickiness (like an audit relationship) is what separates a great service business from a fragile one.

“The worst thing that happens in these businesses is you win a client like Walmart. Let's say they come along and they say, hey, we want to give you $10 million of work over the next year. And so you, you start panicking, you go out, you hire 30 people, and then a new PM takes over that team at Walmart and they just cut your budget.”

The $300K agency acquisition that became a base-hit lead funnel

Wilkinson bought a Spanish web design agency, Z1, for about $300,000 purely to absorb the leads too small for MetaLab. It has since thrown off single-digit millions in profit — not a home run, but a clean base hit.

“We had a lot of success acquiring a company called Z1, which is in Spain. They're a, um, a smaller web design agency. And the theory there was literally just MetaLab gets a ton of leads that are too small for it. So let's buy another smaller agency and let's just send them those leads. And so I think we acquired that business for $300,000 or something, and we've probably made single-digit millions of profit in it. So it's not— we didn't knock it out of the park, but it's just an amazing base hit.”

Steal thisBuy a smaller competitor cheaply to absorb the leads that are too small for your premium brand.

Why AI is making most SaaS un-buyable: 10 competitors becomes 100

Wilkinson has rejected nearly every SaaS company over the past two years because LLMs and vibe coding will multiply competitors in any category, and more competition means margin compression. He only buys SaaS with high switching costs or a defensible moat.

“I just think like LLMs increasingly can build software. And it's not that it's going to put all these businesses— let's say you have a SaaS software company and there's 10 competitors 5 years ago. I just think there's going to be 50 or 100 competitors in the future. And when that happens, competition equals margin compression. So we've basically said no to almost every single SaaS software company we've looked at over the last 2 years.”

SaaS with a hardware mode: integrate into hardware to become un-switchable

Using Serato (DJ software) as the model, Wilkinson argues the most defensible SaaS deeply integrates with hardware. Once a customer buys $5,000 of compatible gear and the manufacturer won't integrate with a random AI upstart, switching costs become enormous and the software becomes the industry standard.

“But once someone really integrates into an ecosystem like Serato, they're buying like $5,000 of hardware. They're not going to switch off really easily. And the manufacturers, frankly, they don't want to integrate with some random college kid who's vibecoded some AI DJ. You know, not to say that people can't come and compete with us. It's just harder because it's not— it doesn't have a hardware mode. So I think SaaS with a hardware mode is pretty incredible.”

Steal thisPick a SaaS niche where deep hardware integration locks customers in and locks AI competitors out.

SaaS with a hardware mode: integrate into hardware to become un-switchable

Using Serato (DJ software) as the model, Wilkinson argues the most defensible SaaS deeply integrates with hardware. Once a customer buys $5,000 of compatible gear and the manufacturer won't integrate with a random AI upstart, switching costs become enormous and the software becomes the industry standard.

“But once someone really integrates into an ecosystem like Serato, they're buying like $5,000 of hardware. They're not going to switch off really easily. And the manufacturers, frankly, they don't want to integrate with some random college kid who's vibecoded some AI DJ. You know, not to say that people can't come and compete with us. It's just harder because it's not— it doesn't have a hardware mode. So I think SaaS with a hardware mode is pretty incredible.”

Steal thisPick a SaaS niche where deep hardware integration locks customers in and locks AI competitors out.

A restaurant is a Rube Goldberg machine — E-tier, just above an MLM

Wilkinson reveres successful restaurateurs precisely because the business is so brutal: for a 6pm meal, someone woke at 3am to bake bread, 30 people had to be trained, and a thousand things had to go right. Low margin and one of the hardest businesses to run.

“Because if you're successful in a restaurant, I just— it is one of the hardest businesses. If you think about for you to go in and eat a good meal at 6:00 PM, people had to wake up at 3:00 in the morning. They had to bake bread. A million things had to go right. They had to train 30 people. It's just like a Rube Goldberg machine of business. So I would rank it as an E, um, probably one of the hardest businesses and low margin and difficult.”

The verb test: the best marketplaces become a verb in your head

Wilkinson's heuristic for a great marketplace is whether the brand becomes a verb that pops into your head automatically — like 'Airbnb' when you think of renting a house. Small marketplaces are lightning-in-a-bottle and most fail; the ones that become a verb are A or B businesses.

“I like a business where it becomes a verb. So Airbnb is a great example. Like if I think like, oh, maybe we should rent a house, Airbnb, the word just pops into my head. I go to the browser, I look up Airbnb. And I'm going to use it, that I would say is probably a, a B or an A business.”

Steal thisTest a marketplace idea by asking whether it could become the default verb customers reach for.

Huberman as a partner brings $20M of free marketing to any business

Wilkinson explains why a trusted health creator is A/B-tier: niche matters because health supplements have high LTV and pay well for ads. He says Andrew Huberman brings roughly $20M of free marketing to any business he joins — their shared yerba mate company grew 300-400% after he got involved.

“I mean, if you think about it, like Huberman, we own, we're friends with, with Andrew. We own a yerba mate business with him. He is able to basically bring, I would call it, $20 million of free marketing to any business he becomes a part of. And so if he takes equity in businesses or owns businesses, he grows them massively. I mean, we took the yerba mate business. I think it's grown 300, 400% since he got involved with us.”

Why Wilkinson avoids real estate: he hates anything with a ceiling

Wilkinson rates plain real estate ownership a C because rents have a ceiling and you can't innovate to grow revenue without massive CapEx. He prefers digital businesses where you can reinvest profits to compound revenue with no cap.

“The reason I don't really do much real estate is because I don't like anything with a ceiling. You know, you, if you buy, let's say you buy a 40-tenant apartment building or something like that, the rent is going to be, let's say, let's say that some old lady owns it. She hasn't increased the rent in, you know, 30 years or something like that. You're going to buy the the building over time, you can get an increased yield by increasing the rent, but there's a ceiling on that rent and you can't innovate to make more money.”

Permanent capital is the real edge in money management

Wilkinson ranks Buffett and Ackman S-tier not for stock-picking but for permanent capital: because their vehicles are publicly traded, investors can't pull their money — they just sell shares to each other. The manager keeps collecting the standard 2-and-20 fees no matter what the market does.

“The structure of hedge funds is typically 2% of managed assets plus 20% of the profits. So let's say that you raise $100 million and you triple it in a short period of time, you can suddenly make, you know, $30, $40, $50 million of carry and fees and stuff. So Those are really tremendous businesses in my opinion. The problem with them is that your investors can pull their cash out. And so what Bill has done that's so smart, and I would rank Bill as S and Buffett as S, and then other asset managers lower, uh, they have permanent capital.”

Steal thisStructure a fund with permanent (publicly-traded) capital so investors can't pull out and your fees compound forever.

Ackman's $25M COVID hedge returned $2.4 billion

Wilkinson recounts that in early 2020 Bill Ackman put $25 million into a derivatives position betting on COVID crashing the market, and it returned roughly $2.4 billion — on top of which he earns management fees on his entire fund.

“He was freaking out about COVID and he had put $25 million into a derivatives position, betting, kind of buying fire insurance against COVID. Dropping the market, he made $2.4 billion of profit or something insane off of that. I think it was $25 million bet.”

Angel investing is roulette; buying businesses is poker

Wilkinson ranks angel investing E-tier, comparing it to roulette versus the better odds of poker. He likens private equity and buying businesses to poker, and warns that founders who 'pay it forward' as angels are usually doing a terrible thing with their money.

“I would put angel investing as an E. I think I view angel investing a little bit like playing roulette. I like to play poker. It has better odds. I look at private equity or buying businesses more like poker.”

Skip the line: buy a working business instead of starting 10 that fail

Wilkinson regrets pouring $10-15M of MetaLab profits into ~10 startups that almost all failed. The lesson: rather than build from scratch, buy an already-working business and improve it — he believes he'd be far ahead today if he'd simply acquired and improved instead of starting.

“I then took almost all my profits and I started like 10 other businesses. And almost all of them failed. It was really exhausting. And at the end of that process, I had one business that I could sell, another one that was kind of alive, but I started 10 and I'd put almost $10 million or $15 million into all these terrible businesses. If I had just taken, you know, the $1 million, $2 million a year and just bought businesses and just improved them, I think I'd be much farther ahead than I am today.”

Steal thisSkip the line: buy an already-working business and improve it rather than starting from zero.

Tiny: $300M+ revenue across 30 businesses, $65M ARR, $40M+ EBITDA

Wilkinson lays out Tiny's scoreboard to answer the trolls: ~$250M revenue, $65M ARR, $40M+ EBITDA in the public company, plus a $200M fund adding another $65M of revenue — over $300M revenue across 30 businesses, all of them profitable.

“We have $65 million of ARR. Uh, we do over $40 million of EBITDA and Chris and I still own the majority of the public company.”

The Courage to Be Disliked — the book that unlocked Wilkinson's cell

Wilkinson credits 'The Courage to Be Disliked' with freeing him from the likability trap. Its core idea: seeking recognition is a trap, you can't make everyone happy, and trying means living someone else's life — so you must have the courage to be disliked.

“And in January I found this book called The Courage to Be Disliked. And it's one of these books where you see the COVID and you just instantly kind of know. Yeah. You're like, okay, like this, I kind of get it. And it's really interesting. It's written in this very odd way where it's a dialogue between like this wise old man and a young, a young guy. And the core idea is just like, seeking recognition is a trap. It's impossible to make everybody happy. And if you try, you're going to end up living somebody else's life. And so you have to be hated. You have to have the courage to be disliked.”

Being unboxable creates a magnet: a 4-hour coffee that bought Letterboxd

Wilkinson argues that refusing to fit a clean box (like Kevin Rose or Tim Ferriss) turns you into a magnet for serendipitous deals. Because he loves movies, a random coffee with the Letterboxd founder in Auckland led him to make an offer for the business within four hours.

“I love movies and I, I tried to invest in film. So I actually like had this period where I was like, flying down to Hollywood and meeting people and looking into investing in movies and stuff. And I looked at it and I was like, I'm going to lose so much money. And at that same time, I happened to be in Auckland with Tim Ferriss randomly. And I, um, I was, I was in town and I went, oh, there's this guy who runs Letterboxd there. I should have a coffee with him. And that coffee, literally that I had coffee with Matt and I made an offer for the business within 4 hours.”

Just rolling out today's AI kills 20% of all jobs

Andrew Wilkinson argues that even if all AI labs were shut down today and we only deployed what already exists, self-driving cars and AI agents would eliminate roughly 20% of current jobs.

“So if we just paused AI, we shut down all the AI labs, and all we focused on was just rollout of what already exists, I think probably between self-driving cars and AI agents, 20% of all current jobs are gone.”

Build a Lindy agent that preps you before every meeting

Andrew Wilkinson uses Lindy (think 'Zapier with thinking in between') to automate admin a human assistant used to do: an hour before any calendar event it pulls a LinkedIn bio via Perplexity and summarizes the relevant email thread, removing the drift that creeps in when a busy human owns the task.

“So the way it would work in this instance is look at my calendar an hour before any event starts, go on Perplexity, go to LinkedIn, and I want you to write me a bio. And then I want you to look at my email inbox and tell me what we're talking about. So that's like pretty basic. And what we're really talking about at this point is removing admin work, right?”

Steal thisWire up a Lindy agent to scan your calendar an hour before each meeting and auto-deliver a bio plus email-thread summary.

Fyxer: AI that triages and drafts every Gmail reply in your voice

Andrew Wilkinson recommends Fyxer (spelled F-Y-X-E-R), a British startup that reads every incoming email, sorts by whether it needs a response, and drafts replies in your own language that improve over time. He also uses Howie.ai for scheduling.

“I use Fixer, F-Y-X-E-R. It's this British startup. It basically reads every single email that comes into your Gmail. It sorts it based on whether you need to respond to it or not. And then it drafts responses. So let's say Sean said, hey, do you want to get coffee? It'll draft a rejection or an acceptance of that in my language, and it gets better over time.”

Claude found a tax move that saved $100K/year in cash taxes

Andrew Wilkinson exported his messy personal holding company books from Xero as a CSV, trained a Claude project on it, and asked for tax-saving ideas. Claude flagged moving an investment between holdcos, saving him $100,000 a year in cash taxes.

“I actually saved $100,000 a year of cash taxes by moving an investment from one holdco to another. Thanks, Claude.”

AI coworkers in Slack within 12 months, 4K video colleagues in 2-3 years

Citing Anthropic's Dario Amodei at Davos, Andrew Wilkinson predicts AI coworkers messaging you in Slack within 12 months, and within 24 to 36 months, 4K video people on Zoom indistinguishable from a human.

“And he basically said in the next 12 months, you will have AI coworkers in Slack. Now, if you just project that out right now, it's text, right? These are not people. But pretty quick, it'll be someone on Slack that you're messaging, hey, can you make some new product images? Hey, do you mind checking out the AdSense? Do you— can you write a report? And I think that within 24 to 36 months, these will be 4K video people that are indistinguishable from a human that you'll talk to on Zoom.”

Vertical market software wins because nobody cool wants to build it

Andrew Wilkinson's thesis on why vertical-market software (funeral home, golf course, dam management) has been the best business for 30 years: no great developer or designer dreams of building it, so there's no competition, you're the only game in town, you can charge what you want, and nobody switches. Constellation Software built a $70B company buying exactly these.

“And where there's been a lot of wealth generated in software is in vertical markets. And so what does that mean? Like, that's like, um, weird niche businesses where nobody is competing. So for example, like funeral home management software, golf course management software, random like dam and infrastructure software. And these are great businesses because not— no, like, amazing developer wakes up and no amazing designer wakes up and is like, I'm going to go and build this software. And so basically, you're the only game in town, you can charge whatever you want, and nobody switches off of you. And so for the last 30 years, that's been the best business ever.”

IREN: a 'fire insurance' AI hedge disguised as a Bitcoin miner

Andrew Wilkinson pitches Iris Energy (ticker IREN), two Australian infrastructure bankers who bought data-center sites next to renewable power and currently mine Bitcoin for ~$500M EBITDA at a ~$2.4B valuation. The misunderstood upside: flipping those scarce, hard-to-permit centers to AI compute for hyperscalers, a low-downside way to capture a fast-takeoff scenario.

“Now the stock trades at about a $2.4 billion valuation, so you can buy it actually quite cheaply based on the Bitcoin thesis, right? And Bitcoin would have to drop by about, I believe, I'm guessing based on some assumptions, but I think it would have to drop about 70%.”

Andrew turned down Slack stock and missed a possible $100M

When Metalab designed Slack (then a failed gaming startup) on an $80K budget, Stewart Butterfield offered to pay partly in stock. Andrew Wilkinson insisted on cash to fund his own productivity software, where he lost $10M. The Slack stake, at a ~$20M valuation, could have been worth ~$100M when it sold to Salesforce for ~$28B.

“So I instead put it into this money-losing productivity software. I could have made $100 million or something crazy because it was at like a $20 million valuation at that time and it sold for $28 billion, I think, to Salesforce.”

From barista to web designer: just copy the guys drinking the espresso

Andrew Wilkinson was making coffee for two web designers who came in daily, working off laptops. He asked what they did, learned they sold $500 websites door-to-door, bought a web design book, and within weeks had quit his barista job.

“And one day I asked them, what do you guys do? Like, don't you have jobs? And, uh, they go, oh, we're web designers. We just walk into random businesses. We ask them if they have a website. And then we say, we'll make one for $500. And so that day I was like, well, forget this. Like, I don't want to make the espresso. I want to be drinking the espresso. I want to be these guys.”

Get paid a lot for what you'd do for free

Wilkinson contrasts his barista job with web design: he went from a small amount of money for something he hated to a large amount of money for something he'd have done for free.

“I was making a small amount of money for something I hated And then I started making a large amount of money for something I would have done anyway for free. Like, it was fun. It was fun designing websites and coding websites.”

Sell other people's time, not just your own

Wilkinson got a $1,000 JavaScript job, subcontracted it to a friend for $500, and pocketed the spread doing no work. He frames this as the leverage jump from self-employed (selling your time) to a business owner (selling others' time).

“And so in that moment, I was like, oh my God, I just made $500 and I did absolutely no work. So that's that crazy transition of going from being a self-employed person selling your time to being someone who can sell other people's time, which to me is like the big leverage point.”

Steal thisSubcontract work you sold, keep the margin, and reinvest the freed-up time into selling more.

The E-Myth: treat your business as a machine

Wilkinson credits Michael Gerber's The E-Myth for the mental model that the business is a machine, the founder is the engineer, and people are swappable widgets — the breakthrough that let him start hiring and scaling past $1M/year personally.

“And around that time, I read this book called The E-Myth. Uh, it's kind of cheesy. It's by Michael Gerber, but I recommend it to everyone. And he really talks about this idea of trying to think of your business as a machine, right? And I think for me, that was the— that was a big breakthrough, that mental model of my business is a machine.”

The light-weights trap: an easy first win breeds overconfidence

Wilkinson says his easy first business was like walking into a gym and picking up light weights, building false confidence. He then spent 5-10 years trying to deadlift 300 pounds — failed e-commerce, a restaurant, software businesses — losing over $10M in one case.

“So I did the equivalent of walking into the gym and I got lucky. I picked up really light weights and it built my confidence. And then for the next 5, 10 years, I would walk into the gym and try and deadlift 300 pounds, but I didn't know that was hard. Right. And so I started an e-commerce business. I started a restaurant. I started multiple software businesses that I bootstrapped and lost in one case over $10 million.”

Wilkinson thought he was doing Shopify a favor — built Pixel Union instead

In 2010 Toby and Harley from a then-small Shopify asked Wilkinson to make themes for their planned app-store-like marketplace. He thought he was doing them a favor and even tried to get paid; the themes started making $10-20K/month almost immediately.

“And at the time Shopify was pretty small and they said, hey, we really love your design work. Would you make some templates, some themes for Shopify? And I was like, oh, you know, I guess we could do these guys a favor. They seem nice. I tried to get them to pay me and they actually said, no, no, no, this is going to be like a store, like the iPhone app store.”

Wilkinson sold Pixel Union for $7M, saw $3.1M hit his account

Wilkinson sold his first business for $7M ($3M upfront, $1.5M earnout, rest in stock). He checked his balance at a strip-mall ATM the day it closed and saw about $3.1M, which triggered his shift from incubator to investor.

“And so I ended up getting an offer to sell that business for $7 million, and it was $3 million upfront, 1.5 earnout, and then the rest in stock in the new business. And I remember I went to the ATM on the day it closed and I checked my balance. I was in like a strip mall and I saw $3 million. It was like $3,100,000 or something like that on the Chit.”

The 20% rule: spend 20% of cash flow, invest 80%

Wilkinson set a personal rule to spend up to 20% of his cash flow and route the other 80% back into investments. On $5M of cash flow that's a $1M lifestyle while always compounding the rest, so he never had to live like a pauper waiting for a big exit.

“So basically I was like, I, I will spend up to 20% of my cash flow personally, and the other 80% has to go back to investing. And so I knew that, you know, on 20% of $5 million, you know, I could live a pretty damn good life spending $1 million a year.”

Steal thisCap personal spending at a fixed percentage of cash flow and auto-route the rest into investments so you compound while you live.

Hire CEOs to run your companies and they double

Wilkinson's breakthrough was realizing he didn't need to be CEO of his own companies. There's a whole class of operators who want stability and to run a company for someone else. When he started installing CEOs and giving only 20% of his time, the businesses doubled.

“And so I realized like there's this whole other class of people where they want to run a company for somebody else. They want to be a CEO. They want to be able to make, you know, millions of dollars, but they don't necessarily need to make like a billion dollars. And that was crazy for me when I started hiring CEOs, because And before I knew it, all the businesses started like doubling.”

Steal thisHire operators who want to run a company for you, then spend your time buying more businesses instead of running them.

Angel investing is roulette; running businesses is poker

Wilkinson reframes his ~$30M of angel bets as roulette — fun, but ~50/50 and soulless. Building and operating businesses is poker: if you're good, the odds tilt in your favor and you feel smart instead of dumb.

“I think of it as roulette. And I think like this period that we're talking about was about me learning how to play poker, right? Poker has way better odds than roulette. If you're good at poker, you can actually win. You've got, you know, 60% odds. When you play roulette, you got 50% odds. It's a terrible game. And angel investing is frankly a roulette table.”

100x the food you need is stressful, not a luxury

Wilkinson's metaphor for overshooting wealth: you have one belly and can only eat so much food, so having 100x what you need is wasteful and stressful — you have to manage it and keep it from going bad. The book is a letter to his younger self saying he didn't need to overshoot.

“It's like, you know, look, you have, you have one, you have a belly and you can only eat so much food. Why do you need 100x that amount of food? If you have 100x the amount of food you need, well, it's actually kind of stressful because A, it's wasteful. You don't want the food to go bad., and you got to do something with the food.”

Pick your annual spend, multiply by 20 to get your 'enough' number

Wilkinson's rule for an 'enough' net worth: decide what you want to spend each year, then multiply by 20. He estimates $3M/year of spending (house, private flights, hobbies) implies a $60M liquid target for an incredible life.

“So call it $3 million bucks. So what's 3 times 20? So $60 million. I think $60 million, if you've got it liquid, that's, you know, you can live an incredible life and spend $3 to $4 million a year. And, uh, and it's awesome. So that's kind of how I think about it.”

Steal thisDecide your ideal annual spend, multiply by 20, and make that liquid number your target instead of overshooting toward billionaire status.

Launchpad, Enough, Life's Work

Wilkinson's three wealth goals: Launchpad ($250K/year passive so you don't need a job), Enough (your annual-spend-times-20 net worth target), and Life's Work (the intrinsically meaningful thing you do once money is the byproduct of your machine).

“So Launchpad is like, how do you make $250K a year, right? And ideally passive. And if you can make $250K a year passive, then you don't need a job and you have the freedom to be generative and start the things that you want.”

Steal thisAim first for $250K/year passive as a launchpad, then build to your 'enough' number, then go find your life's work.

Start a boring cash-flow business instead of a venture lottery ticket

Wilkinson argues most people who want financial freedom should start a boring business — trash hauling, window cleaning — grow it to $1-2M of cash flow, and be set for life, rather than raise venture money for a 1-5% shot at success.

“look, if you just started a boring business, like a trash hauling business or window cleaning business or whatever it is, you get it to $1 or $2 million of cash flow, sell it or hold it, you're set for life. And instead they go off and they raise all this money and they don't realize that they really have a 1%. You know, call it a 1 to 5% chance of success”

Michael Dell accidentally owned the Dallas Stars after a defaulted loan

Andrew recounts meeting $65B Michael Dell, who started a $200M family office doing private credit; one borrower defaulted and Dell ended up owning a professional hockey team without trying.

“He goes, yeah, so about 20 years ago, I took $200 million and I started a family office. And in the family office, I wanted to make like a 10% return. And so I hired these really smart guys and they started doing private credit. And I don't know if you guys know what that is, but usually it's lending to people that the bank won't lend to. So it's higher risk.”

Andrew bought 60% of Letterboxd after blurting out an offer over coffee

Andrew met Letterboxd founder Matt Buchanan in Auckland with no intent to invest, learned it had 10M registered users grown over COVID, blurted out "do you want to sell?", asked for the craziest number, and closed within 48 hours.

“And at the end of the coffee, I literally just blurted out, do you want to sell? And he was like, well, I hadn't really even thought about that. Uh, and I was like, throw me the craziest number you can think of. And so he threw the number out and I said, okay. And I sent him an offer within 48 hours and we just bought that business.”

The money bonfire: small losses you do not notice burn millions

Andrew warns that buying something out of shiny-object excitement with no plan, then letting it lose a small enough amount each month to blend into everything else, turns a tiny ember into a money bonfire; his Castro podcast app lost ~$2M over 5 years.

“And just every month, I, you know, I, I think I bought it for a million bucks and it just lost $10,000 to $20,000 a month. And it was a small enough number that blended into all my other stuff. I just didn't really notice it. It wasn't like an urgent thing. And so this tiny little ember turned into a money bonfire.”

Steal thisAudit small recurring losses; the ones too small to notice are the ones that quietly burn millions.

Why HubSpot bought The Hustle: capture the advertiser margin

Andrew explains the acquisition logic: The Hustle made ~$20M in ad revenue, but advertisers were making $30-50M off that spend, so HubSpot could pay up, redirect the traffic to itself, and capture that downstream margin.

“HubSpot looked at The Hustle and they said, well, right now they're making, call it $20 million. I don't know what the number is, $20 million of ad revenue, but how much are those advertisers making off that $20 million of ad spend? Maybe it's $30 million or $40 million or $50 million. And so they can pay up to buy this business and then they can just direct the traffic to themselves and make all that money.”

Steal thisWhen buying a media business, value the advertiser margin you can capture by redirecting the audience to your own product.

Always be the second owner of a hotel (or house)

Andrew lost 30% building his dream home over 5 years and shares his dad's rule: let someone else go crazy building and overspending, then buy it from them; the same applies to houses.

“And my big lesson is, I remember my dad said, you always want to be the second owner of a hotel, right? You want someone else to go crazy and build it out and then go bankrupt, and then you want to come in and own that. I think the same thing is true with houses. Just go buy a nice house that someone else built.”

Steal thisNever build it yourself; buy the over-built asset from the person who already overspent.

Let a CEO make non-fatal errors, only intervene on fatal ones

Andrew's rule for managing a CEO: let them make their own mistakes and learn, even spending millions on R&D you doubt, because blocking them breeds resentment; only step in when an error is fatal to the business.

“And so we always say, um, we want non-fatal errors, not fatal errors. We'll intervene when they're fatal, right? So I think for you, like intervening when it's something that's going to ruin your reputation, you should jump on that or ruin the business or imperil it. But otherwise, the hard part is you just kind of have to watch them. Make mistakes”

Steal thisLet your CEO make non-fatal mistakes; reserve intervention for the fatal ones.

Pantone: trademark colors and resell the swatch books yearly

Andrew marvels at Pantone, which trademarks colors, has the entire fashion and design world standardized on its swatch books, makes over $100M/year, and tells customers to rebuy the books annually because the colors fade.

“And one of the most genius things about it is they give you that book and they say you need to buy a new book every year because the colors fade, right, from being in the sun or whatever. And so they're just constantly reselling these books. People are licensing these colors and the entire fashion and graphic design world is standardized on Pantone.”

Steal thisBuild a standard the whole industry depends on, then engineer recurring repurchase into the physical product.

AI will erase ~80% of assistant and admin tasks in the near term

Andrew predicts that a well-trained Google AI with access to your Drive, calendar, and email will handle roughly 80% of personal-assistant tasks in the near term, radically changing or eliminating admin jobs.

“I think that, um, if you think about a lot of the tasks that personal assistants do, um, I think a very well-trained Google AI that understands your Google Drive, your calendar, and your email, um, will be able to do probably 80% of those tasks, maybe more. And I think that's coming in the very near term.”

Snipd: AI podcast player that grabs the quote you just heard

Andrew recommends Snipd, a podcast player whose AI transcribes episodes, pulls out key moments, and lets you tap a button in CarPlay to capture the text of whatever was just said.

“And Snipped basically solves that. So what Snipped does is it has an AI that basically takes the transcript. It does like voice recognition on the transcript of the podcast. It pulls out all the key moments.”

Whales only get harpooned when they surface

Andrew Wilkinson's reaction to Kevin Ryan publicly explaining his tax structure: staying quiet about how you minimize taxes is safer than broadcasting it, because visibility invites scrutiny.

“But there's a great saying on this stuff. Whales only harpoon— whales only get harpooned when they surface, right? He just surfaced in a really obvious way. And you know, there's just some anal retentive IRS guy listening to the podcast.”

Sarah Moore: Harvard adoptee who bought eggcartons.com

Andrew's favorite guest of the year, Sarah Moore, had a troubled childhood, was adopted by a wealthy family who put her through Harvard Business School, then bought eggcartons.com. Her arc is held up as proof that anyone can teach themselves to buy and run a business.

“She, um, had a really troubled childhood, basically got adopted by this wealthy family. They ended up putting her through Harvard Business School, and she went out and she bought this business called eggcartons.com. And this story was just incredible. I feel like, um, so many people hear these wild stories about tech bro billionaires, you know, raising a bunch of money and hitting it big, making trillions of dollars. And I think her story is much more realistic for a normal person”

Charlie Munger's 90-year-old billion-dollar side hustle

Andrew's Billy of the Year is Charlie Munger, who at around 90 backed a neighborhood Hasidic kid named Avi who had once tried to convert him to Judaism. Munger mentored him and together they built a billion-dollar LA apartment portfolio.

“And now they own a billion-dollar real estate portfolio of Los Angeles apartments. And he's just this neighborhood kid. Uh, his name is Avi, and, uh, and they built this huge business together. And Charlie started doing this when he was like 90 years old.”

A $1,000/month Philippines assistant to handle your inbox

Andrew breaks up with email entirely: his assistant in the Philippines, costing about $1,000/month, screenshots any important email and he simply dictates what to do, removing the distraction of opening the inbox himself.

“so I have an assistant in the Philippines and it's like $1,000 a month and she does it right. So it's like, it is something that a lot of people could do.”

Steal thisHand inbox triage to an offshore assistant who screenshots only the must-respond emails, so you never open your inbox and fall down a rabbit hole.

How Andrew's no-phone rule cost him a drink with Zuckerberg

In 2010 Andrew left his phone in the car during sushi and missed a same-night invite from Mark Zuckerberg to grab a drink while Zuck was in his hometown of Victoria. By the time he saw it, the last ferry to Vancouver had left. The story haunts him every time he tries a digital detox.

“And I've received an email from Mark Zuckerberg. Mark Zuckerberg at the time was famous, but not famous, famous, not like he is today. And I'd emailed him because I heard he was coming to Vancouver and he didn't respond for 2 days. And then at 8, 8 o'clock at night or 7 o'clock at night, I got this email that said, hey, do you want to go for a drink from him, from Zuck?”

The rich-person dinner-bill dilemma, solved by card roulette

Andrew explains why he and Chris make everyone drop a credit card and let the waiter pick: once you have money, paying the bill signals showing off or that others can't afford it, while not paying makes you an asshole. Randomizing the payer defuses the awkward dynamic.

“What I noticed, one of the weird things about making money is that there's this weird dynamic that happens where when the bill comes, if you pay the bill, you're showing off or you're implying they can't afford it. And if you don't pay the bill, you're an asshole because you can afford to. And so that's why we do that.”

AI Tinder: gamified dating with AI-generated matches

Andrew's idea: generate thousands of photorealistic AI men and women, put them in a Tinder-like app, and make winning them over a casino-style game where you must charm them to exchange photos and keep chatting, knowing they're fake.

“So you basically generate, um, like thousands and thousands and thousands of fake digital men and women, and then you have Tinder, and you basically, um, you make it like a casino, right? So you're swiping, and let's say you match with a, a really hot digital girl, and then you have to text with her, and there's some sort of algorithm where you have to win her over to exchange photos and start talking or whatever.”

Steal thisBuild a gamified dating app stocked with AI-generated matches where users level up by charming bots, framing it as flirting practice rather than deception.

Boring lever pulls beat sexy features for profit

Andrew Wilkinson argues the highest-ROI moves in business are unglamorous one-time changes (raising prices, shrinking packaging, monetizing SEO, parking deposits in T-bills) rather than flashy product launches.

“But one of the things I've realized after running a company for like 20 years is it's really not the sexy stuff that pays off. You know, for example, like we have a bunch of companies and, you know, one increased prices 30% after not increasing prices for 5 years. They massively grew profits, right? That took 10 minutes, a little bit of planning, and that paid off big.”

Steal thisAudit your business for one-time lever pulls (price hikes, packaging, idle cash) before building any new feature.

WeWork Remotely: $1.5M buy 10x-ed to $4M EBITDA

Tiny bought the WeWork Remotely job board (run as a side project by the Basecamp founders) for ~$1.5M at 3-4x earnings, raised the price from $199 to $299, added SEO and email marketing, and grew it from ~$400K profit to ~$4M EBITDA with only two employees.

“So we buy the business, we pay 3 or 4 times earnings or something, which was, you know, a fair price given what it was doing. We immediately take the price from $199 to $299 because that's what all the other job boards were charging. And we hire an SEO consultant. We start doing SEO, we start doing email marketing. That business went from doing about $400K of profit to, I think a couple years ago it did $4 million of EBITDA or something in that range.”

Leave only 2-4 weeks of expenses in each company

Tiny historically left just two weeks of payroll-plus-expenses in each business; the holding company silently backstops cash if needed, but the thin buffer forces urgency on collections and efficiency.

“Yeah. Yeah. So like basically payroll, payroll plus expenses for 2 to 4 weeks max.”

Steal thisCap operating cash at 2-4 weeks of expenses to force discipline; backstop from a separate reserve only when truly needed.

If you ask the dinner guests, they always order steak

A SaaS founder told Wilkinson that CEOs spend the owner's money freely because it isn't theirs: a $300K spend that earns the CEO a $10-20K bonus is a bad trade for the owner but easy for the CEO. Every dollar counts only when you're the owner-operator.

“If you ask the dinner guests what's for dinner, they will always say steak. And I was like, oh my God, that's so true. Right? It's like, why wouldn't they? You know, it's not their money.”

Pay realtors per stink bid to make lowballing worth it

Chris made dozens of lowball offers (e.g. $650-700K on a $1M house); realtors resisted because each offer costs them 30-40 minutes for a tiny chance. Paying $1,000 per submitted offer flipped them to eagerly sending the stink bids.

“And so Chris started saying, hey, look, for every offer you send, I'm going to pay you $1,000. Immediately the guy's totally down to do the stink bids. But before that, he's going, oh, you're going to get a bad reputation in the market.”

Steal thisPay a flat fee per lowball offer submitted so your agent's incentive matches your hit-rate game.

Qualify acquisition sellers with 3 questions, then send a written LOI fast

Wilkinson screens inbound sellers by asking only three things (who runs it, do you want to stay or go, what are your earnings), then immediately quotes a price by email; a formal written LOI with dates and structure makes sellers take the offer seriously.

“So it'll be like, okay, who runs the business, right? Is that you? Do you want to stay or go? And then what are your earnings? And then after that, once I have that info, I say, okay, we would probably pay about X. Right. And if they say, you know, let's talk, then I know I should spend the time and talk.”

Steal thisPre-qualify any acquisition target with operator, intent, and earnings before investing time, then anchor with a written LOI.

$57K charity lunch with Bill Ackman led to a real deal

After getting handed off to a board member, Wilkinson bid $57,000 to win Bill Ackman's charity lunch in a down year for Ackman, expecting no business. Ackman ended up offering to do a deal, and years later invested alongside Tiny in an acquisition.

“And so I ended up bidding $57,000 to go have lunch with him. And my bet was I had no, I had no expectation there'd be any business to do because he's a hedge fund manager. I'm a tech investor, but, but I knew he'd be like an interesting person to meet. And so I went and we ended up connecting. And then at the end of the lunch, he kind of pulled me aside and he's like, hey, I like you. If you ever want to do a deal together, let me know.”

Steal thisBuy access to people you admire when it's cheap (down years, charity auctions) without expecting immediate ROI.

Earn the room you are in; wait until you are interesting

At the Vanity Fair Oscars afterparty everyone glazed over once Wilkinson said he was in tech, teaching him you can't buy your way into a room where you have no value. You should wait until you're genuinely interesting to the people there.

“If I have no value to him or I'm not interesting to him, I should not meet him. You have to wait until you're interesting.”

Be the barnacle on the whale: ride a marketplace for free marketing

Marketing is 15-30% of most businesses' cost. By selling inside someone else's growing ecosystem (Wilkinson built Shopify themes early, owning ~50% of marketplace squares), you inherit their marketing spend and run at far higher margins. Look for unsaturated ecosystems like Discord.

“Most of us are not influencers, but anyone can do that in a different way by being a barnacle on a whale. So here's the story of how we, I kind of stumbled into this. So I was at a conference about 12 years ago. At the time I met Harley and Toby from Shopify.”

Steal thisBuild a product inside a fast-growing platform marketplace early to inherit its marketing and SEO for free.

Sold his best business, then read Buffett and bought it back

Burnt out and feeling broke despite cash flow, Wilkinson sold his Shopify-theme business for relief. Then he picked up a Buffett book on moats and competitive advantage, realized he had just sold a business with all those qualities, stayed on the board, and bought it back.

“And so I pick up a book about Warren Buffett and I start reading about this idea of competitive advantage and moats and what a good business looks like. And as I'm reading, I'm going, oh my God, I just sold the business that has all these qualities. What the hell was I thinking?”

Shopify theme business: $20K start to $260M IPO

Wilkinson's Pixel Union Shopify-theme business started with ~$20K, sold for ~$7M, was bought back for $25M, took ~$10M of M&A, and went public at a $260M valuation, totaling about $36M invested.

“So we, we took it, you know, start, started it for $20K, sold it for $7, bought it back for $25, did $10 million or so of M&A, and then took it public.”

Hanlon's Razor: don't read malice into silence

Wilkinson invokes Hanlon's Razor: never attribute to malice what ignorance or busyness explains. People assume an unanswered important email means rejection, when usually the other person is just busy. Operators fester in silence assuming neglect.

“And basically the idea is it's, um, never attribute to malice what can otherwise be explained by ignorance or stupidity. Right. So never assume negative intent, but everybody assumes negative intent.”

The Laws of Human Nature by Robert Greene

Wilkinson calls Robert Greene's The Laws of Human Nature one of the best books he's ever read; he relistens to the audiobook every year because its patterns recur constantly in hiring and business.

“That's one of the best. That's one of the best books I've ever read. The Laws of Human Nature by Robert Greene. I just got the audiobook and I just keep listening to it every year. It's amazing.”

Use a $29 paywall as a DM filter on a big following

Instead of triaging 100 cold DMs a day, Wilkinson gated his DMs behind a $29/month subscription. Paying that much to buy him lunch self-selects serious people, and he's hired 2-3 people and sourced deals from the resulting group.

“And so when I saw this subscription thing, I was like, okay, this is actually a filter. So what Twitter lets you do is have, um, gated tweets. So you can say anyone who pays to subscribe to me gets these extra tweets. And so what I did is I was like, okay, if someone will spend $29, which is the cost to basically buy me lunch, then they can DM me, then they can message me”

Steal thisGate your inbound DMs behind a small paid subscription so only serious people reach you.

Andrew Wilkinson's gated-Twitter experiment: 550 subs, $16K MRR

Wilkinson charges $29/month for gated tweets, a monthly AMA, and a Telegram group as a filter on his 240K-follower inbound. About 550 paying subscribers produce roughly $16K MRR (~$200K/year) at near-pure profit for ~1-2 hours of work a month.

“I have about 550, um, paying subscribers today. That's growing pretty consistently. Um, that's about $16K of MRR. So about $200K a year. Uh, it's basically pure profit. I probably spend an hour a month, 2 hours a month doing the AMA or whatever.”

Win any room by asking questions (the Dale Carnegie move)

Wilkinson's antidote to status anxiety in elite rooms: find what the other person likes to talk about and keep asking questions. They leave remembering you as a great person regardless of your status.

“I've just realized that everybody wants to talk about themselves and it's the Dale Carnegie thing. Find out what someone likes to talk about. And then talk to them about that and just keep asking questions. And I realized that if they, if I make them feel good, if they get to talk about the thing that they're interested in, they will leave that experience thinking of me as a very positive person regardless of status.”

Steal thisIn any high-status room, just ask the other person questions about themselves and let them talk.

The status game has no end, even at $20B

Wilkinson recounts a multi-billionaire who, asked what Laurene Powell Jobs ($20B) could do that he couldn't, went glassy-eyed and said 'superyacht.' His point: there's always a higher rung, and chasing it is pathetic.

“I remember I was talking to a guy who's a multi-billionaire and he goes, oh my God. Um, you know, Laurene Powell Jobs, Steve Jobs' widow, she's so fucking rich. She's worth like $20 billion. And I look at him and I'm like, what can you not do that she can? And he kind of goes glassy-eyed and he's like, superyacht. I can't do a superyacht yet. And it's just like, that is the most pathetic, insane thing.”

Build the launchpad before you launch the rocket

Wilkinson frames cash-cow businesses (agencies, newsletters) as the 'launchpad' that funds the passion projects you actually want to do. It's not the forever business; it gives you the freedom and capital to chase the real thing.

“I have this whole thing about you want to, you want to, before you launch your rocket, you need a launch pad. Build the launchpad. This is the launchpad business, right? It just provides you the ability to go and do the things you're really passionate about.”

Steal thisBuild a boring cash-cow first to fund the passion business you actually want to run.

The 1-1-100 'airport hot dog stand' for buying businesses

Wilkinson's 1-1-100 framework: if you own a captive source of demand (an audience or distribution), you can acquire a cheap product with a customer-acquisition problem and reliably boost it. A hot dog stand is a bad business, but a hot dog stand inside an airport prints money.

“imagine if you own an airport and there's like 10,000 people in the lobby every day. You know that you can sell them hot dogs. A hot dog stand is not a good business, but if you put a hot dog stand in the middle of an airport, I can guarantee you're going to sell a lot of hot dogs.”

Steal thisBuy a cheap product with a distribution problem, then funnel your captive audience into it.

Maui Nui: turning an invasive deer pest into premium meat

Jake spent ~7 years getting FDA approval to commercially hunt and sell axis deer, an invasive Hawaiian pest the government otherwise machine-guns from helicopters. The regulatory grind created a 7-10 year moat, and the meat is sniper-headshot for ethics and quality.

“he basically spent the last 7 years getting approval to actually hunt and sell this meat. And it's this like super complex problem. So there's this interesting moat in the business. It's going to take someone else like 7 to 10 years to compete.”

Axis deer meat: 20% protein vs salmon 14%, beef 9%

Wilkinson's pitch for Maui Nui's axis deer meat: testing shows ~20% protein content versus ~14% for salmon and ~9% for beef, plus high micronutrients, with the company selling an estimated $10-20M/year of pepperoni sticks and similar products.

“a piece of salmon is like 14% protein. This is 20% protein. Like beef is like 9%. It's good for the environment. The animals live natural lives. And then one day, boom, headshot, gone.”

AG1's moat isn't the powder, it's 15 years of influencer equity

Wilkinson argues Athletic Greens isn't winning on product but on a 1-1-100 distribution moat: 15 years of relationships with the most influential health people, many of whom hold equity. Competitors can copy the powder but not the trust.

“What makes Athletic Greens amazing is that they spent the last 15 years building relationships with all the most influential health people in the world. So it's 1 1 100, right? They have Tim Ferriss. They have all these people who not only they buy ads with, but they also have all these people owning equity in the business.”

Profit First: hide your margin in a separate account on day one

Wilkinson loves the 'Profit First' method: the day $100 of revenue arrives, immediately move your target profit (say $50) into a bank account you can't see, forcing the team to run the business on what's left. It's the 'smaller plate' trick applied to a P&L.

“Let's say that you earn $100 in your business and you want to have a 50% profit margin. You just take the day the $100 comes in, you take $50 and you put it in a bank account that you can't see. And that's it. You just put it away. And so then you and your team are left with $50 to run the business.”

Steal thisSkim your target profit into an out-of-sight account the day revenue lands, and run the business on the rest.

Spend 5% of income, invest the rest, and don't chase an 'exit'

Wilkinson lives on at most 5% of what he earns and invests the rest. His sharper point: many owners of great cash-flow businesses refuse to pay themselves, then suffer a stressful PE sale, when 'the exit was right in your bank account' via dividends.

“Dude, the exit was right in your bank account. You know, you could have just dividended the money out to yourself and then you wouldn't have had this really stressful, horrible experience with private equity and been through all that stuff.”

Steal thisDividend cash out of your cash-flow business to yourself instead of grinding toward a stressful exit.

Bring back 'Negotiation as a Service'

Wilkinson built and sold Buyer (negotiation-as-a-service) to Ramp and misses it: busy operators will pay someone to negotiate cars, furniture, and renovations on their behalf. He pitches it as a perfect Nick Huber-style business to restart.

“I really just, I put this out to the audience. Someone needs to restart that business, Negotiation as a Service. That's a Nick Huber. That's a great Nick Huber business.”

Steal thisOffer done-for-you negotiation on big personal purchases for busy high earners.

The manic 11pm email: 'We're shutting MetaLab down, going all in on Flow'

Wilkinson got so excited about his SaaS side project Flow that one night he emailed the whole staff to shut down the profitable agency and go all in. His CFO calculated they'd be out of business in 3 months and quietly talked employees out of leaving.

“And so I always wanted like a SaaS business, sexy business. And so I started one. I started this productivity business called Flow. It was like a sauna, except we didn't raise any money and we, we had a great product, but it just didn't go anywhere.”

Flow did $300K vs MetaLab's $2M when Wilkinson nearly bet it all

At the moment Wilkinson wanted to shut down the agency to go all-in on his SaaS, Flow was doing only $300K in revenue while MetaLab was doing around $2 million.

“Flow was doing like $300K of revenue and MetaLab was like $2 million or something like that.”

MetaLab almost sold for $15 million ~10 years ago

Andrew Wilkinson and his partner got an offer to sell their agency MetaLab for $15 million about 8-10 years ago, a deal that legally went through but never funded.

“And we got this offer for the business to sell it for $15 million. This is about 8 or 9 years ago, almost 10 years ago.”

Andrew Wilkinson legally sold MetaLab for $15M — the wire never came

Wilkinson spent 4 months negotiating, signed documents, and legally sold MetaLab to a private equity firm for $15M. The wire never arrived because the buyer couldn't close their fund — saving the agency that became the foundation of Tiny.

“And we actually went through the whole process, you know, spent 4 months going back and forth with this private equity firm. We signed the documents, you know, my lawyer calls me in, quivering hand, I sign the documents, and the wire's supposed to come in the next day. And so I wake up, I go to my local bank branch, I go to the ATM, and I look at the balance. My balance is the same.. And I think, okay, it's probably gonna come in later.”

'Every business is a slow-motion knife fight'

Wilkinson quotes Brent Beshore to capture how miserable running a business feels from the inside even when it looks great from the outside — you wake up sweating and fighting to survive.

“But on the inside, there's a great quote by Brent Beshore. He goes, every business is a slow-motion knife fight. Right? Like, you just wake up in the morning, you're sweating, and you're fighting, trying to survive, right?”

Save on percentages, not lattes

Andrew quotes Ramit Sethi's rule: don't sweat small recurring expenses like lattes; the real money is in percentages -- interest rates, mortgage rates, and real estate fees, where a 0.5% difference can be $20,000.

“people think they need to save money on lattes. What they actually need to save money on is percentages. And so he's talking about interest rates on credit cards, interest rates on mortgage, uh, fees in real estate transactions. Like the difference between 2% and 2.5% is like $20,000. And people don't think about that.”

Steal thisStop optimizing $3 expenses; renegotiate the rates and percentages that move tens of thousands.

Procrastinating one signature cost Andrew $500K

Andrew wanted to hedge and lock in the interest rate on company debt, but let the signing documents sit on his desk for a week because he hates paperwork. Rates rose ~1% in that week -- a roughly $500,000 cost from pure laziness.

“And so these documents were sitting in our office and I was like, oh, I'll do it tomorrow. I'll do it tomorrow. I kept putting it off. And then finally I signed it and I realized that between the time that I, it was sitting there for a week. And in that week, the interest rate went up by like 1% and that represented like $500,000 or something insane. And so just me being lazy and not signing that document and not thinking in percentages cost me like 500 grand.”

Rats in the granary: accept that some losses recur

Andrew invokes Charlie Munger's mental model: if you own a granary full of grain, there will always be rats. You can kill them endlessly but they come back, so it's better to accept a baseline of getting-got rather than fighting every one.

“There's what's the Charlie Munger calls it? Um, the rats in the granary, right? If you own a granary, you have a big warehouse full of grain. There's going to be rats. You can keep killing them over and over again, but they're going to always come back and it's better to just accept that there's rats out there.”

Steal thisBudget for a baseline rate of theft and chiseling instead of burning energy fighting every instance.

Buying Girlboss out of the venture scrap heap for a base hit

Andrew's best investment: Sophia Amoroso's Girlboss raised ~$10M, tried to build an impossible social network, and sold distressed to Attention Capital. Andrew bought it cheap, went back to basics (daily newsletter, ads, affiliate, podcast), and it now earns its purchase price in annual profit.

“she ended up running out of cash, getting exhausted. She sold it to Attention Capital and they basically were just like, fuck, we don't know what to do about this. Like, we shouldn't have bought this.. And so they reached out to us and we were able to buy it for really, really cheap just because the business was totally distressed. Um, and so, you know, we looked at it and we were like, okay, like, let's just go back to basics. This business has almost 2 million social followers and email subscribers. Um, and we just did basic stuff. We built a daily email newsletter. Uh, we sold ads, we did social ads, we did affiliate, uh, we've rebooted the podcast, brought on a great CEO. And it's just been this phenomenal base hit.”

Steal thisBuy distressed venture-orphaned brands with big audiences cheap, then monetize with boring basics: newsletter, ads, affiliate.

Founders podcast: business biographies, distilled

Andrew's favorite podcast is Founders by David Senra, which reads business biographies and summarizes them in a tight 1-1.5 hours -- a way to relearn lessons and decide whether a given doorstop biography is worth reading in full.

“So my favorite podcast I'm absolutely obsessed with Founders, which is by David Sennra. And what he basically does is he reads business biographies, um, and then he summarizes them really, really well. So there's a lot of— I've read a lot of business biographies. I really enjoy them, but there's a lot of them where I'm like, I just, I'm not going to spend 15 hours of my life learning about JFK's dad.”

Selling a 50%-growth business for a 14x multiple, then regretting it

Wilkinson sold Pixel Union for $7M (14x its ~$500K profit) before he understood investing. Once he read Buffett and learned to value businesses, he realized a 14x multiple is cheap for something compounding at 50% a year.

“You know, it was growing at 50% a year. And, you know, I thought it was great to get a 14x multiple, but not when it's growing that fast. So I regretted it.”

Steal thisDon't anchor a sale price on the multiple alone; a 14x multiple is cheap if the business is growing 50% a year.

Pixel Union: bought back for $26M, taken public at $260M

Wilkinson bought Pixel Union back for $26M when it was doing ~$4M annual profit, rolled in 460 and other businesses, and took the combined entity public at a $260M valuation as WeCommerce.

“And we paid $26, and then we bought 460 and a couple other businesses,, and then we took it public at a $260 million valuation.”

AeroPress's hidden upside: almost no online sales

AeroPress sold in 95% of gourmet coffee shops but had a tiny percentage of sales online under its older founders. Wilkinson saw the e-commerce gap and hired the SodaStream US president who'd grown that business to $200M.

“There's a reason why if you walk into 95% of gourmet coffee shops anywhere in the world, they sell AeroPress. But when we looked at it, just a very, very small percentage of sales were online. It just wasn't a focus for them.”

Steal thisLook for great products with a neglected channel (e.g. offline-dominant brands with no e-commerce) and supply the missing playbook.

Losing $300K on cat furniture taught him e-commerce margins are brutal

Wilkinson poured ~$300K into HJ Muse, an online cat-furniture store, and learned e-commerce runs on 2-3% margins versus the 30-50% EBITDA of his agency and Pixel Union. Profits kept getting eaten by inventory; he shut it down.

“I just learned how brutal a business e-commerce was that, you know, I was basically eeking out these razor-thin margins, whereas in my agency or in Pixel Union, I was making 30 to 50% EBITDA margins. I was making like 2 or 3%. And the amount of work required to move physical goods around by inventory, I realized that while on paper I was profitable, I was constantly taking my profits and putting them into buying more inventory.”

WeWorkRemotely: an idle SEO-ranked job board bought from Basecamp

Wilkinson's easiest business is WeWorkRemotely, a remote job board bought from Jason Fried and DHH at Basecamp. It ranked #1 for remote jobs off their book and SEO, sat idle, and grew large on a tiny team with simple best practices.

“The easiest business that I own is a company called WeWorkRemotely. This is a job board that we bought from Jason Fried and David Heinemeier Hansson at Basecamp. They had started it and it was like a remote job board. They had written a book about remote and they had great SEO. They ended up ranking number one for remote jobs.”

Steal thisBuy assets with strong incumbent SEO that the owner has stopped tending, then apply basic best practices.

Flow: lost $10M competing against Asana's unlimited budget

Wilkinson poured $10M into Flow, a project management SaaS, competing head-on with Asana. The lesson: fighting a venture-funded competitor with an unlimited budget is like Fiji fighting the United States.

“I basically poured $10 million into it because I was competing with Asana and didn't understand the dynamic of when you're competing against— you're fighting an army that has unlimited budget. It's like Fiji fighting the United States, right?”

Steal thisDon't go head-to-head in a category where a venture-funded incumbent can outspend you indefinitely.

Better to have 10,000 people paying a little than 100 paying a lot

Wilkinson prefers sticky SaaS revenue spread across many small customers: it's resilient because no one rips out a sticky tool, and a yearly bill barely reminds them they pay. Agencies, by contrast, get crunched in downturns.

“I always think it's better to have 10,000 people paying you a small amount of money than 100 people paying you a lot of money.”

An 'advertising sniper rifle' to get on one specific person's radar

Wilkinson's standing idea: a hyper-targeted service that makes one specific person (e.g. an acquirer like Dharmesh) see your company everywhere they go online, so they perceive you as huge. He'd pay $10K/month for it.

“So everywhere Dharmesh goes on the internet, I want him to see stuff about my company and I want him to think we're huge. There's— I forget where the quote comes from, but there's this idea that if someone sees you 5 times, they think you're everywhere.”

Steal thisBuild a service that maps one target's information diet (newsletters, podcasts) and places you in all of it; charge $10K/month.

Tenzing: a modern investment bank for bootstrapped founders

Wilkinson is starting Tenzing, an investment bank aimed at bootstrap founders doing $1-5M EBITDA who can't access capital and don't speak banker language. It helps with credit, debt for M&A, secondaries, and selling.

“Really focused on bootstrap founders because they don't know how to access capital. And so we were starting this business called Tenzing. We started like a month ago.”

Steal thisTranslate an opaque, elite financial service into plain language for an underserved segment that the incumbents ignore.

Dressing up a corner store as the next hot trend to dump on retail

Wilkinson describes a Canadian small-cap fraud pattern: take a tiny business in a hot sector (vertical farming, weed, fake meat), have a banker IPO it, pop it, and dump it on mom-and-pop investors. He met a guy bragging about taking a 2-location business public.

“and I met a guy at a party, um, you know, last, uh, last summer, and he was bragging to me about this IPO that he had done and how much money he made. And I started digging into it and it was literally a the equivalent of taking a corner store public. This was like a 2-location business and he dressed it up to match a trend.”

The non-binary term sheet: cram-down if you miss your numbers

Wilkinson raised for Supercast at a $10M valuation structured so that if revenue didn't hit $1M in two years, the valuation reset to $5M. He missed, crammed himself down 50%, and now offers founders deals where investors can recover their money if milestones aren't met.

“we raised at a $10 million valuation, which at the time was kind of a good, um, you know, angel, angel round valuation. But it was structured so that within 2 years, if the business doesn't do $1 million of revenue, that turns into a $5 million valuation.”

Steal thisStructure a raise so a missed milestone automatically resets to a lower valuation, keeping the deal fair if the business stays small.

PE invests in what is; VC invests in what could be

Wilkinson distinguishes capital types: private equity prices a business off proven EBITDA (assume $10M becomes 11, 12, 13), while venture bets on an unproven trajectory ($200K revenue becomes $2M then $20M). They're fundamentally different forms of capital.

“private equity doesn't take risk on what could be right. Private equity invests in what is. They, they will say your business does $10 million EBITDA. I'm going to assume it's going to be 11, 12, 13, 14, not venture, which is your business does $200K revenue. You're assuming you're going to get to 2 and then 20 over the next 3 years.”

Copying a billionaire's stock pick without understanding his game

Wilkinson read Howard Marks' book, trusted him, and put $100K into a Greek shipping company Marks had bought, only to watch it go bankrupt. He missed that Marks holds hundreds of positions and is a distressed-debt investor betting on the debt, not the equity.

“I'm going to buy into this weird Greek shipping company that he just bought, you know, $50 million of equity in. And so I put like a hundred grand into it., and it goes out of business. And what I didn't understand was two things. One, he has thousands of positions, right? Or hundreds at least. And for him, it's just a tiny little roulette chip that he's put down.”

Steal thisBefore copying an investor's position, understand their strategy and position-sizing; their tiny chip can be your whole bet.

Stress test your business for the worst case before winter

Andrew Wilkinson over-engineers each business for nightmare scenarios. He flags two failure modes: total loss (bankruptcy) and the under-discussed one, missing opportunity because you're illiquid when a cheap acquisition or land-grab appears.

“And so I think you want to stress test and overengineer your business for all the worst-case scenarios. So effectively, that's what I've been thinking about a lot. And I think what people miss is there's two ways that something like this can go bad, right? The worst way it can go bad is total loss, right? You go bankrupt, your business fails, you're embarrassed, it's terrible. I think that's the worst. But the less bad option that no one really talks about is missing opportunity. So you get presented with something incredible and you're illiquid, you can't take advantage of it.”

Steal thisModel revenue dropping 20/50/70% and customers paying 90-120 days late, then keep enough cash to both survive and pounce on cheap deals.

Turn your P&L expenses into standalone businesses

Tiny incubates low-downside companies out of its own cost lines. Wanting better procurement and better credit across its portfolio, it spun up a business for each rather than just cutting costs internally.

“And then the other thing with venture is we've realized too, we can do venture internally by incubating businesses with low downside. So for example, turning our P&L expenses into businesses in and of themselves. So for example, we want better procurement internally. We want to negotiate rates and get our P&L under control. And so we started a business to do that. We want to get better credit across all of our businesses. We started another business to do that.”

Steal thisLook at your biggest recurring expenses and ask which could be productized into a business that also serves outside customers.

Tiny started Buyer for $50K and sold it to Ramp

Andrew describes Tiny's playbook of capital-light bets: it launched Buyer, a software-negotiation service, for about $50K, partnered with a scrappy operator, got revenue in months, and ended up selling it to Ramp.

“So when we started Buyer, which is our, um, negotiation service for software, that we launched 2 years ago and we ended up selling it to Ramp. So I think we started that business for $50K. At the end of the day, we were looking at it and going, this is a very low-risk bet where we're basically finding someone who, you know, they want to start a company, we're giving them all the tools to do it, and we're going to partner with them, provide all the capital. But at the end of the day, we're looking at really, really simple capital-light businesses that can get revenue within like 2 or 3 months.”

Buffett's farm: ignore the yokels yelling numbers

Andrew relays Buffett's parable: if your farm earns $1M a year, a lowball offer is irrelevant unless you're forced to sell. The value of a business only matters at the moment of sale, so don't panic-sell because the market quotes a scary number.

“There's a great Buffett story and he says, Sam, let's say you own a farm and it makes you $1 million a year of profit, and some yokel walks up and goes, "Hey, Sam, I'll give you $50,000 for that farm." You just go, "Go away. No, I'm not going to sell." And then someone else one day comes along and says, "Hey, I'll give you $20 million." Maybe you consider that. But the idea is that at the end of the day, these yokels will yell numbers at you and you don't have to sell.”

Are you playing roulette or poker? Buy businesses, not venture

Andrew frames venture as roulette (near-random) versus poker (known odds in your favor). In a downturn he'd rather buy cash-flowing businesses at a 20-30% earnings yield - paying himself back in 2-5 years - than chase venture bets.

“But I guess the question is, are you playing roulette or are you playing poker? I play poker. I want to play with very good odds in my favor and I want to know the odds. I don't want to play roulette where it's almost totally random. I still think venture is totally random. I do it for fun off the side of my desk.”

DealMaker: outsourced negotiation as a service, paid on savings

Tiny's DealMaker (dealmaker.co) is a procurement-as-a-service business: CC them on vendor emails for office leases, furniture, insurance, and they negotiate, taking a cut of whatever they save you. Andrew built it because wealthy buyers have a target on their back.

“And so we created this business called DealMaker, dealmaker.co. And instead of doing software, we're doing office leases, furniture, insurance, all the random stuff in your P&L. And basically you just CC them and they take a cut of whatever the savings are. And this is the thing I wanted myself because I was going, Oh my God. Like I had the experience of, um, you know, when you're, when you're rich or people know you're rich, they will rip you off if they can.”

Steal thisOffer negotiation-as-a-service where clients just CC you on vendor threads and you take a percentage of the savings you win.

Ramit Sethi's 'I Will Teach You to Be Rich': focus on big levers

Andrew cites Ramit Sethi's book for the point that wealth doesn't come from skipping lattes and budgeting - it comes from the few macro decisions. A 1% difference on a mortgage rate dwarfs years of small frugality.

“There's a great, there's a great book called I Will Teach You to Be Rich by Ramit Sethi. And I read it like 15 years ago and he makes a really good point. He goes, look, you're not, you don't get rich by paying attention to like lattes and like building budgets and like not buying lunch out. You get rich by paying attention to these macro big things in your life. So for example, when you buy a house, there's a massive difference between getting a 3% interest rate and a 2% interest rate, but no one thinks like that.”

Buy put options as an insurance policy on your business

Andrew bought $500K of S&P put options in early 2020 as cheap insurance against Fortune 500 clients not paying; they spiked to $7M before he sold and re-bet (losing the rebet). The reusable move: if your net worth is in one SaaS, buy out-of-the-money puts on a public comp to hedge.

“So the way to think about this, let's say that you own a SaaS business and your entire net worth is in the SaaS business and you've raised money at 20 times revenue or something. You might want to find a SaaS business that's publicly traded that is a comp to you, and you might want to buy out-of-the-money put options or buy a basket of those and basically say, if the market gets crushed, that's probably an indication that the larger economy got crushed too, or my part of the world got crushed and businesses like mine are doing badly.”

Steal thisHedge a concentrated bet by buying out-of-the-money puts on a publicly traded comp, treating the premium as an insurance policy.

Buy put options as an insurance policy on your business

Andrew bought $500K of S&P put options in early 2020 as cheap insurance against Fortune 500 clients not paying; they spiked to $7M before he sold and re-bet (losing the rebet). The reusable move: if your net worth is in one SaaS, buy out-of-the-money puts on a public comp to hedge.

“So the way to think about this, let's say that you own a SaaS business and your entire net worth is in the SaaS business and you've raised money at 20 times revenue or something. You might want to find a SaaS business that's publicly traded that is a comp to you, and you might want to buy out-of-the-money put options or buy a basket of those and basically say, if the market gets crushed, that's probably an indication that the larger economy got crushed too, or my part of the world got crushed and businesses like mine are doing badly.”

Steal thisHedge a concentrated bet by buying out-of-the-money puts on a publicly traded comp, treating the premium as an insurance policy.

Take interest-only mortgages so capital stays in businesses

Andrew hates real estate so much he uses interest-only mortgages and refuses to build home equity, because a business can scale from $1M to $100M of revenue while an apartment building never will.

“I hate real estate so much that I don't build equity in my own houses. So I do interest-only mortgages because I want everything in businesses, because businesses— a business can earn $1 million of revenue and then the next year do $100 million using creativity. There's no apartment building you can buy that'll do $1 million of revenue and do $100 million next year.”

The 'micro SPAC': crowdfund an operator to buy a business

Shaan describes the micro SPAC he and Andrew ran: raise ~$85-100K from random Twitter investors into a shell, then buy a profitable Shopify app on MicroAcquire for an entrepreneur (Daniel) to operate and grow. He frames it as 'just add hustle' to an already-running business.

“And I called it at the time. I said, This is like when you go to buy like cake mix and it's like just add water. This is a like just add hustle. Here's a business. It's here's the code's already written, the business is already running, the revenue is already there, and all you need to do is grow it and you just need to add that hustle into it to grow this thing.”

Steal thisPool small checks to buy a profitable indie business and hand an operator the keys to grow it.

Don't learn to code, learn to manage engineers

Andrew, a non-technical founder, grew a no-code SaaS to $10M ARR by finding one elite overseas engineer (Raymond Chester in China) and hiring all of his friends. His advice for non-technical founders: skip learning to code and learn to manage engineers well.

“I always recommend don't learn how to code, learn how to manage engineers. Properly. And so I ended up just hiring all his friends. So we ended up having like a house for them and they had like 20 engineers in China”

Steal thisIf you're non-technical, find one great engineer, treat them like a brother, and hire their network.

QSBS: pay zero federal tax on the first $10M of a sale

Andrew explains he structured his exit as a stock purchase to qualify for QSBS (Qualified Small Business Stock), which exempts up to the first $10M of gain from federal taxes. He flags it as essential knowledge for anyone selling a business.

“We did a stock purchase, so I benefited from QSBS, which if you're looking to sell a business, look up QSBS. You pay zero federal taxes on up to the first $10 million.”

Steal thisStructure your company so an exit qualifies for QSBS and shields the first $10M of gain from federal tax.

Have the acquirer buy your cash to get QSBS on it

Andrew negotiated to roll $2M of company cash into the purchase price at a 1x multiple. Normally that cash gets distributed and taxed at ~40%; by selling it as part of the QSBS stock deal, he shielded it from that tax.

“typically if you are acquired, you have $2 million cash in the bank account that is divided back out to shareholders and you're taxed at 40%. So we got QSBS on that $2 million cash.”

Steal thisIn a stock sale, fold your bank cash into the purchase price at 1x so it inherits the QSBS tax treatment.

Go boring with money so you can focus on what you're great at

Andrew's investment philosophy after his exit: dump everything into boring index funds, expect ~10% compounded for 40 years, and never check the market. Removing money worries lets him take big swings and focus all his energy on building.

“10% market returns compounded for 40 years, sell when you're 70, you're set. You're going to be balling when you're 70. You're going to be rich. You're going to die with that money. And so for me, I don't like checking the stock market. I don't care to. I don't want to understand it.”

Steal thisPark your exit money in boring index funds and stop checking it, so your focus stays on building.

The future small business will be online, digital, and profitable

Andrew predicts that aspiring entrepreneurs who once would have opened a restaurant or plumbing business will instead start niche SaaS or e-commerce companies, shifting the small business economy toward online, digital, profitable ventures.

“I think the future of the small business economy is going to be online, digital, and profitable. People who used to want to start like a restaurant or like a plumbing business or something like that, Those young entrepreneurs are going to be looking to start a niche SaaS company or a niche e-commerce company.”

The airport business: monetize a captive audience

Sam relays Andrew Wilkinson's 'airport business' concept: like an airport where travelers are stuck for hours and will buy candy and magazines, the best businesses capture an audience that has to be there and sell to them easily.

“with, with, with an airport, you arrive at the airport and you're there. You have to be there for 3 to 4 hours. You're going to buy whatever they have. You're going to— if you're there, it's very easy for that airport to sell you candy, a magazine.”

Steal thisBuild where the audience is already captive, then layer on easy upsells.

The secretive Brazilian billionaire who owns Burger King, Budweiser and Heinz

Andrew Wilkinson's Billy of the Week is Jorge Paulo Lemann, the press-shy Brazilian behind 3G Capital, who buys old, simple, multi-generational brands using piles of debt and runs them better.

“if you think about the businesses that he owns, uh, you would know them. So for Burger King, Budweiser, Tim Hortons, Kraft Foods, Popeyes, Heinz Ketchup, right? So he basically goes out, he finds these amazing, you know, multi-generational businesses that have been around for 50+ years that do something very, very simple. It's just going to grow over time. He goes out, he usually raises a ton of debt, and then he goes and buys them and takes them over.”

PSD hiring: Poor, Smart, and a deep Desire to get rich

At his bank Garantia, Lemann ignored resumes and hired for 'PSD' — Poor, Smart, and a deep Desire to get rich — a screen for hungry talent over pedigree.

“Poor, smart, and deep desire to get rich.”

Steal thisHire for hunger over pedigree: screen candidates for being poor, smart, and possessing a deep desire to get rich.

Skip the banker: call rich people and raise the money yourself

Wilkinson argues bankers, like most realtors, are often useless middlemen who 'build some decks and breathe on the phone' while taking a huge fee. If you have a great business, just call wealthy people directly.

“I think if you've got a great business and you want to raise money, Uh, you should just go and call a bunch of wealthy people and try and raise the money yourself. Because at the end of the day, a lot of the time what bankers do is build some decks and then breathe on the phone while you talk to other people and then take a huge fee.”

Steal thisIf you have a strong business, skip the banker fee and raise money by calling wealthy people directly yourself.

The third-generation buyout: catch a great brand once it gets sloppy

3G's playbook: target proven, simple businesses run by a complacent third generation that has gotten rich and lost discipline, then buy with debt and tighten the operation.

“When they bought Budweiser, it was on the third generation. They'd gotten super rich, right? So it was like the first generation built it. The second generation, like, were amazing. They went to Harvard, they grew it. The third generation took over. They got sloppy, didn't really care about growth. They had fancy offices and private jets and stuff. And so when they bought it, they just look at it and go, oh, it's been run in a kind of a sloppy way and they've lost their discipline. We can buy it with a lot of debt and then we can just make it way better, pay off our debt, and then we own Budweiser.”

Steal thisHunt for proven brands run by a complacent third generation, buy with debt, and win by simply restoring operational discipline.

Sell the private jets first: setting the tone from the top

Whenever 3G buys a company, the first move is selling all the corporate private jets and forcing executives — even hundred-millionaire CEOs — to fly economy and stay in motels, signaling a frugal culture from the top down.

“the first thing they would always do whenever they buy a business is they sell all the private jets immediately. Right. And let's, let's be real. Most Fortune 500 companies have like between 1 and 10 private jets.. And they just say, F that, we don't need those. They sell them and it's kind of a statement. And then from that point on, the new CEO and all the executives, they have to fly economy and they have to stay in motels.”

The one-thesis acquisition: buy on a single insight

Wilkinson's acquisition rule is to enter each deal with one clear thesis (e.g. margins should be 15% not 5%). With Burger King, 3G's single insight was to spin out and franchise corporate-owned locations to pay off the debt.

“we've seen this in our own investing, like often having one thesis, right? So the thesis could be, hey, margins are really shitty. You know, they're, they're 5%, they should be 15%, and we can do that via, via very simple improvements or something simple like this Burger King deal where they went into big debt and they actually paid up a really high price to do it. But the insight they had was, well, as soon as we take over, we're just going to spin out all of our corporately owned locations and franchise them. And by doing that, we're going to raise all the money to pay off our debt.”

Steal thisEnter every acquisition with one clear value-creation thesis you can execute, not a vague hope of improvement.

Deals are easy; finding leaders to run them is the bottleneck

Wilkinson says the hard part of a holding company isn't doing deals — he could do one a month — it's finding and validating enough amazing people to run each business. The real skill is being a 'leader of leaders' (the Warren Buffett playbook).

“The hardest part is recruiting the amazing people. Like, our biggest challenge isn't doing deals. It's like, we could do a deal every month. It's How can we find enough amazing people to run all these businesses? And then how can we validate that they're going to be able to do what we need from them?”

You don't need to be Elon — buy a poorly-run boring business and fix it

Wilkinson's takeaway from Lemann: skip the urge to invent something revolutionary. Take a traditional, poorly-run business — ideally one that's low-risk, growing, and succeeding despite bad management — and simply run it better.

“you don't need to do something innovative and crazy, right? You don't need to be the next Elon Musk or start some crazy technology. You can just choose a traditional business that's very poorly run. And run it better. And I, you know, even better if it's a business that's low risk growing and kind of successful despite bad management or, you know, bloated cost structure or something.”

Steal thisSkip inventing the next big thing: acquire a boring, poorly-managed but growing business and create value just by running it better.

How Capital Daily started: a MailChimp account and a stay-at-home mom

Frustrated that his local Victoria paper had laid off its journalists, Wilkinson started a local news newsletter, Capital Daily, with a stay-at-home-mom writer and a MailChimp account, then discovered ads for local-news subscribers were dirt cheap because no one was competing.

“I went to a friend who is a stay-at-home mom who had some experience doing a bunch of writing. And I said, hey, why don't we just start a MailChimp account and we'll come up with a brand. We called it Capital Daily. And we'll send out a daily newsletter and we'll just summarize like, hey, here's like 3 or 4 stories of things that are happening in town. So we start doing this and, uh, I have a friend who runs a PPC agency and I get him to just go buy ads. And I realized I can buy ads for like nothing. No one's advertising for local news.”

Local news is winner-take-all — so buy your way to scale fast

Wilkinson's local-news thesis: historically there's one dominant paper per city, so he spent $100–200K on ads to race to ~25,000 subscribers fast, then hired a CEO (Farhan) who had scaled Vancouver's biggest local news site to monetize it.

“I realized that in local news, usually there's one winner, right? So historically there's usually been one big newspaper. And so I was like, how do I get this as big as possible, as fast as possible? And I was also just impatient. I was like, I have money. I can afford to do it. I'm just going to spend like $200 grand on ads. And so we spent, I don't know, $100,000, $200,000. And very quickly we got to like 25,000 subscribers.”

Steal thisIn winner-take-all local markets, spend aggressively on ads to grab the dominant audience position before competitors wake up.

$2M spent to build a city's biggest news business that can net $1M/yr

Wilkinson spent just over $2M building Capital Daily — but only ~$250K on ads, with ~$700K from late monetization and ~$500K wasted on wrong hires. He believes the city-level business can do $500K–$1M in annual profit at scale.

“I think at this point I've probably spent just over $2 million, but you have to remember that probably the first $700K was just me, me not monetizing it soon enough and just focusing on building the audience first. So I think we probably spent $200K, $250K in ads. And then we probably burned an unnecessary $500K, like hiring the wrong people and kind of like experimenting. So really, like, at this point, we have the biggest news business in my city for probably $750K to $1 million.”

Roman/Hims for maternal health: build a 'super baby' supplement service

Wilkinson pitches a DTC maternal-health business modeled on Hims/Roman: blood work plus scheduled supplements (DHA/fish, B vitamins, iron) for pregnant mothers, marketed on the fear-hook of avoiding bad outcomes while promising a smarter, healthier baby. He offered to invest his own money.

“There's a huge opportunity to basically do like Roman or Hims but for maternal health. So you do blood work, supplements, they get delivered on a schedule, and it's about building like a super baby.”

Steal thisLaunch a DTC maternal-health brand — blood work plus scheduled prenatal supplements — sold on the fear-hook of protecting and optimizing the baby.

$25–$50K a month is 'enough' — be the casual tennis player, not the Olympian

Wilkinson's 'how much is enough' frame: $25–$50K/month passively, with very low risk, lets you do whatever you want for life. He admires — but doesn't want to be — the billionaire 'Olympian'; he envies people with $10–$25M passively invested and a balanced life.

“let's be honest, $50K a month, even $25K a month is enough to do whatever you want for the rest of your life. And so people often will ask me like, oh, what do you, you know, what do you aspire to be? Or who do you admire most? And I think like Money is like, I used the athlete, like the athlete thing, the example before of like Olympic athletes. I think like billionaires are like Olympic athletes”

The passport photo booth right outside the only passport office

Wilkinson admires a Victoria entrepreneur who put a passport-photo booth directly outside the city's single passport office — a tiny, high-intent location lock that funds a good life and frees him to surf and mountain bike most days.

“he has this business that's a passport photo booth, right? And in Victoria, there's a passport office. It's in the mall. There's only one of them. He has the passport photo office right outside, or sorry, the passport photo place right outside the Canadian passport thing. So as people walk in and they go, oh shit, I need a passport photo. He's got the booth right there.”

Buy media assets, then rebuild the P&L as a 5-person bootstrap

Andrew Wilkinson bought Girlboss only as asset purchase, ignoring its bloated venture cost structure. He valued it on its 2M social followers and audience, then reimagined what the business could do if run lean with about 5 employees instead of a full venture P&L.

“I said, "Look, I will buy it only if I can just buy the assets," because we looked at it and we said, hey, they've got 2 million social followers, they've got a huge newsletter, they've got a massive podcast feed. All the pieces are there, but the cost structure was venture, right? So they had a big P&L, they had a ton of employees, and we looked at it, we went, okay, what if this company had 5 employees? Could you run it with 5 employees?”

Steal thisWhen buying a money-losing media company, value the audience assets and re-underwrite the P&L as if you ran it with 5 people.

Underwrite acquisitions on base hits, not the home runs

Andrew Wilkinson explains his acquisition math: if every big upside fails and only the obvious base hits land (e.g. selling $40-50K/month of ads against 250K subscribers), the deal still returns well. Girlboss could do $3M/year and be amazing, with $20-50M as the upside case.

“if we're wrong about all the big opportunities and we're only right about just base hits, so like, hey, we've got 250,000 newsletter subscribers, can we sell $40,000 or $50,000 a month of ads on that? If we do that, we've got a good little business. And then if we do that on the podcast, we've got a really good little business. And then if we do that on social, again, it's bigger and bigger and bigger. It doesn't need to be huge. Based on the price we paid, it could do $3 million a year in revenue and be an amazing business and give us a good return.”

Steal thisBuy a business so the base-hit scenario already returns capital, and treat every growth bet as free optionality.

Tweeted an $11M rolling fund as an afterthought, filled in 4 hours

Andrew Wilkinson raised one of the largest AngelList rolling funds, around $11M, almost by accident. He tweeted it out as an afterthought and filled the commitments within roughly four hours.

“Yeah, it was insane. We literally were like, we tweeted it out as like an afterthought and we raised it in like 4 hours. It was totally insane.”

Pay any valuation only for proven operators

Andrew Wilkinson argues that indexing into startups at today's frothy valuations would likely lose money, just as it would have in 1999. His rule: ignore valuation only when backing a proven operator you deeply trust, and otherwise stay disciplined.

“And to me, the only way I'll bet on someone at a high valuation is if I know that they're a proven operator. Like if they're a founder who's done really well historically and I have a lot of trust and think they're amazingly smart, I don't worry too much about valuation. But dude, some of the stuff I'm seeing is just wacky, just crazy, crazy stuff.”

Steal thisOnly waive valuation discipline for founders with a proven track record you trust completely.

Braintrust: a no-fee Upwork that pays its network in coin

Andrew Wilkinson describes Braintrust, a freelance marketplace that looks like a polished Upwork but charges no fees. It pays project managers and aligns the network with a token, the way Uber would have if it had granted coin to early drivers, creating lock-in and aligning labor with capital.

“what they do very quietly is they have a coin and so they have a Braintrust coin and they have people who their job is to basically be a project manager on there. Those people get paid in the coin. All the transactions occur in the coin. It's almost like if Uber had issued a coin to all their early drivers,, and then as they participate in the network, they get rich. And so they don't go to Lyft because they're already rich in Uber coin, right? And so it creates this lock-in and it aligns incentives.”

Steal thisIssue tokens to your earliest network participants so their wealth grows with the network and they never defect to a competitor.

MediMap won by selling clinics on saving a phone-answering salary

Andrew Wilkinson recounts dismissing MediMap, a site showing live wait times at every Canadian walk-in clinic, until the founder returned with 25% of clinics signed up. The wedge: clinics field constant 'what's the wait time' calls, so punching wait times into the site lets them cut a medical office assistant.

“Comes back 6 months later and he goes, hey, I've got 25% of all clinics in Canada using this. And I'm like, well, how did you do that? And it turns out that every single clinic every day gets 10 phone calls a minute, and all the phone calls are is, hey, what's the wait time?”

Steal thisFind a directory where the data provider already wastes money answering the same question by phone, then save them that labor cost to get the data for free.

MediMap reached 86% of all Canadian walk-in clinics

After years of losing money to build the network, MediMap has wait-time software installed in 86% of all medical walk-in clinics in Canada, an unassailable moat that Andrew Wilkinson says even a $100M-funded competitor couldn't dislodge.

“So Now, this business has 86% of all medical walk-in clinics in Canada, and every single one has software installed, WaitTime software installed on their computers.”

The airport business: own the chokepoint, then fill the empty stalls

Andrew Wilkinson's mental model for high-moat businesses: an airport is the single chokepoint everyone must pass through, with a captive audience waiting in the lobby. Once you own that chokepoint, you monetize by filling empty 'stalls' (massage, bookstore, sandwiches) one by one.

“I always like to say, you know, we like to buy airport businesses, and an airport is, you know, there's one, there's one airport in a city, if you want to go somewhere and fly, you've got to go and sit in the lobby for an hour. And when you're sitting in the lobby, I'm going to try and sell you a bunch of stuff. So I've got all the stalls and I can put in a massage place and I can put in a bookstore, somewhere to sell sandwiches, whatever. And this is an airport business. And right now all the stalls are empty and we're going to start monetizing it and filling in all the stalls.”

Steal thisBuy the single chokepoint a market must pass through, then layer in revenue 'stalls' against the captive audience.

Euphoria: a Chipotle-vs-McDonald's healthy bakery with no blood-sugar spike

Andrew Wilkinson built a bakery making treats with new sweeteners (allulose, stevia, xylitol) that taste as good but don't spike blood sugar. His framing: bakeries are the unhealthy McDonald's of the '90s, and a healthy version is the Chipotle people will trade up to.

“everyone wants to be healthy right now and they're used to going to a bakery and eating something unhealthy. Given the option, would they choose something that's higher end and healthy but still tastes the same or better? So So think about McDonald's. McDonald's was the standard in the '90s. Now there's Chipotle. If you're a little more health conscious, you go to Chipotle.”

Steal thisTake a category people indulge in guiltily and build the higher-end healthy 'Chipotle' version that tastes the same.

Lost $800K on a pizza restaurant with an alcoholic manager

Andrew Wilkinson's cautionary tale about chasing fun side businesses: he started a pizza restaurant and lost $800,000, plagued by an alcoholic manager sleeping in the restaurant and a sketchy landlord. The lesson he took: the fun is only the beginning, so hire great people and get out quickly.

“I started a pizza restaurant and I lost $800,000 doing it. It was a total disaster. I was getting phone calls. We had an alcoholic manager who was sleeping in the restaurant. We had a sketchy landlord, we had just endless stress and bullshit. And so this stuff is fun to a point. And the key that I've learned is just hiring amazing people. So I only like the beginning. This part is fun, but I got to get out really quick.”

Henry Singleton's capital allocation: issue stock high, buy back low

Andrew Wilkinson explains the Outsiders-era playbook of Henry Singleton: great CEOs win by allocating capital well, not just by innovating. Issue stock when the market is overvalued and sell; buy back stock and invest aggressively when the market is undervalued.

“his whole thing was when the market is overvalued and crazy, that's a great time to issue stock and to sell things. And when the market is undervalued, you want to buying, not only buying back your own company. So if you don't own your entire company, you want to go and buy back more stock and you want to be investing then. And so that approach is very simple. It doesn't sound like rocket science, but I think it's a really important thing for people to be thinking about right now.”

Steal thisTreat your own stock as a currency: issue it when overvalued to buy assets, and buy it back when the market undervalues you.

Sold Shopify themes business in 2013, bought it back at 5-6x in 2019

Andrew Wilkinson's agency started selling $150-250 Shopify themes when Shopify was a small Canadian startup, rode it to a big business, then sold in 2013 before realizing how huge Shopify would get. He bought the business back in 2019 for roughly 5-6x what he sold it for, betting Shopify would keep growing.

“And so we were kind of thinking like, "Hey, it's a small little Canadian company. These guys seem nice. Let's do it." And we started doing it, and Shopify just grew into a behemoth. And we rode the whale and did really well. And we actually sold the business in 2013. We didn't realize how big Shopify would get. And then we bought the business back in 2019.”

Delegate your inbox with rules so only go/no-go emails reach you

Drowning in 200-300 emails a day, Andrew Wilkinson piped his email into tech-support software and gave two assistants ~10 written rules (sign docs under $X, book interviews above Y downloads). Now only friends, CEOs, and investment go/no-go decisions reach him, cutting volume to ~20 a day and saving 2-3 hours daily.

“I pipe my email into it, and I have my assistant, and then we have another assistant we have in the Philippines, and they basically monitor the email and they have a set of rules. So I wrote out, if someone asks me to sign a document, send it to this person on our legal team, they'll review it, and then if they say yes, you can sign it as long as it's below this amount. If someone requests an interview, go and look at the podcast, see how many downloads it gets, and if it's above this, you can schedule it or whatever. And so I made like 10 of these rules, and now I'm getting like 20 emails a day”

Steal thisWrite ~10 explicit decision rules with dollar/threshold limits and hand your inbox to an assistant so only true go/no-go emails reach you.

Turn cold-email asks into a paid monthly AMA for charity

Instead of guiltily ignoring or rejecting young entrepreneurs' cold emails, Andrew Wilkinson routes everyone to a monthly AMA and asks those who can afford it to donate to charity (which he matches). It has raised $58K for charity and saved him 2-3 hours a month.

“What I like to do is I do an AMA, ask me anything every month. And if you can afford to, to donate to charity, you know, just as a way of, you know, paying it forward or whatever. And so if someone's rich, if someone has a big company already, I'm like, hey, go donate some money. If they're a first-time entrepreneur, we don't expect them to. And then Chris and I just do a monthly AMA, and then everyone gets to enjoy the answer we do. So it's— dude, so it's been crazy. So we, we've already donated $58,000 to charity from this.”

Steal thisBatch all advice requests into one monthly public AMA and gate access behind an optional charity donation you match.

Pay to be in the right room: $30K of TED tickets, $10-20M of revenue

Andrew Wilkinson's networking philosophy: pay to be in rooms where everyone is pre-vetted as legit. As a small operator doing ~$15-20K/month he spent $10K on a TED ticket against friends' objections; roughly $30K of TED tickets over three years led to $10-20M of revenue across his businesses.

“I paid $10,000 to go to the TED Conference. And all my friends were like, what the hell are you thinking? You're spending all this money on this? I have this whole thing about paying to be in the right room, right? So when you go to TED, it's like a secret club. If you get into TED, every single person that's there is someone interesting. And at the very least, they've paid a lot of money to be there, so they're legit. And being in the room, if you're in the room, everyone goes, "Oh, they're legit too."”

Steal thisSpend real money to get into pre-vetted rooms; being there signals you're legit and the connections compound into revenue.

Bought a $5M dollar of stock for 65 cents, then $57K lunch with Ackman

Andrew Wilkinson bought into Bill Ackman's Pershing Square Holdings because its blue-chip stock portfolio (Lowe's, Chipotle, Howard Hughes) traded at 65 cents on the dollar. He then spent $57,000 on a charity lunch to 'grill' Ackman as due diligence; the stock later tripled and they ended up doing deals together.

“And for every dollar of stock that was sitting in the holding company, you could buy it for 65 cents because the stock had traded down so much. So it was like buying a dollar for 65 cents. So I didn't necessarily think Bill was a genius. I thought he was a very smart investor. I just thought it was a very cheap stock, and so I bought it. And then when I saw this charity lunch come up, I was like, "Oh, sweet. I can grill this guy and see if I like him."”

Ackman turned a $25M bet into $2.7B

Andrew Wilkinson notes that Bill Ackman invested $25 million in a hedge that turned into $2.7 billion, inside the very Pershing Square holding company Wilkinson is an investor in.

“he had a bet where he invested $25 million and it turned into $2.7 billion. And that was in that holding company that I'm an investor in.”

A podcast is the ultimate networking hack: pre-sold relationships at scale

Andrew Wilkinson argues normal networking means slogging through 5 boring calls for 1 great one. A podcast inverts it: 10,000 listeners already know who you are and opt in if they like you, so you skip the intro pitch and arrive pre-sold to every relationship.

“The problem with networking is you do 5 boring calls and then 1 amazing one, right? So you're constantly talking to people you don't necessarily want to talk where they don't turn out to be that interesting when you think they will be, but it's worth it because there's a diamond in the rough. And I think podcasting is interesting because it lets you— you basically have 10,000 people who kind of learn what you're about, and they can either decide if they like you or not. And if they opt in and they like you, you've already pre-sold them almost, right?”

Steal thisStart a podcast (or public content) so prospects arrive already knowing and liking you, skipping the cold-intro grind.

The four types of entrepreneur: innovator, remixer, scaler, optimizer

Andrew Wilkinson breaks founders into four archetypes using Chipotle: the innovator who rolls the first burrito, the remixer who builds the brand, the scaler who rolls it out to 100 locations, and the optimizer who maximizes an existing machine. Jacobs is the classic scaler.

“I always think there's like, um, 4 different types of entrepreneurs, right? There's the innovators. So let's just take, let's take, um, Chipotle as an example, right? So there's the innovator, there's the guy who rolled the first burrito and was like, oh shit, this tastes really good. Um, then there's the remixer. There's the person who creates Chipotle. They take the burrito, they package it up, they create a brand around it. Then there's the scalers, the person who scales Chipotle to 100 locations. And then there's the optimizer, the person who just sits on top, makes sure it doesn't blow up and gets as much as possible, gets as much juice out of the lemon as they can.”

Steal thisFigure out which of the four founder types you are, then build or buy in the lane that fits you.

The four types of entrepreneur: innovator, remixer, scaler, optimizer

Andrew Wilkinson breaks founders into four archetypes using Chipotle: the innovator who rolls the first burrito, the remixer who builds the brand, the scaler who rolls it out to 100 locations, and the optimizer who maximizes an existing machine. Jacobs is the classic scaler.

“I always think there's like, um, 4 different types of entrepreneurs, right? There's the innovators. So let's just take, let's take, um, Chipotle as an example, right? So there's the innovator, there's the guy who rolled the first burrito and was like, oh shit, this tastes really good. Um, then there's the remixer. There's the person who creates Chipotle. They take the burrito, they package it up, they create a brand around it. Then there's the scalers, the person who scales Chipotle to 100 locations. And then there's the optimizer, the person who just sits on top, makes sure it doesn't blow up and gets as much as possible, gets as much juice out of the lemon as they can.”

Steal thisFigure out which of the four founder types you are, then build or buy in the lane that fits you.

Dan Gilbert: the 'capitalist Batman' rebuilding Detroit

Andrew profiles Dan Gilbert, who went from a struggling Detroit bar family and pizza delivery to founding Quicken Loans, and whose net worth jumped from ~$7B to $57B even as he survived a major stroke; he pours money into revitalizing Detroit.

“He's like a capitalist Batman in Detroit, and I'll talk about some of the cool stuff he's done. And one of the things I like about him as well is that he. He does a lot of stuff that might not work. He takes big swings, takes big risks that he thinks can make the world better. And he invests in all sorts of crazy ideas.”

Gilbert moved 4,000 employees into bankrupt Detroit and bought up downtown

As Detroit went bankrupt in the financial crisis, Gilbert moved his entire ~4,000-person team from the suburbs into downtown, then bought billions of dollars of derelict buildings, ending up owning 20-30% of downtown and pledging to pay off $300M in residents' property taxes.

“he says, "Fuck it, we're moving back into Detroit," and he moves his entire team into Detroit. So he had 4,000 or so employees. If you actually go to Detroit, it's called Campus Martius or something, and it's right in the center of downtown, this huge building, and he moved everyone there.”

Andrew cold-emailed Dan Gilbert at 1am and got a yes in 5 minutes

Andrew's habit of cold-emailing interesting people paid off: he emailed billionaire Dan Gilbert at 1am, got a reply in 5 minutes, and ended up flying to Detroit for a two-day tour where Gilbert spent two hours saying yes to ideas instead of no.

“I have this habit of just cold emailing people I think are interesting. And like 95% of the time, I just don't hear back. But I wrote him an email at like 1 in the morning and said, hey, I'd love to meet you. And I get an email back like 5 minutes later and he's just like, yeah, sure.”

Steal thisCold-email the people you admire; most won't reply, but the occasional yes changes everything.

Andrew got Warren Buffett on the phone for 90 minutes via a random CC intro

While asking someone about philanthropy, Andrew got a surprise CC introduction to Warren Buffett, whose secretary said to call anytime; Buffett picked up and talked for an hour and a half on a landline, exactly the down-to-earth person Andrew hoped he'd be.

“And then he just like CC intro'd me to Warren Buffett, right? It was one of the weirdest things that's ever happened to me. And it was amazing. And I was like kind of nervous, like Warren Buffett's like my hero. Uh, you know, I was never not expecting this. It was just like a random Friday and Warren Buffett's secretary emails me back and just says, oh yeah, you know, call, call him whenever, you know, he'll, he'll pick up.”

Gilbert's barbell: a boring cash-flow business funds the crazy bets

Gilbert pairs a dull, cash-flowing mortgage business with wild venture bets, personally onboards every new hire on culture once a month, and lives by 'isms' like 'yes before no' and 'money follows, it does not lead.'

“he says, there's this great quote. He says, one of our things is that money follows. It does not lead. So we want people that are fired up and passionate about their mission and people that aren't so married to spreadsheets and thinking that kind of voodoo controls the future because it doesn't.”

Steal thisPair a boring cash-flowing business with a portfolio of big bets, and let mission lead money, not the reverse.

Gilbert's barbell: a boring cash-flow business funds the crazy bets

Gilbert pairs a dull, cash-flowing mortgage business with wild venture bets, personally onboards every new hire on culture once a month, and lives by 'isms' like 'yes before no' and 'money follows, it does not lead.'

“he says, there's this great quote. He says, one of our things is that money follows. It does not lead. So we want people that are fired up and passionate about their mission and people that aren't so married to spreadsheets and thinking that kind of voodoo controls the future because it doesn't.”

Steal thisPair a boring cash-flowing business with a portfolio of big bets, and let mission lead money, not the reverse.

Andrew bootstrapped Flow vs billionaire-backed Asana and lost $10M

Andrew built productivity software Flow, choosing to bootstrap like Basecamp, but Facebook co-founder Dustin Moskovitz's well-funded Asana out-built and out-marketed them; Andrew publicly revealed he lost $10 million on it.

“So the story was basically we started productivity software called Flow. I decided to bootstrap it like Basecamp, and we had a big competitor, Asana. And Asana was run by a billionaire, the co-founder of Facebook. He raised a shitload of money. And originally I was like, oh no, we've got a better product. And then they just made their product better and they outspent us on marketing and we got killed.”

Sam: $20 million is enough to live like a king in any city forever

Debating how much money is 'enough,' Andrew pegs it at $5-20M in his city while Sam argues $20 million is the threshold to live a great life in pretty much any city for the rest of your life.

“I think 20 is the threshold that you could live a great life in pretty much any city for the rest of your life with 20”

The 'New Zealand' business: profitable, cult-following, nobody competes with it

Shaan describes the 'New Zealand' type of business (a phrase coined by Andrew Wilkinson): an independent, simple, profitable product with a cult following that nobody bothers to compete with, using Chess.com as the example.

“It really fits the, what we call the New Zealand type of business that Andrew Wilkinson kind of coined that phrase, which is it's this independent thing. It has like a cult following. It's profitable, it's simple, nobody competes with it. It's like New Zealand. Nobody's going to war with chess.com.”

Steal thisLook for simple, profitable niche products with a devoted following that no competitor finds worth attacking.

Mark Leonard: the anonymous $2B SaaS roll-up king

Andrew names Constellation Software founder Mark Leonard his Billy of the Year: worth ~$1.9B from acquiring boring vertical-market software businesses with high switching costs since 1995, while remaining almost completely anonymous online.

“He founded Constellation Software, which is like the OG SaaS acquirer. So over the last 5 years, I think every single person in the world has realized software businesses are good businesses. Everyone's trying to buy them, paying crazy prices. This guy's been doing it since 1995 from up here in Canada. He's been focusing on super boring verticals with low competition.”

Jim Pattison's 'bag of money' monopoly play in signage

Andrew Wilkinson recounts how Canadian billionaire Jim Pattison broke into US signage by paying incumbents three years of revenue in cash upfront at double the rates, then slowly raised prices to build a near-monopoly.

“And so he gave all of his sales guys bags of money and they would walk into all the places that had signs and they'd say, I'm going to give you all the money you would make from the other guys for the next 3 years. In cash right now. I'm going to double the rates and I'm going to give it to you all up front. They dominated throughout different regions in the States, and then over time they started increasing prices again and they basically took over a monopoly down there.”

Andrew turned $10M into $220M buying back a company he sold

Andrew sold his Shopify-ecosystem software company for $7M in 2013, regretted it, bought it back for ~$26M in 2019, then took it public — turning ~$10M of cash into $220M.

“So in 2019, we ended up buying it back for $26 million or so, and then about 2 years later, just a couple of weeks ago, we took it public, and at one point it hit over a billion-dollar valuation. Right now it's at like $600-something million market cap, and so I had about $10 million into that business in cash,, and it turned into $220 million.”

Shaan goes all-in: $25K/day into Bitcoin to hit 25% of net worth

Rather than dollar-cost averaging, Shaan bought the daily maximums on Coinbase ($25K) and Robinhood ($50K) every day until Bitcoin was 25% of his net worth, buying near the all-time high at ~$18K a coin.

“I started buying $25,000 a day, which was the max on Coinbase, and then $50,000 a day on Robinhood, which is the max I could do there, every single day until I accumulated a position that was 25% of my total net worth was moved into Bitcoin. I was doing that at $18,000 a coin, which was almost the all-time high.”

Sell pickaxes to gold miners: own Coinbase, not Bitcoin

Andrew's investing principle: instead of betting on a single asset, own the infrastructure that profits from the whole trend — Coinbase for crypto, Stripe for internet commerce — to capture upside while taking less risk.

“My approach to all this stuff is to sell pickaxes to gold miners. Instead of owning Bitcoin, I'd way rather own Coinbase. I'd rather own Coinbase. It's a way to bet on crypto as a trend versus an individual currency.”

Steal thisBet on a trend by owning the toll-taking infrastructure everyone in the trend must use, not a single speculative asset.

Hyper-local news newsletters to replace the dying local paper

Shaan loves Andrew's idea of running a one-or-two-writer newsletter covering a single city, effectively replacing the local newspaper. Andrew confirms it's cheap and going well, but caps out around a $1–2M/year labor-of-love business per city.

“So creating a newsletter, you know, I live in Lafayette, a city in California, and creating a newsletter for Lafayette, people living in Lafayette about Lafayette that just has kind of like one or two writers and you're basically replacing the local newspaper through newsletters. I love this idea.”

Steal thisLaunch a one-or-two-writer newsletter covering a single city and become the de facto local newspaper.

Raisins and turds: diversifying junk Amazon FBA roll-ups

Andrew is skeptical of Amazon FBA roll-ups (like Thrasio) buying businesses at 1.5–2x earnings, arguing a diversified portfolio of moat-less businesses is still bad — invoking Munger: combine raisins with turds and you still have turds.

“I think Charlie Munger said, what is it? If you put raisins with turds, you've still got turds. It doesn't matter if you group together a bunch of shit, it's still shit. We've looked at tons of these businesses. They're They're sandcastles.”

Bolt a $100/month job board onto any audience site

Andrew's classic move: add a job board to a content site as a low-effort revenue stream. On Girlboss it pulled $5K–$10K/month, spun up with jobboardfire.com for ~$100/month plus an Upwork contractor.

“I think that job board, I think it did $5,000 last month. We did $10,000 the month before, and we just use jobboardfire.com, which is like $100 a month to spin it up. And it's one of those things where you're like, wow, that plus some Upwork contractor to help us, you know, administer it. And we made an extra $5,000. Like, why not?”

Steal thisAdd a cheap job board to your audience site as a near-passive add-on revenue stream.

Influencers should buy dead tools and resell to their audience

Andrew's riff: an influencer with a big audience can acquire a failed marketing tool (that died on customer-acquisition cost) for ~$5,000 on Product Hunt's graveyard, then sell it to their existing followers with free distribution.

“And so you could go on Product Hunt, find something that's failed 6 months ago that's a simple marketing tool because they were trying to acquire people with PPC. And then you just say, great, I'm going to acquire for $5,000 and sell it to my audience. I think there's tons of opportunities like that.”

Steal thisIf you have an audience, buy a dead tool that failed on paid acquisition and resell it to your followers for free.

Feature, not a product: why Fast and Dropbox get absorbed

Andrew's recurring critique: single-purpose tools are features that platforms eventually absorb. Like OSes building in cloud storage to commoditize Dropbox, e-commerce platforms will just make their own checkouts faster, killing standalone one-click checkout startups like Fast.

“So many people miss— VCs, entrepreneurs— the idea of feature, not a product. I think this is something— it's kind of like what's happened to Dropbox. Dropbox has found a niche, but at the end of the day, it was a crazy, amazing product that everybody needed. And then over time, all the OSes just built this in.”

Forwarded-email sales tactic closed $500K in 2 days

Shaan says copying Brex's 'private forwarded email' sales technique let his team close about $500,000 for their investment fund in just two days.

“And we used this tactic to close about $500,000 for our fund in 2 days. We used it for fundraising, but you can pretty much use it for any sales process that happens over email.”

Own the daily newsletter for every town — a mini Murdoch empire

Shaan builds on Andrew Wilkinson's idea: a local news newsletter for a town, run by 2-3 writers, monetized via local classifieds and B2B advertising, with subscribers acquired cheaply through geo-targeted Facebook and search ads. Owning the daily newsletter for many towns could be a very big business.

“And like, can you build like, you know, a little version of Rupert Murdoch's empire? By owning the daily newsletter for every single town. That to me sounded like that wasn't just one of Andrew's kind of pet ideas. That to me sounded like potentially a very big idea.”

Steal thisLaunch a local-news newsletter for one town with 2-3 writers, monetize via local classifieds and B2B ads, then replicate the playbook town by town.

Own 10 car dealerships for 50 years instead of chasing the moonshot

Andrew Wilkinson explains why he deliberately chose the Buffett-style path over the Elon path: most people who set out to innovate fail and live unhappy lives, so he'd rather own boring durable businesses, sit on them, and enjoy a good life.

“So I'd way rather own 10 car dealerships and sit on them for 50 years, live a nice life, have lots of kids, live somewhere I like, hang out with my friends, then spend 50 years trying to innovate and do something crazy and launch rockets to Mars, but have a miserable life, right? I'm glad people like Elon Musk exist, but I don't really want to do that personally.”

Steal thisDecide whether you're playing the durable-cashflow game or the moonshot game, and stop applying one game's strategy to the other.

He built a local newsletter to 40,000 subscribers in a city of 200,000

Frustrated by his dying local paper, Andrew asked a stay-at-home-mom friend to write a daily summary of Victoria news, modeled on The Hustle. Capital Daily grew to 40,000 subscribers in a city of 200,000.

“And so I went to a friend of mine who is a stay-at-home mom. And I said, hey, let's make a newsletter. And we're just going to summarize everything that's happening in Victoria every single day. And, you know, kind of inspired by The Hustle, just super simple. Here's like, you know, kind of a cleverly written summary of what's up. And before we knew it, We just, we just had like crazy numbers of subscribers. Uh, we're at the point. So, well, I mean, it's not hustle level, but we're now at about 40,000 subscribers in a city of 200,000.”

Why a lean local newsletter beats the legacy newspaper it replaces

Andrew's thesis on local news: newspapers fail because of legacy baggage - real estate, printing presses, unions - not because the model is dead. Strip all that out and a two-person virtual newsroom can cover a city profitably while selling ads far cheaper.

“The reason newspapers don't work is because they have legacy. They're cruise ships. It's hard to turn them and change them, and they have these huge real estate portfolios, they have printing presses, all this stuff. When you cut all that crap out, you can actually afford to sell ads for way less, you don't need that much revenue, and you can really just have a virtual newsroom with a couple people and cover a city.”

Steal thisRe-enter a 'dead' industry by stripping out the legacy cost structure the incumbents can't escape.

Buy businesses with product-market fit, then hire someone who's done it before

Andrew's operating playbook: rather than build risky startups, buy businesses that already have product-market fit and real revenue, then hire an operator who has already run something twice the size and align incentives and culture.

“But the advice I always give people is, if you want to build a business that is, you know, going to scale and do well, just find someone who's already done it before, right? So if I'm buying an agency, I'm going to go find someone who's run an agency that's double the size, and I'm going to incentivize them appropriately, make sure the culture is aligned and stuff.”

Steal thisHire the operator who has already run a business twice your size, not someone you hope will grow into it.

Sell newsletter ads as pay-per-lead, not flat sponsorships

Andrew describes converting newsletter ad inventory into lead-gen deals: instead of charging $5,000 for a slot local advertisers don't understand, an automotive lead-gen partner pays per lead delivered, which earns the newsletter far more than a flat ad would.

“But basically we put in their ads and then we basically get paid based on every lead we give them. And a lead is worth like $50 to them. So they can pay us like $25 a lead or whatever. So it's actually significant way more than we'd make if we'd done an ad.”

Steal thisReprice newsletter ad inventory as pay-per-lead so you share in the advertiser's upside instead of a flat slot fee.

Buy abandoned Product Hunt apps for $5K and grow them

Andrew's unexecuted idea: scroll back six months on Product Hunt, find the coolest products that fizzled because the developer couldn't market them, and offer the founder $5,000. To them it's a dead project; to a marketer it could be a $5M business.

“And so what I was thinking is, it'd be smart to go through Product Hunt, go back 6 months, and just look at all the coolest shit that came out, and then start approaching all those developers and saying, "Look, I'll give you $5,000." And to them, they're like, "This is useless to me, I've already shut it down, I don't wanna pay for hosting." to you that could be a $5 million business?”

Steal thisAcquire fizzled Product Hunt apps cheap from developers who can't market, then bring the distribution.

A $10M venture portfolio that would've been richer in the S&P 500

Andrew's blunt take on angel investing: despite a couple of nice returns including a sale to Workday, his roughly $10M venture portfolio would have made him richer, safer, and more liquid had he just put the money in the S&P 500 or Apple. Angel investing is not a good way to make money.

“I probably have a $10 million venture portfolio or something. And if I'd just taken that same money and put it in the S&P 500 or Apple stock or anything else, I would be way richer and it would be way safer. I'd have a more liquid net worth. It would be cash in the bank, right? Like, so I don't think that angel investing is a good way to make money.”

Go where the stupid rich people are

Andrew riffs on Sam's line about real estate: target industries so forgiving that operators succeed even when they're idiots. The presence of 'stupid rich people' is a signal the business is good enough to win regardless of skill.

“I love your line, by the way, about how, you know, the stupid— there's a lot of stupid rich people in real estate, right? I think you want to go where the stupid rich people are because that means that the business is so good that it can succeed regardless of whether you're an idiot.”

Steal thisPick businesses forgiving enough that idiots get rich in them - that forgiveness is your margin of safety.

Mailman: an email firewall that delivers your inbox twice a day

Andrew built Mailman after realizing he wasted whole days in his inbox. It holds email back and delivers it only at scheduled times, snoozes the inbox after hours, and quarantines anyone who hasn't emailed you before - 'an email firewall' that makes life calmer.

“And so we started working on this product called Mailman. And basically what it does is, um, it allows you to kind of snooze your inbox. So you can say, you know what, I get home at 4, I want to hang out with my kids. I don't want to have to use screen time and deal with all this shit. I just want no new emails to come in until 7 in the morning. Um, I want to get email twice a day. I want to get it at 7 in the morning and 1:00 PM.”

Steal thisBatch your inbox to fixed delivery windows and auto-quarantine first-time senders to reclaim your day.

Andrew Wilkinson's Gmail plugin that copies the best of HEY

Shaan praises Andrew Wilkinson's idea for a Gmail add-on that replicates HEY's two best features — screening first-time senders and hiding newsletter clutter — without forcing users to switch email providers. The lesson: deliver the killer features of a new product as a plugin on top of a tool people already use.

“He basically, he took the, he replicated the two features that matter in HEY and hey.com. Like, hey, you could screen, you know, new recipients first before they show up in your inbox. And also it'll just hide all your newsletter cruft in one spot, like better than the core thing.”

Steal thisCopy the two killer features of a switch-required product and ship them as a plugin on the tool people already use.

Amazon FBA is picking up pennies in front of a steamroller

Shaan relays Nassim Taleb's metaphor (via Andrew Wilkinson) for Amazon selling: high probability of steady small gains, low probability of total death when Amazon suspends your account or cuts your category's take rate.

“it's like picking up pennies in front of a steamroller. So, you know, there's a high probability you can make a little bit of money, you know, consistently, every single time you reach down, you pick it up. And then there's, you know, low probability of complete death.”

Steal thisTreat any platform-dependent business as a pennies-in-front-of-a-steamroller bet: keep diversifying off it before the steamroller hits.

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”

Incentive-caused bias: share buybacks line the CEO's own jeans

Wilkinson explains incentive-caused bias using buybacks: CEOs paid in stock options benefit when share price rises, and buybacks shrink the share count to lift price — so a 'return capital to shareholders' move can really be self-enrichment.

“a lot of CEOs are compensated based on share price because they get stock options. So their stock options become more valuable when the share price goes up. And what makes the share price go up but share buybacks? So when you buy back shares, there's fewer shares and each individual share is worth more. So it's actually a way for the CEO to put money in his or her own jeans.”

Andrew Wilkinson zigged: charge SF rates, pay local rates, buy don't build

Shaan breaks down Andrew Wilkinson's two contrarian bets: living in Canada while charging San Francisco prices and paying staff local rates (making his agency wildly profitable), then using that cash flow to buy businesses instead of building them.

“And he was like, no, I'm going to live where I want to live, and I'm going to take advantage of some of the arbitrage opportunities of He charged San Francisco rates to his companies he was doing designs for, but he paid his people local rates for doing the work that they were doing. And so his agency was wildly profitable, and that compounded over like a decade, which is great. So Canada was one contrary decision. The other one was buying businesses versus building them.”

Steal thisSell into a high-cost market while keeping your cost base local, then redeploy the spread into buying cash-flowing businesses.

Buy boring: Tiny acquires simple, profitable, durable internet businesses

Andrew Wilkinson describes Tiny's thesis: a long-term holding company that buys majority stakes in profitable, simple, often boring internet businesses from bootstrapped founders. He deliberately avoids sexy categories like drones, AI, and VR in favor of predictable cash flow.

“So we go out and we find profitable, simple, often boring internet businesses, and we acquire majority stakes and we take over ownership. And we usually buy from founders. Often they're bootstrapped., and usually the businesses have been around for, you know, 5, 10 years. These are longer-term things, and we don't go for sexy stuff. We're not doing drones and AI and VR and all that kind of stuff. We look for businesses that are simple and predictable and boring.”

Steal thisHunt for simple, boring, cash-flowing internet businesses that have already survived 5-10 years instead of chasing sexy categories.

The Buffett-style 7-day term sheet that founders actually love

Wilkinson contrasts the miserable, drawn-out private equity process (months of diligence, last-minute renegotiation, earnouts) with Warren Buffett making multibillion-dollar deals in 7 days. Tiny copies Buffett: fast decisions, no renegotiation, founders get to leave and Tiny takes over management.

“And when we started reading about Warren Buffett, we were like, what the fuck? Like, Buffett makes deals in 7 days and he's doing multibillion-dollar deals. Why can't we just do the same thing? And the businesses we're buying, they're way less complex, way less complex than what Buffett's buying. He's buying factories and stuff. We're buying like these tiny little internet businesses with, you know, 10 to 20 employees. And so we started doing it and people love that. Because founders are high-paced. They want to make a quick decision and get a deal done, and they don't want to waste a bunch of time on it, and they don't want to be renegotiated and dragged through the mud.”

Steal thisWin deals against private equity by promising founders a fast, no-renegotiation close instead of months of diligence and earnouts.

The pessimist's asymmetrical bet: stocking up early on COVID

Wilkinson, a self-described natural pessimist, saw early China news and judged a 1-in-5 to 1-in-10 chance of a global crisis. He treated prepping (a $5,000 grocery run, an isolated office house) as a cheap asymmetrical bet: small cost if wrong, big protection if right.

“And when I started seeing the news pop up out of China, I thought, you know, maybe there's a 1 in 5 chance, 1 in 10 chance this turns into something global and serious. But when I look at the cost of protecting myself so directly with my family, where, you know, I buy $5,000 of groceries or whatever, fortunately I could afford to do that. So me and my business partner rented a house to use as an office. We isolated really early. We stocked up on groceries and hand sanitizer and all that kind of stuff. I just looked at it as an asymmetrical bet where, you know, I spend a small amount of money to protect us. And if we're wrong, then we can laugh about it and look like idiots. But it's pretty low cost.”

Steal thisWhen the downside of being wrong is cheap and the upside of being right is huge, take the asymmetrical bet even at low odds.

Tiny's hands-off CEO playbook: a monthly P&L and a quarterly SWOT

When Tiny buys a company it installs a trusted CEO, hands them a growth playbook, and asks for only two reports: a financials-only update monthly and a SWOT analysis quarterly. No board meetings; some CEOs go six months without contact unless there's a crisis or big investment.

“All you have to do is send us two things. Once a month, you're going to send us a financial-only update. So we get no information about the operations of the business, just the, the numbers, the P&L and the balance sheet. And then on a quarterly basis, you're going to send us a SWOT analysis. So strengths, weaknesses, threats, opportunities in the business. And if there's anything that's really important, you got to call us quickly.”

Steal thisManage portfolio CEOs with just a monthly financials-only update and a quarterly SWOT, escalating only on crises or big bets.

Delegate the work you hate: Andrew stopped flying to close sales

By 2010 Wilkinson had hit his Maslow ceiling around $100-150K/year and refused pain for more money. He hated flying to San Francisco for sales, so he hired people who loved planes and closing, paid them a fortune, and the business grew faster while his life got better.

“And one thing I hated was I hated flying to San Francisco. I'd always get sick, I'd have a bad sleep, I just didn't enjoy it. And that was required to do sales. And so having me do sales meant that I didn't want to get on the plane, I wouldn't go do the meetings, I wouldn't close a deal. And so when I delegated that and I found people who, A, love getting on planes, love closing deals, and only do that, and then I paid them a fuck ton of money for closing those deals, everything in my life got better. The business grew way faster.”

Steal thisIdentify the high-value task you avoid because you hate it, then hire and over-pay someone who loves doing it.

The 'New Zealand business': self-sufficient, no platform risk

Wilkinson's favorite holding, Dribbble, exemplifies his ideal: a 'New Zealand business' that is self-sufficient with no intermediary or gateway. Designers type Dribbble directly into the URL bar, so there's no Google or Facebook risk, and the captive community can be monetized many ways.

“I always say you want a business to be like New Zealand, right? So New Zealand is in the middle of fucking nowhere. Nobody's paying any attention to it. It's quietly successful. It's totally food and energy independent. It could get cut off from the rest of the world and people would eat and be fine. And it's away from nuclear war. Right. And so when I think about a business, I want a business that there's no intermediary, there's no gateway, and you have a fully self-sufficient society.”

Steal thisFavor businesses where customers come directly to you, so no platform (Google, Facebook) sits between you and your audience.

Canada's hiring stack: SR&ED credits, currency arbitrage, free healthcare

Wilkinson explains why hiring in Canada is cheap: the government refunds 15-40% of R&D salaries (SR&ED 'shred' credits), a US dollar converts to ~$1.42 Canadian, salaries are lower, and public healthcare means no health-insurance costs to cover.

“The government will actually give you cash back on that salary. And I mean, depending on the scale of your business, the level of profit and stuff, it can be like 30, 40%. For us now, it's much lower. I think it's like 15% or something. We get it as a tax credit, but it's insane. Like, just, just for everyone's context. So in Canada, we have currency arbitrage, meaning if I get paid a dollar US, I get $1.42 Canadian, right?”

Steal thisHire engineers in Canada to stack SR&ED salary refunds, currency arbitrage, and free public healthcare against US labor costs.

Job boards are just selling a link — if you own the audience

Wilkinson frames job boards as the modern newspaper classifieds: a simple list of jobs a developer can build in three days, where you charge $100-$400 per posting. They're incredible businesses with a captive audience and niche, and horrible ones without.

“They're incredible businesses because at the end of the day, you're just selling a link, right? So these, these websites are very simple. It's a long list of jobs. You might be able to filter by category or whatever. And when you click a job, so it might be like designer for, you know, The Hustle, you click the job and it gives a description and it says you should apply here. Right. And so in terms of software, this is like something a developer can whip up in 3 days. It's very, very basic, it's very easy to maintain, and it doesn't require a lot of engineering. So very low cost to operate, and you can charge a lot for job postings. So just like a classified, you know, you can charge anywhere from $100 to $300.”

Steal thisIf you already own a captive niche audience, bolt on a job board: cheap to build, $100-$400 per post, and high margin.

The Hustle should launch a job board worth ~$1M/year at 80% profit

Wilkinson tells Sam it's a no-brainer for The Hustle to add a job board given its captive audience, estimating it could add about $1M a year of revenue at roughly 80% profit. He notes WeWork Remotely thrives because of audience, while generic job boards Tiny bought petered out.

“I don't understand why you don't have a job board at this point. It's just such a no-brainer. You could probably add like $1 million a year of revenue, and it's like, you know, 80% profit probably.”

Steal thisIf you run a media brand with a loyal niche audience, add a job board as a high-margin revenue line.

No-code gets you to your first $1M before you write deep code

Wilkinson is obsessed with no-code tools like Webflow that let you build and ship a website in five hours with hosting handled. He argues no-code can build a job board, an Airbnb clone, or a marketplace in days, getting you to your first million in revenue to prove the model before writing scalable code.

“And it's not like you're going to build this super scalable business out of this, right? Like it'll, it'll get you your first million dollars of revenue and prove the model and then you can go and build all the deep code. And, you know, maybe, maybe it's not as good of an experience on mobile and all that kind of stuff. But in terms of like proving out MVP ideas, it's absolutely incredible.”

Steal thisBuild your MVP and first $1M of revenue in no-code to prove the model, then rebuild in real code once it's working.

The designer cat furniture flop that taught Andrew to hate e-commerce margins

One of Wilkinson's dumbest ideas: a Shopify dropshipping store selling designer cat furniture, born from his own ugly-cat-furniture problem. He learned how brutal e-commerce and dropshipping margins are, found it impossible to profit without $1M in inventory, and contrasted it with his asset-light 50%-margin digital businesses.

“And so I started an e-commerce store on Shopify that was selling designer cat furniture. And I just, to be honest, I didn't understand how bad e-commerce margins were, and especially dropshipping. And so I spent a ton of money on fulfillment and shipping and all that stuff. And I basically realized it was impossible to make money unless I went out and spent $1 million on inventory.”

Down to $1,500 and buying potatoes in 2008

Wilkinson recounts the depths of 2008, when clients stopped paying and demanded deposits back, leaving him with about $1,500 in the bank — low enough that he went out and bought potatoes. The scare made him permanently conservative with the balance sheet, and diversification now lets him sleep.

“And I got to a point where I had at one point $1,500 left in the bank, and I literally went out and I bought potatoes. Like, this is, this is like the depths of 2008 where all my clients suddenly weren't paying their bills, and, you know, suddenly everyone wanted their security or their deposit back and stuff.”

Subscription podcasting will explode once big personalities catch on

Wilkinson predicts personality-driven podcasters (Howard Stern, Rogan, Maron) will leave platforms like Sirius to run their own subscription feeds charging ~$10/month, with insane margins. His company Supercast builds private premium feeds, and he says creators are building SaaS-like businesses with no employees.

“And I started going like, well, what would stop Howard Stern from leaving Sirius and just starting his own subscription podcast and charging $10 a month? And you start thinking about the scale of something like that where you get Marc Maron or Terry Gross or, you know, Howard Stern or Rogan or whoever. And you just start doing that where they do one extra episode a month or they cut their podcast off after 30 minutes, or whatever it is. I think the numbers are insane on that, and I think that's where it's gonna go once a few people catch on.”

MetaLab threw off ~$7M/year in profit before Tiny started buying

Wilkinson reveals MetaLab was generating roughly $7 million a year in profit when he began acquiring other companies, starting with Designer News in 2013. That free cash flow became the engine for Tiny's acquisitions.

“I think we were doing about $7 million a year in profit or something like that when we started buying businesses.”

Newsletters are New Zealand businesses you can build an empire on

Wilkinson tells Sam that newsletters are an incredible 'New Zealand business' and that owning The Hustle is like owning the modern newspaper. He frames the podcast's affiliation with The Hustle as proof you can stack many businesses on top of a self-sufficient audience asset.

“One of the things I was gonna say is I think newsletters are an incredible business. They're New Zealand businesses, right? Like I think Sam, you own the modern newspaper essentially, and I think that you're gonna be able to unlock so many businesses.”

Steal thisTreat your newsletter as the self-sufficient core asset and stack new businesses (job boards, products, media) on top of its audience.

Tiny Capital: buy profitable companies and live off the dividends

Sam describes Andrew Wilkinson's Tiny Capital, whose portfolio collectively does about $100M in revenue, taking dividends and using the cash flow to buy more companies—a buy-and-hold-for-cashflow model versus chasing exits.

“He owns tiny capital, and they do— they've been doing this. Uh, the companies that they own collectively, I think, do about $100 million in revenue, and he, I think, takes dividends and buys companies with the cash flow, right? And, uh, it's an awesome model.”

Steal thisBuy profitable companies, take dividends, redeploy the cash flow into more acquisitions.

Envato: $300M lifetime sales, $94M revenue, $33M profit in 2017

Sam cites Envato, a marketplace for WordPress themes and plugins, as having grossed $300M in sales since 2008 and doing $94M revenue with ~$33M profit in 2017.

“And Envato, all they are, they probably wouldn't like my oversimplification, but it's basically a marketplace for WordPress themes and plugins. And since 2008, this thing has grossed $300 million in sales. And in 2017, they did $94 million in revenue with something like $33 million in profit.”

Escape the 'fine, good' trap with a specific opener

Instead of 'how's it going?' (which dead-ends at 'fine'), Shaan hits people with a specific observation-based question like 'You look happy, what were you doing right before this?' to get them genuinely talking.

“So I might say, you got a little pep in your step today. You know, what'd you have for breakfast? Or you look happy. What were you doing right before this? Right? So somebody could just pop on a Zoom and I'll hit them with that. You look happy. What were you doing before this? Oh, actually, I was on a call with blah, blah, blah. Or I was actually just cooking food. Doesn't matter what it is. I got him talking.”

Steal thisOpen conversations with a specific observation plus question instead of 'how are you?' to break the cookie-cutter reply.

Easy choices, hard life. Hard choices, easy life.

Andrew Wilkinson's go-to framework (a quote popularized by Tim Ferriss): when you know the right thing to do but are tempted to delay it or make it work, making the hard choice always results in an easier life. Applies across firing, business, and personal decisions.

“Easy choices, hard life. Hard choices, easy life. By this guy, Jersey Gregoric. I think Tim Ferriss famously shared this quote years ago and it always sticks with me. And it most recently has been on my mind. And it's, it's one of those things where you will often find a situation where you know what the right thing to do is.”

Steal thisWhen two options feel equal, pick the harder one — your brain is discounting the hard one to dodge short-term pain.

Why Wilkinson stopped worshiping the Steve Jobs CEO archetype

Wilkinson grew up reading Steve Jobs biographies wanting to be that kind of creative-genius CEO, but realized those people who 'blow their brains out working' often have bad lives or are unhappy. He found he only enjoyed managing 5-10 people max, and anything beyond that forced him into the CEO role he hated.

“I grew up reading biographies of Steve Jobs and worshiping him and thinking I wanted to be that kind of person. And then as I read more and more biographies, I realized that often those kind of creative genius CEOs who blow their brains out working have kind of bad lives or bad dads. Are somewhat unhappy people day to day.”

Why Wilkinson stopped worshiping the Steve Jobs CEO archetype

Wilkinson grew up reading Steve Jobs biographies wanting to be that kind of creative-genius CEO, but realized those people who 'blow their brains out working' often have bad lives or are unhappy. He found he only enjoyed managing 5-10 people max, and anything beyond that forced him into the CEO role he hated.

“I grew up reading biographies of Steve Jobs and worshiping him and thinking I wanted to be that kind of person. And then as I read more and more biographies, I realized that often those kind of creative genius CEOs who blow their brains out working have kind of bad lives or bad dads. Are somewhat unhappy people day to day.”

Don't settle for a B/C hire just because the search exhausted you

Andrew Wilkinson on hiring fatigue: after a 6-month search with no candidate, the easy move is to settle for a B or C player out of exhaustion — and every time he does, it's a colossal failure. The hard, correct move is to keep doing more phone calls.

“let's say that we're doing a hire and we've been doing the hiring process for 6 months and we haven't found the candidate and we have someone that we think is like a B or a C, but we're exhausted at the end of it. The right thing to do is to actually continue the process and do the hard thing and do more phone calls and stuff. But it's so easy to get fatigued and choose the wrong person. And every time I do that, it's always a colossal failure.”

Steal thisNever settle for a B/C hire out of search fatigue — push through and keep interviewing.

Don't settle for a B/C hire just because the search exhausted you

Andrew Wilkinson on hiring fatigue: after a 6-month search with no candidate, the easy move is to settle for a B or C player out of exhaustion — and every time he does, it's a colossal failure. The hard, correct move is to keep doing more phone calls.

“let's say that we're doing a hire and we've been doing the hiring process for 6 months and we haven't found the candidate and we have someone that we think is like a B or a C, but we're exhausted at the end of it. The right thing to do is to actually continue the process and do the hard thing and do more phone calls and stuff. But it's so easy to get fatigued and choose the wrong person. And every time I do that, it's always a colossal failure.”

Steal thisNever settle for a B/C hire out of search fatigue — push through and keep interviewing.

Don't settle for a B/C hire just because the search exhausted you

Andrew Wilkinson on hiring fatigue: after a 6-month search with no candidate, the easy move is to settle for a B or C player out of exhaustion — and every time he does, it's a colossal failure. The hard, correct move is to keep doing more phone calls.

“let's say that we're doing a hire and we've been doing the hiring process for 6 months and we haven't found the candidate and we have someone that we think is like a B or a C, but we're exhausted at the end of it. The right thing to do is to actually continue the process and do the hard thing and do more phone calls and stuff. But it's so easy to get fatigued and choose the wrong person. And every time I do that, it's always a colossal failure.”

Steal thisNever settle for a B/C hire out of search fatigue — push through and keep interviewing.

Andrew thinks the Saudis zero-dayed his phone over a Khashoggi tweet

After tweeting against the Khashoggi killing, Andrew was courted by a fake 'sheikh' investor who grilled him oddly, then sent a WhatsApp fireworks video. His phone began constantly rebooting, and he believes he was hit with a state-grade zero-day exploit.

“And then 24 hours later, I get a video message from him on WhatsApp and it's just fireworks and it says Happy New Year. And I'm like, well, that's a weird— like, what a weird guy. I don't think anything of it. And then for the next week, my phone is constantly rebooting. And around this time it clicks for me and I'm like, oh my God, I probably was identified as somebody the Saudis wanted to like check out and they probably did one of these zero days on me.”

Anthony von Mandl: dirt-floor winery to White Claw, $8B, no VCs

Andrew met a stranger at a neighborhood party worth $8 billion: Anthony von Mandl. He started a wine-importing business, bought a near-bankrupt winery with dirt floors, then created Mike's Hard Lemonade and later White Claw, owning ~100% with no debt.

“it turns out this guy's worth $8 billion and he owns a beverage-focused holding company called Marc Anthony Group. This guy named Anthony von Mandl and his story's pretty crazy. So he started a little like wine importing business in Vancouver and made enough money to buy a winery called Mission Hill, took on a ton of debt. It was like dirt floors, had only a few barrels of wine, turned it around, turned it into a real solid business.”

Wilkinson's CEO hiring hit rate: 60-70%

Across the 15-25 CEO-style roles Andrew Wilkinson has hired for his portfolio of ~20 companies, he estimates his success rate at roughly 60-70%.

“I would say probably 60%, 70%, something like that.”

A Twitter following is reboot insurance you can't lose

Andrew Wilkinson argues a large Twitter following is unseizable capital: when he tweeted about a business he was incubating, he got his first 1,000 customers instantly. You could go bankrupt and reboot in two days off your audience alone.

“I realized that when I talked about a business I was incubating, I had our first 1,000 customers in a split second. And so from my perspective, you know, I talked about last time about being like the Dust Bowl farmer mindset of what if you lose everything? There's such power in that. You could literally go bankrupt. You could lose all your businesses. You could reboot in 2 days with a business idea if you have a Twitter following and no one can take your Twitter following away, obviously.”

Steal thisBuild an owned audience so you can launch to your first 1,000 customers instantly even after a total wipeout.

MetaLab hit $7M in profit by year 7

Sam reads from a public article that by Andrew Wilkinson's seventh year in business, his company (around MetaLab) had reached $7 million in profit before he hired a formal CEO.

“by your 7th year of business, you had $7 million in profit according to this article on like colinkeely.com. So you had a good-sized business.”

Will AI like DALL·E make design obsolete?

Wilkinson openly questions whether, in 5 years, you'll be able to type 'build me a website that looks like this' into DALL·E and iterate by voice — and whether design will still be a profession. He notes he's historically been rewarded for not overestimating such tech near-term.

“You look at DALL·E and you go, okay, in 5 years, will you be able to type into DALL·E, build me a website that looks like this? And then it comes back and you say, oh, more creative, or make the logo bigger, or do this. Will design still be a thing? Right? And I've always been rewarded by not overestimating these things in the near term and just trucking on.”

Will AI like DALL·E make design obsolete?

Wilkinson openly questions whether, in 5 years, you'll be able to type 'build me a website that looks like this' into DALL·E and iterate by voice — and whether design will still be a profession. He notes he's historically been rewarded for not overestimating such tech near-term.

“You look at DALL·E and you go, okay, in 5 years, will you be able to type into DALL·E, build me a website that looks like this? And then it comes back and you say, oh, more creative, or make the logo bigger, or do this. Will design still be a thing? Right? And I've always been rewarded by not overestimating these things in the near term and just trucking on.”

Don't pay a CEO a flat % of profit — peg the bonus to beating your existing growth rate

Wilkinson's early comp mistake was paying 5% of profit, which let the CEO stay lazy and still collect. The fix: if the business already grows earnings ~15% annually, set that as the bar so the CEO is only rewarded for growth beyond what you'd already achieve.

“let's say like a business is already growing your earnings, like 15% annually, you want to incentivize them to at least grow that fast because that's what you're already doing and setting that bar. Whereas I think what I did was I said I had something like, you know, you get 5% of profit or something like that, which is not a good comp model because then they don't really need to grow the business. They can just keep kind of being lazy and enjoying the 5% they're going to get at the current level.”

Steal thisPeg a hired CEO's bonus to growth ABOVE your current annual growth rate, not a flat percentage of profit they'd earn just for showing up.

The chocolate cake model of dopamine addiction

Andrew Wilkinson relays Stanford addiction doctor Anna Lembke's model: a pleasure eaten monthly stays delicious; weekly it dulls and you start craving; daily your brain craves it and you're in pain until you get it, and even then it just removes the pain. Social media works the same way, so she prescribes a four-week dopamine fast.

“if you eat chocolate cake once a month, it tastes amazing and you don't really crave it that much. You don't really think about it that much. It's very pleasurable. If you eat it once a week, you know, it's still enjoyable, but it's not as good. And you start having cravings, you start wanting chocolate cake. If you eat it every day, your brain literally craves it and you're in pain until you eat it. And when you eat it, it's not even that enjoyable. It just makes the pain go away for a little bit.”

Steal thisRun a 4-week dopamine fast: cut social media, podcasts, and news; walk and drive in silence to reset your baseline.

Zero-day cyber weapons cost $1-3M, and budget buys anyone

A former Canadian cyber-command operator told Andrew that with budget he could hack anyone in about two hours. Zero-day exploits go for $1-3 million, and the target doesn't even need to click anything.

“So like these cyber weapons, these zero days, they cost like $1 to $3 million. But if you have the money, you can get anyone you want. You literally just send them a text. They don't even have to click a button and you got them. It's absolutely terrifying.”

Phantom equity over real equity to keep a conglomerate clean

Wilkinson avoids giving real equity in his ~40 corporate entities because it blocks him from moving assets and merging companies for tax purposes. He uses phantom equity instead, and only gives any equity at all when the plan is to eventually sell the business.

“We're moving towards doing more phantom equity if we do do it, because it's really complicated in a conglomerate like we have where you have, you know, 40 or so corporate entities to not be able to move stuff around and, you know, slam companies into one another for tax purposes and stuff. So we're moving more towards phantom equity if we do it. But if a company is at scale, you know, already doing tens of millions of dollars of revenue and profitable, I wouldn't give equity unless the plan is to sell the business.”

Steal thisUse phantom equity instead of real shares so you keep the freedom to restructure and merge entities for tax purposes.

Andrew's two picks for de-biasing your brain

Wilkinson spent years rereading psychology to hammer out his biases. His top two resources: Robert Cialdini's book Influence (anchor bias, comparison, the thinking traps) and Charlie Munger's speech 'The Psychology of Human Misjudgment,' free on YouTube.

“The, my favorite book on it is Influence by Robert Cialdini. It's amazing. It just kind of goes through all of the kind of thinking traps we get into. Um, and you know, it's anchor bias, um, and, uh, you know, um, comparison and, you know, all these, all these kinds of ways that you trick yourself. Um, and then the other great one is The Psychology of Human Misjudgment by Charlie Munger, which is a speech he gave at Harvard.”

Self-bind your phone: leave it home, carry only the Apple Watch

To break phone addiction, Andrew Wilkinson removes the option entirely rather than relying on willpower: he leaves his phone in a drawer and carries only a cellular Apple Watch, so emergencies still reach him but texting is too annoying to do. He frames it like keeping junk food out of the house.

“I mean, how do you not eat junk food all the time and have a good diet? Don't keep junk food in the house. Don't keep booze in the house, right? Self-bind yourself. So, I mean, I just basically screen time the hell out of my phone. And today, for example, I drove to my office. I just have my Apple Watch. I don't have my phone. So, I know if my kids fall down and hurt themselves, my wife can call me, but otherwise I'm not really texting.”

Steal thisCarry only a cellular smartwatch when you leave the house so calls reach you but texting is too painful to bother with.

The capital-call headache that pushed Wilkinson to phantom equity

Wilkinson illustrates why outside shareholders are painful: if a CEO owns 3% and Tiny has to inject $100K into the business, you have to ask the CEO to chip in $3K, they balk, and then you have to dilute them. Phantom equity sidesteps the complexity.

“Let's say we have a CEO and they own 3% of the business and Tiny has to inject money into the business, like loan the business money or something. There's a lot of complexity when you have outside shareholders where you go to the shareholder, like the CEO, and you say, hey, we're loaning $100,000. Can you chip in 3% or, you know, $3K? And they're like, what the fuck? And then you have to dilute them and it just gets kind of complicated. So that's why we're moving towards phantom equity.”

Pay CEOs more if they'll take more risk: trade base salary for variable upside

Wilkinson sizes total comp by how much risk a CEO will accept. A candidate wanting $500K all in salary gets capped, but one willing to take $100K salary with everything else variable can earn far more. He also lets the bonus keep scaling past target (do $15M on a $10M EBITDA goal, get 150% of variable).

“if someone comes to me and they say, Look, you know, I want to make $500K a year. I would say, okay, well, how much do you want to be salary and base salary versus variable comp and bonus? And if they're willing to take more of that in variable comp and bonus, then we can move those numbers up to be bigger than $500K. If they came to me and they said, look, I only want $100K salary and I want everything to be variable bonus. Maybe I would give them way more. And then the other thing we'll often do is we'll say if we set a target, let's say our target is $10 million of EBITDA and you exceed that, let's say you do $15, then we're going to give you 150% of your variable target or your variable bonus.”

Steal thisLet a CEO swap base salary for variable upside, and never cap the bonus — pay 150%+ when they blow past the EBITDA target.

The startup-as-a-house test: which house would you buy?

Andrew Wilkinson frames the venture-vs-boring choice as buying a house: a startup is an 80% chance of zero, 10% break-even, 10% rich; the boring business is an 80% chance of solid returns, 10% zero, 10% poor. Same time invested, very different odds.

“would you buy a house that had an 80% chance of being worth zero, a 10% chance of making your money back and had a 10% chance of making you rich? Right. And then let's say there's another house and that house, there's an 80% chance of giving you a pretty solid return, 10% chance of zero and a 10% chance of a poor return. Which of those houses are you going to buy?”

Steal thisBefore picking a venture, map its probability-weighted payoff against a boring cash-flow alternative for the same time invested.

A big bonus check is good news: comp as a magnet to your desired outcome

Wilkinson reframes large CEO pay: a $400K total comp is really ~$180-250K base plus variable you only pay when targets are hit. He thinks of comp as 'a magnet to whatever outcome you want,' and loves writing huge bonus checks because they mean the business beat expectations.

“I love paying huge bonus checks because if I'm paying a big bonus check, that means that the business is doing well and we're hitting our targets and they're growing faster than I expected to. A lot of people get caught up when they hear, you know, oh my God, I'm gonna pay this person, you know, $400 grand, let's say a year. I'm saying in an at-scale business, let's say it's $400K total comp. And they forget that what that really means is $180, $200, $250 in base and the rest in variable. And you're only paying the variable and bonus if they're hitting targets and the business is growing the way you want it to. So I think of it as like, that's a magnet to whatever outcome you want.”

Steal thisReframe comp as a magnet to your target outcome — structure it so the only way the check gets big is if the business wins.

A big bonus check is good news: comp as a magnet to your desired outcome

Wilkinson reframes large CEO pay: a $400K total comp is really ~$180-250K base plus variable you only pay when targets are hit. He thinks of comp as 'a magnet to whatever outcome you want,' and loves writing huge bonus checks because they mean the business beat expectations.

“I love paying huge bonus checks because if I'm paying a big bonus check, that means that the business is doing well and we're hitting our targets and they're growing faster than I expected to. A lot of people get caught up when they hear, you know, oh my God, I'm gonna pay this person, you know, $400 grand, let's say a year. I'm saying in an at-scale business, let's say it's $400K total comp. And they forget that what that really means is $180, $200, $250 in base and the rest in variable. And you're only paying the variable and bonus if they're hitting targets and the business is growing the way you want it to. So I think of it as like, that's a magnet to whatever outcome you want.”

Steal thisReframe comp as a magnet to your target outcome — structure it so the only way the check gets big is if the business wins.

$1M at 30 compounds to $100M by 60

Andrew Wilkinson's get-rich-slow math: start with $1M at age 30, throw off $300K-$500K a year, reinvest at 10-12%, and you have $100M by 60. The starting number can be small if the time horizon is long.

“So if you have $1 million at age 30 and you can invest, you can produce profits of maybe $300,000 to $500,000 a year at between 10% to 12%. You can have $100 million by 60. With compounding.”

Steal thisReinvest a steady $300K-$500K a year at ~10% from age 30 and let three decades of compounding do the rest.

Pay $15-20K for a deep background check — not the references the candidate hands you

Wilkinson argues normal reference checks are useless because candidates only give you references who'll tell the best story. He pays an expensive firm (~$15-20K) to independently validate every claim — employment history, schools, and the jobs where they got fired.

“So someone says, hey, call my 3 references. They're not going to tell you about the job where they got fired and, you know, they had a horrible, uh, you know, relationship with their boss and they let a bunch of people down. They're going to give you the best possible story. So we have a firm that we use. It's very expensive. I think it's about, 15 or 20 grand, but they will literally get on the phone with the person and they'll validate, they'll write down every single claim they make, walk through their employment history, where they went to school, and they'll validate it.”

Steal thisFor a senior hire, pay a specialist firm to independently verify every claim instead of calling the curated references the candidate hands you.

Pay $15-20K for a deep background check — not the references the candidate hands you

Wilkinson argues normal reference checks are useless because candidates only give you references who'll tell the best story. He pays an expensive firm (~$15-20K) to independently validate every claim — employment history, schools, and the jobs where they got fired.

“So someone says, hey, call my 3 references. They're not going to tell you about the job where they got fired and, you know, they had a horrible, uh, you know, relationship with their boss and they let a bunch of people down. They're going to give you the best possible story. So we have a firm that we use. It's very expensive. I think it's about, 15 or 20 grand, but they will literally get on the phone with the person and they'll validate, they'll write down every single claim they make, walk through their employment history, where they went to school, and they'll validate it.”

Steal thisFor a senior hire, pay a specialist firm to independently verify every claim instead of calling the curated references the candidate hands you.

Jump 1-foot hurdles, not 10-foot ones; swing for base hits

Andrew Wilkinson's pattern: stop chasing businesses that are '10-foot hurdles' requiring lots of people and funding, and instead pick projects inside your circle of competence that are simple to execute. He calls it going back to base hits, a 15-year overnight success that clicks suddenly.

“I used to think I wanted to build all these kinds of businesses, but those were 10-foot hurdles. I don't want to jump 10-foot hurdles. I want to jump 1-foot hurdles. And so if you think about it, all the stuff you're doing, they're in your circle of competence and they're relatively simple to execute. They don't require a lot of people, they don't require funding.”

Steal thisFilter new ideas to ones inside your circle of competence that need no funding or team, then take base hits over home runs.

The third door: skip venture and the dry cleaner both

Andrew Wilkinson rejects both ultra-conservative jobs and venture moonshots, advocating a middle path modeled on Nick Huber: find a niche like self-storage, develop a specific edge, and compound at 15-40% buying boring businesses for a decade.

“So I think what I advocate isn't go uber conservative and go get a salary or go buy a dry cleaner and work there for the rest of your life. It's more what's in the middle, what's the third door. And I like to look at somebody like Nick Huber who found a niche and he said, look, I'm going to go buy a bunch of self-storage businesses.”

Steal thisPick a boring niche with a specific operating edge and compound by buying businesses, not by chasing the venture lottery.

Andrew Wilkinson had his best year ever and was still miserable

Wilkinson took a business public, raised a big fund, and bought great companies — yet felt totally miserable. He traces it to COVID collapsing his day from cafe-hopping in short chunks into all-day Zoom and email, plus a Twitter follower spike that hooked him.

“I had this amazing year. We took a business public, we raised a big fund, we got to work with all these interesting people, we bought some great businesses. I didn't die of COVID All these great things happened, and yet I was totally miserable.”

You have to do it wrong before you do it right

Andrew's rule for entering a new space like NFTs or crypto: don't wait to get it right. Throw spaghetti at the wall, expect to lose money, and treat starting badly as the price of learning to do it well.

“you got to do it wrong before you do it right. Right. And if you know, you directionally want to go into NFTs and crypto, you just kind of have to throw a bunch of spaghetti at the wall and you got to lose a lot of money. And you know, this might make money, might lose money, but just starting, I think is way more important.”

Steal thisWhen entering a new domain, budget for cheap losing experiments rather than waiting to act perfectly.

On paper you're a billionaire; liquidity is what actually matters

Andrew Wilkinson's core warning on the venture path: even if you're a paper billionaire in year two, you typically can't realize it for 10-15 years until an IPO or sale. Cash flow or sellable stock is what truly counts.

“even if on paper you're a billionaire in year 2, my argument is you're not liquid until 10 years, 15 years anyway. Right. It's very rare that you start a business on year 1 and in year 5, you're a liquid billionaire. And to me, ultimately liquidity is what matters so often in these things, right? Either you have cash flow or you can sell your stock, um, or you can use it in some way.”

Fake private-jet photo set rented to influencers at $70/hour

Someone built a fake private-jet interior in LA, like a movie set, and rents it to influencers wanting fake in-flight photos at $70/hour. Andrew estimates it's booked ~12 hours a day, doing $20K-$40K/month at 80%+ margins after a weekend build.

“So some guy, he went and he basically built a fake interior of a private jet in Los Angeles. Like they use like a movie set or whatever, and then they just rent it out to influencers so that they can take photos where it looks like they're on a private jet, but they're not. And they charge $70 an hour. I think it's booked out like 12 hours a day, probably doing like $20,000 to $40,000 a month. And I can't imagine the margins would be less than 80%.”

Steal thisBuild a cheap themed photo set once and rent it hourly to content creators on a studio-listing platform like Peerspace.

Buffett's farm: a lowball bid doesn't change what you own

Andrew invokes Buffett's farm parable to stay calm in a down market: if your cash-flowing farm is worth a million and a jackass offers 50 grand, you just say no. A market quote only matters if you choose to sell.

“Just because some jackass rolls up one day and says, hey, can I buy your farm for 50 grand? You just say, fuck off. No, I, you know, I'm not selling for 50 grand. It doesn't mean you think your farm's worth 50 grand now. Right. And the stock market goes up and down and you get all these bids. You just don't have to sell. So unless you sell your stock at this valuation, it doesn't affect you in any way.”

Tiny bought AeroPress for $70 million

Andrew Wilkinson's holding company Tiny acquired AeroPress, the cult coffee maker, for $70 million.

“The deal was $70 million to buy it.”

Dopamine fasting: the chocolate-cake rule of pleasure and craving

Stanford addiction doctor Anna Lembke's framing: eat chocolate cake monthly and it's amazing with no craving; weekly and cravings creep in; daily and your brain craves it and only feels relief, not pleasure. The fix for overstimulation is a multi-week dopamine fast with quiet, silence, and no constant hits.

“If you eat it every day, your brain literally craves it and you're in pain until you eat it. And when you eat it, it's not even that enjoyable. It just makes the pain go away for a little bit.”

Steal thisWhen something stops feeling good, ration it like chocolate cake — or do a multi-week dopamine fast to reset your baseline.

Debt is the only way an already-rich person loses everything

Andrew lives in fear of debt: he avoids margin on anything volatile, keeps cash on the sidelines to cover loans, and treats leverage as the number-one way someone who is already rich can lose it all.

“But I live in fear of debt. I think it's like, it's the number one way you can lose, you know, you can already be rich and then lose everything. So only way basically.”

AeroPress: buying a category that owns coffee with zero marketing

Andrew Wilkinson describes AeroPress as a category owner like Kleenex or Band-Aid: sold in nearly every gourmet coffee shop, written as a setting on grinders, with fanatical baristas getting tattoos and a World AeroPress Championship. The plan after acquiring it is simply to add a D2C channel that never existed.

“So no one searches like pneumatic tube coffee maker. They just search AeroPress. So, and it's literally written on grinders, right? So like one of the settings on the grinder is AeroPress. So basically, this is an opportunity for us to buy a category of like making coffee, a way of making coffee. And like people are fanatical. There's like World AeroPress Championships. Baristas get like tattoos of AeroPresses.”

AeroPress: buying a category that owns coffee with zero marketing

Andrew Wilkinson describes AeroPress as a category owner like Kleenex or Band-Aid: sold in nearly every gourmet coffee shop, written as a setting on grinders, with fanatical baristas getting tattoos and a World AeroPress Championship. The plan after acquiring it is simply to add a D2C channel that never existed.

“So no one searches like pneumatic tube coffee maker. They just search AeroPress. So, and it's literally written on grinders, right? So like one of the settings on the grinder is AeroPress. So basically, this is an opportunity for us to buy a category of like making coffee, a way of making coffee. And like people are fanatical. There's like World AeroPress Championships. Baristas get like tattoos of AeroPresses.”

The 90/10 reinvestment rule that built a $1B portfolio

Andrew Wilkinson took 80-90% of his agency profits and plowed them into incubating new businesses, living on the rest. One company he sold for $7M was throwing off $600-700K a year; compounding that strategy for 15 years built a portfolio worth over $1B.

“But then I ended up continuing to take that money and just do the 80/20, 90/10 strategy of always investing. And I really started making a lot more money when I went from starting businesses to buying businesses and investing, which I started about 7 years ago.”

Steal thisLive on 10-20% of profits and reinvest the rest into new or acquired businesses, every month.

Wilkinson's businesses together worth over $1 billion

Andrew Wilkinson describes reinvesting ~80% of monthly leftover profit into starting new businesses for 15 years; he says all his businesses together are now worth over $1 billion.

“And I, you know, I've been doing that for 15 years now. And we're— I think, you know, all of our businesses together are worth over $1 billion.”

Agencies are capital-efficient money machines if you skip the fancy office

Andrew's case for agencies: win a contract, then hire the labor just in time, so there's almost no burn and you can bootstrap. The fatal mistake is blowing the cash flow on humongous $5M offices in SF, NY and Spain.

“And then before you know it, you're cash flowing and you're always able to hire people just in time for the work. And so at the end of the day, there's really no burn and it's very capital efficient and you don't need Uh, you don't even need an office anymore.”

Steal thisSell the contract first, hire the delivery talent just in time, and keep overhead near zero.

Buy at 3-10x earnings, then double the business in 1-2 years

Andrew Wilkinson's acquisition playbook: use 20-30% bank debt for leverage, buy businesses at 3-10x earnings, then find ways to double earnings within the first 1-2 years, yielding a 2-5 year cash payback before the multiple-driven value gain.

“And then we were buying these businesses anywhere from 3 to 10 times earnings. And then we would usually within the first 2 years, we would find ways to double the business within 1 to 2 years. So you start to think about it and you go, okay, well, that's a kind of 2 to 5 year payback depending on what's happening.”

Steal thisBuy cash-flow businesses at 3-10x earnings with some bank debt, then double earnings within two years to compress your payback period.

Buy Ackman's holding company at a discount to its own net assets

Pershing Square Holdings is a public vehicle holding blue-chips (Chipotle, Domino's, Hilton, Universal Music) that perpetually trades at a discount to net asset value, ~$70 for $100 of stocks. That discount is a built-in buffer: the market can fall 30% before you lose money, plus you get Ackman managing it.

“And as I dug into it, I realized that it perpetually trades at a discount to the net assets there. So if there's $100 worth of stocks, it trades at about $70, meaning that the market could go down 30% before you've lost any money in the portfolio. And then on top of that, you have Bill Ackman managing your money and he does crazy shit. Like he, last year he turned $25 million into $2.7 billion.”

Steal thisBuy closed-end vehicles trading below NAV so the discount itself is your margin of safety.

Wilkinson compounded at ~40%+ buying small businesses

Andrew Wilkinson says when his firm raised a fund and ran the math, their compounded return was roughly 40-some percent — but he credits small, less-competitive deals and expects bigger deals to slow that down.

“we did the math a couple of years ago because we raised a fund and I think it was like 40-some percent. Now, keep in mind, that was at a time where not that many people were doing what we were doing. So it's gotten more competitive over time and those were small deals. It's really easy to compound at high rates when you're doing small deals.”

AeroPress runs on ~$20,000 of marketing spend

AeroPress, the brand Tiny bought for $70 million, spends roughly $20,000 a year on marketing and has fewer than 10 employees, illustrating how a category-defining product can run on near-zero ad spend.

“Yeah, it's like $20,000.”

Cruise ship vs. speedboat investing

Andrew Wilkinson's mental model for evaluating a business: a startup is a speedboat (exhilarating but you white-knuckle it, might hit a rock, might run out of gas), while a stable cash-flowing business is a cruise ship (slow, predictable, low odds of failure, and you can just buy a ticket via a stock certificate rather than the whole boat).

“A cruise ship is slow and steady. It moves on a straight course. So, you can pretty much estimate where they're going. You can make an educated guess that you'll end up in Hawaii versus Antarctica based on where they're going and what their course is. You can get a comfortable sleep, lots of amenities. There are very low odds of failure. It's not dangerous at all. And best of all, you don't have to buy the whole boat. You just buy a ticket. I was saying a stock certificate, right? So essentially, just as a mental model, when I look at a business, I go, "Is this a speedboat or a cruise ship?”

Steal thisBefore backing a business, ask whether it's a speedboat you must white-knuckle or a cruise ship you can simply board.

Hire 1 to Hire 10

Andrew's biggest hack for scaling Tiny: never hire the ten people yourself, hire the one person who will hire the ten. Founders waste themselves 'swooping and pooping' as the de facto VP instead of hiring the VP.

“And what I realized is you should never ever hire the 10 people. You should always focus on hiring the one person. So that could be a CEO who will then go out and hire all the executives. Or could be hiring an executive who will hire an entire team. But, uh, it's just, it's such a hack, right? It's like 80/20. How do I do 20% of the work for 80% of the result?”

Steal thisStop filling individual roles yourself; hire the one leader whose job is to build the rest of the team.

When you buy a business, make only two decisions

Andrew's operating model for acquired companies: he decides who runs it and how they're incentivized, then fully delegates. He told the AeroPress CEO that hires were now their call—he trusts them 100% unless something goes dirty or the business tanks.

“And so it's complete delegation of when I buy a business, I make two decisions, who runs it and how are they incentivized? And unless they do something dirty or horrible or the business goes to shit, you know, I just leave them to it.”

Steal thisAfter an acquisition, pick the operator and the incentive, then stay out of operational decisions.

Do it wrong before you do it right

Andrew Wilkinson's bias-to-action rule: hire whoever's in front of you and just start, even badly, because it forces you into the industry. His failed restaurant (which lost $800K) is how he met the neighbor whose successful steakhouse he later bought.

“Too many people, um, think they're measuring twice but cutting once and they just never cut. They just measure forever.”

Steal thisStart badly on purpose to force yourself into an industry, learn it fast, and meet the right people through the mess.

Equal risk, equal reward: make them write a check for equity

Andrew says the common losing incentive structure is a partner with upside but no downside. His fix: anyone who wants equity must write a check or take a personal loan, so a failure produces real, felt loss—because people feel losses more than gains.

“The common losing formula is them not being aligned on risk. So for example, if they're able to use my money and I can keep injecting money into the business, but it in no way hurts them. So for example, they don't get diluted. Or they don't have to pay a high interest rate, or, you know, if it goes bankrupt, they don't lose anything. That's a huge problem.”

Steal thisRequire equity partners to put real money at risk so they share the downside, not just the upside.

Wilkinson hired his CFO and 12-year business partner off a bank visit

Andrew Wilkinson met Chris Sparling as the young bank teller helping him get a corporate credit card, hit it off, and blurted out 'do you want to be my CFO?' despite Chris having almost no accounting experience. Chris is now his business partner of 12 years.

“And I just blurt out, do you want to be my CFO? And he's kind of taken aback and he's like, Hey, let's go get a coffee tomorrow. We'll talk about it. And I convinced him to come and be my CFO. He has almost no accounting experience. He worked at a bank. On paper, he's the wrong guy to be a CFO of a business.”

Andrew's ghost-kitchen of sugar-free cookies got killed by regulation

Andrew had a baker friend make near-perfect sugar-free cookies using allulose, stevia and monk fruit, selling them ghost-kitchen style out of his office. The local health authority shut it down because allulose isn't approved in Canada.

“And they just said, hey, you're using an ingredient that's not approved in Canada. And unfortunately, allulose is not approved in Canada. And so you just legally can't serve food with it, even though it's generally regarded as safe and everything.”

Thin desires vs. thick desires (mimetic desire)

From the book Wanting, Andrew Wilkinson explains mimetic desire: thin desires are extrinsic wants modeled by your peers (a Rolex, a sailboat, a raise from Sequoia), while thick desires are intrinsic things you'd enjoy quietly without telling anyone, like gardening. The work is pruning thin desires so you chase what you actually want.

“And so in this book, they talk about thin desires. So these are like extrinsic things coming from the modeling of others, right? So wanting a Rolex because people, you know, that are your peers value Rolexes. And then there's thick desires, which are intrinsic. They come from inside of you. So you enjoy working in your garden. You don't need to tell anyone. You don't post about it. It's not part of your identity. You don't do it to impress anyone. It's just something you quietly enjoy.”

Steal thisAudit your wants: keep the thick desires you'd pursue privately, prune the thin ones copied from your peers.

Find your real rival by asking 'Who do I not want to succeed?'

To surface who you're actually in mimetic rivalry with, Andrew Wilkinson suggests asking the uncomfortable question: who do you secretly not want to succeed? It's usually a friendly peer slightly ahead of you, not a distant celebrity like Bezos. Naming that rival reveals which desires are driving you.

“So the way to figure out who your models are as well is actually to ask kind of an odd question. You say, "Who do I not want to succeed?" And maybe it's deep within you, but it might be that guy on Twitter who you're friendly with and everything's fine, but he kind of bothers you or he's maybe a little ahead of you, has maybe 10,000 more followers, and you just don't want him to succeed. That's probably who you're in mimetic rivalry with.”

Jump 1-foot hurdles, not 10-foot hurdles

Andrew's pattern-matched lesson after years of hard businesses: stay inside your circle of competence and pick simple-to-execute ventures that don't need a lot of people or funding. He no longer wants to jump 10-foot hurdles.

“I used to think I wanted to build all these kinds of businesses, but those were 10-foot hurdles. I don't want to jump 10-foot hurdles. I want to jump 1-foot hurdles. And so if you think about it, all the stuff you're doing, they're in your circle of competence and they're relatively simple to execute. They don't require a lot of people, they don't require funding.”

Steal thisChoose businesses inside your circle of competence that are easy to execute and need little capital or staff.

The gumption test: do they move the ball within 24 hours?

Chris Sparling's hiring filter, per Andrew Wilkinson: when you tell someone the ball is in their court, do they follow up within 24 hours and move the ball forward? Gumption is the single best signal of whether a hire will work out.

“Chris has this thing about— he calls it gumption. It's like if you say to them, hey, ball's in your court, do they follow up within 24 hours? Do they move the ball forward?”

Steal thisAfter a meeting, hand someone the ball and judge them by whether they follow up and advance it within 24 hours.

The Feynman method: you don't understand it until you teach it

Andrew Wilkinson describes the Feynman method for retention: you don't truly understand something until you can teach it, so the best way to remember a book is to summarize it cogently to others, e.g., on a podcast, and keep bringing it up.

“It's basically you, you read the thing and then you teach it and you can't truly understand it until you teach it. So like a, a way of remembering really well would be go on the podcast and in a very cogent way summarize what you've learned and then keep bringing it up for yourself.”

Steal thisAfter reading something important, force yourself to teach it out loud to lock in retention.

Buffett made 97% of his wealth after age 55

Andrew cites that Warren Buffett made ~97% of his wealth after 55 to argue that wealth compounds slowly and quietly. His own model: reinvest 70% of profits, live on 30%, and let 17 boring years compound into a big number.

“I don't know if you know this, but Warren Buffett made like 97% of his wealth after the age of 55. So, so it all happens very slowly. He started in his 20s or whatever, and he wasn't really well known until the '90s.”

The sawmill paradox: you still feel you have to chop wood

Andrew's parable for founder anxiety: you start chopping wood out of restlessness, it becomes a business, and 15 years later you own 15 sawmills and just file papers—yet part of you still beats you up for not chopping wood. The machines do the labor but the need to do labor never leaves.

“And then one day, 15 years later, I wake up and I'm in a sawmill. And I own 15 sawmills and all I do all day is file papers, but there's still this part of me that beats myself up for not chopping wood. I still have this mindset, even though all the machines do all the labor, there's still this part of me that's constantly saying, you need to chop wood, you need to chop wood.”

Tickers make you miserable, so don't run your life on them

Andrew Wilkinson argues that constant metrics, stock tickers, KPIs, daily revenue, Oura Ring scores, glucose readings, are 'tickers for life' that make you miserable when checked hour to hour, and you shouldn't have them for your life the way you don't for a business you want to enjoy.

“Like they're tickers for life and tickers make you miserable. Look at a stock ticker, look at KPIs, look at revenue day to day, hour to hour, and you're miserable. You shouldn't have those for your life.”

Bad guys usually win: the fake $20M-exit mentor

Andrew was mentored, then hired, by a woman who claimed she'd sold her business for $20M. She turned out to be falsifying documents and had never sold anything—but reference-call limits let her keep charming new victims. The lesson: con artists assume you're the bitter ex and keep winning unless they become Elizabeth Holmes.

“And so this woman, you know, I see her on LinkedIn and she's still succeeding and going every year, she's somewhere new. And, you know, people like this, they don't get super rich. They're so short-term. And if they only knew how much money you could make by not being a crook, they would probably be ethical.”

Sparling's 5 Pillars of Happiness

Chris Sparling's simple happiness model, shared by Andrew Wilkinson: see family every day, see friends weekly, be in nature weekly, have a new/novel experience monthly, and do something that satisfies your 'caveman brain' (hunting, sports) once a quarter.

“So he'll say, um, see family every day, right? Obviously. Um, see friends and loved ones multiple times a week, be in nature once a week, new and novel experiences once a month, and then feel like a man or a woman, go out with your buddies, go hunting, sports, whatever makes you feel tough and gritty and ticks that box for your caveman brain once a quarter.”

Steal thisAudit your week against the 5 pillars: family daily, friends and nature weekly, novelty monthly, caveman activity quarterly.

Ask 'what could go wrong?' — 'nothing' means run

Andrew's single best red-flag test: after a super-charming pitch, ask what could go wrong. If the founder says 'nothing,' it's terrifying. Five or six times that one signal preceded a company going to zero, bankrupt, or criminal.

“The biggest one that I've seen is you get this uber charming pitch and then you say, okay, what could go wrong? And they say nothing, right? And you're just like, no, this is insane. This is terrifying. I've had like 5 or 6 different pitches where that was the one signal and it went to zero or bankrupt or criminal.”

Steal thisAlways ask a founder what could go wrong; a 'nothing' answer is a disqualifier, not reassurance.

Win the raise with the first sentence, not a template

Andrew's fundraising-email craft: most pitches are generic Salesforce-style templates that fail. His opener was 'In 2019, I was pissed off,' engineered as a hook so the reader needs to know what he's pissed off about. Few people use copywriting tools to pitch in written form.

“And I always think, like, what I was trying to do with that email is I wanted the first sentence to hook you. And so I think the first sentence in that email was, in 2019, I was pissed off, right? And then they, you know, line one, you're like, what's he pissed off about? What's going on? Right? There's a bit of a hook.”

Steal thisOpen a pitch email with a one-line hook that creates a question, never a generic template.

Blunt one-line replies hurt relationships more than no reply

Andrew's worst habit of the year was firing off blunt one-line responses to DMs and texts. People take more offense at a curt one-liner than at silence, where they can assume you simply didn't see it, so not responding is actually less damaging.

“And it's funny you mention this because I wrote my worst habit of the year is writing blunt one-line responses to DMs and text messages. Because I'm busy, right? I'm just trying to rip through them all and I'm tired. But it's way, it's way better to not respond. At least then you're mysterious and, oh, maybe you didn't see it. The one-liners piss people off so much.”

Steal thisDon't fire off curt one-liners; either reply warmly or wait, because a blunt one-liner reads worse than silence.

Local news's moat: fish where nobody else wants to fish

Andrew's case for local news in 50K-300K cities: it looks like a tiny market, which is exactly the moat. Because it's the stuff nobody wants, you can fish off the beaten path and dominate a local market with little competition.

“But in reality, it's the stuff nobody wants. You're fishing where the fish are off the beaten path and you can dominate a local market.”

Steal thisTarget unsexy markets too small for big players, where you can dominate instead of compete.

Read 'Made to Stick' to learn the wedge-and-hook craft

Andrew credits Made to Stick (Chip and Dan Heath) as the book that made copywriting click for him. He says MetaLab only worked because they'd take a boring topic, find a wedge, pick a fight, and become a topic of conversation that drove client work.

“So I think everyone needs to read the book Made to Stick. That was the book that like really clicked for me.”

Negotiation-as-a-service: $50K start sold to Ramp for millions

Andrew met a scrappy operator who loved negotiating, tested him by having him haggle car and desk purchases (saving ~40%), then co-founded a negotiation-as-a-service business 50/50. They started it for ~$50-100K and sold it to Ramp within a year for single-digit millions.

“And so I was like, okay, dude, this should be a business, like negotiation as a service. You need, you know, a lease negotiation, SaaS software, whatever. So we start this business called Buyer. We go 50/50 on it. I promote it and talk about it, give him the rails and accounting and stuff. Stuff. And we literally, I think we started it for like 50 or 100 grand and we sold it to Ramp about maybe 6 months ago now for single-digit millions.”

Steal thisProductize a skilled hustler's talent into a done-for-you service; pair their hustle with your distribution and back office.