The Hustle

The 'Tesla of X' advertorial angle that printed traffic

Sam wrote advertorials for The Hustle's clients, calling Quip 'the Tesla of toothbrushes.' The angle crushed and advertisers poured money into driving traffic to it, a reusable positioning template for any premium DTC product.

“So I wrote one for them and I called them the Tesla of toothbrushes and that crushed. And they said they spent a ton of money driving traffic to them. Now I'm not going to take credit for it. I actually think I did copy it from someone, but I don't remember. Now the Tesla of like a bed, the Tesla of— yeah, it's— it crushes it.”

Steal thisPosition a premium DTC product as 'the Tesla of [category]' in advertorials to make the angle instantly legible.

The Hustle's signature ad line was stolen from a 1960s piano ad

Sam reveals the 'my boss thinks I'm smart, I'm not' email-newsletter ad line that everyone copied. He adapted it in 2016 from a 1960s piano-lesson ad via his swipe files.

“I wrote that. I wrote that. I wrote that. I stole it from an old ad book. I wrote that in 2016, I think. I stole from an old ad book of like, um, something about a guy being a piano player. Uh, there was like a piano lesson ad from the 1960s about being a great piano player.”

Steal thisKeep swipe files of old ads and adapt proven copy structures to your product rather than inventing from scratch.

Instagram sold for $1B with just 13 employees

Shaan cites Instagram's $1 billion sale at 13 employees (5 hired in the last few months) as evidence that the size of the firm is shrinking, en route to the prediction that one person will eventually create a billion-dollar company.

“it's like, oh, Instagram, when it sold for $1 billion, was at 13 people. That was kind of amazing for 13 people. And really, they hired 5 of them in the last few months. So it really was like 8 people created a billion-dollar company.”

The scholarship lead-gen flow: feel-good front, lead sale on the back

Sam explains Bold.org's model: aggregate scholarships, pay to drive niche applicants (nurses, MBAs) into a sign-up flow, then monetize the highly-qualified list with opt-in offers. The Hustle paid Bold $50k-$100k a month for leads.

“And companies like The Hustle, I would pay them money. I think at one point we were paying them maybe $50,000 to $100,000 a month. Wow. And that's how many leads that they were getting us.”

Steal thisWrap a genuinely useful free offer (scholarships, giveaways) around a sign-up flow, then sell the enriched, niche lead list to advertisers.

Gold/silver/bronze subscribers and cost-per-gold-reader

Sam shares The Hustle's internal acquisition framework: tier subscribers gold/silver/bronze by early engagement, then compare channels by cost-per-gold-reader. Bold-style lead gen yielded a $1 gold reader versus ~$4 from Facebook, more volume but cheaper.

“We'll call it a— we call it— we have a gold, silver, bronze. That's like we internally— so a gold user just costs us $4. Right. Okay. Now let's just say that on bold.org, I've got to get 10 people, but I get those 10 people for a dollar and one of them becomes a gold reader. So I just paid $1 for a gold reader. So you get a lot of volume, but you make up for it because it's cheap.”

Steal thisGrade new subscribers by early-engagement tiers and measure channels on cost-per-top-tier reader, not raw CPA, cheap-but-noisy channels can win.

Sam met Tim Ferriss high on morphine after a kidney stone

Sam's story of how he met Tim Ferriss: riding home high on morphine and OxyContin after a 5am kidney stone, he spotted Ferriss walking and obnoxiously hailed him. He never pitched business, just talked about dogs, until Ferriss later cold-emailed him about The Hustle.

“I see Tim walking in front of my house, and I was on the passenger seat riding dirty with my seat back because I was all high and shit. And I see him walk by and I go, "Hold on, Sarah, back up. Hey, hey, Tim, what are you doing around here, man?" And he goes, "I live down the street." I go, "That's cool. I'm a big fan. Just got a kidney stone. You got any tips for that?"”

The Hustle Asked 30 Onboarding Questions — and Got 98% Completion

Sam reveals that despite his team insisting two questions was already too many, he pushed onboarding to 30 questions and saw a 98% completion rate — and people engaged with the product MORE afterward, not less.

“I would put 2 questions in, and then inevitably everyone at the company was like, oh, that's already too many. I'm like, no, no, no, no, no, put 5. And we put 5, and then we put 10, and eventually we had like 30 questions, and it had like a 98% completion rate. Um, the, the more qu— and not only that, they actually interact with you more after they've answered the this, which is really counterintuitive.”

Recurring evening event + paid community = multimillion in 18 months

Sam describes The Hustle's '2X' evening events, sponsor-funded, that netted ~$15K profit per night and could run monthly across cities. Rinse-and-repeat plus a paid community on top, he argues, builds a multimillion-dollar business inside 18 months.

“This one had 982 people coming. We did $24,000 in revenue, $7,000 in sponsors, $31,000 in total revenue. And then it looks like $16,000 in costs. Frankly, we probably didn't even need to spend that much. And we made $15,000 in profit. And then we would host that almost monthly in a variety of cities. We would do LA, Chicago, yada, yada, yada. One night could make you $15,000. Do that 12 times a year. Then you launch a paid community on top of that. You're, you got yourself a multimillion dollar business inside 18 months.”

Steal thisRun a sponsor-funded evening event monthly across cities, then stack a paid community on top to compound it into a real business.

The case for BitClout: bet on Sam before The Hustle

Shaan makes the emotional pitch for betting on people: he believed in Sam before The Hustle but passed on investing in the media company. If he could have simply bought 'Sam stock' and held the person for 25 years, he says he would have.

“if you could— if I could have just bought stock in you and not bet on— like, for example, I had the opportunity to invest in The Hustle, the media company. I was like, well, I don't know if this is going to be like this humongous billion-dollar company or what. I don't know if this fits my profile, whatever. I don't know about media, but I was believing in you the whole time. And if I could have just bought Sam and owned Sam for 25 years, that's something I want to do.”

Sam's no-audience hit: a Hacker News salary survey that went to #1

With no audience in The Hustle's early months, Sam posted a Google Form titled 'How Much Money Do Founders Make?' to Hacker News, hit #1, and got 300-400 anonymous replies on income, savings, and assets. Hacker News eventually removed it for violating their survey rules, but the anonymized data became hugely popular to both share and read.

“And all I did was I took a Google Form and I posted it on Hacker News. And it went to number 1. They eventually took it down because I think that goes against their terms of service, like have a survey. But I got like 300 or 400 replies and I asked people how much money they have in their checking account, how much they have in their bank account, how much they pay themselves, how much they have in illiquid assets.”

Steal thisBootstrap an audience by collecting and publishing anonymized data people are dying to compare themselves against.

How a porn star turned actress used Reputation.com to bury her past

Sam explains Reputation.com via Sasha Grey, who hired them so her acting work outranked porn when you Google her; The Hustle's article about it got boosted to #1 by Reputation.com as free advertising.

“Sasha Gray is a porn star who became a normal actress, like a Hollywood actress. And she wanted to— when you search her name, instead of porn coming up, she wanted her, like, new work to come up. So she hired Reputation.com.”

Sam faked a bigger team using 4-5 invented personas to launch The Hustle

To make The Hustle look bigger than it was, Sam wrote under invented personas (Sid Finch, Steph Whitfield, Steve Garcia), each a blended in-joke, and notes Ben Franklin did the same by arguing both sides in his newspaper under different names.

“When I launched The Hustle, in order to appear as though I was bigger than I was, I actually had multiple personalities. So I had Sid Finch, I had Steph Whitfield, I had Steve Garcia, which is— so Steph Whitfield is a combination of two friends. Sid Finch is a famous April Fool's joke that Sports Illustrated made, a fake person.”

Media companies buying media: the new acquisition playbook

Shaan frames a pattern: non-media companies acquiring media/community brands to own an audience. Examples include Robinhood buying Snacks, Stripe buying IndieHackers, HubSpot buying The Hustle, and Spotify buying The Ringer.

“Robinhood bought, uh, Snacks, which was like a kind of a media company. So Robinhood, this exchange, not a media company, buys a media company. Stripe bought IndieHackers, right? Stripe, not a media company, bought IndieHackers, this community of kind of makers. HubSpot buying The Hustle. And there's a few other ones that are actually somewhat prominent. Spotify buying, let's say, The Ringer or things like that.”

Steal thisIf you run a software company, consider buying an audience instead of building one from scratch.

HubSpot acquired The Hustle off a single cold email

Kieran explains the deal originated internally at HubSpot, then a teammate named James Gilbert sent The Hustle a cold email to make first contact. That cold outreach is how the entire acquisition got connected.

“So we went and talked to some media companies and I think it was James, no it wasn't, it was someone internally and said, hey, have you thought about The Hustle? And I told James, who's on my team, hey, you go check out The Hustle, talk to The Hustle. And that's how we first got connected.”

HubSpot bought The Hustle for the talent, not the monetization

Kieran admits the real reason for the acquisition wasn't contextualizing HubSpot ads on Hustle content to drive software sales. It was acquiring the team that knows how to build large, trusted audiences in channels HubSpot wasn't good at.

“We were kind of not being honest with ourselves about why we wanted to. We just wanted the talent who could build audience on those properties, and not the monetization of that into software is really secondary to us. It's like, how do you build big audience in these channels? And so the first time we pitched it, I think I just came at an angle that I thought people would like, but wasn't really the honest reason we wanted to do it.”

Selling your company creates an identity crisis

Sam's biggest fear about the sale wasn't the deal falling through but losing his identity. After years of people doubting him and his parents telling him to get a real job, he had fused his self-worth to being 'The Hustle,' and selling forces that identity to evolve.

“my biggest fear was it screws your identity because you've just married yourself to this. I am the hustle or I am whatever I do for a living. That is a weird, weird feeling, right? Like Sean is the guy who runs Monkey Inferno and works out of this fancy office like that. That is him. And you are closing that. It's not ending, but it's evolving.”

Buy vs build is really about opportunity cost and speed

Kieran explains a big company buys rather than builds not because it can't build, but because of opportunity cost. Replicating The Hustle's talent, brand, and community would force HubSpot to put its other plans on ice; buying gets from A to C faster from a higher starting base.

“so I don't know if it's that, uh, we couldn't build it, but there's an opportunity cost, right? Like you would have to, we would have to go and find the talent that you found. We would have to go and create the brand around the podcast, the trans community, the hustle community. Like there's just an opportunity cost that we would have to say, okay, all of this other stuff we have planned, we put on ice cuz we're now going to pivot and start to focus on these things.”

Steal thisTo get acquired, position your company as the fastest way to skip the buyer's years of building.

Sam wanted WeWork or LinkedIn to buy The Hustle, then HubSpot cold-emailed

Sam recounts rejecting private-equity and legacy-media suitors because they felt like a culture mismatch, and how he'd long fantasized about a tech company (WeWork, LinkedIn, Salesforce) buying The Hustle. HubSpot reached out unsolicited last fall and the plan clicked.

“And so in my head, I always thought, you know who should buy us? WeWork. I thought WeWork should buy us, like when they— before we found out that they weren't that great. And then I thought, um, LinkedIn should buy us. And then I started thinking, oh, what about like a Salesforce or like companies like this? And then last fall, HubSpot reached out to me and I was like, oh my God, this is finally happening.”

The Hustle's playbook: build a big free list, profit on ads, reinvest in high-margin products

Sam describes The Hustle's day-one vision as a flywheel: grow a large email list of business-minded readers, monetize early with advertising, then use those profits to launch higher-margin direct products like Trends and eventually invest in members' companies.

“We said that we wanted to build up this really large email list and we're going to do it for like these, this entrepreneurial business-minded person. We're going to make profits early on, which we did with advertising. We had about an 8-figure advertising business. And then as we grow, we're going to use those profits to launch more stuff that we could sell directly to them.”

Steal thisBuild a free audience first, monetize with ads, then plow profits into high-margin products you sell directly to that same audience.

The Hustle's playbook: build a big free list, profit on ads, reinvest in high-margin products

Sam describes The Hustle's day-one vision as a flywheel: grow a large email list of business-minded readers, monetize early with advertising, then use those profits to launch higher-margin direct products like Trends and eventually invest in members' companies.

“We said that we wanted to build up this really large email list and we're going to do it for like these, this entrepreneurial business-minded person. We're going to make profits early on, which we did with advertising. We had about an 8-figure advertising business. And then as we grow, we're going to use those profits to launch more stuff that we could sell directly to them.”

Steal thisBuild a free audience first, monetize with ads, then plow profits into high-margin products you sell directly to that same audience.

One advertiser pulling out after a tragedy cost The Hustle $30K in a day

Sam illustrates the fragility of ad-dependent media: when they covered a shooting, an advertiser refused to run next to the coverage and pulled out, costing them roughly $30,000 that day - his argument for why ads should only be part of the mix.

“And some brand, I don't remember if it was Bonobos, but they were like, you know, we don't want to advertise. So it's like, fuck, we just lost $30 grand that day.”

The Hustle paid newsletters to run ads when Substack wouldn't

Sam recounts that The Hustle went direct to a handful of Substack writers and paid them collectively into six figures to run ads in their emails; those writers made more from the ads than from their subscriptions. He notes ad-monetizing an email usually requires an expensive full-time sales team.

“And so The Hustle, we went direct to a couple of guys, a couple of different people, and we paid them X amount of dollars. I don't even remember. But collectively maybe 6 figures spread out, and they monetized their email with advertisements, and they actually made more from us than they did their subscription. And in order to monetize an email with advertising, you actually have to hire a full-time sales team.”

The Hustle's giveaways revealed an obsessed middle-America bargain-hunter audience

Sam recounts how The Hustle's prize giveaways (a MacBook, a $30,000 Tesla) surfaced huge communities of middle-America stay-at-home moms who chase free contests relentlessly, even when they'd never buy the coastal-branded merch otherwise.

“One time we gave away a Tesla, like a $30,000 Tesla. And when we do these giveaways, there's these websites. I'd have to go and remember what they're called. But it's like Super Savers, or it's like— there is this, and we get so much traffic from it, it's crazy. And if you Google like the Hustle giveaway, there's these huge communities, and we get so much traffic from it. And it's mostly Middle America, stay-at-home moms, and they are doing giveaways like crazy. They are all about saving money.”

Build a lean right-wing news aggregator to replace Drudge

Sam pitches link-aggregation media as a great lean business (The Hustle is an 8-figure version), and argues conservatives engage with news far more 'fervently,' making a right-leaning aggregator a real opportunity now that Drudge has drifted. Snippets-style headline curation is already the most-engaged content in their daily email.

“I think that they can be a really good business if you keep them lean, like 3, 4, 5 people. But particularly, I've always said this, Sean, that the conservatives engage with news way more. I don't know what the right word is. Fervently. Fervently. Yeah. It's— they have a more rabid fan base because usually the right wings, the right-wing folks feel like they're the minority and that they're being pushed down.”

Steal thisRun a 3-5 person news aggregator for a fervent, underserved tribe (e.g. conservatives); rabid audiences engage harder than mainstream ones.

Cheap rent let Sam run a $2K/month burn while starting The Hustle

Because his SF sublet dropped his rent to $300-$400, Sam's total monthly burn while launching The Hustle was just $2,000 a month — the cushion that let him take the startup risk.

“So, but a lot of, when I started the hustle, my monthly burn was $2,000 a month and everyone was like, how do you do that? And I was like, well, cause my rent's $300, $400. That's how, dog. So it worked out perfectly.”

How a content brand should sell product: ask the audience, sell the AV kit

Harley's playbook for a media brand monetizing via commerce: don't slap your logo on a t-shirt. Ask your audience what they need, then sell something genuinely useful. For The Hustle's desk-bound entrepreneur audience he suggests a $250 camera/mic/setup package or an Ember mug collaboration.

“And if there is a way for you to put together a package for $250 that comes with a better camera, a better microphone, and a better setup, that may be something that works really, really well.”

Steal thisDon't sell logo merch; ask your audience what they need and bundle a genuinely useful product around it.

Going remote saved The Hustle ~$250K a year

Sam estimates The Hustle, a 30-person company, saves close to a quarter of a million dollars a year by dropping its San Francisco office (lease was about $15K/year plus extras).

“we're definitely saving probably close to a quarter of a million, and we're a 30-person company, right?”

Hijack trust: license The Hustle's brand to launch new ventures faster

Shaan reframes the licensing model around 'hijacking trust': rather than build a new education company solo and earn trust slowly, license an existing brand like The Hustle for ~6%, letting the brand owner get free expansion of equity they aren't currently tapping.

“what you should be doing is say, cool, this is now Hustle University. I'll give you the brand, you give me 6%, you go do all the work. And, you know, that— and as long as sort of like your brand is not being diluted by the efforts, right? So if you're partnering with a good operator, or in Baccarat's case, like a high-end developer that's going to make a good quality hotel, then you're getting free expansion, um, of using, you know, equity that you already have that you're currently not tapping into.”

Steal thisGot an audience brand sitting idle? License it to a good operator for ~6% and capture value you're otherwise leaving on the table.

Virgin-style: license your audience's brand to operators who build the business

Like Virgin licensing its brand to a cruise CEO, an audience business (e.g. The Hustle) could raise a fund, find operators who know hotels or experiential agencies, and joint-venture: supply the brand, audience, and capital in exchange for ~5% of revenue and ~30% equity while the operator builds and runs it.

“We will give you the capital and we will market and we will give you our brand. And we want 5% of revenue and we also want to own, you know, 30% of the equity. And you guys build the hotels.”

Steal thisMonetize an audience by licensing your brand plus capital to expert operators for ~5% of revenue and ~30% equity, and let them build the business.

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.”

A sales team creates demand: The Hustle went $30k to $200k/mo on the same list

Sam argues a sales team creates demand rather than just harvesting it. At The Hustle he personally got ad sales to $30k/month, then hiring 2-3 salespeople pushed it to ~$200k/month on the same subscriber base. His rule: a good product plus a sales team equals explosion.

“I got us to $30K a month. Then like with the same amount of subscriber base, we went and hired 2 or 3 salesperson and it got to like 200,000 like immediately. And I was like, holy shit, that fucking worked.”

Steal thisIf you have a product that solves a real problem, hire salespeople before assuming you need more demand-gen.

The Hustle's new-tab plugin: one email, 28K lifetime users, ~4 refreshes per session

Sam reveals the numbers on The Hustle's 'Snippets' Chrome extension (a news headline on every new tab). Built once in 2015 and promoted with a single email, it racked up tens of millions of page views, ~28,000 lifetime users with strong retention, and users hit refresh about 4 times per session on average.

“So 30, 40 million page views it's gotten, and it's only had a lifetime of 28,000 users. But I promoted it one time, literally one time, and, uh, look at the retention. That's crazy, right?”

The Hustle's $25K Tesla giveaway pulled hundreds of thousands of users

Sam ran a referral sweepstakes giving away a $25,000 Tesla Model 3: refer friends via your unique link to enter. It collected hundreds of thousands of new subscribers in 30 days, priced well below user lifetime value.

“So we gave away a Tesla in June, and that incentive absolutely worked. We said if you get your friends to join The Hustle using your unique link, you're entered in to win. This thing. And we've collected hundreds of thousands of new users that way in 30 days.”

Steal thisRun a referral sweepstakes priced below user LTV; reward shares with entries.

The three tests of a good marketing enemy

Shaan's criteria for picking a fight: it must (A) make sense, (B) be polarizing, and (C) tell the story of what your brand stands for by being the opposite of what you attack. He notes a PewDiePie-vs-T-Series style feud can grow both sides.

“So I think you got to pick a fight that A, makes sense, B, is polarizing and C, somehow tells the story of what The Hustle is all about by being the opposite of the thing you're hating on.”

Steal thisVet any marketing enemy against three tests: it makes sense, it polarizes, and being its opposite explains what you stand for.

Don't wait until you're rich — think of yourself as an investor on day one

Shaan's biggest angel-investing lesson: the excuse 'I don't have capital' is false. If you're resourceful and persuasive enough, you can access other people's capital, so start treating yourself as an investor immediately rather than waiting to be wealthy.

“the number one advice I would give to you is don't wait until you're rich to do it. Because at that point, you know, the financial returns, it will just be a part of a broader portfolio. It's not going to be that exciting. But if you really want to do this, start thinking of yourself as an investor from day one and find ways to access the capital.”

Steal thisDecide you're an investor before you have money, then go source capital from people who want deal flow.

Charging for free content makes people value it more (Trends NPS ~90)

Sam's playbook for paid information: repackage normally-free content as paid, charge upfront with no freemium, and pack pages densely with info. He cites Trends' NPS of ~90 (versus the free Hustle) as evidence people enjoy content more when they pay for it.

“And so what I've seen with our NPS for Trends versus The Hustle, which is free, the Trends NPS is significantly higher. It's like fucking 90, which is crazy high. And I believe that the content is great, but also people enjoy it more because they pay for it. So I think people, builders out there need to think to themselves, man, there's this weird mindfuck that I can just literally charge for something that normally is free and people will like it more. The second thing is I think people need to charge upfront, no freemium.”

Steal thisCharge upfront with no freemium tier; the price itself raises perceived value.

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.

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.

Why Sam built The Hustle on email: his own 'pirate ship'

Shaan recalls Sam rejecting the hot platforms (Facebook, video, Snapchat) to bet on email because it was a channel he could fully own and not depend on any other platform—calling email list his pirate ship.

“you were like, no, I wanna do email because that's my own little pirate ship that I can own and I'm not dependent on any other platform. I wanna make my own pirate ship and I wanna get my pirate ship to be a big fucking pirate ship.”

Steal thisBuild your audience on a channel you own (email) rather than renting reach on platforms you don't control.

Sam tattooed The Hustle's business plan on his thigh

Sam reveals he recorded a 2015 Hustle SeedInvest video laying out the exact plan—build to a million readers, profit from advertising, reinvest to build and sell more media—and got a pirate ship tattoo reading 'Bold, Fast, Fun' as that plan literally inked on his leg.

“If you Google the Hustle Seed Invest, I explain, I go, we're going to build to a million people, we're going to profit from advertising, and we're going to use all that profit to build more stuff. And we're gonna sell that stuff, and then we're gonna build more media around it. And it is happening exactly.”

The Hustle hit ~$1 million a month in sales

Sam reveals he grew his company to roughly $1 million per month in revenue before realizing he was a poor manager and needed to hand off operations.

“I did a pretty good job of getting us to about $1 million a month in sales.”

The Hustle hit ~$1 million a month in sales

Sam reveals he grew his company to roughly $1 million per month in revenue before realizing he was a poor manager and needed to hand off operations.

“I did a pretty good job of getting us to about $1 million a month in sales.”

The Hustle: $25K saved turned into $60K profit in 6 weeks

Shaan recounts bootstrapping The Hustle with $25,000 of his own savings, generating $60,000 in profit within six weeks and roughly $380,000 in revenue in year one, most of it profit while he paid himself just $2,000/month.

“So When we started The Hustle, I saved up $25,000 to start it. With that $25,000, I made $60,000 in profit in 6 weeks, which is pretty good. And the first year in business was roughly $380,000 in revenue, and most of it was profit because I paid myself, uh, we were in, I think we were an LLC. I withdrew $2,000 a month in salary”

A paper millionaire with no cash: the founder illiquidity trap

Shaan explains that despite a 409A valuation in the single-digit millions, he was taking only $2,000/month and saving nothing — so a tax on unrealized share value would have forced layoffs. Many founders are 'on paper worth hundreds of millions' with only tens of thousands in the bank.

“on paper, I was a millionaire, multiple millionaire. If I had to pay, I think I forget what this— I don't want to like act like I know I'm talking about. Let's say if I had to pay 20% in taxes on that multiple millions of dollars, you wouldn't have had— I literally wouldn't have had any money to do it. Right. Even if I wanted to withdraw money from our business account, I would have had to lay people off”

Shaan's biggest regret: 'I wish I wouldn't have raised money'

Asked his biggest structural regret with The Hustle, Shaan says he wishes he had bootstrapped and owned it all — 'because I would be greedier and richer' — since he ultimately didn't need the capital to make it work.

“Because I would be greedier and richer.”

The year 4-5 burnout mark

Sam shares Jason Lemkin's observation that founders and employees tend to burn out at the four-to-five-year mark; Sam sold The Hustle in year five because he was simply tired, and notes many companies offer sabbaticals at year four to prevent churn.

“Jason told me, um, someone I look up to, that it's at the 4 or 5 year mark where you get burnt out. And I did too, and that's when I took my time. I was like, all right, we sold in year 5 because you're just tired, very tired.”

The unfair advantage of an audience: sell out a workshop with one email

Shaan explains that having an audience makes running a paid workshop nearly zero-work. Neville's list (est. 50K-100K) or even Sam's personal 5K list could sell out a session with a single send; the real cost is the exhaustion of doing the event.

“for anyone listening, there's an unfair advantage of having an audience. Yes. So like, it would be practically no work for us. Yeah. So that's great. Neville, I don't know how many people are on his email list. I don't know this for a fact. I would guess 50,000 to 100,000. Yep. My personal Sam Parr on my email list, well, not The Hustle, probably 5,000, so I could just send out a thing and it would sell out.”

Find any company's real financials via its trademark name

Sam's research trick: scroll to a company's website footer, find the trademark/legal entity name (often different from the brand), then search it in quotes on Google to surface SEC filings and trademark records.

“The first thing that I do is go to the website and I scroll all the way to the bottom and I look at the trademark. I find out the trademark, then I search that with quotation marks in Google. So for example, my company, this company is called HustleCon Media Inc. It's not called The Hustle.”

Steal thisFind a company's legal entity name in its website footer, then search it in quotes to dig up filings.

Charge $10-30K to teach company teams no-code tools

Sam pitches a service that goes into companies like The Hustle or Twitch and charges $10,000-$30,000 for a 2-3 day seminar teaching a department to build their own tools so they never need dev time.

“I would create a business that goes into companies like The Hustle or Twitch and charges $10,000 to $30,000 for a 2 or 3-day seminar and says on the promise of this, hey, head of growth marketing or marketing, or hey, head of this department, I'm gonna make it so your team can move 2 times faster by teaching them just how to make their own stuff. You're not gonna need any dev time.”

Steal thisSell a 2-3 day no-code training seminar to a department head on the promise their team moves 2x faster without dev time.

Sam house-hacked a 4-bedroom to live on ~$1K/month, $15K W-2 income

Early in The Hustle, Sam rented a 4-bedroom house, furnished it with free and used Craigslist furniture, and rented out the other three bedrooms so tenants covered his ~$600 rent. That kept his living expenses near $1,000/month while his W-2 income was only about $15,000.

“And so for the longest time in San Francisco, I had a $600 rent maybe. And I did that because I was able to scrape together some money after selling something. And I rented a 4-bedroom house. I furnished the whole place with used or free furniture on Craigslist, and then I rented it out to people, like the other 3 bedrooms. And that ultimately paid for my rent, which means that on just living expenses, I was able to only spend about a grand a month. And so because of that, the first couple of years my W-2 income was only about $15,000.”

Steal thisHouse-hack a multi-bedroom rental: cover your own rent by subletting the other rooms so you can survive on minimal income while building.

The Hustle: 8-figure revenue, fat margins, targeting $100M by 2025

Sam reveals The Hustle is highly profitable with 8-figure revenue and fat margins, no venture capital taken. He sets a goal of $100M revenue by 2025 and estimates a company like his could sell for $20M-$60M.

“So our business is very profitable. It makes 8 figures in revenue, really fat margins. My goal is to get it to $100 million in revenue by 2025, and I think we'll get there. So it potentially may not be Uber, but it'll be a nice-sized business. It'll be a $100 million business. Companies like ours could probably sell for any— in the huge number, the huge range of $20 to $60 million. And we haven't taken any venture capital.”

The Hustle raised ~$350K from its own readers in 48 hours

After hitting 200,000 users, The Hustle opened investing to anyone on its list. Sam expected $150,000 over 90 days; instead readers put in close to $350,000 within 48 hours.

“And so I thought that we would get $150,000 in 90 days. We ended up getting close to $350,000 in 48 hours.”

Your email list is a pirate ship; building on Facebook is renting an apartment

Sam refused to build The Hustle's audience on Facebook or other platforms, comparing it to building a business in a rented apartment where the landlord keeps raising rent. Instead he calls his email list a 'pirate ship' where every subscriber is wind in the sails.

“I knew from day one that would be a horrible idea. It's like, I've always wanted to be independent, and I felt that building an audience on the back of Facebook was like building a business in a rented apartment where the landlord raises the price every quarter. Like, that's a horrible idea. And so I called my email list my pirate ship, and every subscriber was a little bit of wind in our sails.”

Steal thisOwn your distribution: build your audience on email you control, not on a platform that can raise prices or change the rules on you.

BizNow sold for $60M cash on $20M revenue, $7M profit

At the time of sale, BizNow was doing roughly $20M in revenue and $7M in profit, and sold for $60M in cash — all bootstrapped.

“And he grew it and eventually sold it for $60 million in cash. And at the time of the sale, it was doing like $20 million in revenue, $7 million in profit.”

Two years sick at home reading The Hustle changed his pace of life

Boufarhat says being sick for two years and staying home listening to podcasts and reading The Hustle reset how he approached work. Coming out of remission, he felt he needed to do something fast, and the pace of his life permanently changed.

“because after I was sick for 2 years, I kind of like, and just kind of stayed at home, listen to podcasts, listen, read The Hustle, you know, stuff like that, you know, that you do. You know, I came out of it and I really, it was the perfect time for me to get out of the sickness because when it was through the remission, because I'm like, I kind of felt like I needed to do something very quickly.”

The Hustle raised ~$350K from readers in 48 hours

Once The Hustle hit 200,000 subscribers, Sam opened investment to readers, expecting $150K in 90 days. Instead they raised close to $350,000 in 48 hours.

“And so I thought that we would get $150,000 in 90 days. We ended up getting close to $350,000 in 48 hours.”

Daily Candy, Thrillist, Groupon: billion-dollar companies that started as email lists

Sam relaunched The Hustle as an all-email business in 2016 after studying Groupon, Daily Candy, and Thrillist. The insight: build a huge email list as a distribution channel, then layer products on top.

“if you study the history of Groupon, of, um, Daily Candy, of Thrillist, people may not even know what the last two are, but anyway, I was like, man, some of these like billion-dollar companies all started with an email list. Like, let's do that. Let's build up this huge email list and then start creating more products and use that as a distribution channel. And I think we could build a billion-dollar company that way.”

Steal thisBuild an email list as your owned distribution channel first, then launch products into it.

Don't build on rented land: the email list as a pirate ship

Sam refused to build The Hustle's audience on Facebook, comparing it to renting an apartment where the landlord raises rent every quarter. He called his email list his 'pirate ship' with each subscriber a bit of wind in the sails.

“I've always wanted to be independent, and I felt that building an audience on the back of Facebook was like building a business in a rented apartment where the landlord raises the price every quarter. Like, that's a horrible idea. And so I called my email list my pirate ship, and every subscriber was a little bit of wind in our sails.”

Steal thisOwn your audience channel (email) instead of renting reach from a platform that can change the rules.

Sam's remake playbook: blog, rank, build a list, sell a course

Asked what he'd do at 21 with no network or capital, Sam lays out a concrete playbook: learn something new weekly and blog it daily, use Ahrefs to find what people search, rank for ~2-3K visitors/day, build a 5,000-person email list, then sell a course.

“Start blogging. And when I say start blogging, I would say learn one new interesting thing each week and then just blog about what you learned. Do that every single day, every week for a year. Try to get 2,000 to 3,000 people a day coming to your site through search. The way you find out what to write about is you go to Harefs.com and you buy a subscription and that will teach you what to write because it'll tell you what people are searching for. Try to rank for those words, build up an email list of 5,000 people, and then create a course and sell it to them.”

Steal thisBlog daily on what you learn, use search-volume tools to pick topics, build an email list, then monetize with a course.