Jason Lemkin

Clone yourself: feed 12 years of content into a personal AI advisor

Jason Lemkin ingested everything he and his SaaStr guests ever published (blogs, tweets, LinkedIn, conference videos) into an AI that answers founder questions as a sharper version of him. The pitch: any creator with a deep content archive can build a digital advisor that never forgets.

“And our AI took everything I've written, every tweet I've ever done, every LinkedIn post, every SaaStr video from every speaker for 12 years. Aaron Levy, the week he went IPO for the first Astro Annual to last week when we were talking about AI, all of it ingested in this AI. And so what I instantly saw was as soon as I would talk to this AI, it was much better than me. It was much better than me because I forget stuff.”

Steal thisPipe your entire content archive (RSS, YouTube, Twitter) into Delphi to spin up a digital twin that advises your audience.

AI flipped the SaaS curve: 0-to-1 is easy now, but $100M+ gets disrupted

Lemkin's old 'impossible to inevitable' rule was that 0-to-$1M was impossible but $10M-to-$100M was inevitable. AI inverted it: you can hit $1M in a week or two, but companies at $100-300M are now stalling out in ways that never happened before.

“Now 0 to 1 is very likely in AI. Like, it's like you build an incredible tool that no one else can do. You can do a million in a week or two. But like now everyone beyond $100 million is getting disrupted. There's so many software companies at $100 to $200 to $300 million in revenue that aren't growing anymore. It never used to happen 4 or 5 years ago.”

If you never log into the CRM, what is a CRM even worth?

Lemkin argues that once you just ask ChatGPT for 'the 10 deals to work this week,' the underlying CRM becomes invisible plumbing — and the value of one CRM over another collapses because nobody touches the dated app interface anymore.

“So even if it is benefiting the big guys today, what is the value of, of a CRM if I don't log into the app anymore? If I just talk to ChatGPT and I say, give me the 10 deals I have to work on this week. Like, how valuable is one CRM over another? Or will I even know I have a CRM? Like, it just becomes plumbing in a database.”

Anthropic went from $1B to $3B revenue in 5 months

Lemkin cites Anthropic's run rate jumping from $1 billion to $3 billion in just five months as evidence of how fast AI infrastructure revenue is compounding.

“As crazy as these numbers are, Anthropic went from $1 to $3 billion in revenue in 5 months. They just announced $1 to $3 billion in revenue in 5 months.”

In the AI era, being #4 is dead — only relentless market owners win

Lemkin argues the 2020-21 'happy to be third or fourth and sell for $400M' era is over. Because markets are bigger and software quality compounds every quarter, the best founders now relentlessly aim to be #1 and own the market outright.

“There was a while in 2020, '21 where like being third or fourth was great. Hooray! Like, things were so good that like, you'd be like, well, if I'm number 4 in the market but I don't have to sell a lot of stock and it's calmer and I could sell my company for $400 million, that's better than IPOing. Like, now the best founders today are relentless to being absolutely number 1 and destroying and owning the market, right?”

SaaStr does $5M revenue per employee with just 5 people

Lemkin says his SaaStr media and events business now runs on 5 people generating $5 million per person (~$25M total), after AI replaced designers, content reviewers, and ghostwriters.

“We have 5 people and we do $5 million per person now.”

AI replaced a $5K/mo ghostwriter with a $20 Claude job

SaaStr's ghostwriters charged $5,000/month and took two weeks to produce mediocre session summaries. Lemkin put the same work into Claude and got it done for ~$20 in an hour, then had AI review all 300 conference sessions, decks, and presentations.

“And then I went into Claude and I'm like, this, she just put it in Claude and they start charging us $5,000 a month for this. So like, we can do this for $20 in an hour instead of $5,000 and waiting 2 weeks with our clients, right? So we didn't need the ghostwriters.”

Lemkin's first 5 inbound investments all became billion-dollar companies

Lemkin fell into investing by accident: founders who'd read his blog walked into his office. Pipedrive ($1.5B sale), Talkdesk ($10B), Algolia ($2.5B), and Salesloft ($2.3B cash) all came inbound, and his first five bets all ended up worth a billion-plus.

“So first the founders of Pipedrive came by the week I started, and that was my first investment that sold for $1.5 billion, right? Then other founders started. Then founder of Talkdesk came by. That one was worth $10 billion in its last round. Then the founders of Algolia came by. That's worth $2.5 billion. Then the founder of Salesloft came by. We sold that for $2.3 billion cash in 2021.”

Invest only off a cold email good enough to fund without meeting

Lemkin's rule: he wants a cold email so good he'd invest before ever meeting the founder, with the meeting only confirming the decision. Every good investment he's made, he wanted in before the meeting — a high-intent inbound filter.

“I want them sending me a cold email that is so good that you would invest off the cold email. This is how I invest. I want a cold email that is so good, that is so good that you don't even need, you almost don't even need to meet them. The only point of the meeting is confirming that you want to invest. Like every investment I've done that's good, I've wanted to invest before the meeting.”

Steal thisFilter deals (or hires) on whether the cold outreach alone is good enough to say yes before any meeting.

S-tier recruiting: actually talk to all 200 best people for the role

Lemkin's definition of relentless recruiting (which he says Owner's founder Adam embodies): list the 200 best people in the world for a role and actually contact every one — not pretend to talk to 200 by doing 5 interviews.

“Literally reach out to the 200 best people in the job. Talk to all of them. Set up meetings. Cold, warm, lukewarm, direct, LinkedIn. Who are the 200? Like, talk to everyone in the world. Who are the 200 best CMOs that I could possibly hire? Don't pretend to talk to 200. Don't actually only do 5 interviews and pretend you're doing them. Do 200. That's what the S-tier recruiters do, right?”

Steal thisBuild a list of the 200 best people for a key role and actually contact all of them before hiring.

The smart AI-era play: make $5-10M, cash out, and chill

Lemkin relays a tweet that resonated with him: because nobody can predict where AI goes and today's valuable assets could be worthless later, the smartest move if you can pull it off is to liquidate now, bank $5-10M, and step back.

“He's like, what the smartest play, if you can possibly pull it off today, is to go make $5 or $10 million, cash out, and just chill because you can't predict where it's going to go. Like, this is the world's going to— like, whatever you could do to liquidate your assets now, they may be worthless down the road. So liquidate them right now and chill if you don't, if you don't see the future, because this is the time, right?”

The smart AI-era play: make $5-10M, cash out, and chill

Lemkin relays a tweet that resonated with him: because nobody can predict where AI goes and today's valuable assets could be worthless later, the smartest move if you can pull it off is to liquidate now, bank $5-10M, and step back.

“He's like, what the smartest play, if you can possibly pull it off today, is to go make $5 or $10 million, cash out, and just chill because you can't predict where it's going to go. Like, this is the world's going to— like, whatever you could do to liquidate your assets now, they may be worthless down the road. So liquidate them right now and chill if you don't, if you don't see the future, because this is the time, right?”

Venture has only two modes: a comfy salary job or making $100M+

Lemkin argues there's no middle in VC — you're either in it for the fees and salary (a good job), or you're trying to make at least $100 million in carry. Profits only come from being in three to five $10B outcomes; everything in between doesn't really exist.

“One, it's a great job. One, it could be a mediocre job. It could be a great job, or you could try to make at least $100 million. I think anything else is, it doesn't exist. There's a gap that doesn't exist because you're either in it for the fees and the job.”

Reverse engineer scale: $300K-$400K revenue per employee

Lemkin's rule for judging whether a SaaS model can scale: old software made $1M revenue per employee, the 2021 unicorn low was $100K (less than the fully-burdened cost of a Bay Area employee), and every public SaaS company today sits at $300K-$400K. If your model can't reach that, it isn't real.

“And we reached a low in 2021 of $100,000 in revenue per employee for all these unicorns, $100,000. So we got, we only were 10% as efficient as we used to be. Now the pendulum swung back. So we were historically, we're at $1 million per employee. The low point was $100,000 per employee. When employees in the Bay Area probably cost you $250,000 fully burdened with insurance benefits this and that. So you're losing $150,000 per employee. Now, every public company, at least public SaaS software company, is at $300,000 to $400,000.”

Steal thisStress-test your model: it must have economies of scale that reach $300K-$400K revenue per employee, or it won't scale.

Your second product must be bigger than your first

Lemkin's non-obvious rule: by ~10,000 customers you need a second product that can eventually be bigger than the first. The easy default (a product extension like shampoo + conditioner) never catches a first product that's still growing, so you must build the harder, bigger second product instead.

“If the second— what's easiest, Sam, is to add a product extension. Okay, we sell shampoo in e-commerce. Okay, let's sell shampoo and conditioner. That's the easiest thing because our customers already know us. If they bought shampoo, they'll buy shampoo and conditioner. But the problem is if you, if you, if the second product isn't bigger than the first and the first one's still growing, you never catch up. It's never enough, right? If you're selling 50 million of shampoo and you're growing 20% a year, you're adding 10 million a year, right? And you launch shampoo and conditioner and it does a million its first year, it's great, but it'll never get there. The second one has to be bigger than the first.”

Steal thisBy 10,000 customers, launch a second product engineered to eventually exceed the first, not an easy extension that can never catch up.

Founders underprice; you can fix pricing later for new customers

Lemkin says ~80% of founders underprice because they prioritize getting customers happy and going over optimizing pricing. The fix: pricing is repairable for new customers (just double it), though grandfathered customers are harder to re-price.

“I've underpriced. Yeah. And so have I. And so have 80% of founders. Not all, but it's a— I hate this term, but it's a feature, not a bug, because as painful as it is, you can fix pricing later, at least for new customers. It's harder to fix it for grandfathered customers, right? But for new customers, then just double it to $600 and $1,200 and $1,800 like it is. It's hard.”

Steal thisIf you underpriced, raise prices for new customers immediately, even doubling, and leave grandfathered customers alone.

A great VP of Sales lifts revenue 30-100% on the same leads

Lemkin's case for hiring a VP of Sales: founders can't capture full value, but a great hire running the same playbook on the same leads produces a 30-100% revenue lift in the first 90 days, while a mediocre one actually causes revenue to decline versus founder-led sales.

“Someone with the confidence to ask $30,000 for trends, knowing it's cheap compared to Gartner or Forrester or whatever, they'll take that off your plate if they're good, and you'll see a 30 to 100% revenue lift from someone that's great. Right? Yeah. Someone that's mediocre will rip your customers off and never understand your product and misspell trends and never read it and not know what it is. A mediocre one will actually see a revenue decline from founder-led sales, but a good one will solve— will solve that piece.”

Steal thisHire a strong VP of Sales to capture full price on existing leads; expect a 30-100% lift in the first 90 days.

Let international demand find you, then invest at 5% of revenue

Lemkin's playbook for going global: don't hunt customers abroad. Become a top-2-or-3 vendor in a niche and tech-forward markets (Australia, NZ, UK, parts of Europe) will find you. Once any region crosses 5% of revenue, invest in it; the deeper cheat code is localizing the product early, which 95% of engineers resist.

“And as soon as you cross 5% of your revenue in, in an area, then invest in it. Just invest in it. As soon as you see a cluster in England or New Zealand or somewhere you didn't expect, Chile or Brazil, like support it. Um, and then the cheat code, this sounds obvious. Okay. The one, one is just support it, like make your product open, right?”

Steal thisWatch where overseas customers cluster organically; once a region hits 5% of revenue, invest and localize the product there.

Salesforce got dragged into 10% of revenue from Japan by accident

Lemkin's lesson on international: Salesforce never planned for Japan but got dragged in via partnerships to 10% of early revenue, and Yext was huge in Japan too. The takeaway: don't show up to a market with no traction, but if a handful of your first 100-500 customers come from Japan, treat it as a signal worth chasing, not dismissing.

“But like Salesforce got— had 10% of their revenue in Japan in the early days. 10%. Now they didn't— if you can You can Google it. You can see what Marc Benioff said. They didn't plan it. They got dragged into Japan. Some of it was through partnerships and others. But my point is that wasn't on their day zero plan.”

Anchor pricing to comps; founders' real job is removing friction

Lemkin argues pricing is overdiscussed: buyers already know what software should cost from 200+ apps, so find the closest comps and charge the same way (a smidge lower if nervous, but too cheap signals low value). The founder's daily job is relentlessly removing friction from customer acquisition, since friction (like 'contact me' forms) is only worth adding once you're at tens of millions in revenue.

“So anchor around the comps. If you're truly 10 times more valuable than Riverside, okay, Riverside is very good. We're using it to record the session. If you're 10 times more valuable, maybe charge twice as much. Because you're telling the market we're 10 times more valuable than the leader, right? We're 10 times more valuable. But whatever you do, founders that say there's no one like us, there's no comp, try harder, try harder.”

Steal thisPrice against your closest comps, never claim there's no comp, and make removing friction from the buying process your daily job.

Adding more value for the same dollar beats raising prices

HubSpot's average customer has paid roughly the same (~$10K-$11K) for four years, but the product is now 5x larger and 50x more powerful. Lemkin frames this as the SaaS promise (software as a service, not 'software as a ripoff'): keep adding value for the same dollar instead of pushing price increases with no benefit.

“And this is why HubSpot is one of the reasons it's so successful is they're adding more value for the same dollar. They're adding more value each year for the same dollar. That software is supposed to be a service. SaaS, software as a service. We forgot about it in 2023 and late '22. It became— SaaS became software as a ripoff. Everyone got massive price increases for no benefit, right?”

Steal thisDrive retention by adding more value each year for the same dollar rather than raising prices with no added benefit.

At 3-5% monthly churn you need double-digit monthly growth to survive

Lemkin's churn math: at 3-5% monthly churn, growth feels fine on the way up, but around $10M+ in revenue gravity weighs you down because the leaky bucket becomes nearly impossible to refill. The non-intuitive insight is that you need double-digit growth per month just to overcome that churn at scale.

“You need so much growth to overcome that churn, right? You need like epic, epic, like you can't even— it's not even what your gut says as a founder. You need so— you need double-digit growth per month. Here's the insight. You need double-digit growth per month to overcome that churn at scale, right? You need double.”

Steal thisIf churn runs 3-5% monthly, model the gravity early: you'll need double-digit monthly growth to keep scaling past $10M.

SaaStr Annual costs $10M to 'turn the lights on'

Lemkin's flagship event, SaaStr Annual, draws 12,000 people in the Bay Area each September and costs $10 million before making a single dollar, about $1,000 per attendee fully burdened.

“And so we get 12,000 people in the Bay Area. Now it's every September. It costs $10 million to turn the lights on. That's a stressor. It costs $10 million to turn the lights on. Okay, before you make a dollar.”

SaaStr was an accident: meetups had product-market fit before it was a business

Lemkin built SaaStr around content and community, not as a business. The first 2013 meetup drew 800 great CEOs, the next 1,000 (turning people away), and he outsourced the events for two years without looking at a financial statement. When his partner quit, he had to learn the conference business from scratch in year three.

“Like, this sounds small today, but our first meetup in 2013, we had 800 people come and these were great CEOs, great CEOs, right? CEOs that now are— have gone public or have 9-figure businesses. And they all came. And that— what I didn't know, it would be a business, but I knew we had product-market fit. So I wanted to build. Then I did another meetup and the other meetup had 1,000 and we had to turn people away.”

Money2020 sold for $100M while doing only $10M in revenue

Lemkin cites conference-business comps: ShopTalk sold for $150M at roughly SaaStr's size, and Money2020 sold for $100M when it was only doing $10M in revenue, because both were iconic, top-tier events.

“And ShopTalk was bought for $150 million at about our size, probably under, uh, they got a good deal. And Money2020 sold for a good deal. It sold for $100 million when it was only doing $10 million in revenue.”

Raise over $10M and you're signing up for a billion-dollar exit

Lemkin's framework for fundraising and optionality: a couple million in capital costs only dilution and any exit still works, but once you cross ~$10M raised, you're committing to a billion-dollar outcome and anything less is a disappointment. If you don't feel a billion in your bones, don't raise double-digit millions.

“If you raise more than $10 million, you're signing up for a billion-dollar exit, and anything less than that is a disappointment. It just might not even work out. Like, there's so many variables. You may run out of money. You might not get people. Once you start raising $10 million, you get addicted to burning more money too.”

Steal thisRaise half a million to $2M, one and done, to keep every exit viable; only raise $10M+ if you truly believe in a billion-dollar outcome.

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.”

Jason Lemkin's 5 unicorn signals for SaaS

Sam relays Jason Lemkin's heuristic: a SaaS company at $10M ARR growing 100% year-over-year, with 150% net revenue retention, viral inbound leads, and an NPS of 50 already has a unicorn on its hands.

“if you're at $10 million ARR growing at 100%, so you're doubling or you're going to double, if you have net revenue retention of 150% and a lot of your leads are coming in viral as well as an NPS of 50, you already have a unicorn.”

Steal thisTrack ARR growth, net revenue retention, viral lead share, and NPS as early unicorn signals.

$1M to $10M to $100M is inevitable with retention

Sam summarizes Lemkin's bullish view that with high retention, a SaaS company hitting $1M in revenue will inevitably reach $10M, and from $10M will inevitably reach $100M, so the advice is don't quit and don't sell.

“And he always says if you get to $1 million in revenue and you have high retention, it's inevitable that you're going to get to 10, right?”