Jason Lemkin
Founder of SaaStr, prominent SaaS investor and operator; cited as a Replit power user building lean, AI-driven businesses.
“DJI technology is great for drones. It's the best drone technology... It is banned in the US. It is banned on the thesis that these drones flying in my backyard are going to send confidential information to China... If those drones are banned, this is just my bet. I'm betting that the Chinese models are getting banned, too.”
Source→“If I took that advice, Rory, honestly, all I would have is a maxed out 401k in life. The only reason I have any economic success is that out of obligation, in part, I kept going... Both my startups, certainly I would have quit. I certainly would have quit EchoSign.”
Source→“The violent recovery after the spring sell-off, when SaaStr's Jason Lemkin noted forward software multiples bottomed at 22.7 times, below the S&P 500 for the first time in the cloud era, looks a lot more like an overreaction correcting than a structural death finalizing.”
Source→“The whole thing with the CEO of Cloudflare, just remember founders hold grudges.”
Source→“Every founder today wants to run a startup that's at least a million in revenue per employee or more. They're targeting 2 million... My sense is that roughly over the coming years, startups will be half the size that they used to be for revenue, including enterprise.”
Source→“The majority of Anthropic's enterprise sales are not allowed to talk to a human.”
Source→“They turned around these effing companies. I mean, Evernote was dead and they re-accelerated the growth of Evernote with a fifth of the employees.”
Source→“Lovable hit 500 million of ARR. So 500 million of ARR with 146 employees.”
Source→“Suno raised $400M at $5.4B valuation — doubled in six months — Bond led the round.”
Source→“I know Replit a little bit of the Lovable, but they're the same. They're pushing out a lot of code.”
Source→“I do think we're going to look back in two years and think of this non-persistent AI as almost archaic, right? As almost sort of desktop-like.”
Source→“Devon doesn't argue. Devon doesn't only want to work on interesting problems like most of your best engineers.”
Source→“Participants: Harry Stebbings (Host), Jason Lemkin (SaaStr founder/investor), Rory O'Driscoll (Scale Venture Partners)”
Source→“I had two of my fastest growing portfolio companies saying they already blew through their budget this year... None of my slowest growing companies have said that.”
Source→“He's like, basically we have these AI agents... but the most important agents we have is so that every single person using Klaviyo now is a true expert in marketing, which was impossible for AI.”
Source→“If you want to learn about cost sensitivity, actually study Replit and Lovable because they're under huge pressures right now from their customers.”
Source→“Replit still runs two models. Not for everything you do, but for anything complicated, the architect agent now is Codex that it brings in to check Sonnet. And it works really well.”
Source→“Datadog, which everyone uses, every AI leader uses, up 100% this year.”
Source→“Jeff Lawson was on this show, he said... I'm pretty sure we're going to benefit from AI because agents in AI just need to use more of our voice. And it took a quarter or two, but he's right. Stock's up 57% this year.”
Source→“It's the fastest growing enterprise software startup of all time, of all universe throughout past Alpha Centauri.”
Source→“You want to invest the hour it blows up. The minute it blows up, you want to get the DM and just wire the money in AI. That's the play.”
Source→“Anthropic has done as much in Q1 as all of last year. And OpenAI has done 30% of what they've done last year in Q1. And they're only slightly bigger than Anthropic.”
Source→“It's not just a great revenue business growing at 80%. It's a wildly profitable operating margin business... that's 200 billion of profit a year.”
Source→“This is like that. And you go in, I'm sure Anthropic went in and thinking, we're only going to pay him 1.25 billion for four months. But they're relying on other people building data centers, and life is tricky... you cannot take it away... at 1.25 billion, it's a great deal.”
Source→“If there is efficiency gains from AI across R&D and sales and marketing in particular, everyone's going to be doing 20% layoff just because it's 20% more efficient. My aha is this discussion and the last discussion are, in fact, the same discussion.”
Source→“Jason Lemkin at SaaStr shared how Anthropic rebuilt its commercial sales org from scratch in January 2026.”
“54% of new enterprise logos came through a fully self-serve funnel (real ACV, real terms, real invoicing) without an AE, using Clay and Claude for qualification and Intercom Fin to guide the buyer journey.”
“Google wins whether you use Gemini or whether you use Anthropic now... They have the surplus that they can route between their customers and themselves and others. They win-win here.”
Source→“I think Canva's going to have a wildly successful IPO... But will agents buy? I don't think any chance an agent is going to use Canva.”
Source→“The amount of vendor consolidation that's occurring at the same time as AI growth. Whether you look at Gartner's numbers, 30% to 50% of AI dollars are coming from consolidation. Medallia is a top target.”
Source→“When Ryan Smith sold Qualtrics, I think he made about a billion dollars after 20 years or so. And I believe that billion, most of it went back into the Jazz and it has quadrupled.”
Source→“It's possible you look back and see that as the first disconnect from compute equals revenue.”
Source→“More and more the agent is going to choose what models and just what vendors we use... The agents are going to make the decision on everything.”
Source→“The ones that actually have outperformed, right? The Twilios, the Cloudflares, and others — the agents still have use for it.”
Source→“The ones that actually have outperformed, right? The Twilios, the Cloudflares, and others — the agents still have use for it.”
Source→“Stripe got the highest grade, got the only A+, which is a reason to go along in Stripe. I did not think Stripe would come out on top.”
Source→“there is no place and an agent will never send an email through Outreach, SalesLoft, or Marketo because it will just craft and send a better email itself.”
Source→“If you want to bet on AI today, because we can't buy Anthropic or OpenAI, just buy NVIDIA. That's how you buy AI today. Just buy NVIDIA. Don't even think or spell it. Just buy it.”
Source→“You've got to look at the DAUs and MAUs and WAUs. You've got to in the stealth churn area because if you're feeling all confident because your product's cheap so people don't... But look at those DAUs and WAUs because our DAUs and WAUs and MAUs are zero for Notion.”
Source→“We pay more for Salesforce than we used to... We're down to a couple seats on Salesforce per se, right? Because our team is 20 agents, three humans. But we pay more for Salesforce than we used to.”
Source→“Adam from Owner has quietly done it. Everyone should have a couple ex-founders, if nothing else, to kickstart new things.”
Source→“Aaron Levy was on Harry Stebbins 20VC this week and said there's going to be a whole new category of $500K to $1M new year jobs for operators over the coming years.”
Source→“"Parker Conrad quietly kind of, I think there's hundreds of ex-founders that work at Rippling now, hundreds." — Jason Lemkin [00:47:32]”
Source→“Agent Mail — YC-backed company providing pre-warmed email infrastructure for autonomous AI agent outbound. Jason discovered it via Claude recommendation, set it up in one minute, got immediate high deliverability to inbox.”
Source→“I wonder if it'll make mediocre CS folks even lazier. I, you know, you go solve it, right?... We're just a 20-year-old software platform that charges you $60,000 a year. We don't provide support.”
Source→“He hired an ex-CEO. Like he hired an ex-technical founder who was burnt out on his startup, didn't want to do this for himself anymore, but was technical to be their head of agentic operations. And now he's the one... He said he's had this person now for over a year, like he hasn't gone anywhere.”
Source→“We're down to a couple seats on Salesforce per se, right? Because our team is 20 agents, three humans.”
Source→“Aaron Levy was on 20 Stebbin, Harry Stebbin's 20 VC this week and said, there's going to be a whole new category of 500K to a million dollar new year jobs for operators over the coming years. They're somewhat technical like you. You're not an engineer. You can't really code. But at this point, you're getting somewhat technical.”
Source→“I'm on the board of a startup called Owner that's sort of a next generation agentic toast or so for restaurants. They're at about nine figures in revenue growing triple digits. And the CTO just made a loom... They run headless Salesforce and he built this before they called it headless.”
Source→AI-extracted from podcast / newsletter / paper summaries. May contain errors.