Jason Lemkin
Founder of SaaStr, prominent SaaS investor and operator; cited as a Replit power user building lean, AI-driven businesses.
“you're either in the head of the train, in the new, new thing, everything is possible, or you're in the tail end of the train and life is shitty”
Source→“it's less about being a competitive frontier lab and more about AI sovereignty”
Source→“The winner in the existing world is only worth 50 [billion]. So as you get these bigger market caps like Sierra, you have to go beyond service cloud replacement to be a big company... you have to sell the whole operating system.”
Source→“Wonderful more than doubles to 5 billion in under six months... $170 million in secondary within two years of founding.”
Source→“85% retention for the ring is pretty good... they may not have the Peloton issue for the foreseeable future.”
Source→“IPOs is about distribution... the Robin Hood story... they went basically 10x in the public market... in three years.”
Source→“Waymo is continuing to grind on. There are hundreds of millions of dollars in revenue, but not billions.”
Source→“I actually think it does speak to the argument that they were right not to try and fund this thing at Uber for the last decade too.”
Source→“There literally was 20 posts on this wiki in the last 10 years.”
Source→“The only thing that mattered for the last two years is LLMs do code”
Source→“We're invested in GCAI, which is on the in-house legal side.”
Source→“You've got an all-American software product, and you've got the ability to train it on your data in a totally proprietary way that's not exposed to OpenAI or Anthropic.”
Source→“Things like the OpenRouter report, things like that index of token pricing. Those are the things you look at”
Source→“Jason said last week that if you are not well into your 2027 roadmap already, you are behind.”
Source→“"This has come up a number of times, I think with Jason Lemkin and you — just like the increasing rise in services being a part of software companies."”
Source→“The world is talking about agents. We can have a whole episode on what are agents, what is really an agent, how do you give agency, and how do you control an agent?... When pieces of code can decide what happens next, we're going to have a whole different conversation on how do we secure those agents?”
Source→“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 majority of Anthropic's enterprise sales are not allowed to talk to a human.”
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→“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→“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 whole thing with the CEO of Cloudflare, just remember founders hold grudges.”
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→“I know Replit a little bit of the Lovable, but they're the same. They're pushing out a lot of code.”
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→“Participants: Harry Stebbings (Host), Jason Lemkin (SaaStr founder/investor), Rory O'Driscoll (Scale Venture Partners)”
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→“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→“It's the fastest growing enterprise software startup of all time, of all universe throughout past Alpha Centauri.”
Source→“Devon doesn't argue. Devon doesn't only want to work on interesting problems like most of your best engineers.”
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→“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 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→“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→“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→“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→“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→“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.”
“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→AI-extracted from podcast / newsletter / paper summaries. May contain errors.