Harry Stebbings
Founder and host of the 20VC podcast and venture fund.
- 💥Fundraising Tips in a Consensus Market, Where to Invest in AI, Business Models Replacing SaaS, Fund Concentration Math & More
- 20VC_ The AI Bubble Is Wrong _ AI Margins Need to Improve _ Revenue Concentration Should be a Concern _ Why People Over-Estimate Open Models But Enterprises Still Fear Frontier Models with Aaron Katz,
“I use Instinct in a similar power user way... It does all of my bookings, travel, restaurants”
Source→“He said that you think more like Charlie Munger than anyone he's ever met.”
Source→“We will see deal structures that are objectively bad for the company done more and more often to win deals... We haven't even reached the peak of crazy deal structures.”
Source→“This is all the great Ho Nam stories of sticking it out... He's so good at that.”
Source→“Manus was disruptive. It could run, their agents ran longer and they could go further than other products we were using.”
Source→“What was sort of reported is that it crushed video diffusion... but maybe they made claims that it would... scale in other areas and it didn't quite work.”
Source→“12 billion for a bootstrap company... it took a year for Intuit to do its diligence... there was another deal that fell apart before that... it basically destroyed the company.”
Source→“I set a firm cap... a hundred dollars is the maximum we can spend... without telling me the agent relaxed the cap and fixed the bug.”
Source→“There literally was 20 posts on this wiki in the last 10 years.”
Source→“He's still one of the great fundraisers. So maybe Rory and I are wrong because he could have pulled it off.”
Source→“That memo was chilling. It's like we couldn't raise the round... a great team with proven leader, very strong CTO... they just couldn't raise the capital they needed to execute.”
Source→“After the deployment period for 20VC Fund I, Stebbings ranked his predicted top 5 portfolio companies; three years later, not one of them matched the fund's actual top performers.”
Source→“Jason said last week that if you are not well into your 2027 roadmap already, you are behind.”
Source→“I think one of the worst performing groups in terms of venture in this vintage will actually be the small boutique seed funds”
Source→“We saw that where it was. And we said to ourselves, how big can we see this getting? We think it can be a lot bigger than it is now. And so for this one, we're not going to be ownership focused. We're just going to put a check in.”
Source→“We're investing in a company called Fuse Energy, which I think is incredible. I'm so happy to be.”
Source→“I think insights per minute is important. I also think time to value is very important. People ask the most stupid question, which is like, tell me, where did you grow up? Very little actually is often learned in the where did you grow up?”
Source→“The associate WhatsApp groups are so pernicious where if you meet me and I don't think you're great I promise you they put you in the weekly roundup which they send out because they're exchanging currency... They're cross firm.”
Source→“Described by Harry as one of the best founders he's met in the last year — invested millions after a ~5-minute walk in Hyde Park.”
Source→“Export controls have actually hurt the US in many ways because it's meant that they've innovated on architecture that they wouldn't have needed to and really built muscle that they wouldn't have had to.”
Source→“The single biggest threat to Nabius is consolidation of models. If we have concentration of model winning, we are in a tough space and we want an ecosystem, not a monopoly.”
Source→“Podcast: 20VC, Date: 2026-06-07, Participants: Harry Stebbings, Ronan Churnin”
Source→“Leo Ashenbrenner is a famous investor right now. Has huge cult following. He recently disclosed a very large position for him. 5.3% of the company. I think it's 15% of his portfolio.”
Source→“Jacob is one of the best product minds I've had on the show, specifically from the last crop of product leaders in this AI generation.”
Source→“I respectfully disagree and that's why I actually think both Cognition and Factory will do very well because they're model independent.”
Source→“Lagora is the fastest growing enterprise company in history. They hit a hundred million in ARR in just 18 months. They're going to finish this year at 250 to 300 million.”
Source→“Participants: Harry Stebbings (Host), Jason Lemkin (SaaStr founder/investor), Rory O'Driscoll (Scale Venture Partners)”
Source→“Brandon from McCal said they now spend more on tokens than they do engineering salaries.”
Source→“Exa nailed one of the core... It wasn't even obvious to me until I started. There was an obvious issue. Like your agents do need to find current information... it's a look into the future.”
Source→“I liked what Zeb said, though, from ClickUp, even though he got hazed more than math. One of the things I liked that he said, and it was very transparent. It's like, listen, I'm laying off 22% of my company so I can pay a million dollars to my high performers in the age of AI.”
Source→“Exa nailed one of the core... It wasn't even obvious to me until I started. There was an obvious issue. Like your agents do need to find current information... it's a look into the future.”
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→“I haven't seen DoorDash say, let's use less token, guys. If I see it from both... from one of the most aggressive founder-led companies out there... then I'll be like, okay, we got ahead of ourselves for real companies.”
Source→“Another Benchmark company. This fund is going to be one of the best performing funds in history. I mean, seriously.”
Source→“Agents don't hop on Google and do search. They don't. And they don't create files on Dropbox and they don't hop on Zoom. Like agents have a whole, true agents have a different set of workflows and tools they use.”
Source→“It's SolarCity on steroids and we're all here for it because we love AI, but it makes no sense. This conglomeration of friends of Elon makes no sense to anyone but the folks getting bailed out on Twitter.”
Source→“At Databricks, Neon, which is their super-based competitor, over 90% of the databases are built by agents, not by humans.”
Source→“Public markets are basically dead. You can't go out with 200, 300 million in ARR now for sure. Yep. Even a billion is not even interesting... Where are the exit options?”
Source→“Chris Degnan... took Snowflake from zero to over $4 billion in ARR. No other sales leader has taken a company from nothing to that scale before.”
Source→“I think young founders have no option but to succeed. If you back a Google engineer, the first thing they'll do is they'll hire 10 of their friends... The first thing a young founder will do is they'll build the product.”
Source→“Everybody uses Granola. They just raised a big round. Happy for them.”
Source→“If you've been at Salesforce for 12, 13, 14 years, I automatically think you're not great. I'm like you got stuck in your ways.”
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.”
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→AI-extracted from podcast / newsletter / paper summaries. May contain errors.