The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 110 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable
Harry Stebbings mandates in-office work at 20VC, citing higher productivity
“I made it like mandatory that we're all back in office again. I just think we're so much more productive in office.”
Stebbings: 99% of Guests Given Pre-Release Review Make Zero Edits
“We also tell them that we will send them the episode before it's released. They'll be able to make edits. 99% of people Never make an edit”
Harry Stebbings' $150K Investment From 20VC Fund I Returned $16M
“That one fifty's now done a two X on the fund. And I could have let my ego get in the way there, and that would have been a sixteen million dollar mistake.”
Stebbings' $30M Fund Strategy: Diverse Portfolio and Low Ownership Targets
“Our fund's thirty million. I went for very diverse, low ownership, given the low fund size.”
Stebbings: I write all 20VC questions myself and refuse AI
“I do all questions myself. I would never use AI and I'm very concerned about it because you lose the muscle to me.”
Stebbings: 20VC lost two deals to competitors bidding 3x higher valuations
“We've lost two deals in the last year. And listen, we got outbid, I'm, I don't know if we would have won if we'd paid the same price, I hate people that say that. Yeah. But by like two or three X, we bid one 50, and another we got outbid by 300, another we out…”
Stebbings: Entry price test requires 3x valuation markup by next round
“When we think about our entry price, do we think that we are able to three X that entry price within the next fundraising round?”
Stebbings: 20VC Invested in a Startup Bypassing Apple App Store Fees
“We invested in a company that does, like, rooting away from Apple, just to, like, it's, and it will be a great company.”
Stebbings: 20VC lost two deals to competitors trebling valuation for common stock
“We've lost two deals in 24 months where literally they trebled the price and went to common stock.”
Stebbings: 20VC just raised a $400M venture fund
“We just raised four hundred million dollars for a new fund.”
Stebbings: Regrets pursuing celebrity guests on 20VC during creator economy hype
“We saw the creator economy hype of like the easy wins that you get from having big famous people on the show. And it's like very easy to get big numbers and be very famous, but actually that's not who we are. We are incredible shows with the best entrepreneurs…”
Stebbings: Content business lets 20VC sustain momentum without dealmaking
“We have a cheat with the content business because actually we're able to sustain momentum without doing deals where our competitors have to do deals to sustain momentum.”
Stebbings: 20VC passed on an early ElevenLabs investment at $100M valuation
“We got a tiny check offered to us at like a hundred million price. And I was like, what's the point in doing?”
Stebbings: Delaying 20VC's YouTube launch for six years was my biggest mistake
“The biggest strategic mistake that I made was I waited six years to go to video. I thought that actually people felt much less comfortable on video. I felt that they would close up more and we didn't do YouTube for six years as a result.”
Stebbings: 20VC aims to deliberately shrink its audience for deeper engagement
“I sat down at the start of the year and I said to the team, I want to have a smaller audience. I want us to deliberately get smaller. As a media company, because I want to mean more to fewer people.”
20VC Produced 300 Episodes Before Reaching 1,000 Plays Per Show
“We did 300 shows before we got to a thousand plays per show.”
Stebbings: 85% of 20VC deal flow is AI-first
“I now see 85% of our deal flow now purely as AI first deal flow.”
Stebbings: 20VC Lost Focus by Interviewing Non-Venture Guests Like Pop Stars
“I've never actually spoken about this, but I think actually I lost my way with the content that we did about a year ago. I was overly focused on growth, bluntly, and I started doing things with different guests that weren't venture, and you would have a pop st…”
Harry Stebbings Has His COO Fire Employees Due to Personal Aversion
“I suck at firing so much so that I've had my COO fire people because I don't want to do it.”
Stebbings: 20VC averages 1.3 million plays per episode
“This podcast gets 1.3 million plays per show”
Stebbings holds portfolio companies stuck at $100k ARR despite millions burned
“I'm in many companies that are, you know, a hundred K an arrow after several million dollars burnt and several years.”
Stebbings: 20VC is a data company, not a media company
“I don't think TwentyVC is a media company. I think it's a data company.”
Stebbings: 20VC holds $33M in early-stage fund and $107M in Explorer Fund
“So we have thirty three million in the early stage, and 107 in the, you know, the Explorer Fund, which is really series A and B.”
Stebbings: Most 20VC Portfolio Companies Have Cash Runway Through Mid-2025
“Most of my companies still have money till mid-twenty-five.”
Stebbings: Zero bridge rounds have succeeded in eight years of investing
“I, despite my use and good looks, I've been doing this for eight years, I've never had a bridge around work.”
Stebbings: 20VC partners will never be blocked from pre-seed investments
“I always say to him, I will never block you doing a deal. If you want to do a deal, and I don't want to do it, you can do it, because I don't want to lose the outliers.”
Stebbings forms custom three-founder investment committees for every 20VC deal
“Through the media, I meet the world's most brilliant founders, and with each deal, I create an individual investment committee of three leading founders in that specific space, and I bring their collective minds to make the best decisions together.”
20VC Surpasses 100 Million Total Podcast Downloads
“Hitting a hundred million downloads now for 20 VC”
Stebbings: Distribute Founder Interviews to Their Cap Tables and Boards
“When you release a podcast with a founder, you should also send it to every investor on their cap table. They are incentivized to share it. They have shares in the company. You should also send it to their board. They have a deep relationship with the founder.…”
20VC Produced 300 Unmonetized Episodes Before Reaching 5,000 Plays
“We went 300 episodes with 20 VC before we got to 5000 plays per show. 18 months, 300 episodes. I also did not make a single dollar in that time”
Stebbings: 20VC is passing on 80% of deals we previously funded
“Eight out of 10 deals that we might have done, honestly, we're a very diversified fund, unlike you actually, we're not fucking doing now. It has to be a nine and a half out of 10, and so the bar's just gone up for us.”
Harry Stebbings manages $250M five years after having £50 to his name
“Manage a quarter of a billion dollars, which is a joke, considering when we were five years ago, I had about 50 quid to my name.”
Stebbings: Early-stage VC relies entirely on founders because product is transient
“Market timing, I'm not smart enough to predict it. The product is transient. So all I've got in front of me is Scott and Mike and Jay, and do I fundamentally believe that whatever may happen, they might be the ones to guide it to where it could be.”
Stebbings: Initial 20VC ad revenue was used to fund mother's MS treatment
“The first money we ever made from the show, we made it because my mom has MS and we couldn't afford treatment for her. And the only way that I could pay for it was by putting adverts in the show.”
Stebbings took six years to close a major LP for 20VC
“One of our biggest LPs was a six-year cell cycle.”
Stebbings: 20VC Took Four Years to Reach 1,000 Plays
“It took me four years before I got a thousand plays.”
Harry Stebbings: Being Expelled from School Led Directly to Starting 20VC
“I would never have started the media company. If I hadn't been kicked out of boarding school.”
20VC's Audio Audience Is 10x Larger Than Its Video Audience
“We have 10 times bigger audience on audio than we do on video.”
Stebbings: Not starting 20VC on YouTube ten years ago was a major regret
“But I should have, when we started 10 years ago, if I'd just done YouTube, way better. That's a big regret for me.”
Matt Grimm: I will listen to this interview four times to critique myself
“I guarantee at the end of this, I'm going to listen to this interview no less than four times making notes of different tacks I could have taken or different points I should have made or different arguments I could have gone down.”
Stebbings Used 20VC Earnings to Pay for Mother's MS Treatment
“Well, I, my mother got MS, and I, we didn't make any money from the show, and I said, I'll pay for the show, and we used the podcast to pay for all of her treatment, hundreds of thousands of dollars.”
Stebbings: 20VC podcast intros use AI voice clone instead of real voice
“We don't, people don't know this, but for our intros, it's not my voice, Aaron. Like, not at all.”
Harry Stebbings Recorded 450 Episodes of 20VC Before Making a Dollar
“We didn't make money for two and a half years. It was 450 shows before we made any money. 450 recordings before a dollar.”
The 20VC podcast reaches approximately 500,000 listeners per episode
“So we have, I don't know, half a million listeners per show, whatever it is now.”
Stebbings originally created 20VC for personal learning, not public release
“That's actually why I started it, by the way. I didn't actually intend to release them. People don't know that. Yeah, I just wanted to learn from great people and realize that it was the best way to people to give me time.”