20VC with Harry Stebbings

Search documents
Can Non-Technical CEOs Win?
20VC with Harry Stebbings· 2025-06-18 14:00
For Open AI, you have a CEO and now another CEO that are both not technical. I think it's really weird. And listen, Sam is obviously off the charts genius level.Even though he's lost a lot of people, he can recruit like no one on planet Earth. And maybe that's all that matters as a CEO. But my life experience is non-technical CEOs.Now we have two of them. They can't win at companies like Open. And yet they are winning.But my experience is they almost all fail. Why Fiji built our naps ecosystem at Facebook u ...
How We Made $1BN On Spotify 😮
20VC with Harry Stebbings· 2025-06-18 05:00
So, one of the first employees I hired, he was working as an analyst with me. This is like 2014. I was telling him this story about how my mind exploded when I was in college and I could download Metallica on Napster.And he's like, you know, you've heard of Spotify, right. And I'm like, yeah. He's like, well, maybe we should buy some shares in Spotify.And we started searching around and we found a celebrity that was going through a unfortunate change of life scenario and a divorce and he had like $4 million ...
The Real Problem With Silicon Valley
20VC with Harry Stebbings· 2025-06-17 14:01
I bought into the whole hook, line, and sinker of the entire problem in my opinion of Silicon Valley. What is that problem. Losing focus of what you're hired to do and paying more attention to the lifestyle that comes along with being a money manager and the circles that you roll in and about the deals that you're doing and the money that you're managing versus at the end of the day, the actual value you're creating for your people who have trusted you with their capital and making a difference for your und ...
How We Made $800M on Coursera
20VC with Harry Stebbings· 2025-06-16 17:01
We were the largest shareholder of Corsera through our strategy. We owned 16% of Corsera when it went public. What did it go public.Huh. We sold the stock at 36 bucks a share and it's $8. $800 million back to LP. ...
“We Made Millions on Lyft, But Lost on Uber” 😱
20VC with Harry Stebbings· 2025-06-16 14:01
So when we go down to that first 35, that's how many companies give or take? Like seven. But most of it is Alibaba, Spotify, Palunteer, and Twitter. This is just dumb block. Come on. I'm not that smart. I mean, we made ridiculous sums of money for LPS in that period. We made a ton of money on Lyft and we lost money on Uber. What? Yeah. How does that work? 40% of my third fund went into Spotify. I went back to our LPs and said, "Listen, we weeded up. We need to pivot. We need another 300 million bucks becaus ...
Fiverr Almost Became WHAT! 😱
20VC with Harry Stebbings· 2025-06-14 14:01
One of the strategic opportunities was to create Only Fans many many years before Only Fans and we decided not to do it. How does that come as a strategic opportunity and why did you decide not to do it. The reason why I'm saying that we could have done it is because this was actually bubbling within the first versions of Fiverr organically.We didn't have a category for that. We started noticing this was happening behind the scenes. There were like code words that people spread on social and said, "Oh, go t ...
Can $1BN Companies Fail?
20VC with Harry Stebbings· 2025-06-14 05:00
Some companies that were once worth a billion dollars can go to zero. Easily done. Rich Wong Excel said 20% of unicorns this week will just fail.This is pretty rough and tough, but my gut would be it's roughly 20% will be good enough to get public in the end. 20% will totally maybe 25 in each site just for arbitrary sake. And then 50% in the middle are meaningful enough to be valuable but not so meaningful that they'll get public and they'll be merged.They'll combine with someone else that'll be PE. But it' ...
Duolingo’s Engineer Strategy
20VC with Harry Stebbings· 2025-06-13 14:09
So you're the guy who puts ads in my Dualingo. But I did that. Yeah.Jeem Canu, CPO at Dualingo. Gem leads product strategy for over 90 million monthly active learners. Consumer products live and die in the pixels.Product managers are sometimes viewed as I'm the mini CEO. I decide strategy and then people execute. That is like the worst definition of a product manager that I've ever heard.So if someone is actually creating more output with AI, well, they'll probably get promoted faster. Why would you write s ...
“Circle’s Sellers Missed Out”
20VC with Harry Stebbings· 2025-06-13 05:00
And in the case of Circle, over half of the IPO was sellers, which means you just opted to sell a security at 31 bucks a share and two days later it's trading at 80 bucks a share. That's a lot of money to leave on the table. So, I'm sure if you chose to sell in the IPO, you're sitting back and going, hm, I feel amazing about the outcome, but oh my god, that's a lot of money on the table.Like 20 million shares, I think, were secondary. And you know, at 50 60 bucks of extra dollars a share, that's a billion d ...
“Great Businesses Don’t Need You To Like Them”
20VC with Harry Stebbings· 2025-06-12 14:00
how freaking awesome the US capital system is. I mean, the United States has 4% of the world's people. We have roughly 23% of the world's GDP. We have 67% of the world's market cap.We won. Not just our GDP, our income is higher than our population ratio, but our wealth, our corporate sector is even higher than our GDP. Some companies that were once worth a billion dollars can go to zero.The definition of a great business is when your customers can hate you and still do business with you. The truth is SpaceX ...