20VC with Harry Stebbings

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Why Freemium Beats Paid Acquisition
20VC with Harry Stebbings· 2025-06-22 14:00
If you build an amazing free product, it takes way longer. But what you end up building is an organic growth flywheel. Meaning you tell your friends about Dualingo.I don't know if you do, they can go experience the full thing for free. Whether they appear or not, doesn't matter. If they like it, they will also tell their friends.It just expands the entire pie of people who can use your product. And we have a lot of users that use the app for free for 5 years. Eventually, one January, they're like, "Oh, I'm ...
People Date Using Duolingo?
20VC with Harry Stebbings· 2025-06-21 14:00
There's already signs that people date on Duolingo. We have couples that got married because they met competing on a leaderboard and then they found each other on Facebook and got married. This behavior is already happening.So, it's not out of the question for us to figure out, well, how can we do matching better. Wow, that's pretty cool. I mean, it is out of the question for the record.not doing that. ...
Can the “Old Guard” Still Compete?
20VC with Harry Stebbings· 2025-06-21 05:00
I do believe the old guard can compete in certain circumstances if the situation is right and then they have leadership to just push it through. But I don't think that's the issue here. The real truth about Dropbox shipping or not shipping whatever the product is dash is it doesn't matter.Let me tell you what I mean by that. Typically the old god play is some version of I'm the system of record. I'm already in there.I can add this stuff on top. That's the pitch every time. I'm service now.I can add an agent ...
Duolingo’s Engineer Strategy
20VC with Harry Stebbings· 2025-06-20 14:00
So you're the guy who puts ads in my Dualingo. But I did that. Yeah.Jeem Canu, CPO at Dualingo. Jeem 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 ...
“Microsoft & OpenAI Control The Future Of AGI”
20VC with Harry Stebbings· 2025-06-20 08:38
We're going to hit AGI when Microsoft and Open AI litigate what open AGI is cuz everyone else is using that term loosey goosey. It could be now. It could be 2045.Who the knows. Now half a trillion dollars of value depends on that word. I can tell you that is the only part of the contract where you go ooh cuz it's ambiguous.So you're right. That would be a fun vector of this discussion. ...
Is Scale a Dead Man Walking?
20VC with Harry Stebbings· 2025-06-19 14:00
There's no way that scale can recover from losing its founders. I love you, but it's a dead man walking instantly. I could imagine an entire IPO cycle where once again, neither of the two names decided chose to go out and we get to the end of the year.I'm starting to lose confidence in the old guard. In situations of ambiguity, the person who has the most leverage has the best chance to win. And I would argue Microsoft has quite a lot of leverage cuz it's not existential for them, especially now.I think the ...
How We Avoided Theranos 😬
20VC with Harry Stebbings· 2025-06-19 05:00
How did Theronos happen. The big loss there was for me personally. We signed up to do a secondary at a really good price and met with management.Something didn't feel right. Can't say that I was like, "Oh, it's a great gigantic fraud." I didn't know what it was. Did you meet with Elizabeth.No. The kind of seauite without her. And something just didn't feel right.So, we went back and we had a that form I told you about binding to transact. Oh, no. One page. One page.Simple. Companies love it. So, I ripped it ...
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 ...