20VC with Harry Stebbings
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You Have To Risk Rejection
20VC with Harry Stebbings· 2025-07-08 14:01
Success Factors - Economic and romantic success requires resilience and persistence in the face of rejection [1] - Individuals who consistently ask for opportunities (money, jobs, dates) are more likely to achieve greater wealth and find a higher-quality partner [1] Risk Management - Fearlessness in pursuing opportunities is crucial for outperforming peers [1]
What is the “High Heels Effect”?
20VC with Harry Stebbings· 2025-07-07 17:00
I'm a fan of this podcast called Modern Wisdom from Chris Williamson. He calls it the high heels effect and that is the majority of women will not date a man shorter than them. Distinctive what they say that dating apps show that majority of women will not date a guy shorter than them.Economically women are getting taller every year and men are getting shorter. When you hear people all the time say, "I know all these wonderful, attractive, high character women and they can't find a man." They can find a man ...
Why Young People Are Struggling
20VC with Harry Stebbings· 2025-07-07 14:01
For the first time in our nation's history, a 30-year-old isn't doing as well as his or her parents were at 30. If a man hasn't cohabitated or been married by the time he's 30, there's a one in three chance he ends up a substance abuser. When a young man doesn't have the guardrails of a romantic relationship, he often times channels that energies into video games, porn, and conspiracy theory.If you want to score above your weight class economically and romantically, get out a big spoon. Get ready to eat End ...
Why Melio's $2.5BN Acquisition was Discouraging
20VC with Harry Stebbings· 2025-07-06 14:00
I thought it was discouraging. Melio gets acquired for 2.5% billion. Look, that's a lot of money.But guys, they're at 153 million in AR, growing 127%. 127%. If you knew nothing, would you advise your portfolio company to sell for 2.5% billion.I just got pitched an AI startup at 2 million AR that's only growing that fast, worth the same amount. I could imagine what happened if you guys know the story, but this is not a deceleration story. This is crazy. ...
Why Spotify Won
20VC with Harry Stebbings· 2025-07-05 14:00
Here's a good example. You remember Title? Title. Yeah. Jay-Z Spotify competitor. Yeah. Exactly. They had all the celebrities in the world, you know, the top musicians, Jay-Z, Beyonce, you name it. Like the technology was just as good as Spotify as at the time. And they ended up losing when they should have won because they made all their marketing about Jay-Z and Beyonce are overcoming the music industry and this is the new thing where they are the hero that is going to conquer. Whereas like Spotify is giv ...
The Biggest Question in Venture Right Now
20VC with Harry Stebbings· 2025-07-05 05:00
AI CRM Impact - Replacing CRM with AI CRM without time expansion leads to intense competition for limited resources [1] - AI taking over work and labor dollars suggests an additive effect, which the company believes is the case [1]
Losing $500M in Turkey 🇹🇷
20VC with Harry Stebbings· 2025-07-04 14:00
Financial Losses - The company experienced a loss of approximately 500 million USD in Turkey [1] - The loss was attributed to an investment in a company called UN Roro, a logistics shipping player [1] Investment Risks - The company's investment strategy in Turkey was based on the perception of a strong demographic, innovation, and a growing middle class [2] - The company failed to anticipate the flexible nature of the rule of law in Turkey, leading to unexpected competition and financial losses [2]
“If You Haven’t Grown Because of AI, You’ve FAILED”
20VC with Harry Stebbings· 2025-07-03 14:00
My rule is if you haven't grown because of AI, you've failed. The amount of money we're investing in AI right now at 300 to400 billion dollars a year in capex, will you get the near ROI. Will it be an economically rational decision when you look back 2 3 years from now.I don't know. I think venture is just going to rip. You're getting a lot of money back as an LP, right.Just massive amounts of cash coming back. I mean, if Oracle can get AI native by June 30th and your portfolio of startup can't, I mean, I'l ...
“Larry Ellison is a Genius!”
20VC with Harry Stebbings· 2025-07-03 05:00
At IPO, I think Larry Ellison owned something like 23% of Oracle. Typically, that goes down over time. He now owns 41% of Oracle.What's he done. Every year, he's run that business superbly. It's got 43% operating margins and he's used that cash to buy back shares.He hasn't sold any. So, his ownership has just gone up over time. Two things happened this year.One is the stock really popped 40% and he got a lot of cloud credit. But the interesting thing is this is the year he actually abandoned the buyback str ...
Setter’s Top 30
20VC with Harry Stebbings· 2025-07-02 16:16
Top Risers in Secondaries Market - Perplexity's ranking surged 12 places to number 7, fueled by potential $500 million funding at a $14 billion valuation and acquisition discussions with Apple executives [1] - Kraken rose 15 places to number 11, driven by strong Q1 revenues of $472 million and adjusted EBITDA of $187 million, up 19% year-on-year, with IPO speculation [2] - Curser, Cribble, Crusoe, and Glean are new additions to the list, indicating high demand [2] Top Fallers in Secondaries Market - Figure AI experienced the biggest drop, falling to number 15, due to winding down primary fundraising and scrutiny of its $395 billion valuation against minimal revenue [3] - XAI fell to number 8, despite sweetening its $5 billion debt offering at a 125% yield, due to a high burn rate of $1 billion per month and projected $13 billion losses in 2025 [4] - Shield AI fell four places to number 13, which is surprising given the current strength of the Defense Tech sector [4]