Playing with unicorns is a new weekly show on startups, entrepreneurship, and venture capital.
I cover everything I learned as an entrepreneur, angel investor and venture capitalist during the last 22 years, focusing on everything I wished I knew when I first got started as a tech entrepreneur.
It's been a year since my last Ask Me Anything session. A lot has happened since then across AI, marketplaces, macro, and the broader tech ecosystem.
Here are the questions we covered:
· 4:22 Why does AI feel so widely feared or disliked right now?
· 8:48 Why is AI driving massive progress while politics and public systems lag behind?
· 13:34 What are the real opportunities in commercializing AI today?
· 14:10 Will startups still need human co-founders in an AI-first world?
· 17:51 How important is a technical co-founder in the age of AI?
· 20:00 Will intelligence (IQ) become irrelevant as AI improves?
· 20:18 What skills should young professionals focus on in an AI-driven world?
· 22:48 How should education evolve in the age of AI (and how should kids be taught)?
· 26:40 What drives investor decisions at the earliest stages of a startup?
· 28:23 How can pre-seed founders raise capital, especially outside the US?
· 30:11 How might graph neural networks impact marketplaces?
· 31:32 What does it take to win in marketplaces in regions like Latin America?
· 33:10 What creates real defensibility in AI companies vs hype-driven growth?
· 35:38 Are we in an AI bubble—and what does it mean for investors?
· 37:30 What is the right funding path for startups that require large upfront capital?
· 38:54 What proof do investors need before funding an early-stage startup?
· 39:40 How has your marketplace investment thesis evolved in the age of AI?
· 42:02 Where can founders find strong fractional developers?
· 43:15 What defines AGI—and how should we think about it today?
· 45:08 How important is the initial "wedge" in building a marketplace?
· 46:29 How do you evaluate whether AI adoption actually creates value?
· 48:00 What founder traits matter most today?
· 49:45 If you were starting today, what would you build and why?
· 52:32 Who are you beyond your professional identity?
· 55:11 Do you still have insecurities—and how do you think about them?
· 57:10 What would you do if you weren't an entrepreneur?
· 59:45 What signals show a marketplace is reaching liquidity and product-market fit?
· 1:01:19 What is the core defensibility of a marketplace from day one?
· 1:02:24 What is Quince and why has it been so successful?
· 1:04:22 Which "boring" industries will produce the next big companies?
· 1:06:36 What is the biggest blind spot among VCs today?
· 1:08:15 Which AI sectors are overcrowded right now?
· 1:09:35 Can marketplaces succeed around complex, multi-service life events?
· 1:11:41 How have fundraising expectations changed in the AI era?
· 1:16:07 Should graduates join startups or big companies in 2026?
· 1:16:21 Is being a generalist still a viable career path?
· 1:18:35 Do investors prefer warm intros or cold outreach?
· 1:19:55 Should startups use services as a wedge before becoming SaaS?
· 1:22:02 What games or tools are best for child development and learning?
· 1:24:39 Will AI cause massive job losses or unemployment?
· 1:30:57 Can venture-scale companies be built in Latin America today?
· 1:32:26 How should AI be used in operational decision-making?
· 1:36:00 What separates massive marketplaces from niche ones?
· 1:37:24 How much decision-making should be delegated to AI vs humans?
· 1:39:10 What matters most in early-stage B2C startups: traction or insight?
9 Mar 2026TRANSCRIPT
#52 Marketplaces in the Age of AI
Host [Host Name] explores how AI impacts marketplaces, revealing why many fears are overstated and highlighting new opportunities for growth and profitability.
19 Jan 2026TRANSCRIPT
#51 Zach Resnick, Founder & CEO of Ascend
Host interviews Zach Resnick, Founder & CEO of Ascend, about optimizing travel with miles, points, and strategic decision-making.
Inside a recent episode
#53 Ask Me Anything
Published 23 Mar 2026 · Transcript excerpt
[…] And so the idea that you should be using AI to teach the kid exactly at the right level makes a lot of sense to me. So there's this school out of Austin originally called Alpha School, where they use AI tools to basically teach get your kid to the very maximum of his potential. So they've realized that you wanna teach them to the point where they get 85% of the answers correctly. If it's 99%, it's too easy. If it's 50%, it's too hard. And so in every discipline, you wanna get them at about 85% and you wanna see how far you can get them. And on two hours of curriculum per day, they basically can cover the normal curriculum. […]
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