Podcast

Pivoting one week before YC demo day, growing 20% per month for a year, how to move fast, the benefits of taking on lots of angel investors, how to pick…
Living paycheck to paycheck, investing in Instacart, DoorDash, and Hashicorp's Seed rounds, the struggles of raising his first four funds, how LPs…
Lessons from sponsoring 5,000 influencers, a crash course on the fashion market, why wallets are a terrible category, how to build an enduring brand…
How to pick co-founders, why early customers deserve more credit, Dimitri's experience in YC, using PLG to build a deeper product, going slow to go…
$1.5 million in revenue at 13 years old, why consumer platforms need social inflection points, Medal’s unique approach to in-person / remote work, and…
The history of newsletters, why he spends $0 on growth, how to sell a newsletter, why the NBA commissioner reads his writing, the momentum in US soccer…
The business behind sports, how to raise money for a crazy idea, betting on technological change, how Overtime launched three sports leagues, and why…
1
Competing with 100+ year old monopolies, surviving a 85% drop in revenue, building a moat in CPG, lessons from Facebook's launch strategy, and why…
Why MrBeast Burger failed, bootstrapping to $3 million in profits, how to pitch investors on a unique business model, turning down a nine figure…
Discussing the poor incentives of health insurance, why tech has a negative ROI in healthcare, being Larry Page's right-hand man at Google, and building…
Lessons from selling a company for $45 million, how to get free legal advice, cultural mistakes most startups make, how to fundraise, and the…
How the $1 trillion US K-12 education system works, its broken incentive structures, why teachers are superheroes, how to double their income, and why…