The Post Game Podcast #94 - Vasu Kulkarni: Being Wrong 90% of the Time, Sports, Startups, and Venture Capital
Vasu Kulkarni is a tech entrepreneur, investor, and lifelong basketball fanatic best known as the founder of Krossover, one of the first sports analytics platforms to bring video breakdown and data insights to high school and collegiate teams.
After scaling and exiting Krossover, Vasu moved into venture capital, investing in early-stage sports, media, and technology companies including The Athletic.
He has worked closely with high-profile athletes like Larry Fitzgerald, built a reputation for spotting outlier founders, and now spends his time backing innovative startups and advising entrepreneurs.
What You’ll Learn:
- How Vasu founded Krossover and scaled it from a college project
- The underrated lessons sports teach entrepreneurs
- Why former athletes often thrive in startups
- How venture capitalists choose where to allocate dollars
- Why being wrong 90% of the time is part of the job
- Behind the scenes of working with Larry Fitzgerald
- The art vs. science of venture capital
- How top teams prioritize product features
- What makes certain founders “outliers”
- The story behind the investment in The Athletic and their retention data
- Losing a competitive deal to Andreessen Horowitz
- The key questions he asks early-stage founders
- Vasu’s watch collecting hobby
Timestamps:
(1:30) – Intro to Vasu, childhood, and love for basketball
(5:30) – Getting to Penn & playing JV hoops
(9:30) – Entrepreneurship in his blood
(11:15) – Breaking down the venture ecosystem
(13:00) – Lessons from sports you carry into business
(15:45) – The fine line between quitting & persisting
(18:30) – Why most venture dollars go toward people
(20:30) – Why VCs are wrong 90% of the time
(21:30) – PE vs. VC: What’s the difference?
(25:15) – Working with Larry Fitzgerald
(26:50) – Venture capital: art and science
(27:40) – Prioritizing product features as a founder
(30:20) – Are there true outlier founders?
(31:40) – The Athletic deal & retention numbers
(34:00) – Are founders calling them first?
(35:30) – Why it’s not hard to go 0 for 30 in VC
(37:10) – Early work ethic stories
(39:15) – Vasu’s love for watches
(42:00) – Michael Jordan vs. Steph Curry
Links:
Vasu Kulkarni - Athlete, Entrepreneur, Blogger
The Post Game Podcast:
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