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15
Jay Samit
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Why This Episode Matters
Jay Samit has been called the "Godfather of Digital Media." He started on the internet in 1978, created the first online auction (before eBay), worked with Reid Hoffman to launch LinkedIn, and has advised everyone from Bill Gates to major Hollywood studios on digital transformation.
In this conversation, he reveals why you either have to be the best at what you do or the only one doing it, how YouTube pivoted from a failed dating site, and why the secret to success is solving problems—not selling things.
For entrepreneurs, innovators, and anyone navigating disruption, this is a masterclass in spotting opportunities before they become obvious.
Key Takeaways
Be the best or be the only one doing it
If you're the only one doing something, you're automatically the best. Position yourself where the world is going, and when everyone catches up, you'll look like a genius. Then leave and find the next frontier.
Entrepreneurs solve things, not sell things
The world has endless problems. If you help five people, you have friends. If you help a million, you become wealthy. If you help a billion, you change history. Focus on solving problems at scale.
Failure is just learning on someone else's dollar
Early success can be dangerous because you think you earned it through brilliance. Venture capitalists actually prefer founders who've failed before—they've learned lessons without spending your money.
Most businesses pivot to success
YouTube started as a video dating site called "Tune In Hook Up." Twitter was a music site. When your original idea fails, look at what unexpected behavior the data reveals—that's often your real opportunity.
Nobody's stopping you from joining the innovation club
The same small group of people drives innovation worldwide. There's no gatekeeper. The only thing stopping most people is the fear their parents instilled—take the safe job, avoid risk, don't fail.
Conversation Outline
00:00 — The cocktail answer: be the best or the only one doing it
03:00 — Starting on the internet in 1978 and meeting Bill Gates before he was a billionaire
08:00 — Creating the first online auction (before eBay) and launching LinkedIn with Reid Hoffman
12:00 — The first social network (10 years before Facebook) with Mark Cuban and Eric Schmidt
16:00 — Why failure is learning and early success can be dangerous
20:00 — YouTube's pivot from dating site to video platform
24:00 — Why entrepreneurs solve things, not sell things
28:00 — The Molly Mully story: adopting 22,000 children and changing a nation
35:00 — AI and the future of disruption
40:00 — The magic connection: Robert Houdin and the CIA's head magician
48:00 — Meeting at Davos and the World Economic Forum
Jay Samit
→ Called the "Godfather of Digital Media" for pioneering digital transformation
→ Serial entrepreneur with multiple successful exits
→ Worked with Reid Hoffman to launch LinkedIn
→ Created the first online auction platform (before eBay)
→ Author of bestsellers "Disrupt You!" and "Future Proofing You"
→ Venture capitalist investing in transformative companies
→ Advisor to Fortune 500 companies on digital strategy
Show Notes & Links
Mentioned In This Episode
→ Bill Gates — Samit met him before he was a billionaire, when computers cost as much as cars
→ Reid Hoffman — co-founder of LinkedIn, worked with Samit on the launch
→ Mark Cuban — worked with Samit on the first social network's sports component
→ Eric Schmidt — future Google chairman who worked on Samit's school-wiring initiative
→ eBay — Samit created the first online auction before eBay existed
→ LinkedIn — Samit helped launch with Reid Hoffman
→ YouTube — started as dating site "Tune In Hook Up" before pivoting
→ Twitter — originally a music site before pivoting
→ Davos / World Economic Forum — where Samit and Roberto met
→ Robert Houdin — legendary French magician, father of modern magic
→ CIA — has a "head magician" position Samit learned about
→ Molly Mully — African billionaire who adopted 22,000 children
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