My First Million #148 with Jack Smith - How r/WallStreetBets is Beating Wall Street, Taboola's Billion-dollar Payday, and How Grayscale is Printing Money
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Jan 27, 2021 
Jack Smith, an entrepreneur and founder of companies like Bungle and Ship, dives into fascinating topics. He discusses how WallStreetBets is reshaping Wall Street and the dynamics of retail investing. The conversation shifts to Taboola's billion-dollar success story and the challenges of the ad tech industry. Smith also unpacks Grayscale's influence in the Bitcoin market and speculates on the future of digital identities, touching on the implications of anonymity in online spaces. Finally, they explore how VC firms are venturing into media.
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Jack Smith's Success
- Jack Smith's company, Vungle, sold for hundreds of millions of dollars.
- It was an ad technology company, similar to Taboola.
Future of Identity
- Balaji Srinivasan predicts people will hide their real identities online in the future.
- This is due to social media mobs and cancel culture.
Silk Road's Anonymous Operations
- Silk Road, a multi-billion dollar enterprise, operated with entirely anonymous employees.
- Surprisingly, it had a harmonious work environment.
