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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Taboola's Profitability
- Taboola, a company that places ads at the bottom of articles, has a billion-dollar revenue.
- Despite seeming simple, these ad tech businesses are quite profitable.
Finding Business Ideas
- To find good business ideas, identify the biggest challenges in emerging industries.
- Directly ask potential customers about their pain points.
Beginner's Mind
- Ask experts how something works, but ask beginners how it could work in the future.
- Beginners have a fresh perspective, unburdened by existing paradigms.
