My First Million

#150 - Jason Calacanis Joins The Brainstorm To Talk Robinhood, Gambling and the Opportunities He's Investing In

Feb 3, 2021
Jason Calacanis, an entrepreneur and angel investor known for his early backing of Robinhood, shares his unique journey from journalist to investor. He dives into his gambling experiences and what they reveal about investment strategies. The conversation touches on the demise of tech media, the booming potential of paid communities, and his predictions for the rise of income share agreements and travel startups. With fresh insights on the evolving landscape of entrepreneurship, Jason's thoughts provoke excitement for the future of investment.
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ANECDOTE

Robinhood Investment

  • Jason Calacanis invested in Robinhood after a chance encounter with Vlad Tenev in a bar.
  • Tenev's pitch: getting millennials, often perceived as commitment-phobic, to trade stocks for free.
INSIGHT

Robinhood's Mission

  • Robinhood's mission was to democratize stock trading, making it accessible through a mobile-first, free platform.
  • The GameStop situation represents an unforeseen, extreme edge case, not a reflection of Robinhood's intent.
ADVICE

The Power of Lists

  • Create lists to gain influence in any industry, even if they are somewhat subjective.
  • Ranking individuals or entities sparks debate and draws attention, as demonstrated by Calacanis' Silicon Alley 100.
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