This Week in Startups

Jay Trading, Stripe valuation cut, $NFLX ads, $PTON outsourcing, + more | E1508

Jul 15, 2022
The hosts dive into a new trading segment, analyzing Jason's investment strategy that led to a stock surge for Stitch Fix. They discuss Stripe's significant valuation cut and its impact on employees. Netflix teams up with Microsoft to introduce an ad-supported streaming service, reshaping viewer experiences. Meanwhile, Peloton decides to outsource its manufacturing to Taiwan, reflecting broader market shifts. They also touch on venture capital dynamics and offer insights into navigating economic challenges in investing.
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ANECDOTE

Jason's First Trade

  • Jason Calacanis discusses his first public stock trade, focusing on Stitch Fix.
  • He's shifting from index funds and startup investing to actively trading, citing unique opportunities.
INSIGHT

Insider Influence

  • Bill Gurley's substantial purchase of Stitch Fix shares influenced Jason's decision.
  • Insider buying, especially from respected figures, can signal value.
ADVICE

J-Trading Strategy

  • Follow respected insiders and look for significantly undervalued companies.
  • Consider market downturns as buying opportunities, focusing on long-term growth.
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