The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour

Nov 16, 2020
Stewart Butterfield, Founder and CEO of Slack, shares his remarkable journey from co-founding Flickr to creating a messaging platform used by millions. He discusses his evolving views on wealth, emphasizing the three levels of wealth and how identity shapes entrepreneurship. Stewart reveals his leadership philosophies and the importance of decision-making in business, comparing effective entrepreneurship to parkour. He also dives into the nuances of public offerings, weighing direct listings against traditional IPOs, and shares rapid-fire insights on leadership in tech.
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ANECDOTE

Path to Startups

  • Stewart Butterfield's path to startups began in college with early internet exposure.
  • This led to web development, a dot-com job, and founding Gradfinder, Ludicorp (Flickr), and TinySpec before Slack.
INSIGHT

Three Levels of Wealth

  • Money doesn't guarantee happiness, but reduces stress by easing financial burdens.
  • Butterfield describes three levels of wealth: no debt worries, not caring about restaurant prices, and not caring about vacation costs.
INSIGHT

Vision as Aspiration

  • Company vision should be aspirational, not overly specific, to avoid limiting potential.
  • Butterfield emphasizes the importance of believing in the inevitability of a product's success.
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