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#58 TA McCann – Professional Sailor, Serial Entrepreneur (5x Founder with 3 Exits), Managing Director at Pioneer Square Labs

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T.A. McCann is a serial entrepreneur with an impressive track record. He has founded and served as CEO of several successful companies. Some notable ventures include Senosis (acquired by Google), Gist (acquired by Blackberry), and Rival IQ, a leading company in marketing analytics.

McCann’s expertise extends beyond founding companies. He has also held senior roles at Microsoft, where he led divisions such as Exchange and the Mobile Services divisions. Additionally, he has worked as an EIR (Entrepreneur in Residence) at Polaris Venture Partners and Vulcan Capital.

Full conversation includes:

  • Becoming a professional sailor
  • Working at Microsoft Exchange
  • Starting 5+ companies (3 exits)
  • Working for Paul Allen & building Startup Studio Vulcan Labs
  • Selling Gist to Blackberry
  • Rival IQ
  • Synosis (acq by Google)
  • Pioneer Square Labs
  • Systematic customer discovery & customer development process
  • Advice to entrepreneurs raising capital
  • Is AI a step change?
  • Who will capture value in AI? Big tech or startups?

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Nataraj is a PM at Azure, investor & host of podcast. Follow him on Twitter at


Past guests of Startup Project podcast include Ali Moiz (, Kirby Winfield (, Eric Bahn (Hustle Fund), and many more.