Alex Sink: To Risk, or Not to Risk?


How many investors were almost the Governor of Florida? Not many.

Alex Sink had a 25-year career in banking, followed by a career in politics as the CFO of Florida, a bid for the Governorship for the state, and finally getting heavily involved with startups as an advisor and investor.

On today’s podcast, we talk to Alex and how she shifted her career from banking to politics to helping entrepreneurs bring their fantasies to reality. In this episode, we talk all about her investment journey, what her ideal investment is, and what red flags she watches out for. She’s self admittedly risk-averse, but she’s seen first hand the power of entrepreneurship, and how venture investing can transform personal wealth, lives, and communities.

Listen on Apple Podcasts
Listen on Spotify


Some Questions I Ask: 

  • How did you get involved in investing? (3:32)
  • What technology or business models do you like that influence your investing habits? (10:56)
  • What deal size do you look for? (13:46)
  • How do you look at follow-ons? (17:03)
  • What do you think of pitch competitions? (21:48)
  • How involved do you like to get in an investment? (23:33)

In This Episode, You Will Learn: 

  • About Alex’s transition into investing and her early-stage strategies. (3:44)
  • How to figure out what to invest in as a beginner. (11:06)
  • How Alex chooses what to invest in. (13:54)
  • How Alex deals with investments falling through. (15:07)
  • How Alex evaluates whether or not to participate in follow-on investments. (17:05)
  • What makes & breaks investment presentations. (19:05)
  • Why more women should become investors. (25:16)

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