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Listen in as David chats with Carey Ransom, a serial entrepreneur, venture capitalist and angel investor. Carey begins by explaining how growing up around a family business fostered his entrepreneurial streak.

Carey then discusses what initially captures his interest in an entrepreneurial venture and why he often is skeptical of founders who are in love with their solutions. He and David also spend time delving into the total addressable market (TAM) for a business and why Carey thinks it is imperative to cut that down realistically.

Next Carey tackles the topic of boards for startup companies, as he has served on many of them. He shares that, as a board member or investor, the #1 thing he looks for from the management team is how they learn and adjust.

David and Carey then discuss Bonus, one of the ventures Carey is involved with today.

Carey concludes with his big-picture advice to physicians who may be considering a jump into full-time or part-time entrepreneurial ventures.

What You’ll Learn:

  • How growing up in a family business actually led Carey to be interested in outside businesses
  • Why a founder’s curiosity often is a key factor in getting Carey interested in an entrepreneurial venture
  • Why founders typically need to cut their total addressable market (TAM) estimates realistically
  • What Carey thinks about boards for early-stage companies and how they change
  • Why the ability of a start-up management team to learn and adjust is so important
  • Carey’s DIY vs. delegation perspective on his personal finances – “optimizing for not doing the things I don’t want to do”
  • What Carey’s firm Bonus does and why some physicians may be interested in it
  • Carey’s advice to physicians who may consider a jump into entrepreneurial ventures


  • David Mandell: Bio
  • Carey Ransom: Bio

More about Carey:

Carey Ransom is Managing Director of BankTech Ventures, a newly-closed $100M+ strategic investment and ecosystem fund for community bank technology innovation. With over 100 banks and dozens of bank-enabling technology startups involved, the momentum has grown quickly.

Carey is a technology entrepreneur and investor, and has started, grown and/or led 8 B2B and consumer tech companies. In 2020 he founded Operate, a SoCal-focused venture studio and fund, where he and his team invest themselves into founders of exciting data-centric SaaS and fintech startups – so far with over 25 companies.

Prior to Operate he was COO at Aspiration, the leading “consumer financial firm with a conscience,” where he led the firm’s growth from 20 to 200 people and transition to a FINRA-regulated broker-dealer.  He was also CEO of RealPractice, a venture-backed SaaS company, which he sold to ReachLocal (RLOC); Chief Product & Innovation Officer of Experian Consumer Services; and founding CMO of Happy Money, a venture-backed consumer fintech company (and unicorn) that innovated in lending and financial health.

Carey has an MBA from UCLA Anderson School and a B.A. in Economics from Indiana University. His real education was growing up in a multi-generational retail family business.