Episode 15: Ryan Caldbeck

July 2, 2021
updated on

What does it take to go from small-town kid to successful CEO? To this week’s guest, the answer is simple: never stop learning. A self-proclaimed underdog with a burning desire to make an impact, Ryan Caldbeck describes himself as gritty and a dreamer. In this episode, Ryan discusses growing up in a small town in Vermont, becoming an NCAA basketball champion, finding success in private equity, and eventually co-founding (and stepping down from) CircleUp-and the role each played in his passion for tech entrepreneurship.

Ryan’s small-town upbringing shaped his entrepreneurial spirit. From the time he was young, he would dream about accomplishing something amazing. As his dreams became a reality, though, he found himself struggling both personally and professionally. Reflecting on his journey in admirable detail, Ryan advocates for tapping into your network for support and stresses the importance of mental health.

As someone who is extremely curious and loves to learn and grow, Ryan felt stuck in his career in private equity. That all changed in early 2011, while sitting on a panel where no one could answer the question “How do you raise money for a $5MM business?” At that moment, he knew he wanted to start a company that was going to make an impact-and thus, CircleUp was born. Suddenly, he found himself surrounded by people who loved to learn just as much as him, and it was as if his whole life finally made sense.

In this episode, we talk about Ryan’s intense passion for human connectivity through learning, his journey to CEO, and his ultimate decision to step down. So, what’s next for this lifelong learner? Listen to the full episode to find out.

Favorite Moments

  • (3:20) Passion for learning
  • (8:46) Unlocking the secret door
  • (11:47) Business & basketball
  • (16:08) Post-it notes
  • (26:30) Fatal flaw
  • (47:31) What’s next?

About Ryan Caldbeck

Ryan is the founder and former CEO of CircleUp, an investment platform powered by technology that has helped to revolutionize how data is used in the private markets. CircleUp has helped hundreds of companies to thrive by giving them the capital and resources they need and has won many awards including Top 5 Most Disruptive Companies in Finance by CNBC and Fast Company‘s Top 10 Most Innovative Companies in Data Science. Caldbeck was also a successful investor at top-tier private equity firms like Bain Capital, TSG Consumer Partners, and Encore Consumer Capital, where he sat on numerous boards of successful private companies. A 2005 graduate from the Stanford Graduate School of Business (MBA) and 2001 graduate of Duke University (dual BA in Public Policy and Psychology), Caldbeck was also a member of Duke’s 2001 National Championship Men’s Basketball team under Coach Mike Krzyzewski.

Caldbeck grew up in Shelburne, VT, before moving away to Duke and has lived in Silicon Valley for 18 years. He currently lives in the Bay Area with his wife and three kids.




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