Ryan Caldbeck on Entrepreneurship and the Importance of Lifelong learning

The Altogether Show with Eric Satz

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 life-long learner? Listen to the full episode to find out.