The most important moment of Ryan Caldbeck’s basketball career, perhaps even his life, came when he least expected it. It was during the 1995-1996 season at Rice Memorial High School, and it was the most frustrating game he could ever remember playing. Shots that were normally automatic in practice, normally his bread and butter, were landing anywhere but in the net. He stormed back to the locker room, dejected and frustrated.
What his coach told him next changed his life, putting him on the road to re-unite with his older brother Justin at Duke. “After the game, coach Kevin Cieplicki sat me down with a simple piece of paper outlining a simple plan to improve my game. What was special for me is that the plan symbolized for me how to work hard and smart. It was completely life changing. It showed me the importance of having a roadmap,” said Caldbeck from his office in San Francisco.
Justin Caldbeck was already in Durham, North Carolina on the picturesque Duke campus, having arrived in the fall of 1995 and becoming a student manager on the basketball team. Justin and Ryan both grew up in Shelburne and attended Rice High School before matriculating at Duke, in 1995 and 1997, respectively. Both brothers became student managers of the basketball team as freshmen, beating long odds by sheer persistence and determination. Then, against even longer odds, both brothers were called by then Duke assistant, and current Utah Jazz coach, Quinn Snyder right before practice began in the fall and offered opportunities to walk on.
For Justin, the process was helped along considerably by his one-on-one battles with walk-on Jeremy Hall. “I was a manager and played him one-on-one and did pretty well. I almost beat him. A couple players, especially (current Duke lead assistant) Jeff Capel, took notice and asked us to play again. I eventually started beating him regularly with other members of the team, as well as assistant coaches, watching. The next year I took his spot on the team,” said Caldbeck. Little did Jeremy Hall know that Justin was doing two hours of drills per day with former Duke head coach Pete Gaudette to prepare to beat him. He even had a picture of Hall hanging in his dorm room for motivation. Justin got the call from coach Snyder the next fall and never looked back.
The Caldbecks even managed to make the team, coached by the legendary Mike Krzyzewski, in the same 1998-1999 season, a wildly impressive accomplishment that garnered national attention. The odds of walking on at a program like Duke are minuscule at best, especially in a year in which they had at least five future NBA players and several future NBA All-Stars on the roster.
Doing it in the same year put the Caldbecks solidly beyond everyone’s expectations, where they would stay. Both of them have climbed the traditional steps of corporate America: elite MBAs, stints at elite consulting firms and, later on, private equity firms. Independently of each other, they ended up in Silicon Valley. Now each heads his own investment firm, molded upon the ideals they have developed after years in the business world.
The tipping point for Ryan on whether to make the leap from traditional private equity into his innovative new startup, CircleUp, called to mind his older brother’s decision on where to attend college. Unsure of exactly what to do, but knowing how they felt in their gut, both brothers sat down with a parent for a heart to heart before making the final call.
Justin was deciding between Penn and Duke. Despite wanting to go to Duke ever since he watched Johnny Dawkins play in 5th grade, the Wharton School of Business at Penn loomed large among the possibilities. His mother told him to flip a coin. It landed on Penn. “That made me angry, and that is how I knew Duke was the right choice. I have no regrets,” Justin said.
For Ryan, nearly 20 years later, it had been his father, and there was no flip of the coin. “I told my father I was nervous,” he said from his office in San Francisco last week. “He asked me if I would be more proud of having tried and failed than stayed and succeeded. I said yes, and knew it was the right call. I wanted to make a difference. I wanted to build something, that if people didn’t know I existed, they would still be happy it existed.” What he built was an innovative company that helps successful small retail brands from across the country gain access to the capital they need to expand.
Small consumer brands can apply to be listed on CircleUp, and if they pass through a vetting process, investors can invest money directly. Right now their portfolio is heavy on clothing and food and beverage companies, and includes Bity-Bean of Charlotte, Vermont. Founded in 2012, CircleUp has itself been funded by industry heavyweight Google Ventures, and does 90% of its own investing outside of Silicon Valley.
Justin has recently launched his own smaller, newer firm that is more within the traditional Silicon Valley playbook. He opened Binary Capital with partner Jonathan Teo, and according to Caldbeck, they have been investing in consumer-facing technology since August. They raised a $125 million initial fund, and their typical investment is between three and five million dollars
Both brothers credit much of their success to Shelburne, Rice, and playing basketball at Duke. They both say the lessons they learned through sports have had a direct affect on their success today. . “The resiliency and work ethic and tenacity that I developed in my basketball career are the same things that have helped me get to where I am today. I firmly believe one is related to the other,” Justin said from his office in Silicon Valley.
While Ryan has Coach Cieplicki to thank for his inspiration, Justin found his own in a chance meeting with Coach K his freshman year while working at a Duke basketball camp. After the coach spilled a drink, Justin was ready with a towel, but the legendary Krzyzewski insisted on getting down on the floor and cleaning it himself. He said, “Justin, when you are running your own company someday, always remember, you are never too big to clean up your own mess.”
You can reach Matt Keller at 598-9366 or email@example.com. Follow him on Twitter at @KellerOnSports.