"Ships are safe in harbor, but that's not what ships are for." - John Shedd
Caroline was born in Telluride, Colorado, and allegedly learned to ski before she learned to walk. Her family later traded fourteeners (Colorado’s name for 14,000-foot peaks) for skyscrapers and moved to Chicago, but she refused to become an indoor person. Instead, she found every excuse to be outside: sailing on Lake Michigan, playing lacrosse, and ski racing in Wisconsin (proof that Midwesterners are nothing if not committed).
She studied economics at Dartmouth, where she spent terms working at a fintech startup in London, her first real taste of company building, and backpacking along Australia’s east coast, which, according to extensive research, is more fun than attending class. After graduating, she joined strategy consulting in New York because every economics major has to get it out of their system eventually. One project, in particular, changed her trajectory. A client was deciding between two acquisition targets and leaned toward the obvious, “safe” choice. Caroline wasn’t convinced. She built the model, made the case for the overlooked business, and eventually won everyone over. The client bought the underdog. It worked. Caroline was hooked. That experience led her to equity research at JPMorgan, where she spent her days digging into companies and occasionally betting against consensus.
Armed with an increasingly unhealthy relationship with Excel and a healthy skepticism of conventional wisdom, Caroline eventually made the move west into venture capital. It didn’t take long to realize she’d found her people. It turns out venture capital is one of the few jobs where asking founders an unreasonable number of questions is considered polite. What she loves most about venture isn’t just understanding the numbers. It’s understanding the founders behind them. The best investments come from knowing both. That philosophy sits at the heart of Founders Circle, and it’s what drew her to the firm (although we can’t rule out the legendary CAT ski trips).
Outside the office, Caroline co-leads the San Francisco chapter of Synergist, a national nonprofit that helps young women navigate the early stages of their careers. When she’s not working, she’s usually taking advantage of Northern California’s endless excuses to be outside: running, biking, hiking, or plotting her next mountain escape. Fortunately, her parents eventually found their way back west and now live on a ranch outside Bozeman, Montana, which makes going home a little easier and leaving a little harder.
By Andrew Boston
