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Cack Wilhelm headshot

The Art of Investing

A professional runner turned investor wunderkind, Cack Wilhelm, ’14, shares lessons she’s learned from competitive running, venture capital, and business school.

Cack Wilhelm, ’14, is a world-class athlete who brings her competitive zeal to Silicon Valley venture investment. Wilhelm is the first woman since 1983 to be promoted to general partner at IVP in San Francisco, a venture firm that funds tech startups on the verge of spectacular market growth.

Her path to venture zigged and zagged, from running professionally for Nike and training for the Olympics, to joining a New York investment bank a week before the 2008 crash. She went on to explore sales—first at the database technology company Oracle, and then at the enterprise software startup Cloudera—which gave her an understanding of the kaleidoscopic nature of business. A latent desire to go into venture capital led Wilhelm to Booth’s Full-Time MBA Program so she could broaden her skill set. In venture, she says, every company is a new project with new players. 

In 2022, she was named to Fortune’s 40 Under 40 list for becoming a top investor in data and cloud infrastructure startups, and for helping pave the way for more women to be top decision-makers in the venture space. Recently, she landed the highly sought-after lead investment in the A.I.-powered knowledge engine Perplexity.

There’s a common misperception about venture’s role, that we’re dealing with the day-to-day with our companies. Each of us makes one or two investments per year, which means at any given time we’re involved with six to eight companies. Day to day, week to week, our work is varied. We source new investments, meet with founders, and exercise due diligence. We are not trying to be in the daily mix. Instead, we help management teams think through the big picture, supporting growth and hiring.

There’s an art to investing. It’s more nuanced than facts. You have to have intuition, especially in this dynamic market, where everything continues to seem expensive. The game has gotten harder. Winning comes down to having deep belief and then being right. At IVP, we look to invest in the top 10 to 15 companies of consequence each year, the companies that will make the leaderboards when they exit.

From early on, I’ve believed that founders should lead sales as a way to understand market fit. How many customers have you closed? Delighted? How often? That’s a better mark of value than how much money you’ve raised or how many venture rounds you’ve completed. Sales isn’t a celebrated role, but the business savvy I have I learned in sales.

I shine a light on imbalance because I know it firsthand. I’m the only female general partner at IVP. In the United States, women are about a fifth of all venture partners, and nine out of 10 VC firms have no Black partners, according to the 2022 VC Human Capital Survey. I can’t solve it all, but I can ask a CEO or executive: Why isn’t a given team more diverse? What would it take to double the number of women on the engineering team? That’s an area where we can help; we have the resources to bring a variety of talent on board.

What I learned in competitive running serves me every day. I started competing in track in 7th grade, became an All-American athlete at Princeton, and then continued as a professional athlete for Nike. It took hard work, determination, personal accountability, and team orientation. Sports are character-building, especially in the moments in between when no one is watching. Over and over, I see that business is about character, about being yourself in order to build rapport with others.

“Jobs get boring. That’s why I went into venture capital. We are always looking at what’s new and innovative, and that’s ever-changing.”

— Cack Wilhelm

Cack is a nickname my dad started calling me when I was a kid. My given name is Catherine, which is reputable, fit for a queen. In kindergarten, I declared I wanted everyone to call me Cack. Now I can’t think of being called anything else. It’s just androgynous enough that I get a lot of correspondence addressed to “Mr. Wilhelm.” 

Becoming a mother made me a better executive because it made me think about how I value my time. I’m at my best with a full plate, which I learned as a student-athlete in college. My children are my applied restraints. Without them, I’d work all the time, even though doing more is not always the best thing. To be home for dinner with my family takes my mind away from work. It’s a welcomed reset.

I learned early the value of being in nature and spending time with family without television or devices. My extended family regularly gathers at a cabin in the Wisconsin woods. We’re the seventh generation to use it, which is meaningful. I grew up nearby in Minnesota, so we went there year-round. It’s rustic, pristine; no one would think it’s fancy.

I uprooted myself to go to Booth, leaving my then boyfriend (now husband), and a wealth of friends and colleagues. I’d never taken econ or finance courses. I was a history major at Princeton. Macroeconomics with Anil K Kashyap was my toughest class and, as a result, one of my favorites. He set high expectations but brought out the best in us. I gained fluency in basic economic concepts of inflation, unemployment, and the Fed, which I use to full effect today. Booth gave me skills for life.

At Booth, we had to read the late investor Charlie Munger’s 1994 speech on “elementary, worldly wisdom.” I still have the hard copy. To be a successful investor, he said, you have to have models in your head drawn from experience, both vicarious and direct. This allows you to build a framework, and then build a lattice of those models. His first-rate thinking was an epiphany for me, and I still use his guidance. 

Jobs get boring. That’s why I went into venture capital. We are always looking at what’s innovative and compelling, and that’s ever-changing. Yes, I love making money, but I love winning more. In venture capital, the real win is the exit—be it a public offering or M&A. As a firm we are very driven, day after day, to invest in and work with the 10 companies a year that matter. We’re all born to have a purpose. I’ve found mine.



A modified version of this story appeared in the Fall 2024 print issue of Chicago Booth Magazine.

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