Ryan Caldbeck is the CEO and co-founder of CircleUp, an investment firm that uses new quantitative methods to target consumer retailers in the private market. I sat down with Ryan to discuss balancing the demands of entrepreneurial life, company values, and the advice he’d give to his younger self.
“Try not to let perfect be the enemy of good."
Ryan Caldbeck
Sanyin: Ryan, fill in the blank for us: If we really knew you, we would know that...
Ryan: I spend a lot of time worried about the future of the company. I feel anxious and concerned about the balance that I have between my home life—my family, wife, two kids—and work, and that balance is something I struggle with all the time.
Sanyin: What are some things you’re trying to do to strive for that balance?
Ryan: I grew up in a small town in Vermont, and my mom and dad both made a lot of sacrifices to spend more time with our family. My dad, for example, used to come home and rebound for me every single day when I was playing basketball in high school. My mom would leave work at 3 o’clock to make sure someone was there when I got home from school. Those were really special memories for me.
In San Francisco where I live today, in 2019, that type of balance is really, really hard. It’s hard to do that as the CEO of a 70-person company, CircleUp. That brings a lot of guilt, to be candid with you. I’m extremely proud of what we’re building at CircleUp, but I also feel guilty about the balance I have. It’s hard to unplug as effectively as I’d like. It’s hard to be as present as I’d like to be with my kids and my wife.
But I have a few things I try to do to help with the balance, though I’m not sure anyone’s got perfect techniques. I do transcendental meditation twice a day for 20 minutes. I put it on my calendar—it’s literally blocked off on my calendar so that other people can’t schedule meetings. I’ve found that to be helpful to center myself.
I also work out four times a week. That’s been a great way to escape, and that’s also blocked off on my calendar. My wife does the same thing. She’s a CMO at an education committee called Coursera, and she has a similar workout schedule.
Sleep is a really big and important thing for me, too. I try to get 8 hours every single night. And I’ve tried to unplug more. I’ve deleted Twitter and Facebook off my phone, and I don’t bring my phone with me when I’m with my family.
And then, finally, I try not to let perfect be the enemy of good. When I beat myself up over mistakes, it spirals. I try not to beat myself up too much about mistakes, or only being able to do one meditation session instead of two.
Ryan Caldbeck
Sanyin: Tell us a little bit more about CircleUp and what about CircleUp makes you say, “Alright, this is worth it. I’m going to make these tradeoffs with the blessing of my family.” What is it that drives you to say, “Let’s do this,” and make those tradeoffs in spite of the guilt you might feel?
Ryan: I think the first thing is that I would probably label the guilt more as shame. That’s a word my management coach taught me—the importance of using that word. I feel a lot of shame about that balance. But what fuels me to keep trying to build CircleUp is the desire to have an impact.
CircleUp is an investment platform powered by technology. So, at our core, we are a technology company. We’re backed by some great venture capital firms, including Maveron, Union Square Ventures, Canaan Partners, and Rose Park Advisors. We use technology to find and evaluate consumer companies and then we invest in those companies. We’ve got about 70 people on the team.
What fuels me is less about the application—whether that’s investing or building the technology—and more about the impact. I discovered earlier in my career that I care a lot about impact. The first time I remember caring about this was when I was about 15 or 16 at my home in Vermont, and I remember that JetBlue had just moved to Burlington (meaning that they started flying out of Burlington). Everyone in the state was so excited that this company was flying cheaply from Vermont to other cities, like New York. It doesn’t sound like that big of a deal, but the thought just sort of hit me in my kitchen: Gosh, what if I could create something that made other people this happy? Whether or not they knew my name wasn’t what I cared about. I just remember thinking that it would be amazing if I could have the kind of impact this company had.
And so, CircleUp is one manifestation of that impulse to have an impact on others. Our mission is to help entrepreneurs thrive. It’s that mission—the opportunity to help other people—that fuels me.
Sanyin: How do your company’s values reflect this mission?
Ryan: Our mission is to help entrepreneurs thrive by giving them the capital and resources they need. Every single employee at CircleUp can recite that to you in an instant. Our values, then, are to Do It Right, Be Brave, and Be A Solution. Those values frame the mission and help to remind folks why we’re building what we’re building. The values provide a North Star to help us achieve our mission.
It’s also important to me, in terms of company values, to make sure my employees are able to find balance in their lives. To that end, we give our employees unlimited vacation so they can have the time they need to be with their families. We also provide educational stipends so team members can help further their own personal and professional growth outside of CircleUp. I try to model that by leaving every single day at 5:15. I take vacation. They see my calendar every single day is blocked off from 3:30 to 5:15, and the team knows part of that time is for my meditation and to get email done so that I’m doing less of it at home.
Our employees also see us celebrating and rewarding folks for their impact, not the number of hours they work. Of course, work ethic is important. No matter how smart someone is, if they’re only working an hour a week, it’s hard to have as big of an impact as someone working 50 hours a week. But it’s important to us that people know we value work/life balance.
Ryan Caldbeck
Sanyin: Let’s talk a bit about culture. How do you measure—how do you know—the extent to which everyone has bought into your values? How do you know that everyone is actually expressing those values, or knows what those values mean?
Ryan: Our values are woven into our feedback mechanisms. We have reviews twice a year, and your manager encourages feedback on the incorporation of values. They ask, “Are you demonstrating those values in your work? Were there times when you could have done a better job demonstrating those values, and how?” Everyone in the company also has a one-on-one meeting every two weeks with their manager, and company values are sometimes a discussion point.
And when someone leaves CircleUp, or has a major anniversary, we bring them in front of the company and talk about the ways he or she has lived up to those values and mission. So, the values are pretty central to the workings of the company.
Sanyin: Let's take you back to the time before Ryan Caldbeck was Ryan Caldbeck. What advice would you give to your 21-year-old self?
Ryan: When I was 20, 21, 22, I was a walk-on for the basketball team at Duke. I remember I got a few job offers toward the end of college from three consulting firms—Bain, McKinsey, and BCG. I went to Coach K (Mike Kryzewski) and he gave me some advice: “You should figure out what you’re passionate about and you should do that.” And at 21, to be candid, I did not think that was very good advice. In my head I thought, “Well, Coach, I would love to go coach basketball, but I’m not the best in the world at it like you are.” Everyone doesn’t get to do what they’re passionate about and live this amazing life being the best in the world, making lots of money, living in a great place. Sure, there’s skill and hard work, but there’s also amount of good fortune to be able to do that.
But I missed the point, and I think I missed the point for about a decade of my career. I wish I had realized that Coach wasn’t talking about the application of his passion. I don’t think the application—meaning basketball—is what was really important to Coach K. I think he loves building teams, building connections with other people, and helping to develop those people. Instead of realizing that, I sat there thinking, “Am I really passionate about consulting? No. I’m not. So, Coach, this advice doesn’t apply to me, and I still need to pick a consulting firm.”
What I later realized was that I’m passionate about having an impact on others, and helping others be successful. I took his advice too literally and just assumed that, on the face of it, there was no career I would be as passionate about as Coach is about basketball. It took me longer to know that I could be passionate about the core of something, and that the specific job mattered less than that core. I wish I had taken the time earlier to recognize I was passionate about having an impact on others, and to find applications for that passion.
Takeaways:
– Taking small steps to maintain work/life balance can pay off big.
– Integrate your values into your feedback system at your company. This will keep your values aligned with, and fueling, your mission.
– Don’t be preoccupied with the application of your passion. Find its core and work out of that core.
