Seven Questions with Yong Kim

Yong Kim is co-founder and CEO of Wonolo, an on-demand staffing platform that connects millions of people with flexible work. After immigrating to the U.S. alone at 15 years old, he once ran away from school in the middle of the night, planning to walk to the airport and fly home to Korea—and credits the teachers who rescued him with changing his life forever.

What is something you’ve learned that you lean on daily?

Vulnerability. It took me a while to see it as a sign of courage and true strength. Throughout my life, others seemed to associate vulnerability with weakness or lack of determination. But as I thought about the people who had the most influence on my life, and the people who I admired, many of them had shown vulnerability. Eventually, I learned to open myself up and be authentic, especially when I’m facing a difficult decision or tough conversation.

I’ve had to be transparent with my co-founders, for example, about the fact that I suffer from impostor syndrome. It’s not easy to talk about my fears, but I want them to know that I’m working on them diligently and that I believe I can overcome those fears and evolve into the very best CEO I can be for Wonolo. Before, I had difficulty showing them my full heart—I often held back a lot. Now I feel like they really hear and see me. Being vulnerable allowed us to build a much deeper connection.

What one piece of advice would you give someone starting a company?

The startup journey is unpredictable, but one thing is for sure: Things will go wrong. No matter how much you analyze, plan and engineer, there will still be a constant stream of problems you didn’t anticipate. So when you’re facing a difficult situation, embrace it. Know that it’s part of the journey and believe that there’s a solution out there. Don’t give up – just keep plowing through.

In the book Antifragile, Nassim Nicholas Taleb talks about post-traumatic growth—the idea that when you go through certain difficult events, you come out stronger. We’ve been through multiple near-death moments at Wonolo. At one point in the early days, we had to lay off half the team to survive. Another time we almost didn’t meet payroll right after the Thanksgiving break. It’s never fun to experience those shocks. Yet every time, we focused on a solution and made the best out of it. I’m sure more challenges are waiting for us ahead, but I’m confident that we’ll be able to treat them as learning opportunities and come out stronger again. That’s part of what makes the startup journey so exciting and rewarding.

What small change has made a big difference in your life?

One recent change, which I’m still working on, is to take care of myself before I take care of others. In Korea I grew up believing it was selfish to think about my own needs. And when I came to the States, one of my survival mechanisms was to blend in—to adapt to others’ needs and expectations. That stayed with me. When I would make a difficult decision, of course, I’d still weigh it against my own values. But day to day, I’d become very good at disguising what I really wanted and putting others’ wants first. In a negotiation session, for example, I would always play the good cop.

The breakthrough for me was realizing that when I don’t care for myself, I’m compromising other people’s happiness, not just my own. It’s like putting on your own oxygen mask first so you can help the person next to you. I love working out in the morning, for example, but I never used to do it. My wife and I have three daughters, and I felt guilty leaving her with the chaos of getting them ready for school. Now, I’ve started getting up even earlier so I can go to the gym and be home in time to help. It’s not just that I’m doing both—it’s that I’m so much happier in the process. When we’re helping our daughters brush their teeth or get dressed, I’m in a better mood. Taking care of myself first has made me much kinder to others.

What don’t you know that you wish you knew?

The answers to all of my daughters’ questions. They’re just like me when I was growing up—my nickname as a kid was “Old Man,” because I would drive my parents crazy asking all these deep questions about life. Now that I’m a father, my kids are constantly asking me about everything, from algebra to why the sky is blue to why tigers cannot be vegetarians.

I want them to think I’m smart and cool, so I usually tell them I need to grab something from the next room and go look up the answer on my phone. Then, I come back and tell them the answer as though I knew it all along. Or I tell them to ask their mom, who is much smarter than I am.

What books are on your nightstand right now?

There are a lot. I read multiple books at once, fiction and nonfiction, and go back and forth. I’ve always loved reading—when I was growing up, the library was my sanctuary. My mom would drop me off during the summer, and I would spend all day there. I still do that sometimes. If I’m really stressed at work, I’ll leave the office, go to the library and grab whatever’s on my “to read” list, and stay there all day.

I just finished a novel called The Wife Between Us, by Greer Hendricks and Sarah Pekkanen. It has a lot of plot twists, which is what I like in fiction. For nonfiction, I just finished Never Split the Difference, by Chris Voss. He’s a former FBI hostage negotiator, and argues that compromise is actually the worst outcome—that instead of treating negotiation like a logic problem, your goal should be to show empathy. It’s about EQ, not IQ.

The book that I recommend most is The Culture Code, by Daniel Coyle. It’s had a tremendous impact on me, and helped align everyone at Wonolo around the idea that culture is the most important thing. We talk about it constantly, frame key decisions around it, and go all in on it from the moment we meet a candidate. There are a lot of culture questions in our interviews. For people who might have come from organizations that saw culture as fluffy and intangible, those early introductions have really helped them adjust.

When did you realize you were wrong about something?

I’m wrong most of the time. But aside from morals and ethics, I don’t think much in terms of right and wrong. That framework suggests there’s always a winner and a loser, and wastes what could be an amazing opportunity to learn.

My CTO and I were discussing leadership models recently, and we fell into a debate over what we saw as the right and wrong leadership styles for Wonolo. But when we took a step back and framed it in terms of what we each wanted out of the experience of building the company together, we realized we were perfectly aligned. I said I wanted people to feel a sense of belonging and connection, to feel like they were safe being vulnerable with each other at Wonolo—and that the role of leaders was to create an environment for that. And he said, “That’s exactly what I want, too!” Instead of arguing about who was right or wrong, we were both able to walk out of the room feeling heard.

What unit of time matters the most and why?

Right now. Being present is something I’m really working on. I used to dwell on the past and think about everything I should or could have done differently. Or I’d stay up all night worrying about what might happen in the future. Even when I was with my kids, I’d start thinking about the memo I had to send by 10 p.m. I was never in the here and now, and that limited my opportunity to connect.

Eventually, I realized that everything I was worrying about usually turned out fine and started practicing being in the moment. If I’m with my kids, that’s all I’m doing. I listen to them, enjoy them and try not to think about anything else. It’s been liberating. I’m happier, and I’m making the people I’m with feel more heard, seen and cared for, too.