Some entrepreneurs spend their careers chasing the next big thing. Gene Kwon built his business by paying attention to problems others overlook.
A former collegiate tennis player turned entrepreneur, Kwon has spent decades launching and growing businesses, earning recognition along the way, including Ernst & Young Entrepreneur of the Year and a Forty Under Forty Business Award. Yet what stands out most is not a list of accomplishments. It’s the perspective he’s gained from years of competition, leadership, and working alongside people from all walks of life.
Gene Kwon shares his thoughts on productivity, decision-making, business growth, and why some of the best opportunities come from asking better questions.
What is your typical day, and how do you make it productive?
I don’t really believe in a typical day anymore. The most productive days are usually the ones when I’m talking to people. One conversation can solve a problem that would have taken weeks to figure out on your own. I spend a lot of time listening to customers, partners, and colleagues. The older I get, the more I realize business is really a series of conversations.
How do you bring ideas to life?
I start by paying attention. Most good ideas don’t arrive out of nowhere. They’re usually hiding inside a problem that people have accepted as normal. Once I see something worth pursuing, I try to test it quickly. You learn more from action than endless planning.
What’s one trend that excites you?
I’m interested in how technology is making expertise more accessible. Small companies can now access tools and information that were once reserved for large organizations. That levels the playing field in ways we haven’t seen before.
What is one habit that helps you be productive?
I leave room on my calendar for thinking. Most people fill every available minute. I’ve found that some of the best decisions come from having the time to reflect instead of constantly reacting.
What advice would you give your younger self?
Pay closer attention to people than to plans. The right people can make an average idea successful. The wrong people can make a great idea fail.
Tell us something you believe almost nobody agrees with you on?
I think ambition is overrated. Ambition is useful because it gives you direction, but curiosity is what keeps you growing. Curious people ask questions, challenge assumptions, and stay open to new ideas. Looking back, many of the opportunities that shaped my career came from exploring something interesting rather than chasing a specific goal. Curiosity helps you keep learning, and in a world that’s constantly changing, that’s a huge advantage.
What is the one thing you repeatedly do and recommend everyone else do?
Talk to someone outside your usual circle. Some of the best opportunities in my career came from conversations I never expected to have.
When you feel overwhelmed or unfocused, what do you do?
I try to zoom out. Most problems feel enormous when you’re standing right next to them. I’ll ask myself whether this issue will matter six months from now. That simple question usually changes my perspective.
What is one strategy that has helped you grow your business or advance in your career?
I’ve always paid attention to friction. Whenever I hear someone say, “That’s just how it’s done,” I get interested. Friction usually points to an opportunity. Many successful businesses are built by improving things people stopped questioning.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early in my career, I confused being busy with being effective. I thought leadership meant being involved in everything. Over time, I learned that growth depends on trust. Great businesses aren’t built by one person doing everything. They’re built by teams that are empowered to do their best work.
What is one business idea you’re willing to give away to our readers?
I think there’s a huge opportunity for businesses that help people make sense of information overload. We have more data than ever, but many people feel less informed. There’s value in helping people simplify complexity.
What is one piece of software that helps you be productive? How do you use it?
I’m not someone who constantly chases the newest app. I still get a lot of value from Outlook because it keeps communication, scheduling, and priorities in one place. Sometimes simple tools are the most useful.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
Good to Great by Jim Collins is one I revisit from time to time. The principles are simple, but they hold up. The book focuses less on flashy success stories and more on the habits that create lasting organizations.
What’s a movie or series you recently enjoyed and why?
I enjoyed Drive to Survive. On the surface, it’s about racing, but it’s really about preparation, teamwork, pressure, and competition. Those lessons apply just as much in business as they do in sports.
Key learnings
- Curiosity often creates more opportunities than ambition alone.
- The best business ideas are often hidden inside everyday frustrations.
- Strong relationships matter more than perfectly crafted plans.
- Creating time to think can be more valuable than filling every hour with activity.
- Lasting success comes from building trust and empowering capable people.