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Skillshare’s Michael Karnjanaprakorn on Risk-Taking

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In our risk-taking series, Tulane University and Ashoka U students Katie Smalley and Laura White shed light on the value of risk-taking. By interviewing social innovators about bold steps they’ve taken, they reveal that behavior that appears risky may be the most dependable way to produce innovation, ultimately leading to better solutions to social problems.

Michael Karnjanaprakorn is a serial entrepreneur and philanthropist. Co-founder of All Day Buffet, The Feast, and most recently, Skillshare, as well as a championship poker player, Michael is an expert on risk. Below, Michael shares some of the lessons he has learned.

Dowser: What is the biggest entrepreneurial gamble that you’ve taken that has paid off?
Karnjanaprakorn: As a first-time entrepreneur, quitting my job to pursue a startup full time was a big risk. This is critical because relentless focus is the key to success for any new business ideas. Great successes rarely happen on the side. It’s hard for anyone to take your idea seriously when you’re not even fully committed to it. I can’t tell you how many things fell into place when I took that first leap.

What is the biggest risk that you’ve taken that hasn’t paid off, or at least seemed that way at the time?
I think all entrepreneurs want to start their own company as soon as possible. But, like anything else in life, timing is everything. When I was younger, I felt really rushed to start my own company and worked on a lot of bad ideas. Looking back, I realized that I wasted a lot of time solving the wrong problem, which is a trap that sucks energy and money out of many entrepreneurs. Instead of focusing on the solution, most first-time entrepreneurs need to focus on the problem they will be solving — hopefully it’ll be world-changing and profitable.

What do you think is the most important factor in taking intelligent risks in social enterprise?
For your company, your job is to reduce uncertainty and increase the likelihood of success. You can reduce uncertainty by putting together a great team, finding strong advisors and personal mentors, and solving the right problem with a great idea.

Personally, your job as an entrepreneur is to increase your confidence and risk tolerance over time. Quitting your job should be small potatoes compared to taking your first dollar of investment, or maxing out your credit card to pursue your dreams. Every day, you are faced with hundreds of decisions to make, and you have to be confident that you’ll be making the right decisions, or your company will fail. Increasing your risk tolerance, taking calculated risks, and minimizing uncertainty by making good decisions will ultimately lead to success. And if it doesn’t work out the first time, chalk it up as a learning experience, and move on to the next thing. Our country loves entrepreneurs so it’s a win-win for you. All upside. No downside.

This interview has been edited and condensed.


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