This as-told-to essay is based on a conversation with Kim Perell, author of "Mistakes That Made Me A Millionaire." It has been edited for length and clarity.
Ever since I was a kid living in Oregon, my life has been a roller coaster ride of entrepreneurship.
My parents were entrepreneurs who experienced big highs and big lows. Running their own business created a lot of stress in my household. We never knew if we'd have enough money to turn on the heat during the winter. There was tension between my parents and my two siblings, and I felt it, too.
When we sat down for dinner each night, my dad would ask about the worst part of our day, which always led to him talking about business troubles. He didn't ask about school or sports, but was always up for talking business, so we saw the difficult parts of entrepreneurship up close.
I didn't want to become an entrepreneur until I got fired
I didn't want to be an entrepreneur because I had seen the stress and inconsistency it caused in my family growing up. All I wanted was a stable job with a paycheck every two weeks. So, I went to college and got just that — or so I thought.
After about two years, the company I was working for went bankrupt. I was fired and broke.
That was an important lesson: whether you're an entrepreneur or an employee, there's no such thing as certainty and security. If nothing is guaranteed, the best bet you can make is on yourself.
I waited too long, but then jumped into digital advertising
After that, I was interested in starting a company, but I made the mistake of waiting for the ideal time. I've since learned that launching a business is like becoming a parent: there's no perfect time. You've just got to jump in.
So, I took a $10,000 loan from my grandmother to start a digital ad agency. My grandma didn't understand what the internet was, but she believed in me, and her loan allowed me to start the company at my kitchen table.
I sold my company for $20 million when I was 30
Growing up as a twin, I learned early on to differentiate myself. That gave me a lone wolf mentality that was hard to shake. That's another mistake I made: trying to do everything alone. Once I finally hired help, I was able to grow and scale. The company flourished.
When I was 30, I sold my digital ad company for about $20 million in cash and equity. I remember going to the ATM, and my bank balance had too many digits to print on the receipt. That was the best day of my life. My maxed-out credit cards and 3 a.m. worries had paid off. I had created security for myself.
As a mentor, I aim to normalize failure
I'm 48 now. Since selling that first company, I've become a serial entrepreneur, investor, and business mentor. I speak with my clients not only about my success, but about the failures I've had along the way.
I'm not sure my dad did the right thing by sharing his business woes at the dinner table each night, yet that normalized failure for me. If failure isn't normalized, you can become paralyzed by fear and get stuck. To succeed as an entrepreneur, you need to know you're going to make mistakes and do it anyway.
My failures have contributed to my success
I want my four kids to be comfortable taking risks. Make mistakes; think big; and fail occasionally. That's where you grow. Our children are going to need that adaptability and willingness to try new things in a world that is changing more quickly than ever.
As a young adult, I wanted consistency, but I've learned the only constant is change. Embracing change and failure has led to my biggest successes.
