Don’t underestimate the power of not giving up.
Throughout my life, I’ve founded more than a dozen businesses. I’ve had my teeth kicked in and I’ve also been fortunate enough to take a business from napkin to Nasdaq. The ventures that became successful all had one thing in common: I figured out the right thing to focus on and stuck to it.
I started my first business as a scrappy high school kid: silk-screening bootleg band tee-shirts and selling them in concert parking lots. My business partner was a friend from my neighborhood — a tough part of town in Sacramento, California. That’s when I realized being an entrepreneur was in my DNA.
Next, I started a snowboarding, skateboarding and music ‘zine called Heckler Magazine with my first mentor, John Baccigaluppi. A few years in, I was on a ski lift with John and told him I was leaving the company to pursue a scholarship. He told me, “Don’t go. I have a feeling this Heckler thing is going to be something special. College will always be there, but you can’t pick when opportunities present themselves.” I dedicated the next nine years of my life to Heckler and in return, it gave me the opportunity to visit six continents, make lifelong friends and earn a business education. We sold the company to TransWorld/Times-Mirror when I was 25.
Over the years I also started The Red Rabbit Kitchen and Bar, a restaurant in Northern California; BiteClub, a social network for people in the food and bar industry; a commercial real estate venture; and Requested, a mobile payment app for restaurants. We merged Requested with a food delivery company called Waitr. I became the founding CMO at Waitr, leading a team of 100 and managing branding and customer acquisition and engagement. We took the company public in 2018.
When you’re the CEO, no one tells you what to do. You think you’re building something great and you see a path to your vision. But sometimes you’re on the wrong path or focused on the wrong things. It took seasoning for me to learn when to commit and when to pivot. As an EIR, I tap into that experience to help other entrepreneurs overcome challenges and put together operational plans and resources for growth.
One conversation on a Tahoe ski lift changed the course of my life. A lot of entrepreneurship is like that. I hope to be part of those meaningful decision-making moments for other founders.
What do you think is the hardest part about being a founder?
Share something about yourself that might surprise people:
When I was 15, I trained on the US Junior Olympic Table Tennis team; I’m currently ranked ~1250.
What emerging technology are you most passionate about?
Virtual Reality. We need to embrace it and make sure it becomes a part of human connection, not separation.
What problems in the world would you most like to see solved?
Income equality and financial literacy for under-privileged kids and people, childhood hunger, sex trafficking, access to clean water, and solving our climate imbalance — returning the planet to the unforgiving, healthy state of a natural ecosystem.