From $3.50 an Hour to My First Company
The First Job That Taught Me Responsibility
My very first job was as an usher at a movie theater in California. I made $3.50 an hour. The role was simple—make sure people weren’t misbehaving, and clean up popcorn after the credits rolled. It wasn’t glamorous, but it taught me the basics of responsibility.
The next summer, I worked maintenance at a golf course. If you’ve ever seen Caddyshack, I was basically Bill Murray’s character—cutting grass, fixing things, and laughing about how much life can imitate art.
The Leap Into Business
Fast-forward a few years: after college, I landed a job at a competitor in the insurance space. That’s where I met my future business partner. Within a year, we both left and decided to start our own company.
We were young—23 and 26—and honestly thought everyone else was an idiot. We figured we could do it better. The reality? It took us 14 months to reach profitability.
For the first six months, it was just the two of us, working without pay. I waited tables at a Mexican restaurant at night to make ends meet, and my partner picked up side jobs, from making T-shirts to working in data. Eventually, we hired our first employee to handle administration—processing applications, answering phones, and taking care of customers.
Small Wins and $100 Paychecks
When we finally got to a place where we could pay ourselves, it was $100 a paycheck. That was it. But it meant the business was real. Every little milestone mattered: the first customer, the first hire, the first real paycheck.
What Set Us Apart
We weren’t the cheapest. Our products cost more, and our commissions to agents were lower. But we built a reputation for service. Back when everything was paper-based, we promised agents that if they sent us an application by 2 p.m., an ID card would be in the mail by 5 p.m. That level of speed won us business, even though agents made less money working with us.
Lessons From the Early Days
Looking back, the early grind taught me three lessons that I carry forward:
You don’t need to know everything to start. You just need to start.
Sacrifice is part of the deal. Second jobs, tiny paychecks—those weren’t setbacks, they were the path.
Service beats price. Agents chose us because we delivered faster, not because we were the cheapest.
The foundation we built in those first 14 months set the tone for everything that came after.