Tim Gaspar is the founder and chief executive of Gaspar Insurance Services. Gaspar is a lifelong entrepreneur – he started his first business in high school and went on to run a number of businesses while attending California State University, Northridge.

Today, his company is one of the largest independent insurance firms in the San Fernando Valley and Gaspar sits on the board of various organizations. But things haven’t always been smooth sailing. Here Gaspar discusses a few missteps from his career.

Adventures With Pepsi

I’ve been an entrepreneur my whole life, even before I knew what that word meant. As a kid I used to read the business section in the newspaper with my dad, Entrepreneur magazine, etc. I remember telling my dad the statistic that most entrepreneurs went bankrupt twice on average during their lifetime (not sure if that was actually true or not).

In elementary school I sold candy and toys to classmates, I built a haunted house business in junior high and a party rental business in high school. When I was 19, I started a business manufacturing hide-a-safes that looked like Pepsi bottles. The Pepsi bottle business did well until the nice attorneys at the real Pepsi found out and they were not fans of my little invention and subsequent business. Pepsi seized my company and sued me into oblivion, and I filed personal bankruptcy at 19. Upon hearing the bankruptcy news my dad said, “Good news, you only have to do this one more time.”

Trust But Verify

During my time building Gaspar Insurance I did about half a dozen acquisitions of smaller insurance agencies. I was feeling pretty confident in my ability to size up an opportunity and make a deal when I was approached by the daughter of an insurance agency owner that had just passed away.

During my due diligence I noticed some of the insurance carrier agreements were missing pages or entire contracts. The daughter said she didn’t know where the missing pieces were and some of the files were just a bit of a mess. I foolishly concluded that the contracts were probably “fine” and moved forward with the purchase.

Only after buying the agency did I learn the agency “owner” didn’t actually “own” anything, all the policies were actually owned by another firm. I went back to the daughter who I made the deal with and she was in the wind, I had been swindled. A little bit more due diligence on my part would have kept me from starring in my very own episode of American Greed.

Lessons Learned 

People say success is a lousy teacher and they are absolutely right. It’s these mistakes and ones I will keep much closer to my chest that create the best lessons.