Jason Caras | Crain's Tampa Bay

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Jason Caras


IT Authorities is a leading provider of managed IT services and support to companies in the Tampa Bay region and beyond. IT Authorities specializes in process-driven IT infrastructure solutions and has been recognized by Inc. magazine as one of the country’s fastest-growing privately owned companies.

The Mistake:

I was so ego-fed that I would take crazy risks.

I grew up in Massachusetts and I was a very young entrepreneur. I was selling water filters door to door before I had a driver’s license. And then I started a painting company. I had a whole crew of painters working for me while I was in school. And then I got an opportunity to go into business with my dad. He was an Allstate insurance agent at the time – he’d been with the company for 20 years or so at that point.

Well, Allstate decided to pull out of Massachusetts and my dad had to become an independent agent. He asked if I’d like to help. So when I was 18, we started Caras Insurance Agency in Taunton, Mass. And we killed it. We crushed it. I was 18 years old and really motivated, very driven. But then I decided to start another insurance agency across the street, which specialized in the commercial market, and run both offices.

So a guy comes in, and he says, “You know, I want to start a seafood business.” And he wanted us to insure his truck. We got linked up, and next thing you know, I’m delivering seafood to my insurance clients, restaurants. Our office had the seafood business in one corner, and we were buying and selling medical equipment online. I was also involved in a public-speaking business.

What was feeding me was just pure ego and the excitement of being a young businessman. I decided that I could make money doing anything. I’d say, “Let’s get into X business.” I had the resources and the money, so I could start up a business, no problem.

Well, I ended up doing too many things. I’d spend my entire day driving around town to different offices and checking on things. And I was so ego-fed that I would take crazy risks. It was all double-down, double-down. I tried to set up an IPO but it was a penny stock offering, with a limited partnership offering in Turks and Caicos, which was a tax-free domicile. And all of it just imploded. I ended up losing everything I owned.​

Choose one thing, focus on one thing, and be the best in the world at it.

The Lesson:

Choose one thing, focus on one thing, and be the best in the world at it. Follow your passion, not the dollar, and the rest will follow. Ironically,

I see myself as a success throughout my whole life, even though I’ve lost everything and been penniless three times. I’ve always been very goal-driven, very ambitious.

The problem is that I was making risky mistakes without being focused. I was trying to be all things to all people – diversifying too much. Now, if you’re GE, you can diversify, because you can put the money and the people behind risky ventures, and you can afford to absorb failure. If you’re a small business, you can’t, and you end up being not very good at anything.

My dad always used to say, “Keep the nut small.” And I was like, “You can’t become independently wealthy by keeping the nut small." But you don’t have to risk it all. You leave some behind.

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Photo courtesy of Jason Caras

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