Serial Entrepreneur Building a Luxury Business: Trevor Traina, CEO of IfOnly (Part 4)

Sramana Mitra: Let me see if I got everything. You did two companies after Compare..net One was SchemaLogic and the second was the one you sold to Intuit.

Trevor Traina: Yes, as of 2006.

Sramana Mitra: For both of them, you were Chairman, not CEO.

Trevor Traina: Correct.

Sramana Mitra: Were these your ideas or were these ideas generated by people who came to you for funding? How did you connect with the entrepreneurs?

Trevor Traina: The first one was the idea of someone who worked for me at Microsoft. When I was leaving, I said, “Why don’t we start a company? I’ll help fund it. I’ll be the Chairman. You can run it and be the CEO.”

Sramana Mitra: The second one?

Trevor Traina: The second one was my partner from Compare.net who met a young entrepreneur who had a promising idea but who didn’t know how to build a company out of it. We came together with him and helped him. I was like an Executive Chairman.

Sramana Mitra: What happened to the first company?

Trevor Traina: I sold it to a British company called Smartlogic. That didn’t happen until 2011.

Sramana Mitra: By 2006, you had two more companies where you were either Chairman or Executive Chairman. You funded these companies and you had two more exits.

Trevor Traina: Correct. Then after the sale of StepUp, I co-founded a new company called DriverSide.

Sramana Mitra: What was that?

Trevor Traina: DriverSide was my idea. It was like Mint.com for how to own and maintain your vehicle. It was all the information, skills, and data for knowing what to pay, who to trust, when to do what in order to maintain your vehicle. I was Executive Chairman of DriverSide with two co-founders. We sold that in 2011 to a public company called Advance Auto Parts.

Sramana Mitra: You did your own venture and you sold three more companies by 2011. What are the key lessons from the trenches that you derived out of that journey until 2011. What are some of the core learnings? What are some of the strategic nuances that came out of this portion of the story?

Trevor Traina: There were a number. The first is having the wind at your back is very different than having the wind in your face. There were a couple of companies I had where the category was expanding rapidly and there was lots of interest and attention. There were a couple of companies where the space was not expanding as fast and not as much in demand. What I learned is you can exert the same effort and the result will be very different depending on what the space is like.

This segment is part 4 in the series : Serial Entrepreneur Building a Luxury Business: Trevor Traina, CEO of IfOnly
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