Dwain DeVille | Crain's Orlando

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

Dwain DeVille


Orlando-based Dwain DeVille – whose motto is "I'd rather ride my motorcycle thinking about business than sit in an office thinking about my motorcycle" – is the founder of The CEO Ride, where like-minded CEOs of small enterprises to major universities and corporations come together to enjoy bucket-list routes and peer-to-peer experiences that help their enterprises flourish. He's also the author of "The Biker's Guide to Business."

The Mistake:

Not understanding that all partners have agendas.

When I started my business, I didn’t have enough self-confidence or enough trust that my direction was correct to go it alone. I didn’t feel like I had the entrepreneurial chops. I partnered with someone who I happened to have worked with in the past, who I trusted, as well as someone else who had been an entrepreneur for a long time.

I would look to them for guidance on the big decisions that were being made. And over time it became obvious that – “Wait a minute, they’ve got an agenda.” Not that it was an evil agenda. Not that it was a bad agenda. It just wasn’t my agenda.

They were coming in wanting certain things out of it. And it just wasn’t working for me. What I thought was giving me comfort – not going it alone, having a partner – was actually adding stress. They didn’t have my vision and, as a result, they questioned me. At the same time, my main partner had convinced me that we needed to start another company. It was a quasi-investment company, working with these hot, young tech companies.

So we were working on that when 9/11 occurred. And it crushed all those efforts. I woke up one day and the little venture company we were starting up was dead. And my [other] company was almost dead because I had not been paying attention to it.

And I went through a serious bout of depression. Who doesn’t when you find yourself in the mud? I went and sat on a friend’s boat dock with a yellow pad of paper. So I asked myself, “What are all the things I know how to do to make money?” And I wrote those down. And then, of those, I listed all the things that I was most passionate about doing. And what I realized was that the one thing that I really wanted to do was my consulting business.

We had a meeting for one afternoon to sit down and talk about how to market the company for sale, and one partner walks in and says, “You know, this is really a shame because over the past ten years you’ve helped so many entrepreneurs.”

And I said, “Funny you should say that because I was thinking the exact same thing, and I want to keep the company.” That person turned on a dime on me. He immediately started telling me why I couldn’t run a company, why I couldn’t be in business for myself, why I was a failure, why I was never going to succeed and all of these things. Just obliterated me right there. That partner [realized] there was not going to be a check coming in the not-too-distant future.

The other partner’s response was, “Well I can appreciate that but I don’t want to be in the business anymore.” We made an agreement right there how to get my stock back from that partner, which turned the partner who obliterated me into a bit player, a bit partner, and I just let that be. And I just went my own way.

Everybody who enters into a venture has an agenda.

The Lesson:

In partnerships, you have to have a solid understanding of what you bring to the table. Everybody who enters into a venture has an agenda. If I am CEO and I’m employing 50 people, those 50 people have a separate agenda in working for me, right? They want to come in. They want to earn a salary. They want to have a good job. They want to be able to buy a house, put the kids through school – all of those things.

When we look at potential partnerships, often we don’t sit down and ask them, “What’s in it for you? Because I know what’s in it for me, but I need to know what’s in it for you."

You will never understand [anyone’s] agenda 100 percent, but you can understand what their drivers are for the venture.

Follow Dwain DeVille at @BusinessBiker

Photo courtesy of Dwain DeVille

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