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First one in, last one out

Dave Wechsler '93

A tech startup veteran, Dave Wechsler ’93 (policy studies) founded his first company in 1994, which he later sold in 1999. He’s currently co-founder and CEO of Madison Plus Select—Hey Gorgeous!, an online plus-size fashion boutique.

“Entrepreneurs should not have regrets—they tried. People who want to try but haven’t should have the regrets.” 

How did Dickinson prepare you for your current career/endeavor?
I am a 25-year entrepreneur and started my first business soon after graduating. In 1993 the economy was very bad and entry-level employment opportunities were poor, at best. So I decided to start a tech consulting firm, which eventually evolved into an Internet consulting firm. I am now in my fifth startup. While I had no practical training for the business or technical side of my startup, my solid liberal arts education gave me everything I needed to figure it out. In fact, starting the first business felt very much like a continuation of my interdisciplinary major, policy studies. I found myself using the very same resources I used during my Senior Seminar. To me, nothing is more valuable than a liberal arts education for an aspiring entrepreneur.

What was your "aha" moment?
I have never had an epiphany; it’s more of a “I’m not bored or uncertain of this idea yet, and I’ve been researching it for a while. Let’s do it.” As an entrepreneur, I think of new business ideas daily. Many are frivolous and, fortunately, fade from my mind quickly. However, from time to time one sticks, and I find myself thinking about it more and more. For my current endeavor, it was months of research on multiple ideas—but one really stuck. I found myself coming back to it the most and ultimately, the idea that keeps your passion/attention the best is likely the smartest one to pursue.

“Starting the first business felt very much like a continuation of my interdisciplinary major. I found myself using the very same resources I used during our Senior Seminar. To me, nothing is more valuable than a liberal-arts education for an aspiring entrepreneur. I am now in my fifth startup.”

What inspires you?
Building great businesses through an evolved and usually unique approach. Every business in every industry has incredible and unique aspects. When you look at older, more established industries, they tend to be burdened with the “way we’ve always done it.” Technology and entrepreneurial thinking has changed so much over the past 10 years—every business can be improved, and so many new and incredible business opportunities are yet to be conceived. It’s an exciting time to be alive for so many reasons, but the change we will see in the next 10 to 20 years will be staggering.

What advice would you offer to the entrepreneurs of tomorrow?
It’s a hard way to make a living. Don’t do it unless you are ready for long hours, low pay and extremely low likelihood of success. There is no glamour. There is no play book; in fact, there usually is no right or wrong. Find mentors to help you talk through the ideas that have no right answers. Make mistakes and learn from them—don’t have too much ego you can’t admit when something was stupid. But then learn from that mistake. Have fun. If you aren’t excited there’s a problem. Every day I am in first, brewing coffee, and I leave last, taking the trash out. You can’t have success if you don’t love it.

“I think of new business ideas daily. The idea that keeps your passion/attention the best is likely the smartest one to pursue.”

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Published April 12, 2016

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