When I was 23-years old, my Father and I bought a bar. A dream of every 20-something, right?

The bar was located in a small-ish town about 30 minutes outside of Minneapolis. It was pretty much a drive-thru town, so the only "real" customers were the locals. It got to the point where I was able to order my inventory each week based on which locals I knew were in town that weekend.

We didn't buy the bar to make it into a life-long family business. We bought it because the price was right and we felt we could flip it.

Aside from a few months I spent as a Marketing Manager of a Minneapolis nightclub, neither of us had any experience in the restaurant/bar industry. We were totally green.

I'm not going to lie to you, running that bar and restaurant really sucked.

Employees would constantly drink and bicker with each other while working, cook's wouldn't show up for their shifts, bartenders would steal money, customers would break things, etc.

On top of all that, I was there from the moment we opened until the moment we closed. EVERY day. In fact, often times, I would just sleep there.

It wasn't fun, but it did pay off. About a year after we purchased the bar, we sold it for a profit. I took my share of the earnings and 'retired' for 3 months. But, that's a story for another day.

When I started Wahooly in 2011, a company that gave equity in startups in exchange for influence, I had no idea what I was getting into.

My degree was in marketing, not finance. I knew nothing about the SEC or the (antiquated) rules around investing in private equity. In fact, I don't think I had ever even purchased a single share of a public stock, let alone private.

Every SEC attorney I spoke with told me all of the reasons I shouldn't do it.
I did it anyway because I was naive.

The truth of the matter is, with both of the companies I mentioned above, had I known beforehand what I was going to be up against, I never would have started.

Many people I speak with believe they need to have deep knowledge in something before they can begin. I tend to argue that it may be better if they didn't.

Being an industry expert has its debilitations. It tends to make you into a 'yabut'. Like the SEC attorney's I spoke with--any approach I gave them was met with, "ya, but that won't work because ...".

Having industry knowledge limits your ability to imagine what's possible. It's what would guide you to build a faster horse rather than invent a car.

Being Naive has its advantages. You're not burdened with the norm. You approach problems with a fresh perspective and think in ideals rather than marginal improvements.

Many times being naive is what allows a startup to disrupt an entire industry.

Travis Kalanick was naive and look what happened.

Published on: May 11, 2015
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