In a two-part blog post, we are highlighting the work and wisdom of local entrepreneur and innovator Doug Dayhoff, former President of Upland Brewing Co. In an interview with our Xtern, Anna Carpenter, Doug reflects on his successful business career thus far and discusses some of the highs and lows that he has encountered in the process.

“When I was first starting out, it was so early in my career that I had a very limited network outside of Bloomington. My first job after graduate school at Dartmouth was for a very large Fortune 100 company, and I did not enjoy it. I was forced out of insanity and unhappiness to leave the Fortune 100 corporate setting as a search for meaning and satisfaction, and by process of elimination I ended up in a space that was inspiring to me.

When I was looking for a new opportunity, the first thing I did was reach back into my network, which was largely Bloomington-based. There happened to be an opportunity at that moment, which was very lucky for me. It’s kind of a one in a hundred chance that it lined up that way, given the size of the Bloomington commercial ecosystem and its ability to have mid- and high-level opportunities for professionals.

At the time, I worked with a team that had a greeting card company here, which was step one in getting me to work in small-growth businesses. It also got me out of analyst-level work into leadership work, which I found very rewarding. It took me from predictable commercial situations and pushed me into new, risky, and unpredictable commercial situations. From there, we grew the greeting card company up, and ended up selling it to Hallmark Cards.

We later started a software company, grew that up and shrank it back down, then sold it. When we sold our software company, which was after the 2000-2001 tech market collapse, I really think that we had a profitable business, but we felt like we weren’t going to be able to meet expectations. We felt so disappointed and deflated by that, and we just kind of gave up. We sold it off at a time in which we probably should’ve just doubled down and rode out the storm.”

“Looking back, I would now counsel my younger self to do things much differently. We had a lot of smart people around us, and nobody said anything at the time, so maybe we really didn’t have any opportunity. But in retrospect, we were, after a bunch of layoffs, a cash flow–positive company.  We just weren’t going to be able to execute in a way we originally envisioned.

There are certain benefits of being in the Midwest, but also certain handicaps. I think that Bloomington is a culturally vibrant place, which in and of itself helps drive innovation. I also believe that if you’re intentional about building your own network into high-velocity ecosystems on the coast, you can have both the benefit of a midwestern college town lifestyle here in Bloomington and still be tapped into commercial opportunities that are driven out of the 4-5 innovation centers in the country. You just have to bloom where you’re planted.

On a professional level, I think there’s a big challenge with having access to a large number of candidates who are qualified for mid-level to senior-level management positions in growing companies, particularly in a college town like Bloomington. I think that’s a really difficult thing to deal with. In terms of qualified and available talent pool in this town, I’d say it’s pretty limited, and sometimes it makes it hard to grow your company.”

“One way to address this problem is to build your company to enable remote working, which may be easier than recruiting the talent to come to you.  There’s a chicken-and-egg sort of problem here; businesses sometimes don’t grow here because there aren’t that many people to work within those high-growth companies.  People often feel that it is a risk to move to a small town in the Midwest because there aren’t that many options beyond what they know. However, the more mid-sized growth companies that exist in places like Bloomington, the lower the risk people would perceive in moving here.

It’s a cycle that’s really hard to break. It has posed a challenge to all of our companies. I can’t think of a mid- to high-level management position that I’ve hired for in the last 15 years where I felt like I had multiple great options to choose from.

“We more or less have made a living out of taking risky bets on people who might not have demonstrated qualifications to do the jobs that we’re asking them to do. Sometimes that works out, sometimes it doesn’t. It was never a situation where I wanted to hire all three of the people who applied, I usually had to pick whoever it was that I thought had the highest probability of being able to grow into that ideal candidate that I wish I had.”

Part 1 of 2  | Read Part 2 here