Kevin MacCauley | Crain's

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

Kevin MacCauley


Kevin MacCauley is the CEO and founder of Upper Hand, a company he launched in 2011 to provide cloud-based sports management software and business services. Prior to launching Upper Hand, MacCauley served as vice president of sales at Collect RX for one year. He was also a marketing and sales associate for three years and executive vice president of sales and marketing for two years at ClassWatch. MacCauley founded the Circle of Life Mini Marathon at Indiana University, where students raise funds for the nation’s largest scholarship for cancer survivors.

The Mistake:

My background is around building a company, from conception to operation to achieving profitability as an achievable vision. The mistake we’ve made – and if I only knew then – is that time is the enemy in building a business from the ground up.

If there is a shortage of money, time is against you. There’s only so much money to be invested. There is time in perspective to competitors in the market and those entering the market. Even with employees, you only have so much time to find if you’ve hired the right folks and made the right business decisions.

At Upper Hand, the lesson is that you do not have a lot of time to ponder wrong decisions. In building a company, you’ve got to decide. As I once read, if you’re 70 percent of the way to making a decision, make the decision. If you try to get to 90 percent, you’ve waited too long. If I could have had that mindset from day one, I would probably have had fewer sleepless night when I was going through tough times.

People sometime forget they started with one idea and morphed into something totally different. If you listen to customers, your product is going to change. You could apply the same concept to any publicly traded company.

For us, making the decision to move from the consumer side of sports to software could have been done faster. It took time to get feedback. If we had made the decision faster, we might be further ahead.

It’s easy to forget the context of the period in which you made the decision. When you’re in the context of being out of money or fighting a developer to build the things you need, it’s easy to forget the context of how decisions were made.

Time just happens to be one variable you can’t change, no matter where you are in the process. We pride ourselves on innovation. We’re the only company in our industry focused on the sports life cycle platform. We could have been faster making product decisions and deciding whether we had the right product team in place.

Time is the enemy in building a business from the ground up.

The Lesson:

If you’re talking about time, it’s not just being willing to make rash decisions. You take in as much feedback and opinions as you can from the board, co-founders and employees. But once you touch a dozen or even six opinions, you have to make the best decision moving forward.

That’s your decision. You go from there. There’s no time to debate after the fact. That would be the lesson learned.


Follow Upper Hand on Twitter at @GetUpperHand.

Pictured is Kevin MacCauley. | Photo courtesy of Upper Hand.