An Interview With Upper Hand Founder, Kevin MacCauley | Forbes

Originally published by Forbes, June 15, 2020. Written by Ian Mathews.

Many of the world’s most successful companies started with a founder who had a problem. Google, Uber and Spanx are examples of companies born from a non-existent or inferior product that couldn’t meet a founder’s needs.

Kevin MacCauley saw an opportunity while coaching baseball as a side gig. As a self-employed freelancer, Kevin’s business was largely word-of-mouth with customers paying with cash or check.

MacCauley recalls those awkward transactions, “Rather than talking about how their son developed over the past hour, parents would hand me a hundred bucks and ask when we could do it again. That manner of doing business was very strange.”

And in that vacuum, a software company was born in 2011. Today, Upper Hand is a technology company with 26 employees serving the sport and fitness industry. UpperHand gives owners and staff a competitive edge by automating business operations with an innovative software platform.

I spoke with Mr. MacCauley from his office in Indianapolis, where Upper Hand’s team would typically be working if not for the novel coronavirus. We talked about building a company that helps thousands of sports and fitness companies from individual local small businesses to some of the fastest-growing franchises in the industry.

You’re the second youngest of seven siblings. How did that experience shape you? 

I’ve always seen my older siblings as mentors. And that’s one of the reasons I’ve always loved having conversations with people who are older than me. Older siblings are a blessing because you learn from their experiences without necessarily making the same mistakes.

Can you give me an example? 

I could have played college baseball but I saw how much my brother went through to get drafted by the Oakland A’s. He invested years into baseball, and it ended prematurely with an injury during the 1994 major league baseball strike. I saw that and made a decision to follow my other siblings by going to college and focusing on my career.

What was an early formative experience for you in business? 

I took a job in the appliance department at Sears in high school, and it is still one of my favorite jobs. I earned commission selling appliances. I might sell a $300 vacuum and make 18%, which was great money for a young kid. That job rewarded hard work. You had to approach people and be aggressive. You couldn’t hide behind a computer or not pick your phone up. If a customer was upset, they approached you and it was your job to address it in person.

You have an entrepreneurial spirit but you chose to work for a large company after graduating college. Tell me about that decision. 

I asked myself what I needed to start a business and kept coming back to learning more about sales and marketing. On my first day, I was practicing my cold call pitch with two senior partners. You grow up quickly and learn about accountability. I had great training, and worked with some amazing coaches. When you make 200 calls and one person finally takes your call, it such an adrenaline rush! It is difficult to comprehend unless you have worked in sales.

Tell me about your first experience with a startup. 

My older brother, Ryan, was running ClassWatch, a company that provided graduating seniors an alternative to a class ring. ClassWatch partnered with universities and watch manufacturers to offer a more practical graduation gift of a fine watch with a college logo. I worked with Ryan for two years and learned an incredible amount about angel investing and the challenges that go with it. My brother John joined us and we had a family business.

What role did you take on at ClassWatch? 

Ryan asked me to focus on new partnerships. I had experience prospecting and I was like, “Get me a list of the people that we want meetings with, and I’ll find the phone number.” And then you just start dialing and scheduling. So I learned right out of the gates how to apply my corporate experience to land important meetings.

What was your biggest takeaway from working with family? 

Watching Ryan lead our company through the financial crisis of 2009 was incredible. We were raising money and building a business when the housing market crashed in 2008. And to see his calm when we moved the business to D.C., even when he didn’t know if we were going to make the next payroll – that has always stuck with me in a big way. Many people would have buckled and caved. It was a great lesson to sit next to your brother who’s got so much experience and learn from him every day.

How has the lesson applied at Upper Hand? 

For me, it’s about staying the course on our business strategy and not letting external factors dictate how we run our business. It is so easy to get distracted when the market shifts. I’m tempted to build a new feature or try a new distribution channel because a competitor’s doing it. You want to know what’s happening on the peripheral, but you need to stay focused or you will waste all of your time and money.

What did you miss by jumping right into startups so quickly after college? 

I think you realize quickly, “I’m not an A player.” During that crisis, I needed a coach to help me to the next stage of my career. But I couldn’t expect that in a small startup trying to stay afloat. It is hard to expect one of your two brothers to be your coach. The pace of a startup doesn’t allow for much mentoring. My brothers cared about my development but they also needed me to be more productive immediately, rather than thinking about my next career step.

How did you decide to hire your first employee at Upper Hand? 

The responsibility of making sure you can feed that first employee weighed on us. We asked ourselves, “Are we hiring this person just because we have a short-term problem or are we confident this is a permanent position?” Especially in those early days, the salesperson is also providing product feedback . We were happy with new sales but we also needed to understand why people were saying no. When they say yes, what do they need to us solve? And as they start using it, what did customers like or want more of?

How important were your early customers in forming Upper Hand’s value proposition? 

That feedback was absolutely critical. To this day, my favorite customer is one of our first, a quarterback coach in Virginia. I used to visit him and go to his training sessions. At the time, he was experiencing many bugs with our product. Our feature growth was creating problems operationally and he patiently took his lumps until we figured it out. If you can find those patient early adopters, they will pull your product along if you are honest and communicate well. The value to the customer is having a say in how your product is built.

How are you a different leader today than when you first started the company? 

I listen more, and I’m more comfortable taking a step back if I don’t understand something. At Class Watch, I was brash, and thought I had all the answers. It didn’t work well, and I learned things might be easier if I asked more questions. That is the biggest difference for me. I think divergent perspective and opinions is critical to arriving at the right decision.

What is your philosophy on hiring at Upper Hand? 

We hire for defined core values. One of the worst things for anybody is working in a place you don’t like, right? When we recruit talent, someone might be a great candidate or person, but they just don’t fit our core values. It’s a two-way street in the interview. We want you to feel comfortable because you’ll stay here longer, be more loyal and work harder if you love what you do.

What do you look for? 

We search for grit, resilience, competitiveness and a willingness to be coached. Are they a fun and positive person? Is this somebody that we would want to hang out with after work? Teams enjoy being around fun people.

And what if you learn that someone does not have your core values after you hire them? 

I have made the mistake of holding on to somebody too long. Naturally, you don’t want to be seen as a bad person. I’ve had to learn over time that people want to work around like-minded people. When you have a bad apple in the group, it’s miserable on the team to work next to that person. A sign of waiting too long is the person leaves and their teammates respond with, “Man, we were waiting for that forever!”

What’s the biggest challenge that Upper Hand is facing? 

We are in the awareness phase and our challenge is marketing. We see a path to serious scaling if we can nail the messaging. Also, we need to scale the team behind that growth. We are actively recruiting sales reps and leaders to take us to the next level. Our marketing message is starting to hit and we need great talent to deliver on that promise.

What advice would you give to startup founders who are hesitant to market their product or services? 

To stop waiting. While you wait, your product is not getting the benefit of real customer feedback. You might think you have the perfect product but as soon as it goes to the customer, you will be humbled. If I could do it again, I would have sold faster. I would have said, “Well, we’re taking way too much time writing a business plan for this.” Just get to market, and start getting feedback and iterating as fast as you possibly can. Don’t wait.