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“You can spend all the time you want with your child, but if your attention is on your phone, then mentally you aren’t there” with Kevin MacCauley

Quality most definitely supersedes quantity. You can spend all the time you want with your child, but if your attention is on your phone, then mentally you aren’t there. Experiences like this teach and reinforce bad lessons for children, and can impact various relationships in the long run. I had the pleasure of interviewing Kevin MacCauley, […]


Quality most definitely supersedes quantity. You can spend all the time you want with your child, but if your attention is on your phone, then mentally you aren’t there. Experiences like this teach and reinforce bad lessons for children, and can impact various relationships in the long run.

I had the pleasure of interviewing Kevin MacCauley, the CEO and founder of Upper Hand, the leader in cloud-based sports management software that help sports professionals escape the administrative vortex and focus more on training athletes. As a former Little League coach, Kevin’s impeccable leadership stems from his undeniable love for sports, coaching and technology, which he has leveraged to transform Upper Hand into an industry trailblazer. Its award-winning software has undergone tremendous growth as it continues to reinvent the sports business industry and grow athlete participation worldwide. For more information, please visitwww.getupperhand.com.


Thank you for joining us! Can you tell us your childhood backstory?

As the second youngest of seven brothers and sisters, growing up surrounded by older siblings taught me how to learn from their successes and mistakes. I was lower on the totem pole, which gave me the opportunity to observe what to do and what not to do.

My mother worked at a private school for nearly three decades, and taught me an immense amount of information on the virtue of working hard. In fact, watching the work ethic of my mom over the years is undoubtedly the primary reason I could never sit still and still can’t. However, my love for business was sparked from my dad by watching him take his briefcase with him to work everyday.

In fact, I was so passionate about business that in kindergarten I spent recess making money by using loose leafs of paper to make predictions on Super Bowl teams.

In third grade, I built a real-life field of dreams that was featured in our hometown paper. Two years later, I started my first business called “Tee Time” to host golf tournaments. Then, I started another one that wrote jingles for local businesses to use radio advertising.

Parallel to my love for business was my obsession with baseball. My oldest brother was an All-American at the University of Evansville and eventually went on to play for the Oakland Athletics.

I worked so hard to be better than him that I pushed myself to a new spectrum of burnout. So, instead of going to play at a Division 1 school, I put that work ethic into studying business at Indiana University, which was ranked sixth in the nation for its business program.

In college, I started a non-profit that hosted the first ever collegiate half marathon in the country, to raise money for cancer survivors to go back to college at IU called the IU Mini Marathon.

After college, I got a job at Gartner where I learned how to effectively sell to c-suite executives at Fortune 500 companies. But it didn’t encompass my love for startups. So, I quit to start my first real company with my third oldest brother called ClassWatch to compete in the $4 billion class ring industry, which relocated me to Washington, D.C.

It was then that I started coaching. And, that is when the concept for Upper Hand started.

What brought you to this specific point in your career?

As stated earlier, I’ve been driven by a passion to solving business problems. And I’ll never forget when this seamlessly crossed-over into my coaching profession.

After a pitching lesson with one of my athletes, there was this incredibly awkward moment where mom handed me a papercheck out of her back pocket, directly in front of her kid.

This made me think to myself, “there has to be a better way to do business in the sports industry.” Over the next months, I started researching and building a business plan around this theory. The initial idea, dubbed Book a Coach, was to create an extremely easy way for coaches and trainers to connect with parents and athletes seeking supplementary training.

After getting a product to market, looking at the data and talking with customers, we realized that the opportunity was not in a discovery business model but instead was in the value of creating features for a sports or fitness business to manage their operations. This essentially makes it easier for people to do business in sports and fitness.

This experience and incredible insight led us to pivot from Book a Coach to Upper Hand.

What does your day to day schedule look like?

As long as I’m not traveling or need to get in the office for an early meeting, I start my day with my wife and kids. They are my fuel. My interactions in the morning help you level with reality while making you feel so grateful. It’s like medicine when you’re also going through a challenging time at the office.

I also help my wife (who also works) to take on some morning chores that help everyone get out the door, such as daycare drop off. It’s important to contribute my half, which can also be very difficult to do.

In the startup world, days always end up different than how you end up imagining it to go. It’s very bipolar. One minute, you’ll be celebrating a significant milestone and then someone else will hit you with a major issue that has to be dealt with. You go from ecstatic to frustrated to determined.

I always look forward to the end of by giving my kids a hug and kiss before bed. I always try to be there for dinner, too, which is really important to me.

Then, it’s a workout (if I didn’t get one that morning) or time with my wife to make my mind off of work. And it’s almost always with a cocktail.

Based on experience, why do you think that not spending time with your children can be detrimental to their development?

Based on less research and more instinct, I am a strong believer that parenting is a twop-person. The single parents out there, to me, are like Saints. There are times where I have no idea how people parent solo.

With that said, if you have a choice, two parents who are both completely aligned on teaching their children I believe is critical to their development.

In addition, you cannot be a teacher if you are not in the classroom. So, when you are at home, you have to spend time with your kids to help them grow. As a parent, you are exhausted — just like in sports and fitness. When you need a break, the teammate steps in. However, this can only be achieved if you are fully present as a parent.

According to this study cited in the Washington Post, the quality of time spent with children is more important than the quantity of time. Can you give a 3–5 stories or examples from your own life about what you do to spend quality time with your children?

Quality most definitely supersedes quantity. You can spend all the time you want with your child, but if your attention is on your phone, then mentally you aren’t there. Experiences like this teach and reinforce bad lessons for children, and can impact various relationships in the long run.

In an effort to spend quality time with my child, I always aim to eat breakfast and dinner with my family. This time together is spent without phones and we all devote 100% of our mindshare on one another. We discuss our days and quickly learn who has had a good one, or a bad one — which then enables us as parents to identify potential issues at daycare or in the development of our child and get us thinking about how to tackle that issue together. I’ve outlined a few additional examples of ways I spend quality time with my children while juggling the job of a CEO.

What are 5 ways to be more “fully present” ?

  1. Interview your kids. Sounds goofy, but from day one, take your iphone and at random times interview them. These moments are precious because you’re 100% present, they know you have their undivided attention and you’re also recording memories.
  2. Bring them to the office. When you don’t have deadlines or urgent matters at work, give them a tour of the office and tell them all about what you do there, including the small things like where you make your coffee. Your kids enjoy knowing everything that you do and will take pride in understanding your role in the work world. In fact, those moments will sink in so deep it will amaze you.
  3. Donuts. We live in a society where you can’t eat this, can’t do that. Everything is bad for you. Surprise your children by taking them to a donut shop at 6 or 7 am. Let them go through the whole process. Go up to the glass, order the one they want. Sit there and eat the whole thing together while talking about what the day holds. You can’t do this everyday, so when you do it — they won’t forget it.
  4. Eat meals with your family. This time is invaluable and becomes a treasured component of your entire family’s daily routine. Use meal time to really listen to your children and get to know them, when you open up the floor to allow them to speak freely — they say the funniest, most genuine things.
  5. Get your kid a “Happy S” when you travel. The concept is simple. Often times, when you travel for work, this becomes a “sad” event for children. Therefore, switch the script by returning with a small, thoughtful gift as a surprise for them. The look on their face when you “thought of them” while away is unforgettable, and the excitement this tradition creates is sacred. It also helps soften the sadness when you must leave. They still get sad, but now there’s a surprise at the end if they behave for mom while dad is gone. Or visa versa.

How do you define a good parent?

A good parent is one that actively talks to their kids, but respects their space at times instead of obsessing over them.

Additionally, as a CEO, it’s important to show your kids that working is hard. Kids need to understand it takes time and commitment to succeed in work, which includes having them see you leave for work so they know the importance of going out and working towards what you want in life.

How do you inspire your child to dream big?

When they want to go fast, let them. When they have an idea, help them play it out. Empower them to take the idea and bring it to fruition. Most ideas will be silly or unrealistic, but they will enjoy trying — and you will too.

How do you define success?

I define success by the three rules of Lou Holtz:

  1. Doing your best.
  2. Do what is right.
  3. Treating others well.

If your answer is yes to all three of those every day in pursuit of your dreams and task at hand, then you are succeeding.

Thank you for all of these great insights!

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