As someone who has spent the last 14 summers playing competitive baseball in the Detroit MSBL (Men’s Senior Baseball League) and over 30 years as a business leader, I’ve realized how strikingly similar the journeys of entrepreneurship and baseball are.
Baseball, like entrepreneurship, teaches you that success often comes with a heavy dose of failure. In baseball, if you fail 7 out of 10 times and still hit .300, you’re considered a success. Imagine applying that mindset to business, where failure is often seen as the enemy instead of a stepping stone along your pathway to success.
Here are some of the key lessons I’ve learned from my experiences on the field and in the boardroom and how the ups and downs of both have shaped me into a stronger, more resilient entrepreneur.
Overcoming Hurdles: Lessons from the Diamond
This past season marked a personal and career milestone for me—300 RBIs and 235 stolen bases. Yet, the path wasn’t always smooth. I started playing baseball at 40 and have had my fair share of injuries and challenges. From 2020-2023, I broke my wrist, tore my hamstring off of the bone, and had a stroke in my eye that limited my ability to see the baseball when it was thrown by the pitcher.
The same is true in business. For the first three years of my entrepreneurial journey, I went it alone, trying to shoulder every burden myself. Much like playing baseball without a coach, this led to injuries—financially and mentally. It wasn’t until I became aware of my limitations and sought help that my trajectory changed, both in the game and in business.
In baseball, you don’t dwell on the last pitch—you focus on the next one. Likewise, in business, when something goes wrong, you don’t hang on to that mistake. Instead, you clear the mechanism, refocus, and figure out what’s working at the moment.
The Active Learning Cycle: Rapid Iteration in Baseball and Business
Just like in baseball, business success often comes down to rapid iteration. In every game, every at-bat, and every pitch, I assess what’s going well and what needs to change. This same approach works in business. The active learning cycle—analyze, adjust, and act—can be applied to every facet of running a company. Whether it’s evaluating a new marketing strategy or adjusting your leadership approach, learning from each failure and iteration is what propels you forward.
The parallels between rapid learning in baseball and entrepreneurship can’t be ignored. Baseball is a game of adjustments—just like business. Every at-bat is an opportunity to learn from the last, and every new challenge in business is a chance to improve on the previous one.
Mindset: What’s in Your Control?
One thing I’ve learned over 14 seasons is that there are things I can control and things I can’t. Umpires, other players, the weather, and the team manager’s decisions—these are all out of my hands. In business, you can’t control market trends, economic downturns, or even the decisions of your competitors. But what you can control is your mindset, your preparation, and your resilience.
In baseball, I focus on my exercise routine, diet, and sleep to maintain my performance. In business, I focus on my mental resilience, daily habits, and the health of my company culture. Commitment to improvement is essential in baseball and business. By focusing on what’s within my control, I can better handle the unpredictability inherent in both realms.
Perseverance in the Face of Adversity
Dealing with a fear-based mindset is something I’ve struggled with on and off the field. “What if I can’t get better? What if this is my last chance?” These thoughts creep into my mind every time I face a difficult pitcher or when a big business decision looms on the horizon. But I’ve learned that perseverance—continuing to push through despite uncertainty—is key. Whether it’s the fear of striking out or the fear of failure in business, you have to push through.
And yes, luck plays a role. I didn’t want an injury to end my ability to compete, nor did I want an ugly performance to be my final one. But you can’t let fear of what might go wrong stop you from stepping up to the plate.
Seek Help: The Value of Experience
One of the most valuable lessons I’ve learned is the importance of seeking help from someone more experienced. In baseball, I’ve worked with players and coaches who’ve been where I want to be. In business, I’ve sought out mentors and coaches who’ve already faced the challenges I’m dealing with. Hiring someone who’s been there, someone who’s struggled and emerged stronger, can be the difference between stagnation and growth.
Following my 2023 season, I realized what wasn’t working. I was simply "sucking." I wasn’t the player I used to be due to my numerous injuries, and just like in business, I couldn’t rely on past successes. I had to iterate quickly, adapt, and improve on the fly. I had to reach beyond myself, so I hired a hitting coach. From 2021 through 2023, approximately 102 games, I had a horrendous combined batting average of .248, a measly 24 RBI’s and I struck out 43 times (20 in 2023 alone). In 2024, after investing in a hitting coach, in 30 games, I had a batting average of .452, 29 RBI’s, and reduced my strikeouts to 11.
This is the same advice I give my coaching clients: don’t try to do everything yourself. Find someone who can guide you with a customized approach to your specific challenges. As the person receiving the coaching, take a beginner’s mindset and be open to learning and adapting.
Conclusion: Succeeding on Your Terms
Whether you’re stepping up to bat in a baseball game or leading a business through turbulent times, the lessons remain the same: rapid iteration, focusing on what’s in your control, and never being afraid to seek help.
Baseball has taught me the importance of adapting with each pitch, and entrepreneurship has shown me that failure is just another opportunity to learn.
As I continue my journey in both business and baseball, I’m reminded that success isn’t about avoiding failure—it’s about embracing it, learning from it, and continuing to improve. Whether you’re an entrepreneur or an athlete, the mindset and approach are remarkably similar: clear the mechanism, focus on the next pitch, and keep swinging.
