I’ve been an avid basketball fan for as long as I can remember. It began in the late Jordan years, but not solely because of Michael. To watch him and listen to stories about him was fascinating to me, even at a young age. Little did I know I would later go on to grow up in Chicago and proudly call it home.

A good chunk of my love for the game probably also stems from Kobe Bryant’s NBA Courtside, the first game I got for Christmas along with my Nintendo 64 when I was three. (Jordan was actually so dominant that Courtside didn’t have him in the game. His avatar was a silhouette and referred to as “Player 99”.)

A low-angle shot of a basketball on the ground midcourt of a blacktop with the hoop in the background.
Seeing the parallels between basketball and entrepreneurship has added some new perspective.

Growing up, I continued playing team sports—basketball, baseball, soccer, among others-with friends, in leagues, and any other way I could. And yet, among all the sports I’ve played, basketball has served me the most life lessons. Here’s what I’ve gathered so far:

Get your teammates involved

I was always the shortest kid on the court. And if not the shortest, then the second-shortest. The point is, I didn’t have the height of my peers to be able to back someone down in the post, or finger roll without the fear of being blocked every time, foul or not. If you’ve ever played basketball, you know that the shortest guys are usually the ballhandlers. That was me. I was the guy bringing it up the court. Not every single time, but a good chunk of the time.

What I did differently though, was study the game. Most of the time, and particularly when you’re younger, your teammates automatically feel the need to score if they have the ball. Not only that, but they feel the only way to score is to break the defender’s ankles or throw up a prayer when their ankles are still intact. In other words, they want to score individually. At that elementary age, many haven’t understood that basketball is ultimately a team sport. In high school, it was sometimes even worse. Egos were flying higher than the hormones. One person can carry a team and might be a crucial ingredient, but no one person can make the team. Unfortunately, I’ve played with people who never learned this lesson, even at their 40+ age.

What I did manage to learn at an early age was the importance of getting my teammates involved. I was a good scorer-not always the #1 scorer (though never the worst), but very solid, and unstoppable if I was on a hot streak. I had developed a quick-trigger jumper, so if I was making it rain from deep, it poured. But as the unofficial guard for whatever team I was on, getting my teammates involved always came first. Here’s what I noticed when I put my teammates first:

Two basketball teammates high fiving in an indoor basketball court wearing white uniforms.
Team sports are very different from individual sports because of the multiple variables at play.

You're forced to lead
Whether you want to lead or not, it’s always good practice to do so. At one point or another in your life, you’re going to be responsible for leading something or someone.

Once you become the leader, you're also ultimately to blame for a lot, if not everything

This is reminiscent of good CEOs: When things are going well, they give credit to their employees. When the ship is sinking, they blame no one but themselves. This is a key topic in Jim Collins’ bestseller Good to Great.

Your team moves the ball better

Developing trust is integral, and a pillar of teambuilding. If your team is less reliant upon one person (e.g. you) to get things rolling, your team is stronger and more independent of what you do.

San Antonio head coach Gregg Popovich is the greatest example of this outcome. If you’ve ever watched the Spurs play, you know that everyone touches the ball at least once on the vast majority of possessions. Some critics call their style of play boring-but you know what? They are one of the most consistent playoff-bound teams. Ball don't stick!

As I mentioned earlier, I was always one of the shortest guys on the court, which meant there was always a mismatch. But what I lacked in height, I made up in speed, agility, and shooting. And in all those pickup games I played where I had to defend someone bigger, taller, and stronger than me in the post, not once did I relent solely because of their size advantage.

In fact, some of those bigger guys will underestimate what a smaller guy can do. While those bug guys were backing me down in the paint, I was pulling the chair on them, or doing one quick move to steal or strip the ball. But before even doing all of those things, I was focused on not letting them get into position at all.

If your game is inside, I’m going to force you to take a jump shot. If you start making me pay for them, I’ll adjust. But you’d be surprised to find out just how much people are thrown off by simply preventing them from getting into their spots. Fortunately, I did have good reactions, so even if they were fighting for position, a lob to them would have to be perfectly placed for them to begin their work in the post.

Team dynamics are ever-changing, especially if you play pickup ball. Everyone has their strengths and their weaknesses. And influencers of our generation will often advise playing your strengths, rather than focusing on your weaknesses. Or at least use Pareto’s Principle and apply an 80/20 strategy, with 80% of that time being focused on your strengths and only 20% on your weaknesses.

A pen laying on an open notebook with glasses next to the notebook.
The same way you take note of something in a sport is the same way you take note of something when you're building something new.

I have noticed this to be the case on the court, myself included. Before I developed handling with my left, I was quite insecure dribbling with my left. I knew I didn’t have it, and I did not pretend that I did. The defense would often notice this, which would automatically eliminate a part of my game. I noticed it with others when defending, too-which helped shape me into a very good defender even at my comparably short size. The point is, I didn’t let my lack of a left hand dribble stop me.

Improvements are made in the gym. In the offseason. On a court when no one is looking. Because I couldn’t improve my left then and there in-game, I simply focused on what I could do offensively, which was shoot, create, and move the ball well.

I’ve played with older people who are not the most athletic but can shoot the lights out. Others work well in the post, and only the post. Some use their quickness and agility, and others use their strength. But one thing is clear: Those who know their role together go far.

I played my best basketball in college, and not just because we had an indoor court and a Wilson Evolution basketball for a change. But knowing that I would never be a professional athlete from an early age, I kept my eyes on something else: Coaching. I would sit through countless hours of videos watching the best coaches, their strategies, disagreements, interactions with their players, and so much more.

Among these hours were also classic games and teams, like the Showtime Lakers, Larry Bird’s Celtics, and of course Michael Jordan’s Bulls. Allen Iverson’s 76ers and the 2004 Detroit Pistons were also some of my favorites, particularly because they got so far with comparably less talent than other teams.

Through many hours of observation, I would pause, rewind, and study all elements of the game. In fact, it’s how I stopped focusing on the numbers so much. I don’t think people realize just how subjective every statistic is.

Literally everything matters:

  • Who that person is defending.
  • Who is or isn’t playing.
  • What the person ate that day.
  • Which shoes they are wearing.
  • What personal issues the player was facing that particular day, week, or month.

There is absolutely nothing that does not account for a specific outcome.

During our pickup games in college, I naturally put my study of the game to work. My group of friends and I would often surpass the necessary 10-player limit for a 5-on-5, so we would play against each other a lot. And sure enough, we learned each other’s playing styles.

Defenders knew they had to pick me up at half court, or I was going to let it fly. I knew if I forced somebody left, they were still going to end up going right because they could not dribble with their left. But despite everything going on inside my head, I made a clear effort to vocalize how we could improve.

This helped not only my teammates, but I almost felt a sense of “validation” in my coaching abilities. Now, I know what you’re thinking: “Hiram, you were 19 and played pickup basketball with your friends. Get real.” And I agree with that—I have no credible track record, and will never be Phil Jackson or Gregg Popovich. I understand. However, it does not change the fact that had I put in all those hours to study the game, and when it came time to put it into action, it made a significant difference.

A birds-eye view of an outdoor basketball court.
Everyone sees the same game with different angles, with different perspectives, opinions, and biases.

The same is true in business. Do you want to become a better investor? Then it’s time to read some books and listen to Warren Buffett. Do you wish you were a social media expert? Time to get on platforms out there and start posting 2–3 times a day and engaging with the communities that live inside those social platforms. Study, read, learn, absorb. But also do. There’s only so much you can learn outside of just doing.

Some of you who are great players, great business people, great artists, might be thinking: “Hiram, if I give others my knowledge and expertise, they could just use it to do their own thing and crush me.” I have not found this to be the case at all. In the previous section where I wrote about coaching, I implied that I gave away some of my best secrets to my teammates. It didn’t matter if we switched it up the game afterward and I was playing against the person who I just revealed something to. And aside from my love of helping people, I legitimately wanted my friend/teammate to improve. Chances are if they’re improving, they’ll want to keep improving and continue to play ball.

Here’s the best part: If they do become better than you, or are at least giving you a consistent challenge every game, it’s good news for you. You know why? Because you’re going to be forced to improve. Does Jimmy know that you can’t lay it up with your left hand? Then you better develop that left hand. Perhaps Danny knows you can’t shoot, so he has no reason to guard you near the three-point line. Better improve that shot and make him pay.

Use your advantages

I had a friend who was about 6'2" and over 200 pounds, but weak in the post. I took the time to show him how to use his size to his advantage in the post, and he began to give me trouble in the paint. He became a drastically better rebounder, not because he improved his vertical, but because he learned how to use his size. That challenged me to approach rebounding and attacking the basket differently. My improvements on and off the court have come primarily from playing against people who are better than me because I learn from them.

Sometimes we have more information than we know what to do with it. Some of the best leaders and most admired people in the world often put their best ideas forward.

Build bridges, not walls.

One of the best things about basketball is that anyone can beat anyone at any time. It just has that probability. You’ve heard players in the league say it multiple times, and it is absolutely true. It often comes up when a statistically bad team beats a top team in the league. Sometimes teams will get just a bit too cocky and think the game is going to be a walk in the park, but that 7–32 team comes out with everything they've got and pulls out the win.

Are there any other activities you’ve found that translate into business and entrepreneurship lessons? Would love to hear about it. Reach out here: