Stop worrying about losing. Play to win.

How I learned to love risk and why the best small business owners do too

As a kid, I obsessed over sports.

Before I even started playing baseball, I wore a baseball uniform (cleats and everything) around the house, when I was playing outside, while doing my newspaper route — everywhere I went, I wore the uniform. I read everything I could about baseball. I studied the teams and players.

When I finally got to play baseball, I was eager to please. I wanted to do well, I wanted my coaches’ approval, and I feared letting my team down by making mistakes. I was good, but playing not to mess up kept me from being great.

In high school I started playing basketball. I was one of the better players on the team. I played basketball with the same attitude I played baseball: do well, try hard to win the game, don’t make mistakes. I practiced constantly, shoveling snow from the court daily during Michigan winters. I tried to be a leader in practice and for the team. I did everything that was expected of me. I shot when I was open, I made the safe pass, I tried to keep teammates happy all the time.

People Only Remember The Shots That Go In

One day, after a game, my coach pulled me aside. He told me, “shoot the ball whenever you can.” He saw that I didn’t want to be a ballhog or miss important shots. He said, “I only remember the shots that go in.”

At that moment a light went on. I realized that I needed to do everything I could to win. I needed to use the skills I had developed in all that practice. I began to do amazing things — challenging shots, aggressive defense, a risky pass when it made sense, and occasionally yelling at a teammate. It worked. I was a far more effective contributor and the team benefited.

I always loved to win and hated to lose, but I played to not lose. When I stopped worrying about mistakes I made more mistakes, but I also made more big plays that more than made up for it.

I took that attitude with me off the court. Be aggressive, play to win, and don’t focus on avoiding the downside. This has served me well in all areas of life — with the possible exception of my rec basketball league, where I shoot way too much (all that practice stopped a few decades ago).

When Entrepreneurs Don’t Play to Win

Today, I work with hundreds of small business entrepreneurs and I see the same two approaches. Some play to win, some play not to lose. I understand. Nobody likes to lose. Everyone likes to win. But the approaches are not equal. Chasing wins beats hiding from loss.

One of the smartest, most driven entrepreneurs I know lost unmeasurable business opportunities because he stopped playing to win.

At first, he was able to build a great business on his own. He went from nothing to a successful enterprise almost overnight. Then, falling victim to this mentality, he plateaued. He owned several businesses and was always thinking of his next venture, but he wasn’t playing to win in the most important category: he refused to pay for good talent. He didn’t believe that anyone would be worth paying over a certain salary — end of story. I watched as he burned through employees, all of them realizing after a matter of months that they were overworked and undervalued. His business simply couldn’t grow. Just like any entrepreneur, he’s only one person, and without highly motivated, talented employees on his team, he could only take his business so far.

His mistake? He let a salary range dictate how successful his business could be.

When I realized that paying more for high-quality talent was the only way I could truly grow my business, I did whatever it took to get those people. I paid people more than their work was worth to the business in the short term, taking a huge hit to my personal finances. After that, I took out loans from a bank for as much as they would give me in order to compensate highly motivated and talented people. Each time I did this, the business improved almost overnight, paying back the risk and investment immediately. My business wouldn’t have grown the way it did if I tried to skimp on talent. Taking the risk to pay someone highly valuable has always had enormous return on risk and investment.

Don’t let the fear of losing get in the way of winning. Losing $20,000 on a more expensive employee’s salary is nothing compared to their invaluable contributions to your business — in fact, it’s a bargain.

How You Can Play to Win (in Business)

Attributes of a small business entrepreneur who plays to win:

• They maximize their own time.
• They invest in the best people possible as quickly as possible.
• They view spending on their business as an investment, not an expense.
• They are more excited about growth than they are afraid of decline.

Maximizing your time means realizing you’re uniquely great at a small number things. These typically encompass domain expertise, leadership, or selling. While fully capable of doing nearly everything for the business, you choose to only spend your time on the things that bring the business the most value.

When you’re an entrepreneur, it can seem risky and uncertain to find someone to run areas of your business for you when you can do it all just fine yourself (and without paying anyone!), but part of being a next-level entrepreneur is finding people to take over the roles that you’re doing a good job on so they can do a great job. And more importantly, free you up to focus on the things you can to a great job on.

While I admire most small business entrepreneurs, those who truly inspire me play to win without worrying about losing. They build businesses where their time is maximized, and their teams, customers, and communities benefit from their boldness.

Forget about losing — play to win.