Two Sided Coin

Monday evenings this summer meant flag football for our Son. One night, near the end of the season, I watched my son walk to center field as the captain for the coin toss. The flip went up and down but we didn't know the results (the kids are soooo quiet talking to the refs!). He came jogging back with the ball, tossed it to his coach, and said, “We’re on offense.”

The coach told him, “Good job.”

Puzzled, my son replied, “Why? We lost!”

You see, he’s played long enough to know most teams prefer starting on defense so they can get the ball after halftime. If you knew his coach though, you would know this didn't actually matter. He just loves football. Offense or defense didn’t matter - he was ready to play.

The moment stuck with me. Literally 50/50 chance of offense or defense. Just like in life, sometimes you find yourself in a position with a 50/50 chance. It could be any number of things, but maybe it’s big. Moving out of state. Two different job offers. Or like a Hallmark movie, two different life paths. Hopefully its not like the movie No Country For Old Men where your faced with a coin toss for life or death, but maybe it seems like it. It's that feeling of, "This could go either way."

This summer, I was in one of those coin-flip moments. By July, I was deep in due diligence on a business acquisition as I mentioned in my 120 check-in. LOI signed, banks engaged, seller interested. But at the same time, I knew how fragile these deals are. Just as likely as a closing was a collapse. Heads or tails, both futures seemed possible and even probable.

The debate became freedom vs structure. Staying on my current path meant flexibility, exploration, and building things like Radio Chatter apps and partnerships with wholesalers. Acquiring a business meant more structure, a team, and steady income. Both were entrepreneurship, but one was build, the other was buy.

In the middle of all this, my wife and I did a deep dive on our finances. We pulled everything up on the TV with coffee in hand because my son was away for the weekend and we could have one of those slow mornings. I wanted to make sure she was fully in the loop, but what hit me was how long our emergency runway actually stretched. That is, if we didn’t acquire the business. Longer than I thought.

That realization reframed the choice.

As I looked at it, I kept coming back to something I’d underlined in The Young Entrepreneur’s Guide to Starting a Business:
“Entrepreneurship is about freedom, too—the freedom to work how and when you want, and the freedom to make your career truly enjoyable and rewarding.”

Yet the “freedom” looked different on each side of the coin. That was the choice. One side: the freedom to build, experiment, and follow my own momentum. The other: the freedom of ownership with (presumable) cashflow and stability, but tethered to employees, customers, and schedules. Angel on one shoulder, devil on the other.

By August, the acquisition fell through. Financing terms couldn’t come together, collateral demands were too heavy, and we walked away. What I thought was a coin toss resolved itself.

And here’s the part I didn’t expect: some relief. As I mentioned to my business partners as it was falling through in front of us, I said I enjoyed the ebbs and flows of what I was working on. So, looking at our runway, the flexibility I’ve had, and the projects I’ve already pushed forward, I began asking a new question. What can I build in the time we have before that runway runs out?

The answer: possibly anything. Especially considering some building leads to some income. Runway extended. Without meetings and updates. Without reporting structures. Without deadlines, timelines, and places to be. Just the freedom to experiment, create, and double down on what excites me. It’s not a coin toss anymore. The coin is still in the air, but I’ve realized, I don’t have to call it until it lands.