Chalk Up: Taking the Leap into Business

I had a working prototype. At least, it worked for me. But was it a business? That question loomed larger than the product itself. I’ve always wanted to own my own business, to be my own boss. My notebooks were filled with ideas—real solutions to real problems. Porta-Hang was just one of many. But did this idea have what it takes? More importantly, did I have what it takes?

Self-doubt had been my companion for years. Straight out of college, I dreamed of starting a website development business and then a real estate venture. Both ideas could have been successful, but instead, I took a job. A decade drifted by while I played it safe.

I did take a risk once by joining someone else’s startup. When that fizzled, I joined another—only to discover the owner was stealing. Disillusioned, I returned to the comfort of a steady paycheck, spending six more years collecting a salary instead of chasing my dreams.

Porta-Hang was tabled, just another idea gathering dust. It's funny, really. I could climb a wall at Red River Gorge or tackle a six-pitch odyssey at Smith Rock, but starting a business? That felt like the riskiest thing I could do. Losing my life savings, not being able to pay rent, or struggling to feed my teenagers—that was a fear I couldn’t just shake off.

Facing the Odds

The stats didn’t help, either. Four in five businesses fail within five years. Of the remaining, only half ever turn a profit. That meant only 1 in 10 businesses would actually succeed. Those numbers were sobering.

But then I remembered something Teddy Roosevelt said:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.”

It was a powerful reminder that the greatest failure isn’t falling short; it’s never trying at all. At 45 years old, I felt like I still had something to prove—not to anyone else, but to myself.

Chalk Up and Make the Send

I made a deal with myself: Either I take the leap and start Porta-Hang, or I hang it up for good and accept a lifetime of working for someone else.

I chose to chalk up and make the send.

My goal was modest: sell 100 sets. If I could do that, I’d count it as a win, close down, and use the experience to start something new. I thought I had it all planned out.

But, as with any climb, the route ahead wasn’t what I expected.