How a Conversation on a Plane Saved My Startup
In 2003, my startup was days from shutting down. We had a strong product, a brilliant team, and a handful of loyal customers — but not enough cash to stay alive. I had already maxed out my credit, stretched every invoice, and delivered the hardest message a founder can deliver: “We may have to close the doors.”
That week, I boarded a flight back to Dallas from what was supposed to be our last shot — a pitch meeting with a promising client in Vermont. The meeting went well… but they weren’t ready to sign. And time was the one thing we didn’t have.
On the flight home, my laptop was dying. Back then, not all seats had outlets. I asked a teammate to switch so I could plug in. That simple switch — the decision to trade seats — changed my life.
I ended up next to a man I had never met. We started talking. He was a seasoned entrepreneur, and as I shared our story, I admitted I thought we’d have to shut everything down.
Before we landed, he asked me a question I’ll never forget:
“Are you sure you’ve done everything you can to keep your company alive?”
I said, “I think so.”
He looked me in the eye.
“Because you keep saying you think… and I believe God put me in this seat to ask you three times. So I’ll ask once more: Have you really done everything in your power?”
That was the moment.
I got teary. I felt the weight of it. And I realized — I hadn’t.
The next morning, I woke up before the sun and started calling everyone I knew. Customers. Partners. Anyone who might be willing to help. By that afternoon, I was on a flight to California to visit the CEO of our first client.
He met with me in his office and surprised me with something I didn’t expect: a check. Not a donation. Not a loan. But $150,000 in prepaid licensing fees they had originally planned to pay over three years.
That check saved us.
We stayed open. Closed the deal in Vermont. Added more customers. And in 2005, we were acquired.
It’s been more than 20 years since that day, and I still believe that man on the plane wasn’t just a coincidence. He was sent — a divine interruption, at just the right time.
That’s why I wrote my book, The Outlet That Changed My Life. It’s short. It’s true. And it’s my way of saying: if you’re out of options, keep going. If you think you’ve done all you can… ask yourself one more time.
The answer might surprise you.
📘 The Outlet That Changed My Life is now available on Amazon for just $2.99. It’s a short, powerful read — and if you’ve ever faced a turning point, it might be exactly what you need.
If it resonates with you, I’d love to hear what you think — and if you know someone going through their own “one more try” moment, feel free to share it.
