By Jeff Gilder — Founder, WingDing MEDIA™
I’ve been an entrepreneur, in one way or another, since I was twelve years old. Over the decades, I’ve had days, weeks, and even months when I doubted myself, my ideas, and the path I chose. I’d love to say those days are behind me, but the truth is—when you’re driving forward, there will always be times that don’t go your way. Entrepreneurship isn’t a straight line. It’s a roller coaster of victories, lessons, and resilience.
The Racing Lessons That Shaped My Business Mindset
One of my greatest mentors, Paul Lewis, was my crew chief during my short racing career. He taught me two lessons that have stuck with me to this day.
“When you stop getting better, you cease being good.”
That one still echoes in my mind whenever I start feeling comfortable. Growth is a moving target—if you’re not improving, you’re falling behind.
The second lesson hit even harder. Paul once told me, “There’s not one single thing you can do that will make you a champion.” I’ll admit, that stung a little at first. Then he added, “It’s the combination of all the little things you do that make you a champion.”
That truth applies perfectly to business. Success rarely comes from one big move—it’s the accumulation of consistent small efforts done well. In racing, that meant dialing in every bolt, every lap, every adjustment. In entrepreneurship, it means refining every product, conversation, and decision. The details matter.
The Myth of the Overnight Success
Several years ago, during a podcast I hosted, Forrest Lucas of Lucas Oil shared something I’ll never forget:
“After twenty years of working night and day, Charlotte and I had become an overnight success.”
That line perfectly captures what most people never see—the years of unseen effort behind every “sudden” success story. I’ve always paid attention to people like Lucas, Gary Vaynerchuk, and other straight-talking entrepreneurs who remind us that the grind is the only path. The best don’t just hustle for a season—they build stamina for decades.
The Question That Hurt the Most
I once had a loved one ask me, “Why don’t you just quit?”
That question hit me harder than I expected. But quitting was never an option. One sure way to fail is to quit. The only way to succeed is to keep going—especially when you don’t feel like it.
With Paul Lewis’ guidance, I won a championship, sat on fifteen poles, won half the races we entered, and held a track record for years. And we did all that in a car people said was obsolete, driven by a guy they said was past his prime.
That experience taught me a lifelong truth: the grind works.
The Strength You Don’t Realize You Have
I’ve been so broke in business that I didn’t think I could make it another week. I remember the anxiety, the exhaustion, and the temptation to give in. But I didn’t. Looking back now, I realize how much strength that took—and how essential those moments were to becoming who I am today.
Entrepreneurship will test you, break you down, and rebuild you stronger—if you let it. It’s not about the product, the pitch, or even the money. It’s about perseverance. It’s about believing in something long enough to see it become real.
Final Lap
If there’s one thing I’ve learned, it’s that the journey of entrepreneurship never really gets easier—you just get better at handling it. You learn to ride the ups and downs. You learn that every small improvement matters. And you realize that success is never instant, but it’s always possible.
A Word to Every Entrepreneur, Creator, and Dreamer
To every person out there with an idea, a vision, or a dream—keep pushing. The road gets bumpy, the nights get long, and doubt will always whisper louder than belief. But remember: you’re not alone in the grind. I’ve been there, and I still am.
If you ever need encouragement, advice, or just someone who understands the journey—reach out. I’m always here for those who dare to chase the dream and challenge the grind.
— Jeff Gilder
Founder & CEO, WingDing MEDIA™