Why My Worst Business Decision Was the Best Thing That Ever Happened
(Posted on Tuesday, June 17, 2025)
Decades ago, I walked away from a comfortable corporate role and did what many dream of doing:
I started my own company.
At the time, I was successful in media and finance. I’d built a career, built a network, and thought:
“I’ve figured out harder things than this. I can make a business work.”
I also loved cars. So naturally, I thought—why not go into the car parts business?
New and used parts.
No background in the industry.
No real strategy.
Just an idea… and confidence.
Spoiler: it didn’t work.
From Corporate Confidence to Cold Reality
The plan was simple—on paper.
Buy a couple of shops.
Turn them around.
Build something scalable.
But what I lacked was industry knowledge. I underestimated how different this world was from the environments I was used to operating in—finance, media, high-growth businesses.
And more than anything, I didn’t approach it with the discipline I was known for in other areas of my career.
I took shortcuts. I skipped due diligence. I relied on belief instead of a real plan.
And it failed.
The Emotional Cost of Failure
I lost money.
But more than that, I lost confidence—for a time.
It was the first time I had fully committed to something professionally… and watched it fall apart.
It didn’t just sting. It shook me.
At that moment, it felt like the biggest mistake I’d ever made.
And yet—today, I see it differently.
The Blessing of Not Succeeding
In hindsight, I’ve come to believe the worst-case scenario wasn’t failure.
It was moderate success.
If that business had worked—just well enough—I might have spent the next 20 years running a couple of small parts stores.
I might’ve stayed in the business simply because it was “fine.”
But fine isn’t what I was built for.
That failure forced me to pause.
To reassess.
To reconnect with what I’m actually good at—and what gives me energy.
And that path brought me back to raising capital, advising businesses, and operating in spaces where I could create real impact.
The Hidden Cost of “Good Enough”
So many people get trapped in lives and careers that are “good enough.”
- The business that pays the bills but drains your energy.
- The job that’s stable but uninspiring.
- The venture that kind of works—but not enough to grow.
What’s dangerous isn’t failure—it’s comfort.
And when you’re good at a lot of things, it’s easy to coast on competence.
But growth rarely lives in that space.
Fulfillment doesn’t either.
According to research by the Harvard Business Review, those who pursue meaningful work—not just high-paying work—report higher levels of long-term satisfaction and career resilience. And yet, the vast majority of professionals stay in roles that no longer stretch them because… things are going “okay.”
Sometimes, failure is what forces us out of okay—and into something better.
What I Learned From Losing
Here’s what that car parts business taught me:
- Just because you’re successful in one field doesn’t mean you’ll be successful in another—without preparation.
- Confidence is important, but it can’t replace strategy and industry insight.
- Failure is feedback. And when you listen to it, it can steer you back into your lane of real strength.
Most of all?
It reminded me that I’m built to create momentum—not just manage operations.
I’m at my best when I’m building, advising, connecting capital to opportunity—not running inventory for brake pads and alternators.
And that realization changed the course of my career.
Final Thought: What’s One Failure You’re Grateful For?
Looking back, I can confidently say that one of my biggest failures turned out to be one of my greatest gifts.
Because sometimes failure clears the path that success would’ve trapped you in.
So I’ll leave you with this:
What’s one failure in your career that turned out to be a blessing in disguise?
You might be surprised at how much it taught you—and how far it took you.