Losers Are Winners: What Twelve Entrepreneur Success Stories Taught Me
When I launched the Losers Are Winners series, I didn’t know exactly where it would take us, but I knew I was hungry for real stories.
I wanted the messy middle: the mistakes, the missed signals, the pivots no one plans for, and the perspective that only comes from being deep in the trenches of business and life.
Over the course of twelve episodes, I sat down with builders, designers, business owners, and entrepreneurs who were willing to talk about what didn’t go right, what almost broke them, and what forced them to stop, reassess, and rebuild.
What I didn’t expect was how much I would personally take away from those conversations, and how many common threads would start to show up, episode after episode.
Core Values That Actually Matter
If there’s one thing every guest in this series had in common, it was vulnerability.
These were raw, honest reflections. And I think that’s exactly why these episodes resonated the way they did.
Another constant was resilience.
Time after time, guests shared moments where quitting would’ve been the easier option. But instead, they chose the strategic decision to rebuild, sometimes from the ground up. Whether it was Alyssa Abbott reworking her team after burnout, or Chris Freytag reinventing her entire fitness business for the digital world.
And then there was authenticity.
In an industry that can sometimes reward ego, image, or bravado, these conversations were a reminder that being real is what actually builds trust.
“People connect with you, not just what you build.”— Alyssa Abbott, Episode 1
What Failure Teaches (If You Let It)
Across the series, certain themes came up again and again, sometimes in totally different contexts, but always pointing toward the same bigger lesson.
Creative risk was a big one.
Several guests hit a point where they could’ve stayed safe in their small business but chose not to. They launched new brands, doubled down on passion projects, or walked away from something successful because it no longer aligned.
Entrepreneurial success takes courage.
“I could’ve kept doing what worked. But I wasn’t proud of it anymore.”— Nathan Marsala, Episode 4
Another recurring thread was growth mindset.
Failure wasn’t framed as the end, it was framed as information on the way to business success. Adam Copenhaver talked openly about learning from hiring mistakes. Brad Leavitt shared how personal challenges reshaped his purpose and leadership. These stories reframed loss as something that sharpens you, if you’re willing to pay attention.
And then there were the pivots.
Nearly every guest had a moment where the business model they built just… stopped working. Sometimes it was the market. Sometimes it was internal misalignment. But the solution was rarely a small tweak, it was a full reinvention.
Painful? Yes. Necessary? Absolutely. That's when they became business innovators.
“Burnout was the wake-up call. But reinvention was the cure.”— Mark D. Williams, Episode 5
Conversations I’m Still Thinking About
Every episode brought something different, but a few stories have stayed with me:
Chris Freytag shared how navigating massive tech, digital platform, and SEO shifts nearly wiped out her business ventures, forcing her to build a stronger digital foundation and entirely new revenue streams.
Caleb Macdonald talked candidly about losing a major deal and how it taught him more about boundaries and red flags than any business book ever could.
Morgan Molitor opened up about motherhood, leadership, and reimagining how a business can function when life changes overnight.
These were the kinds of conversations that make you rethink how you’re showing up in your own work.
I learned just as much from these episodes as I hope our listeners did.
Why Losers Are Winners Mattered
When we titled this series Losers Are Winners, it was meant to be a little tongue-in-cheek. But after twelve honest, thoughtful, and deeply human conversations, I believe it more than ever.
Failure is part of the game. But who you become because of it? That’s the win.
So here’s to the guests who shared their truth, the listeners who saw themselves in these stories, and to everyone out there building something real one lesson (and one loss) at a time.
If you haven’t listened yet, now’s the time. Start at Episode 1 and work your way through. It’s not just good business advice, it’s a masterclass in being human.
