The Reluctant Entrepreneur Podcast

Most entrepreneurs don’t fail because their idea was bad. They fail because they didn’t understand the unglamorous parts of business—the parts no one talks about until it’s too late. Payroll. Taxes. Compliance. Risk. Today’s guest has spent decades living in that world—and helping entrepreneurs survive it. My guest today is Charles Read, a CPA, author, and the founder of GetPayroll. Charles has bu...

What if the reason your marketing is not working has nothing to do with your funnel, your ads, or your budget, but everything to do with how you sound? My guest today is Ryan Clark, and his journey into entrepreneurship started from a place many founders know all too well. He invested money he did not have into a program that failed, went completely broke, and was forced to confront a hard truth. ...

Starting and running a business requires far more than a good idea. It demands strong communication, effective leadership, and the ability to stay productive without burning out—skills that are rarely taught, but absolutely essential. My guest today, Kim Miller-Hershon, has built her career helping leaders and organizations strengthen exactly those skills.  Kim is an executive coach, leadership an...

Most entrepreneurs believe they control their brand through their website, marketing, and personal interactions. But today, that’s no longer entirely true.  Increasingly, AI-driven systems—search engines, knowledge panels, and digital assistants—are shaping how entrepreneurs and their businesses are understood, often before a conversation ever happens. If you don’t clearly define who you are and w...

Building a successful business doesn’t automatically mean you’re building a sustainable life. My guest today built, scaled, and exited a company, but along the way, he discovered that success can come with a hidden cost most entrepreneurs don’t talk about. My guest today, Craig Cooke, knows that firsthand.  Craig is a serial entrepreneur who built and scaled a digital agency through years of growt...

In this episode of Reluctant Lessons: Where Businesses Go Wrong, we take a closer look at Blockbuster LLC—a company that once dominated home entertainment with over 9,000 stores worldwide… and then disappeared. This isn’t just a story about Netflix winning. It’s a story about business model dependence, hesitation, and the danger of protecting what once worked. We break down the real factors behind...

Starting a business is hard. Starting one with your spouse means there’s no separation between work and life—and no place to hide when things get difficult. Today’s episode is a great example of something I talk about often on this show, how entrepreneurship doesn’t always start with a clear plan. Sometimes, it starts with action, commitment, and figuring things out as you go. My guests today are...

There’s a point in nearly every entrepreneurial journey where success begins to feel like a trap. The business is growing. Revenue is up. Clients keep coming. And yet—you’re working longer hours, carrying more responsibility, and wondering how a business you built for freedom slowly became dependent on you for everything. My guest today understands that moment well. Joe Patneaude is an executive a...

What happens when a company invents the future… and then chooses not to embrace it? That’s the story of Kodak. At its peak, Kodak didn’t just lead the photography industry, it owned it. Nearly 90% market share. A business model that printed money. A brand so strong it became part of everyday language. The “Kodak moment” wasn’t just marketing, it was culture. They even had songs written about them....

I’m excited to introduce a new series on The Reluctant Entrepreneur Podcast: Reluctant Lessons: Where Businesses Go Wrong This series takes a different approach to business failure. We’re not talking about fraud. We’re not talking about scandal. We’re talking about real businesses that made strategic decisions that, at the time, seemed reasonable… but ultimately led to significant decline, loss of...

There’s a common belief that if you’re not technical, you can’t build technology-driven businesses. That belief quietly stops a lot of people before they ever start. My guest today is proof that assumption is wrong. My guest today is Colin Hirdman, a serial entrepreneur who has built multiple companies across growth services, software, and now AI-enabled platforms, without coming from a traditiona...

What happens when the very traits that drive your success start working against you? Discipline. Grit. Relentless drive. For many entrepreneurs, those qualities are celebrated—until the lack of sleep, constant pressure, and nonstop pace quietly take their toll. Today, I’m joined by Tim Thomas, whose journey spans elite performance, personal reckoning, and entrepreneurship. Tim served in Australian...

Most entrepreneurs don’t fail because their idea was bad. They fail because the business grows… and they don’t. What started as freedom slowly turns into dependency. Every decision runs through you. Every problem lands on your desk. And instead of building a company, you become the system that’s holding it together. Today’s guest has built a career helping founders recognize that moment — and more...

Some of the most capable entrepreneurs I know don’t struggle just with their business — they also struggle with being seen. Not because they lack expertise, but because self-promotion feels uncomfortable, forced, or inauthentic. My guest today built a business helping others solve that exact problem. On this episode of The Reluctant Entrepreneur, I’m joined by Kelly Schuknecht—a marketing strategi...

Not every entrepreneur sets out with a master plan. Many find themselves running a business simply because an opportunity appeared, a problem needed solving, or a career took an unexpected turn. But once you’re in it, growth is no longer optional—it’s strategic. Today’s guest, Steve Anderson, has spent years studying how one of the most influential companies in the world approached growth, risk, a...

Most entrepreneurs work incredibly hard to build something valuable—but far fewer truly understand how to price that value. We’re taught how to sell. We’re taught how to market. We’re even taught how to scale. But pricing? For many founders, it’s still a mix of gut instinct, fear of losing customers, and copying what competitors are doing. And that hesitation often leaves money on the table, limit...

Most entrepreneurs chase success assuming fulfillment will follow. Today’s conversation explores what happens when a pivotal life event forces you to redefine what success actually means. Today’s guest is Alan Lazaros, founder and CEO of Next Level University, a global personal development brand and one of the most prolific podcasts in the space. But Alan’s story isn’t just about podcast rankings...

What if the biggest threat to your business isn’t competition, the economy, or lack of sales — but the fact that you don’t truly understand your numbers? Welcome, or hopefully welcome back to the reluctant entrepreneur podcast. On today’s episode I’m joined by Manny Skevofilax,  a CFO strategist, consultant, author, and speaker who has spent more than two decades helping business owners uncover hi...

Most entrepreneurs don’t set out to build unicorns. They’re just solving a problem they understand—until that solution turns into a business, then a company, and eventually a set of decisions they never expected to face: growth, capital, pressure, and exit. Today’s episode is about what really happens after the dream collides with reality. On this episode of The Reluctant Entrepreneur, I’m joined...

Entrepreneurship is rarely a straight line. It’s shaped by experience, mistakes, hard-earned lessons, and the perspective that only comes from time in the trenches. Today’s guest, Dr. Mark Young, is someone who understands that reality firsthand.  Mark’s entrepreneurial journey spans decades, multiple ventures, and a steady evolution in how he thinks about business, leadership, and relationships....

What if building a strong brand doesn’t require louder marketing, bigger promises, or constant hustle, but instead starts with clarity, empathy, and purpose? My guest is Hanna-Mari Kirs, a brand story strategist and coach who helps empathic entrepreneurs communicate their value with authenticity and confidence.  With more than a decade of experience in product management, marketing, and sales in e...

When digital platforms support revenue, serve massive audiences, or operate as mission-critical infrastructure, downtime and poor performance aren’t minor issues—they’re business-ending risks.  My guest today built a company specifically to solve that problem. This is the show that looks past the highlight reels and digs into the uncertainty, the hard decisions, and the lessons that only come from...

A book doesn’t automatically make you an authority. But the right book, written for the right reason, can change how people see your business entirely. My guest today is Ally Machate, a publishing professional with more than two decades of experience in the book industry.  Ally has worked inside traditional publishing, including roles with major publishing houses, and today she is the founder of T...

Baseball teaches you very quickly that you cannot argue your way out of a bad call. The pitch is thrown, the call is made, and whether you agree with it or not, the game moves on. There is no replay in the moment, no time to dwell on what just happened. You step back into the box and prepare for the next pitch. That mindset translates directly to business. Deals fall apart, ideas miss the mark, an...

My guest today is Dr. Christiane Schroeter. She began her career in academia as a marketing professor, surrounded by well-structured assignments, strong theories, and students who were doing everything right, at least on paper.  But over time, she began to see a gap between performance and real learning, between checking boxes and creating meaningful growth. That realization led her beyond the cla...