The Reluctant Entrepreneur Podcast

Mike Konrad
  • 5.0 (2)
  • Entrepreneurship
  • Updated Semimonthly

I’m your host, Mike Konrad, the author of The Reluctant Entrepreneur - Anatomy of a Business Start-Up - From Uncertainty to Unstoppable, available on Amazon as a paperback, e-book, and an audible book, and I’m excited to share real stories that reveal the many paths people take to build their own businesses.  Whether you stumbled into entrepreneurship or you’ve always known it was your calling, this podcast is for you. Let’s start with what it means to be a reluctant entrepreneur. Many entrepreneurs don’t set out with a grand plan to build a business.  Maybe you worked for a company that didn’t value your vision, and one day you thought, “I could do this myself”, that was my story. Or maybe life pushed you in an unexpected direction—losing a job, facing a personal crisis, or discovering a passion that grew into a business. Reluctant entrepreneurs often find themselves starting a business not because they always dreamed of it, but because it was the best—or only—option available.  And then there are intentional entrepreneurs. These are the people who’ve known from the start that they were meant to create something of their own.  They may have planned meticulously, crafted their vision, and followed a well-laid path to build a business. Intentional entrepreneurs are often seen as risk-takers, those with a drive to innovate, disrupt, and lead in their industries.  But even with all the planning in the world, intentional entrepreneurs face their own share of unexpected challenges, setbacks, and doubts. On The Reluctant Entrepreneur podcast, we celebrate both types of entrepreneurs—the ones who jump in with both feet, and the ones who tiptoe cautiously into the water.  So, join me as we explore the many ways people navigate the complex and rewarding world of entrepreneurship.  Whether you’re here for inspiration, advice, or just a great story, I hope you find something valuable in every episode of The Reluctant Entrepreneur Podcast.

  1. 8h ago

    The Numbers Don't Lie: Max Emma on Bankruptcy, Bookkeeping, and Building a Franchise

    A lot of entrepreneurs dream about success. They dream about freedom, control, growth, income, and building something they can call their own. But very few dream about the part where the business fails. Very few dream about bankruptcy. Very few dream about rebuilding from the wreckage of a company they once believed would define their future. My guest today has lived that story. Max Emma is a Certified Franchise Executive, franchisor, franchise consultant, and co-founder of BooXkeeping.  His journey began with immigrating to the United States from the former Soviet Union. From there, he built a career in corporate accounting and finance, eventually left that world behind, built a family-run landscape maintenance business, and then experienced the kind of business failure that leaves a mark. But bankruptcy wasn’t the end of Max’s story. In many ways, it became the beginning of a much more informed one. That experience gave him a front-row seat to one of the most important lessons in business:  if you don’t understand your numbers, your business may be telling you something critical, and you may not hear it until it’s too late. Max later co-founded BooXkeeping, a bookkeeping business that grew into a franchise.  Today, he also helps aspiring entrepreneurs evaluate franchise opportunities and better understand whether franchise ownership is the right path for them. So this episode fits perfectly into our normal two-part format. In the first segment, we’ll talk about Max’s entrepreneurial journey: immigrating to America, leaving corporate life, building a business, losing a business, rebuilding a business, and most importantly, what he learned from that experience. In the second segment, we’ll talk about franchising, bookkeeping, financial clarity, and how entrepreneurs can decide whether buying a franchise is the right path for them. BooXkeeping https://www.booxkeepingfranchise.com

    The Numbers Don't Lie: Max Emma on Bankruptcy, Bookkeeping, and Building a Franchise

  2. 3d ago

    The Business of Giving a Damn: Justin Ricklefs on Purpose, Culture, and Entrepreneurship

    A lot of entrepreneurs leave corporate life because they’re chasing freedom. Some are chasing money. Some are chasing control. But for many entrepreneurs, the real story is more complicated. They leave because something inside them says, “There has to be another way to work, lead, build, and live.” Today’s guest, Justin Ricklefs, knows that tension well.  Justin spent years in the front office of the Kansas City Chiefs, building relationships, partnerships, and revenue inside one of the most recognized sports organizations in the country.  But eventually, he stepped away from that familiar world and took his first swing at entrepreneurship. It didn’t go the way he hoped. In fact, Justin describes that season as painful, humbling, and filled with lessons. But the story didn’t end there. Justin eventually returned to Kansas City, went back to familiar ground, and then made the leap again. This time, he launched what became Guild Collective, a human-first brand consultancy focused on helping companies tell better stories, build healthier cultures, and close the gap between what they say they believe and how they actually operate. He’s also the author of Give a Damn: The Catalyst for Caring Companies, a book built around a simple but powerful idea: care can be a competitive advantage. In this episode, we’ll talk about leaving comfort behind, what failure teaches us when we’re willing to look at it honestly, why storytelling matters in business, and how curiosity, compassion, clarity, and consistency can shape not only a better company, but a better entrepreneur. Guild Collective: https://guildcollective.com Justin's Book: Give a Damn THE CATALYST FOR CARING COMPANIES https://a.co/d/03XF7DRh

    The Business of Giving a Damn: Justin Ricklefs on Purpose, Culture, and Entrepreneurship

  3. 6d ago

    From Business Operator to Business Multiplier: Tom DuFore's Franchise Strategy

    Most business owners dream of growth. But growth can become a trap. More locations, more employees, more customers, more complexity.  Before long, the business that was supposed to create freedom can start consuming every available hour. So the real question is not just, “How do I grow?” It is, “How do I grow without building a business that depends entirely on me?” My guest today is Dr. Tom DuFore, founder and CEO of Big Sky Franchise Team.  Tom has spent more than two decades helping business owners think beyond the single-location, owner-dependent model and explore whether franchising could be a path to smarter, more scalable growth. Through Big Sky Franchise Team, Tom and his team help entrepreneurs determine whether their business is truly franchiseable, how to build the systems needed to replicate success, and how to avoid the common mistakes that can turn growth into chaos. He is also the host of Multiply Your Success, a podcast focused on helping growth-minded entrepreneurs, investors, and franchise companies learn from the misses, makes, and multipliers of business success. Today, we are going to talk about Tom’s own entrepreneurial journey, what he has learned from helping hundreds of companies expand, why franchising is often misunderstood, and what business owners should think about before trying to multiply what they have built. Big Sky Franchise Team https://bigskyfranchiseteam.com

    From Business Operator to Business Multiplier: Tom DuFore's Franchise Strategy

  4. 6d ago

    Lessons From a Reluctant Entrepreneur - The Myth of Being Your Own Boss - Episode 1

    I’m launching a new series from The Reluctant Entrepreneur Podcast called Lessons From a Reluctant Entrepreneur. This series is based on stories and lessons from my book, The Reluctant Entrepreneur: Anatomy of a Business Startup, From Uncertainty to Unstoppable. Episode 1 is titled The Myth of Being Your Own Boss. People often say, “It must be great being your own boss.” And I get it. From the outside, entrepreneurship can look like freedom. No boss. No time clock. No one approving your vacation. No one telling you what to do. But once you start a business, you quickly learn the truth. You don’t eliminate bosses. You multiply them. Customers, employees, vendors, banks, landlords, tax collectors, regulations, the economy, and cash flow all get a vote. And somehow, every problem eventually finds its way back to your desk. That’s the reality of entrepreneurship, and that’s what this series is about. Lessons From a Reluctant Entrepreneur isn’t about business theory or motivational slogans. It’s about the real entrepreneurial journey. The uncertainty, mistakes, fear, ego, resilience, decisions, failures, lessons, and occasional moments of clarity that shape the people who build businesses. In this first episode, I talk about the myth of being your own boss and why the real reward of entrepreneurship isn’t freedom from responsibility. It’s growth through responsibility.

    Lessons From a Reluctant Entrepreneur - The Myth of Being Your Own Boss - Episode 1

  5. Jul 22

    Coaching the Coaches: Adam Roach on Clarity, Confidence, and Building a Real Business

    Some entrepreneurs build one business and stay in that lane forever. My Guest today is not one of those entrepreneurs. His journey started on the tennis court, eventually led to building a tennis business in Beverly Hills, and later moved through real estate, franchise ownership, recruiting technology, and now coaching coaches. Along the way, he built businesses, led teams, helped support hundreds of real estate agents, created tools that impacted recruiting across North America, and learned that entrepreneurship is rarely a straight line. It’s a series of transitions. Some planned. Some unexpected. Some exciting. Some painful. And each one teaches you something, if you’re willing to pay attention. My guest today is Adam Roach, Founder and CEO of I Love Coaching Co., a company built to help coaches of all types turn their experience, knowledge, and expertise into a real business.  Not just athletic coaches, but business coaches, life coaches, leadership coaches, consultants, advisors, and other experts who know they can help people but may not yet have the structure, clarity, or confidence to turn that knowledge into a sustainable business. Adam’s own entrepreneurial path gives him a unique perspective on that work. He was a collegiate tennis player, launched his first business in his twenties, built a successful tennis club in Beverly Hills, moved into real estate, operated Keller Williams franchises, built recruiting technology, and eventually created I Love Coaching Co. We’re going to break this conversation into two segments. In the first segment, we’ll talk about Adam’s entrepreneurial journey, the highs, the lows, the reinventions, and everything in between.  In the second segment, we’ll dig into his area of expertise: helping coaches and experts build businesses with clarity, conviction, and a model that actually works. I Love Coaching Co. https://ilovecoachingco.com

    Coaching the Coaches: Adam Roach on Clarity, Confidence, and Building a Real Business

  6. Jul 20

    The Business That Runs Without You: Alane Boyd on Automation, Exits, & Finding Purpose After Success

    What happens when you finally build the business you dreamed of, grow it, sell it, and then discover that freedom doesn’t feel quite the way you expected? My guest today is Alane Boyd. She’s a serial entrepreneur, growth strategist, keynote speaker, AI and automation expert, and co-founder and CEO of Biggest Goal.  She’s built and led multiple SaaS companies, grown a tech company into an 8-figure business, and successfully exited two companies. On paper, that sounds like the entrepreneurial dream. But as we’ll talk about today, the dream has a second side.  After one of those exits, Alane experienced the silence that can come after years of constant motion. The business was gone, her identity tied to the business had changed, and the next chapter wasn’t immediately obvious. Alane now helps business owners tackle their biggest operational challenges through systems, automation, AI, and workflow design.  She also co-hosts the podcast Automate Your Agency, where she and Micah Johnson help founders systemize and automate their businesses so they can scale more efficiently without being trapped in the day-to-day grind. So today, we’ll break this conversation into two segments. In the first segment, we’ll talk about Alane’s entrepreneurial journey, the wins, the stress, the burnout, the exits, and what success really felt like once she got there.  In the second segment, we’ll shift into her area of expertise: AI, automation, workflow design, and how entrepreneurs can build companies that don’t depend on them being in the middle of every task, every decision, and every emergency. Biggest Goal: https://www.biggestgoal.ai Automate Your Agency Podcast: https://www.youtube.com/@BiggestGoalAI

    The Business That Runs Without You: Alane Boyd on Automation, Exits, & Finding Purpose After Success

  7. Jul 17

    The Strength Within You: Jay Setchell on Resilience, Responsibility, and Never Giving Up

    What do you do when life gives you every reason to stop, but something inside you refuses to quit? My guest today is Jay Setchell, a Marine Corps veteran, serial entrepreneur, inventor, author, and the voice behind Never Quit Trying. Jay’s life story is not theoretical inspiration. It is lived experience. He grew up on a working farm, served in the Marine Corps, survived multiple near-death experiences, and has endured more than seventy surgeries.  His book, The Strength Within You: It’s Always Too Soon to Quit, explores the power of mindset, preparation, faith, resilience, and personal responsibility in the face of overwhelming adversity.  But this conversation is not just about survival. It is about what we do after the setback, after the accident, after the diagnosis, after the business failure, after life changes the plan.  For entrepreneurs, Jay’s message is especially relevant because building a business often requires the same thing rebuilding a life requires: discipline, ownership, courage, and the willingness to keep going when motivation is gone. Jay's Website: Never Quit Trying https://neverquittrying.com

    The Strength Within You: Jay Setchell on Resilience, Responsibility, and Never Giving Up

  8. Jul 15

    From Filmmaker to Al Founder: Jason Sherman on Reinvention and Resilience

    Most entrepreneurs do not fail because they lack ideas. They fail because they fall in love with the idea before they prove there’s a market, a customer, and a path to revenue. My guest today is Jason Sherman, and he has spent much of his career helping founders avoid exactly that trap. Jason is a technology entrepreneur, author, filmmaker, startup advisor, and AI founder. He is the author of Strap on Your Boots, a practical startup guide built around the lessons founders need most: validating ideas, understanding target markets, building MVPs, making data-driven decisions, and turning a concept into a real business. But Jason’s story is not just about startups. It is about reinvention. He has worked as a filmmaker, journalist, author, podcaster, teacher, software developer, and entrepreneur.  Today, he is also connected to the world of artificial intelligence through Vengo AI as their co-founder & CEO, where the focus is helping businesses use AI to engage customers, search company knowledge, and create more effective sales conversations. In this episode, we will talk about Jason’s own entrepreneurial journey, the mistakes he sees founders make again and again, how storytelling shapes business success, and how entrepreneurs can use AI without losing sight of the human problem they are trying to solve. VENGO AI https://vengoai.com SPINNR https://spinnr.app Strap on Your Boots https://tinyurl.com/bdh3s79z JASON SHERMAN's Website https://jasonsherman.org

    From Filmmaker to Al Founder: Jason Sherman on Reinvention and Resilience
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5
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About

I’m your host, Mike Konrad, the author of The Reluctant Entrepreneur - Anatomy of a Business Start-Up - From Uncertainty to Unstoppable, available on Amazon as a paperback, e-book, and an audible book, and I’m excited to share real stories that reveal the many paths people take to build their own businesses.  Whether you stumbled into entrepreneurship or you’ve always known it was your calling, this podcast is for you. Let’s start with what it means to be a reluctant entrepreneur. Many entrepreneurs don’t set out with a grand plan to build a business.  Maybe you worked for a company that didn’t value your vision, and one day you thought, “I could do this myself”, that was my story. Or maybe life pushed you in an unexpected direction—losing a job, facing a personal crisis, or discovering a passion that grew into a business. Reluctant entrepreneurs often find themselves starting a business not because they always dreamed of it, but because it was the best—or only—option available.  And then there are intentional entrepreneurs. These are the people who’ve known from the start that they were meant to create something of their own.  They may have planned meticulously, crafted their vision, and followed a well-laid path to build a business. Intentional entrepreneurs are often seen as risk-takers, those with a drive to innovate, disrupt, and lead in their industries.  But even with all the planning in the world, intentional entrepreneurs face their own share of unexpected challenges, setbacks, and doubts. On The Reluctant Entrepreneur podcast, we celebrate both types of entrepreneurs—the ones who jump in with both feet, and the ones who tiptoe cautiously into the water.  So, join me as we explore the many ways people navigate the complex and rewarding world of entrepreneurship.  Whether you’re here for inspiration, advice, or just a great story, I hope you find something valuable in every episode of The Reluctant Entrepreneur Podcast.

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