The Reluctant Entrepreneur Podcast

Mike Konrad
  • 5.0 (3)
  • 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. 4d ago

    The Entrepreneur’s Next Move: Build, Buy, or Both? Karl Hughes on Growing a Business

    What does it take to grow a business by building it, buying one, or combining both approaches? In this episode of The Reluctant Entrepreneur, Karl Hughes shares his path from leading software teams to founding Draft.dev, which grew to $2.5 million in revenue within two years. He also discusses his move into acquiring and growing podcast production companies, including the lessons he learned from bringing established businesses together. We talk about the challenges of rapid growth, how to decide whether to build or buy, what entrepreneurs should focus on after an acquisition, and how Karl’s definition of success has changed along the way. One entrepreneur. Eight questions. Thirty minutes. Lessons you can use. Draft.dev https://draft.dev The Podcast Consultant https://thepodcastconsultant.com

    The Entrepreneur’s Next Move: Build, Buy, or Both? Karl Hughes on Growing a Business

  2. Oct 13

    WHEN FEAR BECAME MY BUSINESS PARTNER - IT COST ME 49% OF MY COMPANY

    WHEN FEAR BECAME MY BUSINESS PARTNER IT COST ME 49% OF MY COMPANY One of the most expensive decisions I ever made didn’t cost me anything on the day I made it. I gave away 49 percent of my company. My business partner agreed to work for the first year without a salary in exchange for sweat equity. His contribution was legitimate, and when I decided to buy him out, I paid him the salary he had deferred. But the ownership negotiation was another matter. He demanded $200,000. The company had only $10,100 in the bank. I withdrew $10,000 in twenty-dollar bills, leaving the company with just $100. During a meeting with our attorneys, I slowly built a pyramid of cash in the center of the conference table. “That’s it. That’s all the money I have. Take it or leave it.” His attorney called it a cheap stunt. My partner took the money. This episode isn’t about blaming my former partner. The mistake was mine. I allowed fear, insecurity, and assumptions to influence one of the most important decisions an entrepreneur can make. In Episode 6 of Lessons From a Reluctant Entrepreneur, I share what happened when fear disguised itself as sound business judgment and why a temporary insecurity can create a permanent obligation. Before making a major decision, ask yourself: Would I make this same decision if I weren’t afraid? #Entrepreneurship #BusinessLessons #Leadership #BusinessOwnership #ReluctantEntrepreneur

    WHEN FEAR BECAME MY BUSINESS PARTNER - IT COST ME 49% OF MY COMPANY

  3. Oct 8

    Protecting the Margin: Viktor Popovic on Payments, Pressure, and Founder Decisions

    Every entrepreneur loves the sound of a sale being made. The customer says yes, the invoice gets paid, the transaction goes through, and for a brief moment, everything feels like it’s working. But then comes the part we don’t always talk about. The fees. The margins. The systems. The hidden costs of getting paid. And for many business owners, those small percentages add up to something much larger than they realize. Today’s guest is Viktor Popovic, President of Avendo, a company focused on helping businesses rethink the way they process payments, protect margins, and build smarter systems around one of the most basic parts of business: getting paid. But this conversation isn’t just about payments. It’s about the entrepreneurial journey behind the solution. Viktor has built, sold, and returned to business ownership. He understands the pressure of making big decisions without perfect information, the importance of resilience, and the challenge of building a company that doesn’t depend entirely on the founder. In this episode, we’ll talk about how his early life experiences shaped his view of risk and leadership, what motivated him to jump back into entrepreneurship after selling his first business, and the moment he recognized that the payment industry needed a better answer. We’ll also talk about systems, margins, founder dependency, and what entrepreneurs can do before they’re forced to adapt under pressure. Avendo https://www.avendo.tech

    Protecting the Margin: Viktor Popovic on Payments, Pressure, and Founder Decisions

  4. Sep 26

    THE BUSINESS THAT COULDN'T BE SOLD - LOUIS SWART ON BECOMING THE BOTTLENECK

    Most people start a business because they want more freedom, more control, and the opportunity to build something of their own.  But somewhere along the way, many entrepreneurs discover that they haven’t created freedom at all. They’ve created a demanding job with an unreasonable boss: themselves. My guest today is Louis Swart, a business builder, coach, author, and founder of Ironbrij. Over a career spanning more than 35 years, Louis has built and sold companies, managed hundreds of employees, and learned firsthand what happens when a business becomes too dependent on its owner. His first business taught him a painful lesson when he discovered that it had little value without him.  He later applied those lessons to build more scalable companies, including one that sold for $5 million and another that grew to approximately $35 million in revenue with 450 employees. Louis is also the author of The B Myth: How Successful People Accidentally Build Businesses That Steal Their Lives. Today, he helps entrepreneurs escape the daily operational grind through smarter delegation, practical systems, virtual assistants, and the thoughtful use of artificial intelligence. IronBrij https://ironbrij.com.au

    THE BUSINESS THAT COULDN'T BE SOLD - LOUIS SWART ON BECOMING THE BOTTLENECK

  5. Sep 26

    The Weight No One Sees: Joshua Lee on Building a Business and Becoming a Leader

    Sometimes the career that looks safest is the one quietly taking you in the wrong direction. The résumé gets stronger. The paychecks keep coming. Every outward measure says you’re succeeding.  But somewhere inside, you realize that each step forward is carrying you farther from the work you were meant to do. Joshua Lee grew up in a small Alaskan town as the son of Korean immigrants. His family faced physical disabilities, financial hardship, and the kind of uncertainty that teaches you how to become resourceful long before you understand what entrepreneurship means. Joshua went on to build an impressive career spanning finance, technology, venture capital, consumer products, and e-commerce. After investing more than $70 million in startups, he launched an Amazon brand in 2017 and exited it two years later.  He eventually founded First Light Studios, where he helps established product brands grow across Amazon, Walmart, Shopify, and other digital channels. But Joshua’s story isn’t simply about building and scaling brands. It’s about recognizing when the path you’re successfully following is no longer the right one.  It’s about the loneliness of entrepreneurship, the strain our decisions can place on the people closest to us, and what Joshua calls the “leadership weight” that few founders are prepared to carry. Today, we’ll explore the experiences that shaped Joshua, the decision to leave a secure career, the lessons he learned by becoming an operator, and what established brands must do to compete in a marketplace increasingly influenced by algorithms, advertising, and artificial intelligence. First Light Studios https://flstudios.website

    The Weight No One Sees: Joshua Lee on Building a Business and Becoming a Leader

  6. Sep 18

    The Problem Everyone Accepted: Tina Larsson on Building a Business by Asking Why

    Most people who discover that their building is wasting hundreds of thousands of dollars complain about it. My guest today helped organize a board takeover, fixed the problem, and accidentally discovered a business opportunity hiding inside the chaos. Some businesses begin with a carefully researched idea, a detailed plan, and a founder determined to become an entrepreneur. Others begin with a frustrating question: Why do the costs keep going up when no one can explain where the money is going? My guest today wasn’t searching for a business opportunity. She was trying to understand why her New York City co-op had raised its fees year after year while the building continued to be poorly managed. Drawing on their backgrounds in financial analysis, she and her husband began examining the building’s operations.  What they discovered led them to organize their neighbors, replace the majority of the board, and uncover hundreds of thousands of dollars in unnecessary expenses. But solving the problems in their own building revealed something much larger.  Co-op and condo boards throughout New York were facing similar challenges, often without the experience, information, or time needed to address them. That realization became the foundation of The Folson Group, a consulting firm that helps New York City co-op and condo boards reduce expenses, oversee major projects, improve governance, and protect the value of their buildings. Tina Larsson is the co-founder and CEO of The Folson Group. She’s also the author of Living the High Life: How Smart Co-op and Condo Owners Protect Themselves and Their Investment. Today, we’ll talk about how a Wall Street analyst became an accidental entrepreneur, what it took to turn one building’s problems into a successful consulting company, and why some of the best business opportunities are hiding inside problems everyone else has learned to accept. The Folson Group https://www.thefolsongroup.com Living the High Life: How Smart Co-op and Condo Owners Protect Themselves and Their Investment https://a.co/d/0fIJoH6A

    The Problem Everyone Accepted: Tina Larsson on Building a Business by Asking Why

  7. Sep 14

    The Exit Trap: Matt DiFrancesco on Planning Before It’s Too Late

    Successful business owners rarely ignore exit planning because they don’t care about the future. They postpone it because the business is thriving, customers keep coming, and leaving still feels years away. But waiting too long can reduce a company’s value, limit an owner’s options, and turn an expected transition into a difficult financial and personal crisis. We’ve explored exit planning with other guests, but this conversation examines it through a very different lens. Matt DiFrancesco is a Financial Advisor and Certified Exit Planner™ who has built his practice around the collision repair industry. These businesses often combine family ownership, expensive equipment, rapidly changing technology, skilled labor challenges, industry consolidation, and complicated succession decisions. In this episode of The Reluctant Entrepreneur, Matt explains why successful owners fall into the exit trap, what makes a business valuable without its founder, and why preparing for an eventual transition can improve a company long before the owner intends to leave. We also discuss Matt’s entrepreneurial journey, the advantages of serving a highly specialized market, and what business owners in every industry can learn from the challenges facing collision repair shops. High Lift Financial https://highliftfinancial.com

    The Exit Trap: Matt DiFrancesco on Planning Before It’s Too Late

  8. Sep 11

    Build the Moat First: Scherrie L. Prince on Protecting What Entrepreneurs Create

    Most entrepreneurs spend their time thinking about how to build a business. How do I find customers? How do I increase revenue? How do I grow faster? ' But far fewer stop to ask a different set of questions. What happens if my partner and I have a falling-out? What happens if the business is sued? What happens if I become seriously ill or die? And what happens to everything I’ve worked so hard to build if I never created a plan to protect it? Those aren’t particularly exciting questions. They don’t generate the same enthusiasm as launching a product, closing a major sale, or reaching a new revenue milestone.  But ignoring them can turn years of entrepreneurial success into years of financial and emotional pain. My guest today understands these risks from both sides of the desk. Scherrie L. Prince is an attorney, entrepreneur, asset protection coach, speaker, and host of the Play Big Faster Podcast.  She is also the founder and managing partner of Prince & Associates, where she helps entrepreneurs navigate business structure, contracts, regulatory compliance, asset protection, litigation, and succession planning. But Scherrie’s path into law was anything but conventional. She grew up on a farm in Mississippi, lost her mother when she was only 16, and later watched a painful family dispute unfold after her grandparents died without an adequate estate plan.  Before becoming an attorney, she worked in communications and operations, became a real estate broker and mortgage broker, and entered into a business partnership based largely on a handshake. The business performed well, but the partnership ultimately failed because it lacked the structure needed to survive. Then came the mortgage crisis of 2008. Scherrie lost her business and found herself starting over while raising two very young children.  That experience prompted a dramatic pivot into law school and eventually gave her a new mission: helping entrepreneurs protect the businesses, families, and legacies they’re working so hard to build. Today, Scherrie teaches entrepreneurs how to merge their business plans with their estate plans and create what she calls a moat around their assets. During the first part of our conversation, we’ll explore her unconventional journey from entrepreneur to law student, attorney, and business owner, including the personal and professional setbacks that shaped her work. Then, in the second part, we’ll discuss the legal and structural mistakes entrepreneurs commonly make, why forming an LLC isn’t enough, and how business owners can build companies that aren’t only positioned to grow, but structured to endure. Prince & Associates: https://scherrieprince.com Play Big Faster Podcast: https://www.youtube.com/@scherriespeaks

    Build the Moat First: Scherrie L. Prince on Protecting What Entrepreneurs Create
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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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