The Reluctant Entrepreneur Podcast
Business & Finance
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.
Episodes
- Rocky Lalvani: Why So Many Businesses Run Out of Cash. Profit on Paper Doesn't Mean Cash in the Bank - Episode 82
Rocky Lalvani, founder of Profit Comes First, explains common cash flow problems and the Profit First philosophy. He shares insights from his entrepreneurial journey and advises on managing business finances to prioritize profit.
- Building a Brand Without Big Retail: Kate Assaraf's Main Street Strategy - Episode 80
Kate Assaraf, founder of DIP, discusses building her sustainable haircare brand into a seven-figure business. She shares her strategy of focusing on Shopify, building a loyal community, and supporting small, local retailers instead of trad…
- Growing the Founder: Andrew Poles on the Leadership Gap in Entrepreneurship - Episode 79
Andrew Poles joins The Reluctant Entrepreneur Podcast to discuss the leadership challenges entrepreneurs face as their businesses grow. He shares insights on how founders can develop the skills needed to lead larger teams and scale their c…
- Thinking Beyond Borders: How Bobby Casey Helps Entrepreneurs Build Global Businesses - Episode 78
Bobby Casey, guest on The Reluctant Entrepreneur Podcast, discusses how he helps entrepreneurs build global businesses. He shares his expertise in international tax strategy and global business structuring, focusing on protecting assets an…
- Entrepreneurship Without Borders: Brian Samson's Nearshoring Revolution - Episode 77
Brian Samson, founder of Plugg Technologies, shares his journey from traveler to entrepreneur, focusing on nearshoring and building global teams with Latin American tech talent. He discusses the insights gained from building companies acro…
- From Startup and Sale to M&A Advisor: Marty Fahncke’s Journey - Episode 76
Marty Fahncke, an experienced M&A advisor, shares his journey from startup and sale to advising on mergers and acquisitions. He discusses using acquisitions for company growth and strategies for maximizing business sale value.
- Seven Books and 5 Million Listeners: Dr. Lee Baucom’s Platform-Building Journey - Episode 75
This episode features Dr. Lee Baucom, a marriage therapist who became an entrepreneur. He shares his story of writing seven books and growing his podcast to 5 million listeners, discussing how expertise can lead to unexpected entrepreneuri…
- The Dog Days of Startup Life: How Courtney Honda and Slava Borisov Built Pupte - Episode 81
This episode features Courtney Honda and Slava Borisov, founders of Puptqe, a pet business that emphasizes community and experiences for dog lovers. They discuss their entrepreneurial journey and how they built a brand focused on human-dog…
- The Toy Store That Became a Case Study: Toys "R" Us and Where It Went Wrong - Episode 7
This episode examines the factors behind Toys "R" Us's decline, including its struggle to adapt to market evolution, supplier relationships, e-commerce challenges, and the impact of a leveraged buyout.
- Growing the Founder: Andrew Poles on the Leadership Gap in Entrepreneurship - Episode 79
Andrew Poles joins The Reluctant Entrepreneur Podcast to discuss the 'leadership gap,' the challenge entrepreneurs face in developing the skills needed to lead at scale. The episode covers the pressure of business growth and the importance…
- The Accidental Entrepreneur: How Renee Hastings Turned Executive Support Into a Business - Episode 74
Renee Hastings explains how she founded Executive Help Now by leveraging her executive assistant skills to help entrepreneurs delegate tasks. The episode covers her transition into entrepreneurship and the importance of delegation for busi…
- The Airline That Defined an Era - Why Pan Am Couldn’t Survive the Next One - Episode 6
This episode discusses Pan American World Airways' pivotal role in shaping global aviation and the challenges it faced after deregulation. It examines how the airline's premium model became unsustainable when air travel shifted to a price-…
- Why Smart Entrepreneurs Still Struggle With Sales - With John Lester - Episode 73
This episode features John Lester discussing the common struggles entrepreneurs face with sales, identifying discomfort as an emotional and mindset issue rather than a skill gap. Lester, through his work at Attitude Selling, focuses on cha…
- Building a Business You Don't Lose Overnight: Lessons from Cybersecurity - With Michele Novack #72
In episode 72 of The Reluctant Entrepreneur Podcast, guest Michele Novack discusses cybersecurity as a leadership problem for entrepreneurs. She explains how small businesses are vulnerable and the dangers of assuming cybersecurity is hand…
- What Most Entrepreneurs Miss About Scaling:Lessons From Ivan Vislavskiy - Episode 71
This episode discusses common mistakes entrepreneurs make when scaling, emphasizing the importance of systems and leadership over pure growth. Ivan Vislavskiy shares insights on shifting from operator to owner and building a sustainable bu…
- Why High Performers Burn Out and How to Avoid It: Chaz Wolfe's Lessons from the Top - Episode 69
This episode features Chaz Wolfe discussing the hidden costs of entrepreneurial success and the tension between achievement and fulfillment. Wolfe shares lessons on redefining the entrepreneurial win beyond financial milestones.
- The Unsexy Side of Entrepreneurship That Can Kill a Business - With Charles Read - Episode 68
This episode features Charles Read, founder of GetPayroll, discussing the crucial, often overlooked aspects of business operations like payroll, taxes, and compliance. Read shares insights on entrepreneurial risks and the importance of add…
- From Broke to Breakthrough: Ryan Clark on Strategic Messaging and Reluctant Entrepreneurship - #67
Ryan Clark shares his entrepreneurial journey, starting from bankruptcy due to ineffective messaging. He developed a contrarian marketing approach focusing on messaging foundations, which has helped clients generate over $35 million in sal…
- Rethinking Leadership Norms:Kim Miller-Hershon on What Actually Moves the Needle - Episode 66
This episode features Kim Miller-Hershon, an executive coach and leadership expert, who shares insights on essential business skills including communication, leadership, and productivity. The discussion covers practical advice for entrepre…
- If You Don't Define Your Brand, Al Will: Jason Barnard on Modern Entrepreneurship - Episode 65
Jason Barnard explains that AI systems, not just entrepreneurs, are defining brands today. He advises founders to take control of their digital narrative to ensure clear, consistent, and credible representation across modern search and AI…
- What Success Really Costs:Dr. Craig Cooke on Leadership, Growth, and Balance - Episode 64
In episode 64 of The Reluctant Entrepreneur Podcast, guest Craig Cooke discusses the hidden costs of entrepreneurial success, sharing insights from his journey of building and exiting a digital agency. He also explores conscious leadership…
- Reluctant Lessons: Where Businesses Go Wrong – Blockbuster: From 9,000 Stores to Bankruptcy - Episode 3
This episode analyzes Blockbuster's failure, highlighting its reliance on late fees, the missed Netflix acquisition opportunity, and resistance to change as key factors. It serves as a lesson for current businesses on the dangers of clingi…
- Becoming an Entrepreneur After You Start - Brittany & Michael Martin's Journey - Episode 63
Brittany and Michael Martin share their entrepreneurial journey, detailing the founding of Anchorfish Printing and the challenges of business ownership as a couple. The episode explores how entrepreneurship can begin with action and evolve…
- The Hidden Cost of Growth—and How Smart Entrepreneurs Avoid It - With Joe Patneaude - Episode 62
Joe Patneaude, an executive and business coach, discusses the challenges entrepreneurs face when success leads to longer hours and increased dependency. He shares insights on scaling businesses without burnout, transitioning from operator…
- Kodak: From 90% Market Share to Bankruptcy - Episode 2
This episode discusses Kodak's fall from a 90% market share and cultural dominance to bankruptcy. Despite inventing the digital camera, Kodak hesitated to embrace the future, choosing instead to protect its existing successful business mod…
- Reluctant Lessons: Where Businesses Go Wrong - Rubbermaid - Episode 1
This episode of The Reluctant Entrepreneur Podcast examines the downfall of Rubbermaid, detailing strategic errors like customer dependency and pricing miscalculations that led to a significant loss of value and control. It highlights the…
- How to Be a Non-Technical Founder in a Technical Industry: Lessons from Colin Hirdman - Episode 61
Colin Hirdman, co-founder of Rainmaker and founder of Wrappt, discusses his journey as a non-technical founder in the tech industry. He shares insights on building companies, leveraging AI, and overcoming the belief that a technical backgr…
- When High Performance Breaks You:Tim Thomas on Recovery and Reinvention - Episode 60
Tim Thomas shares his journey from Australian Special Forces to entrepreneurship, detailing his personal recovery from high-pressure performance and how it led to a business focused on breathwork, sleep, and recovery.
- Building a Business That's Bigger Than the Founder - With Brandon Moon - Episode 59
This episode features Brandon Moon, COO at TD Pine Advisors, who shares insights on building scalable businesses that are not dependent on the founder. He covers moving from chaos to clarity, owner-dependency to sustainable companies, and…
- The Reluctant Spotlight: How Kelly Schuknecht Built a Business Helping Others Be Seen - Episode 58
This episode features Kelly Schuknecht, a marketing strategist who helps entrepreneurs, authors, and experts gain visibility. She discusses her entrepreneurial journey, the challenges of self-promotion for capable business owners, and how…
- Risk, Growth & The Amazon Playbook with Steve Anderson - Episode 57
Steve Anderson, author of The Bezos Letters, joins The Reluctant Entrepreneur to discuss applying Amazon's principles of growth, risk management, and long-term thinking to businesses of all sizes. The episode explores how calculated risk a…
- The Entrepreneur's Secret Weapon: Smart Pricing with Per Sjöfors (AKA The Price Whisperer) - Episode 56
Per Sjöfors, also known as The Price Whisperer, joins The Reluctant Entrepreneur Podcast to discuss the importance of strategic pricing for entrepreneurs. He shares insights on making data-driven pricing decisions, challenging the common p…
- The Crash That Changed Everything: Alan Lazaros on Turning Tragedy into Transformation - Episode 55
In this episode of The Reluctant Entrepreneur Podcast, guest Alan Lazaros discusses his journey of redefining success following a near-fatal car accident. He explores the importance of fulfillment, self-awareness, and mindset in both profe…
- Revenue Is Loud, Profit Is Quiet:Emmanuel Skevoilax on the Truth Behind the Numbers - Episode 54
Emmanuel Skevoilax joins The Reluctant Entrepreneur Podcast to explain why revenue growth doesn't guarantee success. He shares insights on understanding financial numbers, simplifying decision-making, and building a resilient, profitable b…
- From the Fairway to the Boardroom: Lessons Building & Exiting a Sports Tech Startup - Spencer Dennis
Spencer Dennis, former competitive golfer, shares his unexpected journey founding and exiting a global sports technology company. The episode covers the realities of startup growth, capital, pressure, and exit strategies, drawing from his…
- The Making of an Entrepreneur: Mark Young on Growth, Failure, and Perspective - Episode 52
Dr. Mark Young shares his decades of entrepreneurial experience, discussing how growth, failure, and perspective shape business building. He emphasizes building trust and long-term value, drawing from his book 'Date Your Clients' and his w…
- Brand Storytelling for Purpose-Driven Entrepreneurs:Insights from Hanna-Mari Kirs - Episode 51
This episode features brand strategist Hanna-Mari Kirs discussing brand storytelling for purpose-driven entrepreneurs. They explore how clarity, empathy, and purpose can build a strong brand, moving away from traditional hustle-driven mark…
- When Clients Operate @ Scale, Failure Isn't an Option - A Conversation w/ Ndevr Founder, Matt Dorman
Matt Dorman, founder of Ndevr, joins The Reluctant Entrepreneur to discuss building high-performance, scalable, and reliable web platforms. The conversation covers his entrepreneurial journey and the critical importance of speed and reliab…
- From Manuscript to Market:The Journey of an Entrepreneurial Author with Ally Machate - Episode 49
Publishing professional Ally Machate joins host to discuss her transition from traditional publishing to entrepreneurship. The episode also offers practical guidance for entrepreneurs on writing strategic books that provide value to their…
- Playing the Long Game:How Baseball Shaped Uri Geva's Approach to Entrepreneurship - Episode 48
Uri Geva, co-founder of Cookie Dough Bliss, discusses how lessons learned from professional baseball, such as accepting bad calls and moving on, translate to entrepreneurship. He shares his journey from baseball to business, the challenges…
- From the Classroom to the Real World: Dr. Christiane Schroeter's Entrepreneurial Pivot - Episode 47
Dr. Christiane Schroeter shares her journey from academia to entrepreneurship, launching Petite Practice to promote growth through small, intentional actions. The episode explores her transition, challenges, and how professionals can apply…
- From Self-Destruction to Systemization: Todd Hagopian's Entrepreneurial Reckoning - Episode 46
Todd Hagopian discusses his entrepreneurial journey, detailing how personal challenges and self-destructive behavior led him to develop systematic approaches for business transformation, focusing on eliminating stagnation and complexity to…
- An Entrepreneur's Journey to Fix What Business Owners Misunderstand About Money with Jen Fizer - #45
Jen Fizer, CEO of MKB & Co., shares her entrepreneurial journey and explains how business owners can achieve financial clarity. The episode covers cash flow, common bookkeeping errors, and leveraging accurate financial data for informed de…
- Why Engagement Matters More Than Ever in Business With Anders Boulanger - Episode 44
Anders Boulanger, CEO of Engageify and author, shares insights on re-humanizing business engagement using performance psychology. The episode explores how to create meaningful connections and build trust in an increasingly digital world.
- The 10X Leap Mindset: How to Overcome Barriers and Scale with Purpose With Steve Walsh - Episode 43
Steve Walsh, founder of Bison Equity Group and author of "Make the 10X Leap," joins The Reluctant Entrepreneur Podcast to discuss how founders can overcome personal growth barriers to scale their businesses. The episode covers the differen…
- Blueprints and Business Plans: Lance Cayko on Leading a Design-Build Firm - Episode 42
Lance Cayko, co-founder of Colorado-based F9 Productions, shares his career path from carpentry to architecture and co-founding his firm. He discusses balancing creativity and profitability, and lessons learned in leadership, risk, and gro…
- Comedy Meets Tech: Leanne Linsky's Journey from Stage to CEO - Episode 41
Leanne Linsky, founder of the live online comedy club platform Plauzzable, discusses her unique career path from business student and comedian to tech entrepreneur. The episode covers her journey, challenges, and insights gained from build…
- Be Different or Be Dead: Roy Osing on Audacious Leadership and Execution - Episode 40
Roy Osing, a former company president and author, shares insights on audacious leadership and execution with The Reluctant Entrepreneur Podcast. He details his journey from startup to billion-dollar sales and his philosophy on achieving ex…
- The Business of Patents: One Attorney's Path to Entrepreneurship - With Austin Bonderer - Episode 39
Austin Bonderer, a patent attorney with over 690 issued U.S. patents, discusses his entrepreneurial path from government service to founding his own firm. The episode covers the patent process, idea patentability, and common mistakes in in…
- Trading Madison Avenue for Main Street: Lindy Nowak’s Leap into Entrepreneurship - Episode 38
Lindy Nowak, former creative director for major brands, founded Up in a Day to help small businesses rapidly establish an online presence with professional websites. She shares insights on her transition from corporate life to entrepreneur…