Durable Entrepreneurs

Pride and weak accountability nearly pushed Eric Dingler’s business into bankruptcy. In this conversation, Eric tells Sean O’Hara how a side hustle grew into a digital marketing agency—and what he learned about leadership, hiring, and building a business that can operate beyond its founder. Eric began a business as a way to help fund his family’s international adoption. As the company grew, he had...

Episode Description David Nassief: From Two Years Away From Broke to a Seven-Figure Portfolio At 63, David Nassief was fired after 18 years with the same company—and realized his family could be broke by the time he turned 65. Six years later, at 69, he had built a seven-figure portfolio. In this episode of the Durable Entrepreneur Show , host Sean O’Hara talks with David about the difficult decis...

One letter can be the difference between owning a brand and watching someone else copy it. In this episode of The Durable Entrepreneur Show , intellectual property attorney and entrepreneur Richard Gearhart explains how founders can protect what they’re building—and why a promising idea needs more than a patent to become a successful business. Host Sean O’Hara speaks with Richard, founder of Gearh...

In this episode, Sean is picking the brilliant "social media mind" of nationally-recognized social  media expert, Shannon McKinstrie. Most businesses are making social media harder than it needs to be. Shannon reveals the simpler way to build attention, trust, and sales online without forcing yourself into a content machine that feels fake, exhausting, or random. If you have been posting...

Most side hustle entrepreneurs are trying to do the impossible on the wrong schedule. Alan Lazaros breaks down the hybrid model that lets you keep your day job, build your dream, and avoid the burnout that kills most early-stage businesses.  Sean O'Hara sits down with Alan Lazaros, founder and CEO of Next Level University and host of a top 100 podcast, for a brutally practical conversation ab...

Most entrepreneurs fear failure. Alisa Sparks nearly got crushed by success. In this conversation, the founder of Linden Creek home staging reveals how rapid demand, not collapse, nearly broke her business and how she built the systems, staffing, and mindset that turned a one-woman operation into a nationwide franchise. Sean O'Hara sits down with Alisa to unpack the real mechanics behind dura...

EPISODE DESCRIPTION - Most speakers try to be professional. Conor Cuneen proves that being memorable matters more - and that a well-placed smile can transform the way people trust, buy, and remember you. In this conversation, Sean O'Hara sits down with Conor, the voice behind Irishman Speaks , to unpack how a corporate setback became the launchpad for a speaking career built on resilience, hu...

In this episode, Sean interviews serial entrepreneur Scott Curry about his journey from struggling through five years of failure to building multiple successful online businesses. Scott candidly shares how a heartbreaking moment with his crying toddlers shifted his motivation from seeking personal independence to prioritizing family time, leading him to aggressively pursue automated income streams...

In this episode of the Durable Entrepreneur Show, host Sean welcomes Ally, a seasoned expert in the publishing industry, to discuss the evolving landscape of book publishing and its significance for entrepreneurs. Ally outlines the four main paths to publication—traditional, hybrid, supported indie, and DIY—while sharing her personal journey from a lifelong book lover to an editor at Simon & S...

Ever feel like you’re one "revelation" away from spending six months in a hoodie coding something nobody actually wants? Andrew Ackerman joins the show to explain why enthusiasm without experience is a trap and how a simple pack of index cards can save your business before it even starts. We dive deep into the "Wizard of Oz" approach to faking your product to prove pricing, the...

In this episode, Sean O'Hara sits down with AI expert Chris Hood to discuss the realities of artificial intelligence in business. Chris, who has advised Fortune 500 companies and worked at major corporations like Google and Disney, shares his insights from over 25 years in the tech industry. The conversation covers the newfound accessibility of AI, comparing its current adoption phase to the...

In this episode, Sean sits down with Damon Darnall, a lifelong aviation enthusiast and the founder of the Sky Eye Network. Damon shares his incredible entrepreneurial journey, which began in 1976 with a homemade drone that took 13 months to build and crashed in just seven seconds. Through sheer grit and perseverance, Damon transitioned from those early childhood failures to pioneering massive indo...

In this episode, Sean sits down with public relations master Jill Lublin to uncover the true power of PR for early-stage entrepreneurs. Jill clarifies the important distinction between posting on social media and securing genuine publicity, emphasizing that true PR involves being interviewed or featured as a thought leader.  KEY TAKEAWAYS Posting on your own social media channels is not publicity;...

In this episode, Sean welcomes Chief Profitability Advisor Rocky, who discusses why traditional financial statements often fail small business owners. He explains that standard profit and loss reports and balance sheets are primarily designed for IRS tax filing, not for optimizing real-world business strategy. Rocky introduces a critical mindset shift based on the Profit First system, advocating f...

Sean sits down with Chad Jenkins, a master of collaboration and the founder of SeedSpark and CoLab. Chad shares his journey from a curious kid on a South Carolina farm reading The Art of the Deal to launching over 50 successful businesses. They take a look at the 'who' deficiency that plagues most entrepreneurs and how to solve it by leveraging existing resources rather than starting fro...

In this episode, Sean welcomes Andrew Poles, a three-time founder and seasoned business coach with over 20 years of experience. Andrew discusses the critical transition from being a grinder to becoming an effective leader. He shares a deeply personal story of missing a milestone in his daughter's life to attend a meeting, which became a turning point in his understanding of professional succe...

Today, Sean sits down with franchise coach and consultant Adam Goldman to explore the world of franchise entrepreneurship. Adam shares his personal journey from selling a business in Europe to finding his niche in the U.S. and debunking common misconceptions about franchising, including the idea that it is limited to fast food or requires millions in capital. Their conversation dives deep into the...

In this episode, Renee Hastey, founder of Executive Help Now, joins Sean to discuss the pivotal moment that nearly broke her as an entrepreneur and how it led to a revolutionary shift in her business operations. Renee shares her raw experience of working multiple jobs on just three hours of sleep, the toll it took on her health and work quality, and the life-changing decision to hire her first vir...

In this episode, Sean sits down with Jenna Monahan, a seasoned operational expert and the founder of Steady Ground Strategies. Jenna shares her fascinating career journey, from managing massive logistical projects in major healthcare systems (like moving an entire hospital while patients were in beds!) to scaling a high-end jewelry startup. Jenna discusses the universal principles of operational s...

In this episode, Sean sits down with Colin Sanburg, a serial entrepreneur and the founder of Finn Elevate. Colin shares his journey into entrepreneurship, which began unexpectedly at 21 when he joined his stepfather's struggling business. He discusses the pivotal role a ‘firefighting’ CPA mentor played in teaching him the financial foundations of business success. They dive deep into the stra...

In this episode, Sean sits down with Kelly Schuknecht, the founder of 2 Mile High Marketing, to discuss how early-stage entrepreneurs can harness their unique voices to become industry-recognised thought leaders. Kelly shares her personal transition from a 20-year career in publishing and marketing to launching her own agency after a sudden layoff. The conversation dives deep into her strategic fo...

Today, Sean sits down with Matt Person, founder of Town Square Advisors and author of the upcoming book, ‘The Culture of Alignment: How to Intentionally Design High-Trust, High-Performance Organizations’. Matt shares his personal journey from a high-stakes career in professional sports management to founding his own consultancy. He introduces the Square Management System, a transformative framewor...

In this episode, Sean O'Hara sits down with Chad Link and Rob Brower, the co-founders of Swyvvl. Swyvvl is a revolutionary real estate marketplace designed to disrupt the traditional industry model by putting money back into the pockets of homebuyers and sellers. Chad and Rob share their entrepreneurial journeys, including the personal and professional challenges they’ve overcome, such as Cha...

In this episode, Sean welcomes back former MMA fighter and Special Forces soldier Tim Thomas. Their discussion centers on the transformative power of breathwork, particularly its role in optimising recovery, enhancing sleep, and managing PTSD. Tim shares his personal journey from hitting rock bottom, facing undiagnosed PTSD, severe fatigue, and relationship breakdowns, to discovering how breathwor...

Today, Sean sits down with Paul Pape, a creative powerhouse known as the ‘Santa for Nerds’. Paul shares his incredible 20-year journey from inventing pop-out architectural furniture to creating viral custom collectibles and props for giants like The Tonight Show, Disney, and Nickelodeon. They discuss the critical ‘Bend, Don't Break’ mindset that saved Paul’s career when technology threatened...