Durable Entrepreneurs

Durable Entrepreneurs

Welcome to Durable Entrepreneurs – the podcast built for those who don’t just want to succeed, but want to last. Entrepreneurship is tough, but you don’t have to go it alone. Each week, we bring you raw, real, and practical insights from battle-tested entrepreneurs and sharp industry experts who’ve been through the trenches – and came out stronger. From breakthrough stories to road-tested strategies, we share the tools, mindset, and grit you need to build a business that not only grows, but endures. No fluff. No fake hype. Just powerful conversations to help you thrive long-term. Let’s build something that lasts. Welcome to Durable Entrepreneurs.

Episodes

A Tech Entrepreneur Talks AI Threats, World-Class Customer Experience, and ROI - with Orion Stewart

August 19, 2025 • 48 mins
What does it really take to build a business where customer service isn’t just a buzzword, but the heartbeat of everything you do? In this episode, Sean O’Hara sits down with Orion Stewart, co-founder of MSP Shift, to unpack his entrepreneurial journey and the lessons he’s learned along the way. From knowing when it’s the right time to bring in IT support, to why outsourcing often makes more sense than hiring in-house, Orion share...
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Planning Your Business Growth and Adapting to Change - with Claire Pickens.

August 12, 2025 • 54 mins
In today's episode, Sean sits down with Claire Pickens, a seasoned entrepreneur and founder of a successful veterinary hospital. Claire shares her remarkable journey from starting her veterinary practice, Your Family Veterinarian, to exiting it after 12 years, and her subsequent role in helping another startup grow from 20 to 127 locations in just four years. Throughout the conversation, Claire discusses the challenges she faced, t...
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Amp Your Productivity with 1 Surprising Habit Change - with Steve Frazier, Part 2.

August 5, 2025 • 59 mins
In this episode, Sean continues his insightful conversation with Steve Fraser, a seasoned entrepreneur who transitioned from the restaurant industry to the world of online natural health. Steve shares his personal journey, including the challenges he faced when his wife was diagnosed with Lyme disease, which led to the creation of a gluten-free pasta brand. The duo also discuss Steve's new book, "Release the Coffee Cuffs," where he...
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Brutal Truths and Big Wins - with Lifelong Serial Entrepreneur, Steve Frazier.

July 29, 2025 • 47 mins
In this episode, Sean interviews Steve Frazier, a seasoned serial entrepreneur with extensive experience in the restaurant industry. Steve shares his journey of owning and operating six different restaurants, starting from his first venture at the age of 28. He discusses the challenges and triumphs he faced, offering invaluable insights and actionable advice for early-stage entrepreneurs. Steve also emphasises the need for resilien...
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How to Show Up Strong for a Business Loan - with John Ward.

July 22, 2025 • 47 mins
Today, Sean sits down with John Ward, co-founder of CapitalPro Partners, to discuss the intricacies of financing for early-stage entrepreneurs. John shares his journey from the medical and banking industries to becoming a durable entrepreneur himself, emphasiszing the importance of understanding credit and the challenges business owners face when seeking financing. He provides valuable insights on how entrepreneurs can better posit...
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Prepare Your Team to Grow with You - with Tony Moore, The Culture Architect.

July 15, 2025 • 62 mins
In this episode of Durable Entrepreneurs, Sean sits down with Tony Moore, also known as the "culture architect," to discuss the critical importance of developing leadership within organisations. Tony shares his journey from a stable corporate career to becoming a successful entrepreneur, driven by a desire to impact more people. He acknowledges the common pitfalls of promoting leaders without adequate preparation and the need for a...
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Build a Powerful Business Network - with Tiffany Anderson

July 8, 2025 • 52 mins
Today, Sean engages in a discussion with Tiffany Anderson, a community engagement strategist and networking expert, focusing on the art of effective networking for early-stage entrepreneurs. Tiffany shares valuable insights on how to approach networking with a strategic mindset, emphasising the importance of building genuine connections rather than merely transactional interactions. She discusses the significance of preparation bef...
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Ed Gillcrist, USMC Helicopter Pilot and Co-Founder. Know Your Clients and their Problems!

June 30, 2025 • 61 mins
Sean sits down with Ed Gillcrist, a U.S. Marine and co-founder of the Shackleton Group, a leadership and organisational development firm. Ed shares his journey from being a Marine helicopter pilot to establishing a successful consulting business over two decades ago. He discusses the importance of leveraging existing networks, adapting business models to meet market needs, and the critical role of hiring the right people. Ed emphas...
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Profitably Tackling the "Most Wicked" Problems - with Paolo Narciso.

June 23, 2025 • 45 mins
In today's episode, Sean sits down for a conversation with Paulo Narciso, a seasoned entrepreneur and author of "The Founder's Journey." Paulo shares his insights on the importance of focusing on sustainability over scalability for early-stage entrepreneurs, emphasising the need for a mindset shift from founder to CEO as businesses grow. He discusses his role as a Build Fellow at Stand Together Ventures Lab, where he tackles some o...
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8 Start-ups and a 9-Figure Exit - with Lee Benson

June 17, 2025 • 48 mins
In this episode, Sean interviews Lee Benson, an accomplished entrepreneur and author of the best-selling book "Your Most Important Number." With a remarkable track record as an eight-time founder and seven successful exits, Lee shares his journey from being a high school cook to building a thriving aerospace business that saved customers over $200 million. Their conversation delves into the concept of value creation, emphasising th...
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CFO Insights. Make Better Informed Decisions & Watch the Cash Flow - with Bruce Smith

June 10, 2025 • 44 mins
Today, Sean sits down with Bruce Smith, a seasoned C-suite executive with over 30 years of experience in leadership roles across start-ups and large corporations. Bruce shares invaluable insights on leveraging data and business analytics to create actionable plans, emphasising the importance of transforming raw data into meaningful information. He discusses strategies for entrepreneurs in the prelaunch phase to validate their busin...
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Solopreneur Spotlight. Start a Daycare with Grant Funds. Ultimate Mom WFH Biz - with Delaney Mikolaycik.

June 3, 2025 • 40 mins
In this episode, Sean sits down with Delaney Mikolaycik as she shares her inspiring journey as the owner of Little Wildflowers, an in-home childcare business. Delaney discusses her background in working with children and how the challenges of the COVID-19 pandemic led her to discover grant funding opportunities for starting her day care. She provides valuable insights into the process of securing grants, navigating licensing requir...
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Win Government Contracts. Protect Quality of Life. Know Your Exit Strategy - with Chris Adams.

May 27, 2025 • 44 mins
In today's episode, Sean O'Hara sits down with Chris Adams, founder and CEO of Adams Engineering Solutions and Adams Business Coaching. Chris shares his journey from being a computer technician in the U.S. Air Force to launching his own successful IT services firm that supports federal agencies and private sector clients. He discusses the challenges he faced in building his business, the importance of mentorship, and the strategic ...
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Employee to Co-Founder. Winning with Strong Industry Partnerships - with Dan Gleissner.

May 20, 2025 • 41 mins
In this episode, Sean sits down with Dan Gleissner, co-founder of Ally Medical Partners, a medical real estate brokerage firm in Colorado. Dan shares his journey from being a sales representative to launching his own business, emphasising the importance of leveraging relationships and experience. He discusses the unique challenges of tenant representation in the healthcare sector, the significance of strategic partnerships, and the...
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From Snow Shovels to Coffee, Beer Festivals, and Venture Capital - with Matt Wilson.

May 20, 2025 • 40 mins
Today, Sean interviews Matt Wilson, an accomplished entrepreneur and venture capital investor. Matt shares his inspiring journey, starting from his early entrepreneurial ventures as a child shoveling driveways and running a coffee business, to his innovative role in launching Calgary Beer Week and a successful craft beer membership program. As the founder of Allied Venture Partners, Matt offers valuable insights into the world of a...
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Persistence and the Path to the Inc. 5000 - with Kyle Francis.

May 20, 2025 • 40 mins
In this episode, Sean interviews Kyle Francis, the founder of Professional Transition Strategies, a firm dedicated to assisting dentists in buying, selling, and creating their practices. Kyle shares his entrepreneurial journey, which began in a family of entrepreneurs and evolved through various experiences in the dental industry. He discusses the importance of strategic employment, the value of building relationships, and the less...
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Immigrant to Citizen to Pittsburgh Pirates VP - with Nayli Russo

May 20, 2025 • 57 mins
In this episode, Sean sits down with Nayli Russo, founder and CEO of Russo Leadership, a leadership consulting firm dedicated to helping organizations achieve their goals without fostering a burnout culture. Nayli shares her inspiring journey from being a pharmacist in Venezuela to becoming a prominent leadership consultant for Fortune 500 companies. She discusses the importance of intention, adaptability, and resilience in entrepr...
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Start Here. Meet Sean O'Hara, Your Durable Entrepreneurs Show Host

May 20, 2025 • 6 mins
In this very first episode of Durable Entrepreneurs, we meet host Sean O'Hara, who shares his extensive background in sales, business development, and entrepreneurship. With over two decades of experience, including founding a successful advertising agency and learning valuable lessons from a less successful energy drink vending machine venture, Sean emphasises the importance of resilience in business.  KEY TAKEAWAYS Sean has o...
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25 Years of Consulting Growth and a Surprising Approach to Landing Big Name Clients - with Jim Sartain.

May 20, 2025 • 54 mins
In this episode, Sean sits down with Jim Sartain, a seasoned entrepreneur with 25 years of experience in business consulting. Jim shares his unique journey from corporate leadership to founding two consulting firms, discussing the challenges and valuable lessons he learned along the way. He emphasizes the importance of having a clear "why" for entrepreneurship, the significance of leveraging networks, and the necessity of being ada...
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