Durable Entrepreneurs

Sean O'Hara, MBA
  • 5.0 (16)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. Delegate to Accelerate Your Business Growth - with Renee Hastings

    4D AGO

    Delegate to Accelerate Your Business Growth - with Renee Hastings

    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 virtual assistant. We dive deep into the mindset shifts necessary for founders to overcome the fear of letting go, the importance of aligning with a team that shares your core values, and practical strategies for identifying which tasks to delegate first. Renee’s journey is a powerful testament to the idea that true success isn't found in doing it all yourself, but in empowering others to help you scale sustainably while protecting your peace. KEY TAKEAWAYS Hiring support isn't just about business efficiency; it's a critical investment in a founder's mental health and overall well-being. High personal standards can lead to burnout if you don't have the capacity to maintain them. Perfectionism shouldn't be a barrier to growth. Founders should spend the majority of their time on activities that move the needle financially. Everything else is a candidate for delegation. When building a support team, aligning on core values and work ethics is more important than just technical skills for long-term success. Effective delegation replaces negative, overwhelming stress with ‘eustress’, a positive stress that fuels innovation and excitement for the future. BEST MOMENTS "When you're operating on three hours of sleep, the quality of your work starts to suffer. You start to miss opportunities because you're burning the candle at both ends." "Delegation is not just a business move; it’s self-care. It’s an investment in your own mental health." "I had to battle my own fears of delegating and allowing someone else into my private circle, my bubble of life." "You should be spending all of your time in revenue-generating activities. Anything that is not a revenue generator is something that should be delegated." "A team could look like one person doing one thing or two people doing several things. All of it takes things off your plate so that you can focus on the things that you built the business for." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner.   This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    46 min
  2. Encore Episode: Transform Your Business Operations for Transformational Growth - with Jenna Monahan

    MAR 3

    Encore Episode: Transform Your Business Operations for Transformational Growth - with Jenna Monahan

    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 success, explaining why systems and ‘clear language’ are the bedrock of any sustainable company. KEY TAKEAWAYS Jenna emphasises that once you cross the ‘starting line’ of a project, the opportunity for deep planning vanishes. Front-loading the effort saves resources and prevents burnout. Whether it’s moving a surgical department or managing custom jewelry orders, the fundamental need for unified software, clear documentation, and consistent training remains the same. Leaders often dictate from the top, but the ‘genius ideas’ for efficiency usually come from the people on the front lines. Successful transformation requires their presence at the planning table. Businesses thrive when they move beyond mere transactions and build a brand that creates ‘fans’. This starts with an internal culture where every employee understands and believes in the company's ‘heartbeat’. Many founders become their own bottleneck because they try to do everything. Bringing in fractional leadership allows a founder to return to their ‘value-added work’ while an expert handles the operational heavy lifting. BEST MOMENTS "You can't spend too much time or you'll never get anything completed, but you lose that preparation once you start over the starting line; you'll never get that planning opportunity again." "There's no way that anybody in the executive suite or HR is going to be able to pluck those genius ideas that [frontline staff] are seeing the redundancy in." "The world has [other companies], the world needs us. And we need to make sure that we get loud and amplify the things that make us unique." "Customers will never love your company until your employees do." "The founders who succeed in the long term are the ones that stay agile and they're able to bend but not break and turn challenges into opportunities." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    49 min
  3. Get Your Pricing and Business Model Right - with Colin Sanburg, FinElevate Founder

    FEB 24

    Get Your Pricing and Business Model Right - with Colin Sanburg, FinElevate Founder

    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 strategic importance of premium pricing, the differences between starting a business from scratch versus acquisition, and why simple, forward-looking financial models are superior to dense accounting reports.  KEY TAKEAWAYS Successful entrepreneurs rarely operate in a vacuum; seeking out mentors who have already walked the path can dramatically shorten your learning curve. Unless you have the massive scale of a company like Amazon, a low-cost model is often a ‘race to the bottom’ that prevents you from investing in quality and talent. Buying an existing business allows you to ‘buy altitude’ by leveraging established momentum and revenue, which is often easier than creating momentum from thin air. Move away from dense, multi-page financial reports; focus on a high-level, six-line P&L to identify which parts of the business are actually driving growth. Durable entrepreneurs must be willing to ask ‘What did I do wrong?’ whenever a mistake occurs, rather than blaming employees or external circumstances. BEST MOMENTS "I would rather be the one in control. Give me that control, and I can at least trust myself that with my back against the wall, I'm going to do the right things." "The scary thing is, think how dumb the average person is and realise half of them are dumber than that. Once I was in a room full of people, I kind of thought, 'Okay, I can hang here.'" "You’re a man when you can do the work of a man, all the adults in the room have no idea what they're doing." "Easy choices, hard life. Hard choices, easy life." "A leader goes out and understands the complexity of the world so they can come back and simplify it for their team." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    48 min
  4. Power-Up Your Influence, Thought Leadership, and Personal Brand - with Kelly Schuknecht

    FEB 17

    Power-Up Your Influence, Thought Leadership, and Personal Brand - with Kelly Schuknecht

    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 four-step framework for building authority, leveraging LinkedIn, podcasting, public speaking, and book publishing. KEY TAKEAWAYS Building thought leadership is most effective through a tiered progression: establishing a presence on LinkedIn, guesting on podcasts, engaging in public speaking, and finally, publishing a book. Podcasting is not just about reaching a new audience; it is a critical tool for entrepreneurs to refine their messaging by learning what questions their market is asking. Kelly admits to a significant fear of public speaking but overcomes it by shifting her focus from herself to the value of the message she is providing the audience. Writing a book is a mountain many entrepreneurs fear, but ghostwriting services allow experts to extract their deep knowledge into a professional format without the time-consuming burden of writing it themselves. Successful entrepreneurship involves leading through the "messy middle," which requires business owners to manage their own stress so it doesn't negatively impact the health and productivity of their team. BEST MOMENTS "I believe that every business leader has an influential voice, you can grow your business by flexing your voice to become a recognised thought leader." "It's really about me refining my message, as you're asking me questions, I learn what people don't know about what I know."  "The fear is really just this internal thing that we have to get over because we have so much to share. It's not about you, it's about the message." "A lot of times people have built their business to a certain point and they're like, 'I know I need to do other things to continue growing, I just don't have the time.'" "I have to control my own need to get stuff done and move fast, because sometimes you've got to slow down to make sure you can keep moving forward." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    45 min
  5. Scale Your Business Without Chaos - with Matthew Person, Founder of Town Square Advisors.

    FEB 10

    Scale Your Business Without Chaos - with Matthew Person, Founder of Town Square Advisors.

    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 framework designed to help early-stage entrepreneurs navigate the complexities of scaling their businesses while maintaining a healthy, high-performing company culture.  KEY TAKEAWAYS This is defined as the known degree to which an employee can action their own ideas within set guardrails; defining this ‘box’ is the essence of corporate culture. True durable success is impossible without alignment across the staff; misalignment is tangible, creates friction, and often leads to organisational failure. Culture happens by default if it isn't designed by intent; without a structured framework, employees will set their own ‘squares’, leading to inconsistent ‘fiefdoms’ across departments. A well-defined culture acts as a screening tool for hiring; 50% of new hires fail within 18 months, often because they were hired for ‘gut feel’ rather than a specific fit for the company's ‘square’. BEST MOMENTS "If you don't actively design and build your company culture, your business will likely never achieve its highest potential." "The degree to which you constrain an employee's independence, is actually corporate culture." "An incomplete square is so common because they haven't figured out how to put the whole thing together. That is how you get fiefdoms and different ways of doing things." "Once you have trust, and I trusted and everyone trusted that they were in the same box, it allows you to not ask questions. You just know." "People don’t start their first day disgruntled, but 50% of them don’t make it 18 months. It’s obviously not working." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    47 min
  6. Meet Swyvvl. The Disruptors Coming for the Real Estate Giants.

    FEB 3

    Meet Swyvvl. The Disruptors Coming for the Real Estate Giants.

    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 Chad’s experience of sleeping in his office and car to keep his first brokerage afloat. They dive deep into how Swyvvl eliminates high referral fees charged by corporate giants like Zillow and Redfin, allowing real estate agents to compete by offering a portion of their commission back to their clients. KEY TAKEAWAYS Swyvvl is a nationwide home search platform that connects buyers and sellers with agents who compete by offering a portion of their commission, often ranging from $5,000 to $20,000, back to the client. The platform aims to eliminate the 30-50% referral fees that agents typically pay to large corporate platforms like Zillow and Redfin, redirecting that money to consumers to help with down payments and closing costs. Chad Link shares a powerful story of sleeping on his office floor and in his car for over a year during a divorce to ensure his business survived, emphasising that entrepreneurs must be willing to make extreme sacrifices. The success of Swyvvl relies on the synergy between Chad’s 20 years of real estate expertise and Rob’s background in technology and digital media. Swyvvl uses a blind ‘Share Experience’ bidding process where agents bid to represent clients based on home data without seeing personal details, ensuring a fair and competitive environment. BEST MOMENTS "If you're going to be an entrepreneur, you are going to walk that razor's edge more often than you want, whether that's financially, mentally, time-wise, or family-wise." "You better have that type of tenacity, if you're not willing to do it, don't start it, don't do it, because you're going to be one of these people that are going to wash out." "We are creating a new marketplace that allows homebuyers and sellers to be able to negotiate with real estate agents regarding that commission, rather than sharing it with a company that has absolutely nothing to do with the actual transaction." "It's almost like a marriage. We've got to respect each other's opinions, we've got to be able to trust one another." "You have to get comfortable being uncomfortable, there's not really a school for it, and they can be brutal on you." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    56 min
  7. Live Like an Energetic Millionaire - Tim Thomas (Part 2).

    JAN 27

    Live Like an Energetic Millionaire - Tim Thomas (Part 2).

    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 breathwork could rebuild his life and performance. Sean also reveals the results of his own challenge to implement Tim’s techniques, discussing how prioritising sleep and simple breathing exercises significantly improved his energy, mental acuity, and overall quality of life. KEY TAKEAWAYS Quality sleep isn't a luxury; it's a non-negotiable biological necessity. Sleep deprivation severely impacts mental health, increasing the likelihood of issues by 200-300% and hindering the body's ability to clear waste products from the brain. Engaging in simple breathwork exercises can interrupt the body's stress response (‘survival mode’), helping to regulate the nervous system, reduce anxiety, and transition the body into a state of rest and recovery. True high performance is built on a base of rest, recovery, and healing. Focusing solely on output (business goals, targets) without a solid foundation of recovery leads to burnout and diminishing returns. A simple ‘biohack’ for calming the nervous system involves splashing cold water on your face. This triggers the mammalian dive reflex, which instantly lowers heart rate and signals the body to conserve energy and reduce stress. You don't need hours of meditation. Consistent, small actions, like 15 minutes of breathwork before bed or taking three deep breaths during a stressful workday, can lead to massive improvements in sleep quality, mood, and mental clarity over time. BEST MOMENTS "Sleep is the soil that everything in your life is nourished in and grows from." "I was one of those guys who built his life on pushing hard, cashing in my tomorrows to live today, and eventually my tomorrows started catching up to me." "I realised if my team's having a bad day, I'm having a bad day. So simply by accessing breath, accessing better sleep. All of a sudden everything just became a whole lot more workable." "True high performance is built on a base of rest, recovery, and healing art forms. The top looks nothing like the bottom." "If you think life is hard, it's possibly hard to be around you. You're possibly the one in a crappy mood." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    50 min
  8. Say Yes, Figure It Out Later: The Creative Path to Breakthrough Opportunities - with Paul Pape.

    JAN 20

    Say Yes, Figure It Out Later: The Creative Path to Breakthrough Opportunities - with Paul Pape.

    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 his first business, and his ‘Say Yes, Figure It Out Later’ approach that landed him a high-stakes project building a life-size LEGO Seinfeld set.  KEY TAKEAWAYS When the market shifts or technology renders your product obsolete, you must be willing to pivot immediately. Standing rigid like a redwood will only lead to the collapse of your business; flexibility is the key to longevity. Growth often comes from accepting challenges you aren't fully prepared for. Whether it’s building a trophy for a worm-charming competition or a LEGO set for Jerry Seinfeld, trusting your ability to learn on the fly can open massive doors. Perfectionism kills momentum. Don't wait until a product is flawless to release it. Get it to a ‘done’ state, ship it, and refine it through future iterations based on real-world feedback. In the age of social media vanity metrics, entrepreneurs often obsess over viral fame. Paul argues you don't need millions of followers; you need 100 true fans who resonate with your specific passion to build a sustainable business foundation. In a crowded marketplace, your product is often just a commodity. The true differentiator is your story and your identity. When you sell who you are, the money becomes an exchange of value for your unique magic, not just a transaction for goods. BEST MOMENTS "You'll never be satisfied with perfect, you just gotta be satisfied with done." "Bend, don't break. I know too many people who stand as redwoods with their ideas, their ideologies, and their products. And what happens is when the seasons change, they can't adjust." "Quit selling your sh*t, sell yourself. You are the wizard. You are the magic item maker." "If you can run a lemonade stand, you can run a business. You just need to understand scaling. It's all it is." "There's 8.3 billion people on this planet. If you can find those 100 people [who love what you do], they will be your fans." HOST BIO Meet Your Host: Sean O’Hara, MBA – Entrepreneur, Sales Strategist, and Relentless Business Optimist. With over 20 years in the entrepreneurial trenches—guiding scrappy startups and Fortune 1000 giants alike—Sean brings a rare mix of strategic insight and real-world experience to every conversation. Known for his sharp sales acumen and down-to-earth style, he doesn’t just talk business—he lives it. Sean’s superpower? Asking the right questions, then stepping back to let the wisdom flow. His curiosity-driven interview style unlocks actionable insights, powerful stories, and the kind of truth today’s entrepreneurs actually need. If you’re serious about building a business that lasts, Sean’s the guide you’ll want in your corner. This Podcast has been brought to you by Disruptive Media. https://disruptivemedia.co.uk/

    49 min
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5
out of 5
16 Ratings

About

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.

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