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Durable Entrepreneurs

Durable Entrepreneurs

By: Sean O'Hara MBA
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 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. Economics Leadership Management & Leadership Personal Development Personal Success
Episodes
  • 12.Building a Powerful Business Network with Tiffany Anderson

    12.Building a Powerful Business Network with Tiffany Anderson
    Jul 8 2025
    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 before attending networking events, the power of shared values in fostering relationships, and the concept of leaving a positive "echo" that enhances one's personal brand. KEY TAKEAWAYS Simply showing up to networking events is not enough. Entrepreneurs need to approach networking with a clear strategy, treating it with the same importance as other business activities. Successful networking is about making meaningful connections rather than just transactional interactions. Establishing rapport and shared values can lead to long-term relationships that benefit both parties. Before attending an event, do your research on the organisation and its members. Prepare a few key points about yourself and questions to engage others, which can help ease nerves and facilitate conversations. The impression you leave on others is crucial. Your reputation and the way people talk about you after the event can significantly impact your networking success. Aim to create a positive echo that resonates beyond the initial meeting. Not every connection will be an ideal fit, but every interaction can lead to new opportunities. If a conversation doesn’t align with your current goals, consider how you can connect that person with someone else in your network, keeping the door open for future possibilities. BEST MOMENTS "Showing up is no longer the end goal. Showing up is step one in a list of best practices." "It's not about only the people in the room. It's about every single person that they're connected to." "If you don't know what your values are as a business, you need to start there." "The echo that you leave behind, and the way that people talk about you, matters." "If you're treating networking like an extra thing, that's exactly what it's going to be." 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/
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    53 mins
  • 11. Ed Gillcrist, USMC Helicopter Pilot and Co-Founder. Align with the Problems that Need Solving.

    11. Ed Gillcrist, USMC Helicopter Pilot and Co-Founder. Align with the Problems that Need Solving.
    Jun 30 2025
    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 emphasises the necessity of having difficult conversations, including letting go of employees who don't fit, to ensure the overall health of the organisation. KEY TAKEAWAYS Building a business is often more effective when you focus on your existing relationships and networks. This allows you to gain insights into the specific challenges potential clients face, enabling you to tailor your solutions to meet their needs. Successful entrepreneurs must be willing to pivot their business model based on market demands. Initially focusing on training systems, the Shackleton Group shifted to organisational development because that was what their network needed. When building a team, prioritise hiring individuals you trust and who demonstrate the potential to grow within the organisation. Establish clear criteria for hiring and ensure that the interview process is genuine and relevant to the roles being filled. Effective leadership involves not only rewarding good performance but also holding team members accountable. This includes making tough decisions, such as letting go of employees who are not a good fit for the organisation, to ensure the overall health of the team. In both military and business environments, sound judgment is crucial. While systems and procedures are important, they should never override the need for critical thinking and adaptability in complex situations. BEST MOMENTS "We unfortunately stuck our hand in the blender a few times over the years and hopefully we can share some of this stuff and it helps people realise, ouch, that hurts, don't need to go there." "By focusing on your existing network, you have more access to the problems and the challenges that they're specifically facing." "Hire people you'll trust. And then trust the people you hire." "Sometimes you gotta cut a man loose. You have to be willing to look at people and fire them." "None of the procedures or statements or steps in this book is intended to ever usurp good judgment and good thinking." 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/
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    1 hr and 1 min
  • 10. Paolo Narciso. Profitably Tackling the "Most Wicked" Problems.

    10. Paolo Narciso. Profitably Tackling the "Most Wicked" Problems.
    Jun 23 2025
    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 of society's most pressing issues, particularly in healthcare. KEY TAKEAWAYS Founders should prioritise the sustainability of their business rather than merely aiming for rapid scalability. This involves ensuring that the organisation can endure over time while maintaining its culture and achieving its original vision. Transitioning from a founder to a CEO requires a significant shift in mindset. Founders must acknowledge their new responsibilities and develop the necessary skills, both hard and soft, to lead an organisation effectively. Founders should engage in self-reflection to understand their motivations for growth and the changes they need to make. This internal change is crucial for external success and helps in building a sustainable organisation. It is essential to continuously monitor the effectiveness of strategies and be willing to adapt them based on real-time feedback. Regular evaluation helps ensure that the organisation is on the right path to achieving its objectives. As organisations grow, founders must learn to delegate responsibilities and trust their team members. This involves hiring individuals with diverse skills and allowing them to contribute in ways that enhance the overall success of the business. BEST MOMENTS "The moment you recognise that need for growth is the moment of self-reflection." "Sustainability is about how do I create that future, not scaling." "If the ladder is not leaning against the right wall, every step just gets you to the wrong place faster." "The most successful founders are the ones that scratch their own back." "Change doesn't happen if somebody doesn't internalise it." 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/
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    45 mins
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