Durable Entrepreneurs

Sean O'Hara, MBA

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. Turn Your Expertise Into a Book That Wins Clients and Builds Your Business - with Ally Machate

    20H AGO

    Turn Your Expertise Into a Book That Wins Clients and Builds Your Business - with Ally Machate

    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 & Schuster. The conversation delves into the strategic importance of writing a business book, emphasising how it can enhance credibility and open doors for entrepreneurs. Ally also highlights the critical timing for writing a book, the process of identifying a winning topic, and the essential steps for launching a book effectively. Five Key Takeaways Four Paths to Publication : There are four main options for publishing a book today: traditional publishing, DIY self-publishing, hybrid publishing, and supported indie publishing. Each has its own advantages and trade-offs, allowing authors to choose the best fit for their goals. Timing and Strategy : Writing a book can be a powerful tool for entrepreneurs, but it’s crucial to determine the right time to write one. Authors should have a clear understanding of their business and audience before investing time and resources into a book. Authority Through Authorship : Having a book can enhance an entrepreneur's credibility and authority in their field. It serves as a powerful marketing tool that can open doors to speaking engagements, partnerships, and client acquisition. Importance of Audience Focus : Successful books are those that not only reflect the author's passion but also address the needs and interests of the target audience. Authors should shift their perspective from what they want to say to what their audience wants to hear. Marketing and Reviews : The first 30 days after a book's launch are critical for gaining visibility on platforms like Amazon. Authors should have a strategic plan in place to gather reviews and promote their book effectively to maximize its impact and reach. 5 Direct Quotes "There are four paths to publication... traditional publishing, total DIY publishing, hybrid publishing, and supported indie publishing." "A book gives you a certain gravitas as a thought leader and as an expert." "If you're still trying to generate cash flow, a book is really not the right tool for that job." "The main difference is strategy, being really strategic about thinking about the book and how you want that book to work for you out in the world." "The first 30 days of that book's publication is really critical for Amazon's algorithm." 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
  2. How to Validate Your Startup Idea Before Spending a Dime: From Index Cards to Unicorns - with VC Andrew Ackerman

    MAY 5

    How to Validate Your Startup Idea Before Spending a Dime: From Index Cards to Unicorns - with VC Andrew Ackerman

    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 reality of surviving elite accelerators like Dreamit, and why the best entrepreneurs are actually "method actors" who master the art of customer empathy. Whether you’re pivoting a blog into a billion-dollar company like SeatGeek or just trying to nail your first elevator pitch, this conversation is a masterclass in durable entrepreneurship. 5 Key Takeaways Validate for pennies: Use a pack of index cards to mock up your app and watch real users interact with it before writing a single line of code. The Wizard of Oz Hack: Manually perform the "tech" behind the scenes with interns or spreadsheets to prove people will pay for the solution. Pivoting is progress: SeatGeek started as a blog curation site; a failed 0.2% conversion rate on their "Buy Now" button led them to their billion-dollar gold mine. Apply early: When applying to accelerators, get in before the directors have seen 800 other decks and lost their patience. Empathy is a business tool: Success comes from the ability to step out of your own head and truly feel the pain points of your customer. 5 Direct Quotes "There's a lot we can do before you spend six months with your hoodie up coding." "Avoid dead ends. Simply avoiding dead ends is a huge cost savings." "Money is oxygen to a startup. You run out, you're dead." "The problem with most business books is they're deathly boring." "The best entrepreneurs have that sense of empathy. Sometimes it's innate, sometimes they cultivate 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/⁠

    48 min
  3. Surviving the AI Gold Rush: A Guide for Small Businesses with Chris Hood

    APR 28

    Surviving the AI Gold Rush: A Guide for Small Businesses with Chris Hood

    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 launch of the iPhone. KEY TAKEAWAYS The Accessibility Revolution: AI has been around for a long time, but it has only recently become highly accessible to the general public. This shift is comparable to how mobile phones existed for years before the iPhone revolutionized their everyday use. Rapid Prototyping for Founders: Non-technical entrepreneurs can leverage AI tools to rapidly draft comprehensive business plans. These models can also help outline marketing strategies and generate the initial code required for a minimum viable product. The Scaling Barrier: AI is a highly effective tool for building an initial proof of concept. However, specialized human expertise remains essential for scaling software to support massive user bases and for creating true market differentiation. The Dangers of Degenerative AI: Over-relying on AI tools can significantly diminish human critical thinking, decision-making, and writing skills. Furthermore, when AI models are trained on their own generated content, it causes a degradation or "flattening" of human language. Prioritizing the Customer Experience: Businesses should avoid forcing AI automation on their customers if it does not actually improve the user experience. Instead, companies should offer clear choices, such as allowing users to easily bypass AI to speak with a human representative. BEST MOMENTS "We are seeing the same thing with AI where AI's been around for a while, but it wasn't until it became accessible through ChatGPT and OpenAI that all of a sudden now we have the power of this tool in our hands." "There are a lot of people out there that believe software developers are eventually going to go away. We're not going to need software developers because AI will be so good at doing the coding..." "Right now generative AI is a drug and people are addicted to it and they are unwilling or unable to see how it's impacting their lives." "If you rely on the AI to tell you what to do... you lost your opportunity to actually have a conversation with another human being who may have the exact same experience and to say, 'Which one would you get?'" "All of these names that people are tossing out to try to brand as something beyond what they are is solely an attempt to increase market and it's all marketing." 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
  4. The Drone Boss: Turning a Childhood Hobby into a Multi-Million Dollar Empire

    APR 21

    The Drone Boss: Turning a Childhood Hobby into a Multi-Million Dollar Empire

    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 indoor advertising blimps for the Dallas Stars, and eventually to training over 14,000 entrepreneurs on how to launch their own successful drone businesses. KEY TAKEAWAYS Perseverance is Your Greatest Asset: Damon’s very first drone crashed into pieces a mere seven seconds into its maiden flight. By choosing to spend the next six months rebuilding it rather than giving up, he learned early on that sticking with your vision through severe setbacks is the only way to achieve victory. Don't Accept "No" as Final; It Usually Just Means "Not Yet": When pitching his indoor blimp advertising concept, Damon faced rejection from 106 different promoters.  Sell the Vision and the Benefit, Not the Product: Many drone pilots fail because they introduce themselves by simply saying, "I fly drones." To succeed, you must position yourself as a problem solver.  Drones Have Profound Humanitarian Applications: Beyond commercial marketing and inspections, drone technology is actively saving lives. Damon's account of using a thermal-equipped drone to locate a missing Alzheimer's patient in 110-degree Texas heat in just 11 minutes highlights the critical, real-world impact of the industry. The Barrier to Entry is Incredibly Low: Unlike many traditional businesses that require massive overhead or brick-and-mortar investments, you can start a highly lucrative drone business with a $1,500 piece of equipment.  BEST MOMENTS  "That taught me such a powerful lesson that if you really wanted something bad enough and you just stuck with it regardless of what comes up or what tests you, you can ultimately become victorious." "I could have given up 106 times and never had it, and never figured it out, and just said everybody that said you can't make money with your hobby is right." "It wasn't a 'no,' it was just 'they don't understand yet.' They don't know that they need it yet, or they don't see the benefits yet. It was always a 'yet'." "The older we get, we forget what it's like. We learn to give up faster." "What we're offering with drones, you literally get to help almost any business make more money, save money, get more customers, introduce efficiencies, and oftentimes save lives." 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/

    51 min
  5. APR 14

    Become the Expert the News Media Wants to Interview- with Jill Lublin

    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; true PR occurs when you are interviewed or featured by a third party, which builds genuine thought leadership. Instead of simply talking about what you do, frame your pitch around "the problem today is" to offer direct value and benefit to the audience. When presenting a problem to the media, always follow up with three actionable solutions, keeping your language simple enough for a five-year-old to understand. Calculate the ROI of your media features by determining exactly how much it would have cost to pay for that same exposure or airtime as a traditional advertisement. Earning a spot on a local TV affiliate allows you to put major network logos (like ABC, NBC, CBS, or Fox) on your marketing materials, instantly elevating your credibility ahead of the competition. BEST MOMENTS "Social media is not publicity. [...] However if you're being interviewed by somebody, that's publicity." "The mistake that most people make is they talk about what I do. No, it's about the problem today is... and frankly giving them value and benefit." "I like uh three solutions. Why three? People can remember in threes, it's simple and most importantly actually keep it simple. Five-year-old language." "Anytime you're featured in media what we do as public relations professionals is measure it if you had paid for that space." "You want to be saying to people I've been featured in. It puts you way ahead of the competition and engenders trust." 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/

    30 min
  6. Flipping the Profit Equation: Sales Minus Profit Equals Expenses - with Rocky Lalvani

    APR 7

    Flipping the Profit Equation: Sales Minus Profit Equals Expenses - with Rocky Lalvani

    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 for the equation of sales minus profit equals expenses. KEY TAKEAWAYS Traditional accounting reports are typically designed to minimize effort for IRS tax returns rather than to help owners run their businesses effectively. Business owners should adopt a Profit First mentality by prioritizing their own profit before allocating funds to operating expenses. You can troubleshoot your business by breaking it down into main drivers like sales, profit, and cash flow. Diagnosing a struggling business is very similar to systematically finding the broken part in a washing machine. Increasing your prices slightly can lead to a disproportionately large increase in your gross profit due to the leverage effect on overhead costs. Many business problems arise because owners fail to measure vital metrics. This failure is akin to ignoring universal, predictable principles like gravity. BEST MOMENTS "If the report is sent to you in a PDF, I honestly think it's useless because you can't manipulate any of the data." "Those reports weren't created for business owners. They were created for accountants, for investors, for the IRS, not for you." "If you discounted and offered them 30 days, you just gave away your profit right to get a sale and now you have to deliver all that work." "We focus on gross profit. And the reason we focus on gross profit is that is what you have to run your business and pay yourself." "Because if you make more profit you have to pay more taxes. And who do you yell at when you pay more taxes? You don't yell at your Congressman or Donald Trump, you yell at your CPA." 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
  7. Collaboration Collapses Time on the Road to Success - with Chad Jenkins

    MAR 31

    Collaboration Collapses Time on the Road to Success - with Chad Jenkins

    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 from scratch. Chad breaks down his VCR Formula (Vision + Capability + Reach) and explains why the future belongs to those who can master Collaborative Intelligence in an increasingly AI-driven idea economy. KEY TAKEAWAYS Most business hurdles aren't caused by a lack of ideas, but a lack of specific talent, reach, or resources. Instead of hiring or building from zero, find a partner who already has that asset. Partnerships are about doing something together (often leading to legal disputes), while collaboration is about becoming something together where both parties maintain their equity and entities. Massive growth is a simple math equation: Vision (the idea) + Capability (the infrastructure to make it real) + Reach (access to the target audience). By leveraging established resources (like a partner's existing client base or manufacturing plant), you can launch and generate revenue in days or weeks instead of months or years. As AI takes over repetitive tasks, an entrepreneur’s value shifts from ‘task completion’ to ‘imagination and combination’, the ability to see how disparate resources can be combined for new value. BEST MOMENTS "Entrepreneurship is a grind, but you’re all about changing that mindset and that strategy completely." "I believe I was meant to be born where things move just a little bit faster. I had to learn leverage at a very early age." "If you and I are going to partner, we're going to go do something together. If we collaborate, we become something together." "The robots are coming, what’s going to be left? You came factory-installed with what you need to win in the Idea Economy: your imagination." "How do you relax and unwind? It’s not very sexy. I thirst for knowledge and I thirst for patterns." 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/

    52 min
  8. Your Story Drives Growth - with Andrew Poles

    MAR 24

    Your Story Drives Growth - with Andrew Poles

    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 success versus personal fulfillment.  KEY TAKEAWAYS While early-stage entrepreneurship often requires intense hours and "hustle," relying on that same mindset as the business grows prevents a founder from becoming a true leader. Success is hollow if it comes at the cost of irreplaceable personal moments. Andrew highlights how a single missed event at his daughter’s senior prom forced him to re-evaluate his "loyal soldier" mentality. The skills required to be a high-performing individual contributor are fundamentally different from the skills needed to lead a team.  Effective delegation requires "slowing down to speed up." Investing time in thorough training and clear context today prevents the need for micromanagement and "fixing" work later. A founder's primary job is to be the "Chief Storytelling Officer," providing the "Why, What, and How" that gives team members the context they need to think and act independently. BEST MOMENTS  "The pain of violating something important to you... is the fire that ultimately transforms you." "Not everything is actually existential. Not every single thing is a make-or-break moment for your company." "The skill set of being a hard worker and knowing how to personally produce results is completely, totally different from the skill set required to lead or manage other people." "You can't typically be successful if you don't know how to grind... but if that's the only thing you know how to do, you will get trapped." "Human beings are fundamentally, neurologically story-based in our interaction with the world... we act on the stories." 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
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.