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iwon™ podcast with Michael J Thomas

iwon™ podcast with Michael J Thomas

By: Michael J Thomas
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IWON™ (It Wasn’t Over Night) is a long-form podcast for ambitious founders. Wherever you are at in your business journey, you'll get something from every episode and each guest. These are the people who been there and done it. If you want to understand what it actually takes to build and scale a successful company, iwon™ is worth listening to. Each episode features honest, in-depth conversations with founders, operators and growth leaders who have built, scaled, exited or survived in the tech world. Iwon™ is hosted by Michael J. Thomas. He is an experienced marketing strategist, Cambridge-accredited coach and founded DARWIN™ Works Marketing in 2011. This isn’t surface-level advice or recycled LinkedIn BS. It's the real stories. We go deep and unscripted with every episode and every guest. It’s the real story behind: • Early mistakes and failures • Fundraising realities and financial pressure • Product and growth decisions that changed everything • Sales lessons that cost years to learn • Mental health, leadership and resilience • What genuinely moves the needle From first customers to $750m exits, IWON reveals the thinking, trade-offs and hard-earned lessons you rarely hear in public. If you are building a SaaS or tech company, leading a product or growth team, or trying to grow without chaos, this podcast will give you perspective, clarity and practical insight from people who have done it for real. New episodes every two weeks. The names iwon and DARWIN are registered trademarks. This podcast and the opinion-based content herein are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd. Copyright 2026.Copyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd. Economics Leadership Management & Leadership
Episodes
  • AI Skills and Future of Work - Building a Gold Standard That Doesn't Exist (Yet) | Aatish Thakerar | iwon™ podcast Ep. 9.

    AI Skills and Future of Work - Building a Gold Standard That Doesn't Exist (Yet) | Aatish Thakerar | iwon™ podcast Ep. 9.
    Jun 25 2026
    AI is moving at a rapid pace. Most education institutions, schools and companies cannot keep up with it.While technology continues to reshape industries, careers, and the future of work, many education systems are still trying to figure out how to respond.In this 9th episode of the iwon™ podcast, Michael J. Thomas sits down with Aatish Thakerar, Co-Founder of Pedagogue, to discuss one of the biggest challenges facing education today: preparing the next generation for a world powered by AI.A former British Army Reservist, engineering leader, and startup founder, Aatish brings a unique perspective on technology, learning, leadership, and the realities of building a business in one of the fastest-moving industries on the planet.Before launching Pedagogue, Aatish founded and exited an AI startup before spending four years helping scale Climate X through multiple stages of growth. Along the way, he learnt first-hand what works, what doesn't, and why timing, distribution, and economics often matter more than founders realise.Together, Michael and Aatish explore AI literacy, startup lessons, product-market fit, education reform, future careers, large language models, agentic AI, and why schools must rethink what "elite education" means in the age of artificial intelligence.If you're a founder, educator, parent, student, or simply curious about where AI is taking us next, this conversation is packed with practical insights and thought-provoking ideas.In This Episode• Why AI is advancing faster than most education systems can adapt• What "elite education" looks like in the age of AI• Lessons from building and exiting an AI startup• Why timing, distribution, and economics matter in startup success• Product-market fit and knowing when to pivot• Why education became Pedagogue's focus• The future of work and the skills students need most• The opportunities and risks of large language models• Agentic AI, automation, and what comes next• Why founders should avoid outsourcing all of their thinking to technology• Leadership lessons from the British Army• Why human creativity still matters in an AI-powered futureChapters00:00 AI Is Moving Faster Than Education00:36 Welcome to the iwon™ podcast01:40 Building and Selling an AI Startup04:18 Startup Lessons, Risk, and Luck07:07 The UK vs Silicon Valley12:00 Product Market Fit and Enterprise Challenges14:14 The Palantir Problem16:17 Why Education Became the Focus17:34 What Is Elite Education Today?20:24 Why Schools Must Teach AI23:16 Why AI Could Increase Inequality25:49 Why Not Start With Government Contracts31:31 Is Pedagogue the Right Solution?34:00 The AI Boom and Startup Reality36:52 Why Most People Misunderstand AI38:00 Teaching AI Without Platform Bias41:08 Agentic AI and the Future46:00 How Founders Avoid Overengineering50:41 Leadership Lessons Beyond Technology54:28 Think Long Term and Compound56:00 Are We Outsourcing Thinking?57:50 Unknown Unknowns and Human Creativity58:52 Final ThoughtsConnect with Aatish ThakerarLinkedIn:https://www.linkedin.com/in/aatish-thakerar/Pedagogue:https://pedagogue.io/Pedagogue on LinkedIn:https://www.linkedin.com/company/pedagogue-schools/Connect with Michael J. ThomasLinkedIn:https://www.linkedin.com/in/realmjt-in/Stuck where you are with your SaaS or B2B tech product?Michael and the team at DARWIN™ Works help founders simplify their message, sharpen their positioning, and accelerate growth.Find out more:https://darwinworks.com/Learn More About the iwon™ podcastWebsite:https://www.iwonpodcast.comLinkedIn:https://linkedin.com/company/iwon-podcastSuccess isn't overnight.That's why we tell the real stories.Takeaways:Artificial intelligence is advancing rapidly, while educational systems struggle to keep pace with these developments.The incorporation of AI education in countries like China begins at a remarkably young age, highlighting deficits in the UK and US educational frameworks.The role of schools extends beyond traditional education; they must prepare students for the future of work, integrating technology into their curriculums.Founders must navigate the complexities of funding and commercial viability, particularly in the fluctuating landscape of AI and technology startups.Companies mentioned in this episode:PedagogueClimatexPalantirClaudeGrokBase44ReplitAnd many more.Disclaimer: The views expressed in this podcast are those of the individual speakers and do not necessarily reflect the views of the producers or associated organisations.This podcast is provided for informational and entertainment purposes only and should not be considered financial, legal, or professional advice.Trademarks and Copyright: The IWON™ Podcast is produced by DARWIN™ Works, a trading name of BlueEyed Digital Marketing Ltd.IWON™ and DARWIN™ are registered trademarks.All content is copyright © BlueEyed Digital Marketing Ltd 2026.
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    59 mins
  • The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8

    The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8
    Jun 11 2026
    Instagram wasn't an overnight success.Facebook required enormous funding.Most success stories take years.Most people see success and assume it happened quickly.Elizabeth Dodson knows better. What does it take to build a software company for 14 years without giving up?What looks like an overnight success story is actually the result of decades of learning, one successful software exit, countless pivots, thousands of conversations, and 14 years building HomeZada into a platform helping homeowners manage more than 100,000 properties.In this episode of the iwon™ podcast, Michael J. Thomas sits down with Elizabeth Dodson, Co-Founder of HomeZada, to discuss the realities of building a category-defining software company, creating strategic partnerships, navigating growth, and why success rarely happens as quickly as people think.Before HomeZada, Elizabeth helped grow and eventually sell Meridian Systems, a leading commercial construction project management software company.But it was a simple homeowner problem that sparked her next venture.After a costly hot water heater failure, she began searching for a way to manage home maintenance, inventories, warranties, and important property information. Despite the existence of sophisticated software used to build stadiums and skyscrapers, she couldn't find a solution designed for homeowners.So she decided to build one.In this conversation, Elizabeth shares the realities of creating an entirely new software category, the lessons learned from scaling multiple companies, and why persistence matters more than most founders realise.In This Episode• How HomeZada was born from a personal frustration• Why founders should hire people smarter than themselves• The importance of contracts, negotiation, and protecting your interests• Building strategic partnerships that create value for everyone involved• How A/B testing and customer language transformed HomeZada's growth• The challenge of educating a market when your category doesn't exist yet• Why technical founders often underestimate marketing• The truth about "overnight success"• Protecting customer data and maintaining trust• Setting boundaries and avoiding founder burnout• Why persistence matters more than most people realiseChapters00:00 Why Most Startups Fail00:36 Welcome to the iwon™ podcast01:48 The Problem That Led to HomeZada04:18 The Hidden Cost of Homeownership05:39 The Hot Water Heater That Changed Everything07:51 Searching for a Better Solution11:53 Lessons From Building and Selling Meridian Systems14:30 Contracts, Negotiation, and Protecting Yourself19:59 Why You Should Hire People Smarter Than You23:53 Learning an Entirely New Market30:10 The Challenge of Creating a New Software Category31:55 A/B Testing, Messaging, and Finding What Works35:54 Handling Naysayers and Unhelpful Praise39:31 Finding the Right Customer42:08 Why HomeZada Pivoted to Busy Professionals42:49 Don't Quit Too Soon43:40 Starting Again With a Blank Whiteboard44:26 Playing the Long Game45:34 The Growth Mindset Advantage46:55 The Myth of Overnight Success50:46 Building Something You're Proud Of52:30 Copycats, Competition, and Patience53:59 Life After a Successful Exit55:40 Why Being an Outsider Can Be an Advantage58:51 Protecting Customer Data and Privacy59:55 The Negotiation Trick Nobody Talks About01:01:59 Building Win-Win-Win Partnerships01:04:05 Why Many SaaS Companies Aren't Enterprise Ready01:06:53 Work-Life Boundaries as a Founder01:09:41 Not Every Fire Is an Emergency01:13:08 Advice for Technical Founders01:15:14 The Marketing Touchpoints Most Founders Ignore01:18:18 Final ThoughtsConnect with Elizabeth DodsonElizabeth Dodson, Co-Founder of HomeZadaLinkedIn:https://www.linkedin.com/in/edodson/HomeZada:https://www.homezada.com/Connect with Michael J. ThomasLinkedIn:https://www.linkedin.com/in/realmjt-in/Stuck where you are with your tech or software product?Michael and the team at DARWIN™ Works help SaaS and B2B technology companies create clarity, sharpen their positioning, and drive growth.Find out more:https://www.darwinworks.comLearn More About the PodcastOfficial Website:https://www.iwonpodcast.com
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    1 hr and 19 mins
  • Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7

    Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7
    May 28 2026
    This iwon podcast episode revolves around the entrepreneurial journey of Tolu Salami, the award-winning founder of LetPlant. He's an ex Google and Accenture employee with an innovative solution to plant care, combining software and hardware.This discussion dives into many of the challenges faced by founders and highlights the stark reality that only 1 in 200 entrepreneurs succeed, emphasizing the necessity for clarity in problem-solving.Tolu shares his personal experiences, including the pivotal moment that inspired him to create LetPlant after struggling to keep his own plants alive.He talks about the importance of validating ideas through customer engagement, suggesting that aspiring founders should not hesitate to seek feedback before fully developing their products. The episode serves as an invaluable resource for those interested in starting their own business, improving their current one and is a tactical entrepreneurship masterclass, offering insights into perseverance, the significance of understanding market needs, and the role of effective communication in achieving success.In this enlightening podcast episode, Tolu's personal entrepreneurial journey serves as a springboard for a broader discussion on the intersection of technology and sustainable living, as Tolu recounts how he discovered a community of individuals grappling with similar challenges through platforms like Reddit.This discovery not only validated his personal frustration but also illuminated the market gap that LetPlant seeks to fill by leveraging technology to assist users in maintaining their plants. The dialogue further explores the critical importance of validating business ideas before embarking on product development.Tolu highlights the importance (and tactics) to engage with potential customers to gather insights and understanding their needs, a practice he believes is crucial for any aspiring entrepreneur. He cautions against the common misstep of building a product in isolation, advocating instead for a strategy rooted in customer feedback and iterative design. The episode also touches upon the challenges Tolu faced in securing partnerships, particularly with Morrisons, illustrating the resilience required to navigate the competitive landscape of entrepreneurship. In conclusion, this episode serves as a rich tapestry of insights into the entrepreneurial process, emphasizing the need for authenticity, customer engagement, and the willingness to iterate based on feedback.Tolu's journey is a testament to the power of turning personal challenges into innovative solutions, inspiring listeners to cultivate their entrepreneurial spirits with a focus on real-world problem-solving and community-driven approaches.Takeaways:The podcast aims to unite founders who are innovating compelling solutions to complex problems.Tolu's venture, Letplant, addresses the prevalent issue of plant care through innovative technology.Validation of a business idea should stem from genuine customer interactions and feedback, not assumptions.The entrepreneurial journey is fraught with rejections, but perseverance is crucial to achieving success.Links referenced in this episode:letplantreddithenleybusinessangelspitchukCompanies mentioned in this episode:letplantGoogleMorrisonsHenley Business AngelsBootcareAccentureEnjoyed This Episode?If you found this conversation valuable, follow the show so you don’t miss future episodes with founders and growth leaders building in SaaS and tech.Leaving a 5-star review on Apple Podcasts or Spotify helps more aspiring entrepreneurs and founders in the trenches right now to discover the show. And, it supports the growth of the IWON™ community.About the HostMichael J. Thomas is a marketing strategist and Cambridge-accredited coach. He founded DARWIN™ Works Marketing in 2011, helping SaaS and tech companies overcome growth hurdles and build sustainable momentum.Learn more about Michael and DARWIN™ here:https://darwinworks.comAbout IWON™IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company.Find out more about the podcast: https://iwonpodcast.comInterested in being a guest? https://iwonpodcast.com/guests/Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/Michael J ThomasCopyright 2026 - iwon and DARWIN are registered trademarks. This podcast and those trademarks are wholly owned by, property of, and produced by - and is a DARWIN Works Production - a trading name of BlueEyed Digital Marketing Ltd.
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    36 mins
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