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iwon™ podcast with Michael J Thomas

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by Michael J Thomas

9 episodes
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Podcast Overview

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.

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Publishing Since

3/3/2026

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Recent Episodes

Episode thumbnail for The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8

June 11, 2026

The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8

<p>Instagram wasn't an overnight success.</p><p>Facebook required enormous funding.</p><p>Most success stories take years.</p><p><strong>Most people see success and assume it happened quickly.</strong></p><p>Elizabeth Dodson knows better. What does it take to build a software company for 14 years without giving up?</p><p>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.</p><p>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.</p><p>Before HomeZada, Elizabeth helped grow and eventually sell Meridian Systems, a leading commercial construction project management software company.</p><p>But it was a simple homeowner problem that sparked her next venture.</p><p>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.</p><p>So she decided to build one.</p><p>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.</p><h2>In This Episode</h2><p>• How HomeZada was born from a personal frustration</p><p>• Why founders should hire people smarter than themselves</p><p>• The importance of contracts, negotiation, and protecting your interests</p><p>• Building strategic partnerships that create value for everyone involved</p><p>• How A/B testing and customer language transformed HomeZada's growth</p><p>• The challenge of educating a market when your category doesn't exist yet</p><p>• Why technical founders often underestimate marketing</p><p>• The truth about "overnight success"</p><p>• Protecting customer data and maintaining trust</p><p>• Setting boundaries and avoiding founder burnout</p><p>• Why persistence matters more than most people realise</p><h2>Chapters</h2><p>00:00 Why Most Startups Fail</p><p>00:36 Welcome to the iwon™ podcast</p><p>01:48 The Problem That Led to HomeZada</p><p>04:18 The Hidden Cost of Homeownership</p><p>05:39 The Hot Water Heater That Changed Everything</p><p>07:51 Searching for a Better Solution</p><p>11:53 Lessons From Building and Selling Meridian Systems</p><p>14:30 Contracts, Negotiation, and Protecting Yourself</p><p>19:59 Why You Should Hire People Smarter Than You</p><p>23:53 Learning an Entirely New Market</p><p>30:10 The Challenge of Creating a New Software Category</p><p>31:55 A/B Testing, Messaging, and Finding What Works</p><p>35:54 Handling Naysayers and Unhelpful Praise</p><p>39:31 Finding the Right Customer</p><p>42:08 Why HomeZada Pivoted to Busy Professionals</p><p>42:49 Don't Quit Too Soon</p><p>43:40 Starting Again With a Blank Whiteboard</p><p>44:26 Playing the Long Game</p><p>45:34 The Growth Mindset Advantage</p><p>46:55 The Myth of Overnight Success</p><p>50:46 Building Something You're Proud Of</p><p>52:30 Copycats, Competition, and Patience</p><p>53:59 Life After a Successful Exit</p><p>55:40 Why Being an Outsider Can Be an Advantage</p><p>58:51 Protecting Customer Data and Privacy</p><p>59:55 The Negotiation Trick Nobody Talks About</p><p>01:01:59 Building Win-Win-Win Partnerships</p><p>01:04:05 Why Many SaaS Companies Aren't Enterprise Ready</p><p>01:06:53 Work-Life Boundaries as a Founder</p><p>01:09:41 Not Every Fire Is an Emergency</p><p>01:13:08 Advice for Technical Founders</p><p>01:15:14 The Marketing Touchpoints Most Founders Ignore</p><p>01:18:18 Final Thoughts</p><h2>Connect with Elizabeth Dodson</h2><p>Elizabeth Dodson, Co-Founder of HomeZada</p><p>LinkedIn:</p><p><a href="https://www.linkedin.com/in/edodson/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/edodson/</a></p><p>HomeZada:</p><p><a href="https://www.homezada.com/" rel="noopener noreferrer" target="_blank">https://www.homezada.com/</a></p><h2>Connect with Michael J. Thomas</h2><p>LinkedIn:</p><p><a href="https://www.linkedin.com/in/realmjt-in/" rel="noopener noreferrer" target="_blank">https://www.linkedin.com/in/realmjt-in/</a></p><h2>Stuck where you are with your tech or software product?</h2><p>Michael and the team at DARWIN™ Works help SaaS and B2B technology companies create clarity, sharpen their positioning, and drive growth.</p><p>Find out more:</p><p><a href="https://www.darwinworks.com/" rel="noopener noreferrer" target="_blank">https://www.darwinworks.com</a></p><h2>Learn More About the Podcast</h2><p>Official Website:</p><p><a href="https://www.iwonpodcast.com/" rel="noopener noreferrer" target="_blank">https://www.iwonpodcast.com</a></p>

Episode thumbnail for Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7

May 28, 2026

Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7

<p>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.</p><p>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.</p><p>Tolu shares his personal experiences, including the pivotal moment that inspired him to create LetPlant after struggling to keep his own plants alive.</p><p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>Takeaways:</p><ul><li>The podcast aims to unite founders who are innovating compelling solutions to complex problems.</li><li>Tolu's venture, Letplant, addresses the prevalent issue of plant care through innovative technology.</li><li>Validation of a business idea should stem from genuine customer interactions and feedback, not assumptions.</li><li>The entrepreneurial journey is fraught with rejections, but perseverance is crucial to achieving success.</li></ul><br/><p>Links referenced in this episode:</p><ul><li><a href="https://letplant" rel="noopener noreferrer" target="_blank">letplant</a></li><li><a href="https://reddit" rel="noopener noreferrer" target="_blank">reddit</a></li><li><a href="https://henleybusinessangels" rel="noopener noreferrer" target="_blank">henleybusinessangels</a></li><li><a href="https://pitchuk" rel="noopener noreferrer" target="_blank">pitchuk</a></li></ul><br/><p>Companies mentioned in this episode:</p><ul><li>letplant</li><li>Google</li><li>Morrisons</li><li>Henley Business Angels</li><li>Bootcare</li><li>Accenture</li></ul><br/><h2>Enjoyed This Episode?</h2><p>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.</p><p>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.</p><h2>About the Host</h2><p>Michael 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.</p><p>Learn more about Michael and DARWIN™ here:</p><p><a href="https://darwinworks.com" rel="noopener noreferrer" target="_blank">https://darwinworks.com</a></p><p></p><h2>About IWON™</h2><p>IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company.</p><ul><li>Find out more about the podcast: <a href="https://iwonpodcast.com" rel="noopener noreferrer" target="_blank">https://iwonpodcast.com</a></li><li>Interested in being a <strong>guest</strong>? <a href="https://iwonpodcast.com/guests/" rel="noopener noreferrer" target="_blank">https://iwonpodcast.com/guests/</a></li><li>Want to <strong>sponsor</strong> IWON™ and help the community thrive? <a href="https://iwonpodcast.com/sponsors/" rel="noopener noreferrer" target="_blank">https://iwonpodcast.com/sponsors/</a></li></ul><br/><p>Michael J Thomas</p><p>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.</p>

Episode thumbnail for From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6

May 14, 2026

From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6

<p>Sarah Eggleston's journey from her two-decade tenure at IBM to the establishment of her own startup encapsulates the multifaceted challenges and triumphs inherent in the entrepreneurial landscape.</p><p>In our conversation, she articulates the harsh reality that merely building a product does not guarantee its success; potential customers must be aware of its value and relevance to their needs.</p><p>Throughout the discussion, we explore the nuances of transitioning from corporate life to entrepreneurship, highlighting the importance of understanding consumer pain points and the necessity of proactive engagement with potential users before investing resources into product development.</p><p>Sarah's insights serve as a clarion call for aspiring founders, emphasizing that fear should not deter one from pursuing their ambitions.</p><p>Ultimately, the episode underscores the importance of community engagement and the iterative process of refining one's vision based on real-world feedback.</p><p>Takeaways:</p><ul><li>Sarah Eggleston emphasizes that merely building a product does not guarantee its success; effective marketing is essential.</li><li>The journey from corporate life to entrepreneurship involves significant challenges and requires resilience and adaptability.</li><li>Networking and engaging with potential customers can provide invaluable insights before committing to product development.</li><li>Successful founders often begin their ventures while still employed, balancing their time and resources effectively.</li><li>Inclusivity in technology and software development is crucial for opening pathways for diverse talent across industries.</li><li>Understanding the needs of customers and validating ideas through conversations is paramount for any aspiring entrepreneur.</li></ul><br/><p>Companies mentioned in this episode:</p><ul><li>IBM</li><li>fflow</li><li>Treehouse</li></ul><br/><h2></h2><h2>Enjoyed This Episode?</h2><p>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.</p><p>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.</p><h2>About the Host</h2><p>Michael 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.</p><p>Learn more about Michael and DARWIN™ here:</p><p><a href="https://darwinworks.com" rel="noopener noreferrer" target="_blank">https://darwinworks.com</a></p><p></p><h2>About iwon™ podcast</h2><p>IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company.</p><ul><li>Find out more about the podcast: <a href="https://iwonpodcast.com" rel="noopener noreferrer" target="_blank">https://iwonpodcast.com</a></li><li>Interested in being a <strong>guest</strong>? <a href="https://iwonpodcast.com/guests/" rel="noopener noreferrer" target="_blank">https://iwonpodcast.com/guests/</a></li><li>Want to <strong>sponsor</strong> IWON™ and help the community thrive? <a href="https://iwonpodcast.com/sponsors/" rel="noopener noreferrer" target="_blank">https://iwonpodcast.com/sponsors/</a></li></ul><br/><p>Michael J Thomas</p><p>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.</p>

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What is iwon™ podcast with Michael J Thomas?

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.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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