iwon™ podcast with Michael J Thomas

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• AI Skills and Future of Work - Building a Gold Standard That Doesn't Exist (Yet) | Aatish Thakerar | iwon™ podcast Ep. 9. 25.06.2026 58min

  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.
• The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8 11.06.2026 1u 18min

  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
• Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7 28.05.2026 36min

  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.
• From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6 14.05.2026 28min

  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.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.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.Sarah's insights serve as a clarion call for aspiring founders, emphasizing that fear should not deter one from pursuing their ambitions.Ultimately, the episode underscores the importance of community engagement and the iterative process of refining one's vision based on real-world feedback.Takeaways:Sarah Eggleston emphasizes that merely building a product does not guarantee its success; effective marketing is essential.The journey from corporate life to entrepreneurship involves significant challenges and requires resilience and adaptability.Networking and engaging with potential customers can provide invaluable insights before committing to product development.Successful founders often begin their ventures while still employed, balancing their time and resources effectively.Inclusivity in technology and software development is crucial for opening pathways for diverse talent across industries.Understanding the needs of customers and validating ideas through conversations is paramount for any aspiring entrepreneur.Companies mentioned in this episode:IBMfflowTreehouseEnjoyed 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™ podcastIWON™ (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.
• Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5 30.04.2026 1u 3min

  Summary of this episodeIn this conversation, Scott Truitt shares his journey from a comfortable career in enterprise software to pursuing his passion for music through his start-up, Sawtooth. He discusses the challenges of the music industry, the importance of artist compensation, and the need for a transparent platform that connects artists directly with their fans. Scott emphasizes the significance of embracing uncertainty, recognizing patterns in business, and balancing passion with financial realities. He believes in creating hope while defining reality, and he aims to build a music platform that prioritizes artists and their connection with listeners.What we discuss (Takeaways for Founders/CEOs)Scott's journey began in the late 90s, rooted in a passion for music.He transitioned from enterprise software to music entrepreneurship.The idea for Sawtooth emerged from a desire to support artists fairly.Scott emphasizes the importance of community and connection in music.He faced scepticism from industry veterans but remained determined.Embracing uncertainty is crucial for entrepreneurs.Pattern recognition helps identify opportunities in business.Scott aims to create a transparent music platform for artists and fans.The music industry is risk-averse and conservative, making change challenging.Scott believes in the importance of honoring one's passion and purpose.Chapters00:00 Introduction to Scott Truitt and Sawtooth vs Spotify01:26 The Journey Begins: Passion for Music04:46 The Evolution of an Idea10:23 The Call to Action: Leaving Comfort for Passion15:26 Navigating Uncertainty in Entrepreneurship21:58 Taking on Spotify: The Vision Behind Foreplay29:47 Balancing Hope and Reality in Business32:40 The Journey of Belief and Passion34:08 Embracing Failure as Experience36:33 Pattern Recognition in Business41:24 Building a Community Around Music45:16 The Economics of Music Consumption48:17 Navigating the Music Industry's Challenges52:26 Creating a Sustainable Business Model01:00:26 The Future of Music and OwnershipKeywordsScott Truitt, Foreplay, music industry, entrepreneurship, Spotify, artist compensation, music platform, business challenges, pattern recognition, transparency, iwon podcast, Michael J Thomas, founder podcast, business podcast, real, authenticEnjoyed 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.Companies mentioned in this episode:SpotifyWarp RecordsNapsterKleiner PerkinsHerokuInstagram
• £1M to £5M Revenue: It Could Kill Your SaaS Company | iwon podcast Episode 4 | Mark Blakemore 16.04.2026 36min

  Mark Blakemore, a seasoned financial expert with extensive experience in the SaaS sector, elucidates the critical financial pitfalls that SaaS founders frequently encounter. He introduces the concept of the "SaaS death zone," a precarious stage of growth where companies struggle to secure funding between one and five million in annual recurring revenue. Blakemore emphasizes the importance of maintaining a clear focus on cash flow, cautioning against the allure of overestimating sales prospects and the detrimental effects of slashing marketing budgets during challenging times. He advocates for founders to recognize their strengths and consider hiring specialists for areas outside their expertise, underscoring that financial prudence is paramount in navigating the complexities of scaling a SaaS business. Through this discussion, he provides invaluable insights for founders striving to survive and thrive in a competitive landscape.Mark Blakemore's appearance on the podcast provides invaluable insights into the financial intricacies of managing a SaaS company, particularly during critical growth phases. He introduces the concept of the 'death zone,' a term that encapsulates the struggles of startups with annual recurring revenues between one and five million dollars. This stage is marked by heightened difficulty in securing funding, as investors tend to shy away from companies that have not yet established full product-market fit. Blakemore's extensive experience as a CFO allows him to articulate the common financial missteps that can lead to a company's downfall, such as overly optimistic sales forecasts that fail to reflect actual buying intent. Blakemore stresses the importance of cash flow management, illustrating how essential it is for founders to maintain a clear understanding of their financial position. He advises establishing rigorous cash forecasts and maintaining a buffer to avoid financial crises. In addition, he warns against the temptation to slash marketing budgets during tough times, explaining that such cuts can have long-term repercussions on a company's growth trajectory. His recommendations advocate for a return to core competencies, urging founders to consider outsourcing financial responsibilities to specialists to enhance operational effectiveness. The conversation serves as a critical reminder of the need for prudent financial discipline in the fast-paced world of SaaS.Takeaways:SaaS companies often enter a challenging phase known as the death zone, which is marked by difficulty in securing further funding between one to five million in annual recurring revenue.It is crucial for founders to maintain a realistic outlook on their sales pipeline and avoid the trap of believing overly optimistic projections provided by sales teams.Effective cash flow management is vital; founders should establish detailed cash forecasts to avoid running out of cash unexpectedly.Marketing expenditures should be safeguarded, even during tough times, as cuts can lead to long-term adverse effects on lead generation and sales opportunities.Hiring specialists for areas outside of their expertise allows founders to focus on their strengths, leading to better outcomes for their businesses.Founders must approach potential investments with thorough forethought and not rely solely on optimistic forecasts from sales teams, fostering a culture of accountability.Links referenced in this episode:homerunfinance.co.ukContact Mark directly - mark at homerunfinance dot co dot ukCompanies mentioned in this episode:Home Run FinanceKingston CommunicationsEnjoyed 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.
• This Blind Spot Ruins Product-Market Fit & Growth | Scott Byrne-Fraser | iwon podcast 02.04.2026 1u 3min

  What if the thing slowing growth is not your product team, your marketing, or your users... but a founder blind spot?In this episode of the iwon™ podcast, Michael J Thomas speaks with Scott Byrne-Fraser about the hidden assumptions that cause founders to build the wrong features, chase the wrong outcomes, and lose touch with what customers actually need.Scott shares lessons from his work across product and UX, including experience with Amazon, BBC and DAZN, and explains why customer lifecycle thinking, retention, and real user behaviour matter far more than most teams think.You’ll learn:What the founder blind spot isWhy solving the wrong problem kills growthHow to think in outcomes, not just featuresWhy customer journey mapping mattersWhat DAZN’s Japan launch taught Scott about assumptionsWhy retention is one of the most overlooked growth levers in SaaSWho this is for:SaaS foundersTech foundersProduct leadersUX and CX professionalsTeams trying to improve retention and reduce churnWatch or listen here 👇YouTube: https://www.youtube.com/@realmjtApple: https://podcasts.apple.com/gb/podcast/iwon-podcast-with-michael-j-thomas/id1882021798 Spotify: https://open.spotify.com/show/629GCCMNKOJNblEtz99YbpEnjoyed 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™ PodcastIWON™ (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.Takeaways:The founders blind spot often leads to entrepreneurs focusing on the wrong problems, which can hinder their product's success.It is crucial for founders to understand the specific problems they are solving and for whom, as assumptions can lead to misguided development efforts.Recognizing and measuring customer behavior outcomes is essential for driving product improvements and ensuring user satisfaction.Founders must prioritize understanding their customer lifecycle and the associated metrics to maintain focus and avoid losing track of important goals.Companies mentioned in this episode:AmazonBBCDaznHundo
• From Zero to $750 Million: How to Build a High Performing Sales Team | Alex Sullivan Lepaffe | iwon podcast with Michael J Thomas 19.03.2026 40min

  This podcast episode features a compelling dialogue with Alex, a sales specialist who took one team and company to a $750m exit as sales person number one.He is also an investor, who wants to help founders and their sales people succeed.Believe it or not, the average failure rate of new salespeople is as high as 80 percent. Yet, Alex and his team have a remarkably high 95 percent success rate.80% of salespeople fail.That is the norm in many start ups.In this episode of IWON, Alex Sullivan Lepaffe CEO at The Sales People shares what founders consistently get wrong about hiring, sales leadership and scaling revenue.Alex has been there and done it. He was Sales Rep #1 at WorldFirst, which grew from zero to a $750m exit. He now helps founders design repeatable go-to-market systems that actually work.We discuss:Why hiring more reps rarely fixes salesThe VP of Sales mistake that can burn a year of runwayWhy inconsistent revenue is a warning signalHow to build demand generation before scaling headcountWhy great sales reps can fail in poorly designed systemsHow founders accidentally sabotage sales performanceIf you are building a SaaS company or scaling a B2B tech business, this episode will help you think more clearly about how to build a sales engine that scales.Connect with Alex:https://www.linkedin.com/in/alex-sullivan-lepaffe-21a7985/https://thesalespeople.co/Learn more about IWON, sponsorship and apply to be a guest:https://iwonpodcast.comThe 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.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.Takeaways:The podcast discusses the alarming 70-80% failure rate for new salespeople and how addressing hiring practices can significantly improve success rates.The speaker emphasizes that hiring for attitude and aptitude is crucial, as skills can be taught later, allowing for better team dynamics and overall performance.Founders are advised to closely monitor the mental wellbeing of their teams, as a healthy mindset is essential for sustained performance in high-pressure sales environments.The conversation highlights the importance of creating a supportive culture in sales teams, where feedback is encouraged and team members feel integral to the business's success.
• This Will Save You Years in Your Business | Christian Zigler (£24m + Multi-Exit Founder) on VCs, Hiring & AI 16.03.2026 54min

  This episode could genuinely save you years in business.Christian Zigler, my guest is a serial entrepreneur who previously founded and exited for around £24m. He has built, scaled, IPO’d and exited multiple companies across Europe.Christian shares hard-earned lessons for founders, start up leaders and tech entrepreneurs who want to avoid the most common early mistakes.Christian is a multi-exit tech founder and CEO at Tapp.He knows the mistakes that cost founders time, money and momentum. In this conversation, we talk honestly about what really builds a company and what quietly destroys one.We cover: Why success is usually a seven-year overnight storyThe real meaning of patience versus fail fastHow the wrong VC firm can derail your visionWhy corporate hires often struggle inside start upsThe danger of chasing big enterprise clients too earlyThe Steve Jobs Rule of Ten hiring principleWhen dilution is actually the smart moveWhy AI must sit at the core of your business, not bolted on later If you are building a SaaS company, launching a start up or leading a tech team, this conversation will sharpen how you think about growth, hiring, venture capital and product decisions.About Christian Zigler Christian is a serial tech entrepreneur with multiple exits and IPO experience.He is now building Tapp, an AI-driven platform delivering proactive intelligence and business insights.Connect with Christian Zigler on LinkedIn.Learn more about Tapp.About IWON This is Episode 1 of IWON. IWON, It Wasn’t Over Night, is a long-form podcast for ambitious founders who want the real story behind building and scaling technology companies. No hype.No overnight success myths. Just honest conversations about what it actually takes.Prefer to watch this episode? You can watch it all here: Youtube.Learn more about the iwon podcast.Work with Michael J Thomas and DARWIN Works Marketing.If this episode helped you, subscribe and turn on notifications.New founder conversations every two weeks. 00:00 Intro and Why Success Takes 7 Years02:18 Founder Stupidity and Patience07:04 The VC Mistake That Cost Millions14:12 Why Enterprise Clients Can Kill Startups20:30 Hiring Corporate Talent vs Startup Builders28:15 The Steve Jobs and the Rule of Ten35:48 Protecting Runway as a Founder45:22 AI Hype vs Real Competitive AdvantageCompanies mentioned in this episode:TapPhilip KotlerElon MuskMark ZuckerbergTinderAirbnbJeff BezosAmazonShopifyRevolutStripeSquareDojoMicrosoftThe 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.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.
• Welcome to IWON™. Because "It Wasn’t Over Night". It rarely is. 03.03.2026 1min

  Most successful tech companies don’t happen overnight.IWON™ (It Wasn’t Over Night) is a long-form podcast hosted by Michael J. Thomas, featuring honest, in-depth conversations with tech founders, operators and growth leaders who have built, scaled, exited or survived in the world of SaaS.This isn’t surface-level advice or recycled growth hacks.It’s the real story behind:• The early mistakes• The near failures• The fundraising pressure• The sales lessons that cost years• The mental health toll• The decisions that changed everythingFrom first customers to $750m exits, IWON explores what it actually takes to build a successful tech company.If you are building in SaaS, leading a growth team, or trying to scale without losing yourself in the process — subscribe and follow.New episodes every two weeks.Enjoyed 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™ Works Marketing 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.