iwon™ podcast with Michael J Thomas

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

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: * IBM * fflow * Treehouse 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 HOST 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. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT IWON™ PODCAST 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.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas 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.

Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5

SUMMARY OF THIS EPISODE In 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. CHAPTERS 00:00 Introduction to Scott Truitt and Sawtooth vs Spotify 01:26 The Journey Begins: Passion for Music 04:46 The Evolution of an Idea 10:23 The Call to Action: Leaving Comfort for Passion 15:26 Navigating Uncertainty in Entrepreneurship 21:58 Taking on Spotify: The Vision Behind Foreplay 29:47 Balancing Hope and Reality in Business 32:40 The Journey of Belief and Passion 34:08 Embracing Failure as Experience 36:33 Pattern Recognition in Business 41:24 Building a Community Around Music 45:16 The Economics of Music Consumption 48:17 Navigating the Music Industry's Challenges 52:26 Creating a Sustainable Business Model 01:00:26 The Future of Music and Ownership KEYWORDS Scott 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, authentic 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 HOST 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. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT 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.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas 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. Companies mentioned in this episode: * Spotify * Warp Records * Napster * Kleiner Perkins * Heroku * Instagram

£1M to £5M Revenue: It Could Kill Your SaaS Company | iwon podcast Episode 4 | Mark Blakemore

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.uk [https://homerunfinance.co.uk] * Contact Mark directly - mark at homerunfinance dot co dot uk Companies mentioned in this episode: * Home Run Finance * Kingston Communications 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 HOST 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. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT 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.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas 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.

This Blind Spot Ruins Product-Market Fit & Growth | Scott Byrne-Fraser | iwon podcast

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 is * Why solving the wrong problem kills growth * How to think in outcomes, not just features * Why customer journey mapping matters * What DAZN’s Japan launch taught Scott about assumptions * Why retention is one of the most overlooked growth levers in SaaS WHO THIS IS FOR: * SaaS founders * Tech founders * Product leaders * UX and CX professionals * Teams trying to improve retention and reduce churn Watch or listen here 👇 YouTube: https://www.youtube.com/@realmjt Apple: https://podcasts.apple.com/gb/podcast/iwon-podcast-with-michael-j-thomas/id1882021798 [https://podcasts.apple.com/gb/podcast/iwon-podcast-with-michael-j-thomas/id1882021798] Spotify: https://open.spotify.com/show/629GCCMNKOJNblEtz99Ybp [https://open.spotify.com/show/629GCCMNKOJNblEtz99Ybp] 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 HOST 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. Learn more about Michael and DARWIN™ here: https://darwinworks.com [https://darwinworks.com] ABOUT IWON™ PODCAST 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.com [https://iwonpodcast.com] * Interested in being a guest? https://iwonpodcast.com/guests/ [https://iwonpodcast.com/guests/] * Want to sponsor IWON™ and help the community thrive? https://iwonpodcast.com/sponsors/ [https://iwonpodcast.com/sponsors/] Michael J Thomas 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. 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: * Amazon * BBC * Dazn * Hundo

From Zero to $750 Million: How to Build a High Performing Sales Team | Alex Sullivan Lepaffe | iwon podcast with Michael J Thomas

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 sales * The VP of Sales mistake that can burn a year of runway * Why inconsistent revenue is a warning signal * How to build demand generation before scaling headcount * Why great sales reps can fail in poorly designed systems * How founders accidentally sabotage sales performance If 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://www.linkedin.com/in/alex-sullivan-lepaffe-21a7985/] https://thesalespeople.co/ [https://thesalespeople.co/] Learn more about IWON, sponsorship and apply to be a guest: https://iwonpodcast.com [https://iwonpodcast.com] 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 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.