iwon™ podcast with Michael J Thomas cover art

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

    From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6
    May 14 2026

    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

    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
    • Interested in being a guest? https://iwonpodcast.com/guests/
    • Want to sponsor IWON™ and help the community thrive? 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.
    Show More Show Less
    29 mins
  • Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5

    Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5
    Apr 30 2026
    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

    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
    • Interested in being a guest? https://iwonpodcast.com/guests/
    • Want to sponsor IWON™ and help the community thrive? 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
    Show More Show Less
    1 hr and 4 mins
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