iwon™ podcast with Michael J Thomas copertina

iwon™ podcast with Michael J Thomas

iwon™ podcast with Michael J Thomas

Di: Michael J Thomas
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A proposito di questo titolo

 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. Economia Gestione e leadership Leadership
Episodi
  • 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.
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    29 min
  • 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
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    1 ora e 4 min
  • £1M to £5M Revenue: It Could Kill Your SaaS Company | iwon podcast Episode 4 | Mark Blakemore

    £1M to £5M Revenue: It Could Kill Your SaaS Company | iwon podcast Episode 4 | Mark Blakemore
    Apr 16 2026
    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.
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    36 min
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