<![CDATA[iwon™ podcast with Michael J Thomas]]>bb9ebd59-199b-5203-a39e-8ad56ef40ae4Thu, 11 Jun 2026 15:00:18 +0000Captivate.fmMichael J Thomashttps://artwork.captivate.fm/78e0df71-6a34-4faa-be2b-db5177e1d316/Michael-J-Thomas-iwon-podcast-cover-art-6.pngiwon™ podcast with Michael J ThomasMichael J ThomasMichael J ThomasIWON™ (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.https://www.iwonpodcast.comtrueepisodicnopodcastStratford-upon-Avon, United KingdomThe Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8The Real Overnight Success Story: Elizabeth Dodson's 14-Year Journey Building HomeZada | iwon™ podcast | Episode 8Instagram 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 realise

Chapters

00:00 Why Most Startups Fail

00:36 Welcome to the iwon™ podcast

01:48 The Problem That Led to HomeZada

04:18 The Hidden Cost of Homeownership

05:39 The Hot Water Heater That Changed Everything

07:51 Searching for a Better Solution

11:53 Lessons From Building and Selling Meridian Systems

14:30 Contracts, Negotiation, and Protecting Yourself

19:59 Why You Should Hire People Smarter Than You

23:53 Learning an Entirely New Market

30:10 The Challenge of Creating a New Software Category

31:55 A/B Testing, Messaging, and Finding What Works

35:54 Handling Naysayers and Unhelpful Praise

39:31 Finding the Right Customer

42:08 Why HomeZada Pivoted to Busy Professionals

42:49 Don't Quit Too Soon

43:40 Starting Again With a Blank Whiteboard

44:26 Playing the Long Game

45:34 The Growth Mindset Advantage

46:55 The Myth of Overnight Success

50:46 Building Something You're Proud Of

52:30 Copycats, Competition, and Patience

53:59 Life After a Successful Exit

55:40 Why Being an Outsider Can Be an Advantage

58:51 Protecting Customer Data and Privacy

59:55 The Negotiation Trick Nobody Talks About

01:01:59 Building Win-Win-Win Partnerships

01:04:05 Why Many SaaS Companies Aren't Enterprise Ready

01:06:53 Work-Life Boundaries as a Founder

01:09:41 Not Every Fire Is an Emergency

01:13:08 Advice for Technical Founders

01:15:14 The Marketing Touchpoints Most Founders Ignore

01:18:18 Final Thoughts

Connect with Elizabeth Dodson

Elizabeth Dodson, Co-Founder of HomeZada

LinkedIn:

https://www.linkedin.com/in/edodson/

HomeZada:

https://www.homezada.com/

Connect with Michael J. Thomas

LinkedIn:

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.com

Learn More About the Podcast

Official Website:

https://www.iwonpodcast.com

]]>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 realise

Chapters

00:00 Why Most Startups Fail

00:36 Welcome to the iwon™ podcast

01:48 The Problem That Led to HomeZada

04:18 The Hidden Cost of Homeownership

05:39 The Hot Water Heater That Changed Everything

07:51 Searching for a Better Solution

11:53 Lessons From Building and Selling Meridian Systems

14:30 Contracts, Negotiation, and Protecting Yourself

19:59 Why You Should Hire People Smarter Than You

23:53 Learning an Entirely New Market

30:10 The Challenge of Creating a New Software Category

31:55 A/B Testing, Messaging, and Finding What Works

35:54 Handling Naysayers and Unhelpful Praise

39:31 Finding the Right Customer

42:08 Why HomeZada Pivoted to Busy Professionals

42:49 Don't Quit Too Soon

43:40 Starting Again With a Blank Whiteboard

44:26 Playing the Long Game

45:34 The Growth Mindset Advantage

46:55 The Myth of Overnight Success

50:46 Building Something You're Proud Of

52:30 Copycats, Competition, and Patience

53:59 Life After a Successful Exit

55:40 Why Being an Outsider Can Be an Advantage

58:51 Protecting Customer Data and Privacy

59:55 The Negotiation Trick Nobody Talks About

01:01:59 Building Win-Win-Win Partnerships

01:04:05 Why Many SaaS Companies Aren't Enterprise Ready

01:06:53 Work-Life Boundaries as a Founder

01:09:41 Not Every Fire Is an Emergency

01:13:08 Advice for Technical Founders

01:15:14 The Marketing Touchpoints Most Founders Ignore

01:18:18 Final Thoughts

Connect with Elizabeth Dodson

Elizabeth Dodson, Co-Founder of HomeZada

LinkedIn:

https://www.linkedin.com/in/edodson/

HomeZada:

https://www.homezada.com/

Connect with Michael J. Thomas

LinkedIn:

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.com

Learn More About the Podcast

Official Website:

https://www.iwonpodcast.com

]]>45d5ac4e-25d6-4fe1-8f25-7271fe65e61bThu, 11 Jun 2026 16:00:00 +010001:18:33truefull88Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7Idea to Impact: From Google to Becoming a Startup Founder - Tolu's Salami's Journey | iwon podcast | Episode 7This 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:


Companies mentioned in this episode:

  • letplant
  • Google
  • Morrisons
  • Henley Business Angels
  • Bootcare
  • Accenture

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.


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 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:


Companies mentioned in this episode:

  • letplant
  • Google
  • Morrisons
  • Henley Business Angels
  • Bootcare
  • Accenture

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.


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.

]]>1b200be7-bb0b-4462-b85b-70d8b20502eeThu, 28 May 2026 12:00:00 +010036:22truefull77From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6From IBM to Entrepreneur: Sarah Eggleston's Inspiring Founder Journey | iwon™ podcast episode 6Sarah 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.


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.

]]>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.


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.

]]>a54d5e18-380e-44b3-b0f9-e905e96248efThu, 14 May 2026 12:00:00 +010028:49truefull66Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5Why I’m Taking on Spotify: Scott Truitt’s Plan to Fix a Broken Industry | iwon podcast | Episode 5Summary 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.


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

]]>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.


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

]]>dd89ee59-3882-4d3e-8262-2302b741f65eThu, 30 Apr 2026 12:30:00 +010001:03:36truefull55£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 BlakemoreMark 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:


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

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.


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.

]]>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:


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

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.


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.

]]>7ea2fddc-3487-4c9a-bb76-625b01b2fafcThu, 16 Apr 2026 12:00:00 +010036:17truefull44This Blind Spot Ruins Product-Market Fit & Growth | Scott Byrne-Fraser | iwon podcastThis Blind Spot Ruins Product-Market Fit & Growth | Scott Byrne-Fraser | iwon podcastWhat 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

Spotify: 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

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.


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

]]>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

Spotify: 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

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.


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

]]>e4cbe52b-fb62-4936-896c-97b9deb14dcaThu, 02 Apr 2026 12:00:00 +010001:03:04truefull33From Zero to $750 Million: How to Build a High Performing Sales Team | Alex Sullivan Lepaffe | iwon podcast with Michael J ThomasFrom Zero to $750 Million: How to Build a High Performing Sales Team | Alex Sullivan Lepaffe | iwon podcast with Michael J ThomasThis 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://thesalespeople.co/

Learn more about IWON, sponsorship and apply to be a guest:

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.

]]>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://thesalespeople.co/

Learn more about IWON, sponsorship and apply to be a guest:

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.

]]>fbafb8d0-8180-4e16-9e11-3a53b9abeb58Thu, 19 Mar 2026 11:45:00 +010040:09truefull22This Will Save You Years in Your Business | Christian Zigler (£24m + Multi-Exit Founder) on VCs, Hiring & AIThis Will Save You Years in Your Business | Christian Zigler (£24m + Multi-Exit Founder) on VCs, Hiring & AIThis 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 story
  • The real meaning of patience versus fail fast
  • How the wrong VC firm can derail your vision
  • Why corporate hires often struggle inside start ups
  • The danger of chasing big enterprise clients too early
  • The Steve Jobs Rule of Ten hiring principle
  • When dilution is actually the smart move
  • Why 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 Years

02:18 Founder Stupidity and Patience

07:04 The VC Mistake That Cost Millions

14:12 Why Enterprise Clients Can Kill Startups

20:30 Hiring Corporate Talent vs Startup Builders

28:15 The Steve Jobs and the Rule of Ten

35:48 Protecting Runway as a Founder

45:22 AI Hype vs Real Competitive Advantage

Companies mentioned in this episode:

  • Tap
  • Philip Kotler
  • Elon Musk
  • Mark Zuckerberg
  • Tinder
  • Airbnb
  • Jeff Bezos
  • Amazon
  • Shopify
  • Revolut
  • Stripe
  • Square
  • Dojo
  • Microsoft

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.

]]>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 story
  • The real meaning of patience versus fail fast
  • How the wrong VC firm can derail your vision
  • Why corporate hires often struggle inside start ups
  • The danger of chasing big enterprise clients too early
  • The Steve Jobs Rule of Ten hiring principle
  • When dilution is actually the smart move
  • Why 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 Years

02:18 Founder Stupidity and Patience

07:04 The VC Mistake That Cost Millions

14:12 Why Enterprise Clients Can Kill Startups

20:30 Hiring Corporate Talent vs Startup Builders

28:15 The Steve Jobs and the Rule of Ten

35:48 Protecting Runway as a Founder

45:22 AI Hype vs Real Competitive Advantage

Companies mentioned in this episode:

  • Tap
  • Philip Kotler
  • Elon Musk
  • Mark Zuckerberg
  • Tinder
  • Airbnb
  • Jeff Bezos
  • Amazon
  • Shopify
  • Revolut
  • Stripe
  • Square
  • Dojo
  • Microsoft

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.

]]>89acca43-0642-493e-ad0e-cd70d055b47bMon, 16 Mar 2026 11:45:00 +010054:35truefull11Welcome to IWON™. Because "It Wasn’t Over Night". It rarely is.Welcome to IWON™. Because "It Wasn’t Over Night". It rarely is.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 everything

From 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 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™ Works Marketing 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.


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.

]]>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 everything

From 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 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™ Works Marketing 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.


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.

]]>78628acd-9481-4009-a0c9-97a082144853Tue, 03 Mar 2026 16:15:00 +010001:52truetrailer