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.

• 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.

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

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

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.

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

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

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.

• 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

• 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

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.

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

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.

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

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.

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:

1. Why success is usually a seven-year overnight story
2. The real meaning of patience versus fail fast
3. How the wrong VC firm can derail your vision
4. Why corporate hires often struggle inside start ups
5. The danger of chasing big enterprise clients too early
6. The Steve Jobs Rule of Ten hiring principle
7. When dilution is actually the smart move
8. 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:

1. Tap
2. Philip Kotler
3. Elon Musk
4. Mark Zuckerberg
5. Tinder
6. Airbnb
7. Jeff Bezos
8. Amazon
9. Shopify
10. Revolut
11. Stripe
12. Square
13. Dojo
14. 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.

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.

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.

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

IWON™ (It Wasn’t Over Night) is a long-form podcast exploring what it really takes to build and scale a successful technology company.

1. Find out more about the podcast: https://iwonpodcast.com
2. Interested in being a guest? https://iwonpodcast.com/guests/
3. 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.