The $100 Million Mindset

Todd Liles

Welcome to The $100 Million Mindset, the source for business owners who aspire to scale, grow, and reach their full potential. Whether you're aiming for $5 million, $10 million, or $100 million, Your hosts are Alan O'Neill, the Irish Plumber who scaled Abacus Plumbing and Cooling to over $100 Million and Todd Liles, a coach to high-performing business leaders and the owner of Service Excellence, are going to help you think bigger, act smarter, and take your business to the next level.

  1. You Can't Systemize What You Don't Understand - Ryan Fenn, CEO of Chiirp

    JAN 27

    You Can't Systemize What You Don't Understand - Ryan Fenn, CEO of Chiirp

    Founders don't struggle because they lack systems. They struggle because they try to systemize work they don't fully understand yet. In Part Two of this conversation on The $100 Million Mindset, Todd Liles sits down with Ryan Fenn, CEO of Chiirp, to unpack a hard-earned truth about scale, leadership, and growth: You can't systemize what you don't understand. This episode goes deeper into why founder-led hustle isn't something to escape, it's how clarity, conviction, and real systems are built. Ryan shares what he learned by staying close to sales, messaging, and execution before ever handing things off. These aren't theories. They're lessons earned the hard way. 👉 If you haven't watched Part One yet, start there first: https://youtu.be/V7Am26KHI-0 In this episode, you'll learn: Why systems fail when founders skip firsthand understanding How hustle creates the blueprint for scale The danger of delegating before conviction exists When it's actually safe to build systems Why founders must carry the message before handing it off How clarity, not tools, becomes the real constraint on growth If you're building systems right now, this episode will help you ask the most important question first: Do I understand this well enough to scale it? If this episode hit home, follow, review, and share it with a business owner who's ready to grow with purpose. The $100 Million Mindset isn't for the average—it's for those bold enough to lead, scale, and leave a legacy. Resources & Links: 📌 Connect with Todd Liles: Website | Instagram | Linkedin 🔗 Full show notes and resources: www.toddliles.com/mindset

    54 min
  2. Why Your Hustle Isn't Scaling (and How Systems Will Save You) - Ryan Fenn, Founder of Chiirp

    JAN 20

    Why Your Hustle Isn't Scaling (and How Systems Will Save You) - Ryan Fenn, Founder of Chiirp

    Most business owners don't lose because they're lazy—they lose because they're reactive. In the Season 2 premiere of The $100 Million Mindset, Todd Liles and Alan O'Neill sit down with Ryan Fenn, founder of Chiirp. Ryan shares his incredible journey from being a "broke founder" who couldn't pay for a sandwich to building a company with a multi-million dollar valuation by mastering one critical shift: moving from pure hustle to intentional systems. In this episode, you'll learn: The "Leadership Tax": Why avoiding hard decisions quietly compounds cost, stress, and confusion. Systems vs. Hustle: Why your business breaks when lead flow increases if you don't have a consistent follow-up process. The Power of Qualification: How Ryan whittled down 300 leads a day to the 5 most qualified buyers using automated funnels. Identity Before Performance: Why believing in your "superhuman capabilities" is the first step to removing limits on your growth. The "Right Way" Premium: Why doing things ethically might cost you in the short term but is the only way to protect your peace and long-term success. Featured Guest: Ryan Fenn: CEO and Founder of Chiirp, who started his entrepreneurial journey with a $400 windshield repair kit and a drive to provide for his family. If this episode hit home, follow, review, and share it with a business owner who's ready to grow with purpose. The $100 Million Mindset isn't for the average—it's for those bold enough to lead, scale, and leave a legacy. Resources & Links: 📌 Connect with Todd Liles: Website | Instagram | Linkedin 🔗 Full show notes and resources: www.toddliles.com/mindset

    1h 21m
  3. What Happens After You Win? Leadership, Legacy, and the Cost of Building Big

    JAN 6

    What Happens After You Win? Leadership, Legacy, and the Cost of Building Big

    Most leadership content talks about how to build, grow, and scale. Very little talks about what happens after you win. In this special $100 Million Mindset compilation, Todd Liles and Alan O'Neill step into a quieter, harder conversation, the personal toll of leadership once the business is built. This episode pulls together some of the most replayed moments on: Burnout that shows up after success The emotional weight of selling or stepping back Identity loss when the company no longer needs you Family strain, relief, grief, and purpose after control Why legacy isn't what you build, but who you build You'll hear honest reflections from leaders who've lived it, including Matt Michel and Paul Kelly, alongside Todd and Alan's own hard-earned perspective on stewardship, succession, and sustainability. This isn't about exit strategies. It's about meaning. It's about leadership after momentum fades. And it's about building something that lasts without costing you everything else. In this episode, you'll learn: Why leaders often feel empty after the build is complete The emotional reality behind selling a business Why relief and grief often arrive together How identity gets tied to control What real legacy actually looks like in practice If you're building something big, or already built it, this episode will hit closer than you expect. If this episode hit home, follow, review, and share it with a business owner who's ready to grow with purpose. The $100 Million Mindset isn't for the average—it's for those bold enough to lead, scale, and leave a legacy. Resources & Links: 📌 Connect with Todd Liles: Website | Instagram | Linkedin 🔗 Full show notes and resources: www.toddliles.com/mindset

    21 min
  4. Leadership That Scales: Training, Coaching & Building the Leaders Who Carry Your Growth

    12/16/2025

    Leadership That Scales: Training, Coaching & Building the Leaders Who Carry Your Growth

    Scaling a business isn't about adding more trucks or pushing harder. It's about building leaders who can carry the growth, protect the culture, and make decisions with clarity when the pressure rises. In this curated collection of 100 Million Mindset's most impactful conversations, Todd Liles and Alan O'Neill revisit the moments that shaped their thinking on scalable leadership — featuring insights from operators and leaders across the season. You'll hear from guests who lived the weight of fast growth, rebuilt their organizations, trained up their people, and learned what happens when the leadership bench is too shallow to support the vision. In this episode, you'll learn: Why companies stall when leadership doesn't scale What great coaching and training really look like How leaders spread clarity instead of chaos The difference between delegating tasks and developing ownership How to build leaders who think and decide the way you would Why the next stage of growth depends on the people you elevate This episode is a reality check for every founder and leader who wants to scale without breaking their business — or themselves. Because growth doesn't rise to the level of your ambition…it rises to the level of your leaders. If this episode hit home, follow, review, and share it with a business owner who's ready to grow with purpose. The $100 Million Mindset isn't for the average—it's for those bold enough to lead, scale, and leave a legacy. Resources & Links: 📌 Connect with Todd Liles: Website | Instagram | Linkedin 🔗 Full show notes and resources: www.toddliles.com/mindset

    20 min
5
out of 5
5 Ratings

About

Welcome to The $100 Million Mindset, the source for business owners who aspire to scale, grow, and reach their full potential. Whether you're aiming for $5 million, $10 million, or $100 million, Your hosts are Alan O'Neill, the Irish Plumber who scaled Abacus Plumbing and Cooling to over $100 Million and Todd Liles, a coach to high-performing business leaders and the owner of Service Excellence, are going to help you think bigger, act smarter, and take your business to the next level.

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