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

• 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

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

Company culture rarely fails overnight. It erodes quietly—through what gets ignored, excused, or left unaddressed.

In this $100 Million Mindset compilation episode, we pull together key conversations from across the series to examine why company culture breaks down—and what it actually takes to rebuild it intentionally.

This isn't about slogans, perks, or values decks. It's about:

• Identity before performance

• Behavior before policies

• Standards before scale

You'll hear why culture is always being built—either by design or by default—and how leaders shape it through what they tolerate, reinforce, and model under pressure.

If your business feels harder to manage as it grows, if standards feel inconsistent, or if performance drops when stress rises, this episode will help you see culture for what it really is—and how to take responsibility for shaping 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

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

Leadership doesn't just cost time, money, or energy. It costs emotional bandwidth, relationships, health, and presence.

In this special compilation episode of The $100 Million Mindset, Todd Liles and Alan O'Neill pull together the most replayed moments that reveal the human toll of leadership — the part most leaders never plan for.

Across these conversations, you'll hear:

• How stress follows leaders home, even when they think it won't

• Why burnout and fatigue quietly sabotage decision-making

• How ambition can strain marriages, families, and health

• Why leadership becomes lonely without real partnership

• What sustainable growth actually requires beyond hustle

This episode isn't about slowing down your ambition.
It's about surviving it.

If you've ever felt like the bottleneck…If success hasn't felt the way you thought it would…If the weight of leadership is heavier than you expected…

This conversation will feel uncomfortably familiar — and deeply grounding.

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

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

Every leader dreams of growth. Few prepare for what growth demands.

This episode brings together the breakthrough moments leaders replayed the most — the stories where ambition collided with reality, where numbers told the truth leaders were afraid to face, and where the foundation proved more important than momentum.

You'll hear Ellen Rohr describe the day she realized she didn't actually understand her business — and how clarity rebuilt everything.

You'll hear Mike Wilson explain how a recession layoff reshaped his identity and forced him to rebuild from the inside out.

You'll hear Wyatt Hepworth reveal why you must hire for the company you want, not the one you currently operate.

And you'll hear Todd and Alan explain why simplicity, fundamentals, and financial literacy are the only paths to sustainable growth.

This episode isn't about scaling.

It's about strengthening what must exist before scaling is even possible.

If your business feels heavier than it should…

If your growth created more confusion than opportunity…

Or if you're finally ready to see what your numbers are really saying...

This conversation will steady your footing.

You'll learn:

• Why leaders fall apart before businesses do

• How financial clarity protects you from disaster

• Why "confidence without numbers" is a liability

• How overcomplication destroys momentum

• The truth about hiring for your future, not your present

• Why foundation—not ambition—determines how far you can grow

Growth rewards those who prepare. Reality humbles those who don't. This is the episode that helps you build something that will last.

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

The moment every leader grows is the moment they finally confront the truth about profit.

This highlight episode brings together the clips that forced owners to stop guessing and start leading with clarity.

These are the most replayed moments of Season 1 — the conversations that hit hardest, exposed hidden weaknesses, and showed owners that survival and growth both rest on the same foundation: margin discipline.

You'll hear the realizations that changed careers and companies:

The operator who thought he was profitable until he saw the real numbers…

the team that discovered underpricing was silently draining their growth…

and the executives who learned that profit isn't greed. It's responsibility.

This episode is the playbook for every leader who wants to build a company that's strong, stable, and built on truth instead of hope.

• Why revenue creates illusions but profit creates clarity

• The emotional moment leaders see their true numbers

• How underpricing slowly destroys healthy companies

• The fundamentals of margin discipline and responsible pricing

• Why raising prices is a leadership test, not a math problem

• How forecasting protects you from chaos, fear, and surprises

• Why profit is the real measure of health, stability, and growth

If you want a business that grows without breaking — and survives the mistakes that take others down — these are the lessons you can't afford to miss.

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