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