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