Is growth always the goal, or is there wisdom in slowing down? Dan Sullivan and Jeffrey Madoff share how real breakthroughs happen when you pause, build new capabilities, and stop chasing cookie-cutter success. True progress as an entrepreneur means playing your own game and having the freedom to shape your life, not just your business.

Show Notes:

Growth comes in two forms: expanding outward and building new capabilities internally.

It's difficult to maximize your existing capabilities and create new capabilities at the same time.

Lasting breakthroughs often start when entrepreneurs get bored and look for new challenges.

Every capability, even the ones learned under pressure, adds to your entrepreneurial tool kit.

Treating your capabilities as unique assets, rather than just checking off boxes, leads to bigger, better opportunities.

Strategic Coach® draws inspiration from the entertainment industry, not the corporate world.

Not every business needs to scale endlessly; staying small can give you more freedom and satisfaction.

A tightly scheduled entrepreneur can’t transform themselves.

Most people want to retire because they need time off, but entrepreneurial growth happens when you realize you can take time off now.

If you want your business to support the life you want, be deliberate about choosing both growth and downtime.

Resources:

Learn about Strategic Coach®

Learn about Jeffrey Madoff

The Entrepreneur's Guide To Time Management

Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage

Who Not How by Dan Sullivan with Dr. Benjamin Hardy

Always More Ambitious by Dan Sullivan

Are you navigating division in your business or community? Dan Sullivan and Jeffrey Madoff explore how entrepreneurial thinking helps bridge the gap between opposing sides, keeps innovation moving, and fosters practical empathy. Learn how to find common ground, how to stay curious during challenging times, and why focusing on what you can control leads to real progress.

Show Notes:

American identity is complex, shaped more by shared beliefs than by politics.​

Deep divisions often go back generations, but most people want similar things: safety, health, and prosperity.​

Entrepreneurial thinking is about agency—owning your choices, not chasing quick money.​

Entrepreneurship is a patriotic act, showing belief in the country you’re in and its future.

The entrepreneurial journey is a lifetime commitment; few ever return to “normal” jobs.​

Genuine curiosity and empathy help bridge gaps between differing viewpoints.​

In many ways, being American feels almost like having a shared faith—it’s deep, personal, and instinctive.​

Americans define themselves by their nationality, while Canadians mostly just know they aren’t American; there’s less focus on a single national identity up north.

Informed, vigorous debate is healthier than shutting out people who disagree with you.​

Find common ground with others; sometimes, a practical approach gets the bills paid and the team moving forward.​

Agency and passion, not money, are what keep entrepreneurs motivated over the long haul.​

Challenging experiences build empathy, resilience, and a shared humanity among entrepreneurs.​

Resources:

Learn about Strategic Coach®

Learn about Jeffrey Madoff

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Curious questions change everything, especially when hiring and building teams. Dan Sullivan and Jeffrey Madoff swap stories about how great conversations reveal true fit and why creating space for engagement and originality beats chasing predictability every time. Discover why the best teams are cast for creativity and growth, not just to fill a role.

Show Notes:

What makes a good conversationalist is what makes a good salesperson—curiosity that invites a real exchange.

The best salespeople don’t pitch; they ask questions that spark new thinking.

If candidates show up knowing the company and armed with questions, they instantly set themselves apart.

When people engage with you and the moment, they tend to show up fully in everything they do.

Seeing an owner enjoying their work is the best advertisement for joining a team.

If you’re hiring for predictability, you’re going to structure things in such a way that unpredictability can’t happen.

The best test for any team member: Would you hire them again, knowing everything you know now?

Context matters—people shine brightest when the environment is right for their talents.

Leadership happens where new capabilities are created, not from job titles or louder voices.

Resources:

Learn about Strategic Coach®

Learn about Jeffrey Madoff

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Always Be The Buyer by Dan Sullivan

The Talent Delusion by Tomas Chamorro-Premuzic

Growing Great Leadership by Dan Sullivan

The Impact Filter™