How much does your upbringing still shape you? Dan Sullivan and Jeffrey Madoff explore how childhood worldviews, even those you barely remember, set the foundation for your decisions and relationships. Learn why combining old perspectives with new insights helps entrepreneurs understand themselves, connect with others, and identify opportunities in a world that keeps on changing.

Show Notes:

The beliefs you formed as a child still shape how you approach life and business today.​

Kids once had the freedom to explore, play, and learn without constant supervision.​

School is often a miniature version of society, full of social experiments and life lessons.

Asking older generations about their youth is a great way to deepen connection and spark fresh insight.

History reminds us that opportunities and limitations were shaped by things like gender and culture.​

The strongest relationships fill gaps in our lives, giving us things we needed but didn’t have.​

A narrow worldview can make it hard to accept new ideas or be open to others.​

Everyone wants to feel seen, valued, and understood.

Parents often struggle with self-reflection because busy lives leave little room for introspection.​

Resources:

Learn about Strategic Coach®

Learn about Jeffrey Madoff

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Who Not How by Dan Sullivan with Dr. Benjamin Hardy

Unique Ability®

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