How did you land your first customers, and how did that shape your entrepreneurial journey? Dan Sullivan and Jeffrey Madoff share their origin stories, from life insurance referrals to fashion industry breakthroughs. They explain why longevity in business comes from curiosity, calculated risks, and a relentless focus on making your future bigger than your past.

Show Notes:

Thinking about your thinking is beneficial no matter who you are or what industry you’re in.

There’s no recipe for creativity.

Risk and excitement are two sides of the same coin—you can’t have growth without embracing both.

The first person you have to sell an idea on is yourself.

If you have an advantage in a competitive industry, you won’t tell your competitors about it.

When experimenting with a new solution, you have to start by making sure it works for one person.

Longevity is something to be proud of.

If you have a successful approach, you can keep it, and just add more experience to it.

There are two types of support: moral and financial.

Longevity in business isn’t about luck; it’s about staying alert, curious, and adaptable to new opportunities.

Your number one job is to always make your future bigger than your past.

The more committed you are to something, the less you care about the obstacles.

Resources:

The Impact Filter™

Thinking, Fast and Slow by Daniel Kahneman

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

Do you ever notice how some people obsess over things, gossip about others, or recycle old ideas? Why is it that true innovators think differently? Dan Sullivan and Jeffrey Madoff break down the four levels of thinking and explain why thinking about your thinking fuels creativity, collaboration, and breakthroughs.

Show Notes:

Most people spend their lives fixated on things, people, or others’ ideas, but true innovators think about how they think.

People who think about their thinking are looking for other people who are doing the same thing.

The highest level of thinking isn’t competitive—it’s collaborative. Two original minds create a third idea neither could alone.

Nearly every meaningful innovation stems from that fourth level of thinking, where you examine how and why you think the way you do.

Some of the most creative people don’t even realize how they think—they just do.

The moment you care more about stuff than ideas, you’ve lost the game.

Like casting a play, the best teams are built when you assign people roles based on their unique strengths, not rigid job descriptions.

If your team fears being wrong, they’ll never risk being right. Defensiveness is the enemy of breakthroughs.

Corporations reward conformity, but entrepreneurs win by asking, "What if we did the opposite?

Resources:

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Thinking About Your Thinking by Dan Sullivan

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

Do you chase external success or internal fulfillment? Jeffrey Madoff and Dan Sullivan discuss ambition versus passion—how they differ, intersect, and fuel entrepreneurs. Learn why passion sustains long-term commitment while ambition alone falls short, and discover how to combine them for lasting impact.

Show Notes:

Passion is your internal drive, while ambition translates that drive into measurable success.

Ambition without passion burns out because external milestones like money and fame hollow out without the joy of the process.

Passion is what fuels long-term commitment because it’s what you can’t not do.

True passion creates freedom—doing what you want, when you want, with whom you want.

Childhood clues reveal your passion. What lit you up as a kid often points to your lifelong strengths.

Great entrepreneurs fuse principle (passion) with strategy (ambition).

Retirement is the enemy of passion.

Getting people to talk about their experiences is a great way to learn a lot about the world.

If you ask people questions that connect their experiences, they get very excited.

Resources:

Everything Is Created Backward by Dan Sullivan

How to Win Friends & Influence People by Dale Carnegie

The Power of Positive Thinking by Dr. Norman Vincent Peale

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®