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®

What if predictability is the ultimate competitive advantage? Dan Sullivan and Jeffrey Madoff dissect how standards and intent create unshakable trust in business and in life. Learn why elite entrepreneurs prioritize dependable relationships over short-term gains, how to spot (and avoid) toxic partnerships, and why money is just a metric—not the mission.

Show Notes:

Humans don’t like unanswerable questions.

You can't seek answers unless you have questions, and you have to ask the right questions.

Prediction is necessary for survival, which is why we’re always looking for things we can count on in the future.

A lot of power comes with the belief that your intelligence is better than someone else's intelligence.

Thought is a luxury. Only those freed from survival mode can engage deeply with creativity, innovation, and purpose.

Humans aren’t information processors—they’re meaning makers.

Purpose is created out of greater and greater freedom of money, time, and relationships.

Money is the scorecard, not the game.

The greatest contribution you can make to another person is your standards.

Teams thrive when they know your standards are non-negotiable, even if it’s uncomfortable.

Resources:

Same As Ever by Morgan Housel

You Are Not A Computer by Dan Sullivan

The 4 Freedoms That Motivate Successful Entrepreneurs

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

What effect do the games we play have on us—and what do our motivations for playing them say about us? Dan Sullivan and Jeffrey Madoff discuss the kinds of “games” that are interesting and beneficial to entrepreneurs, and why you don’t have to choose between passion projects and commercial projects.

Show Notes:

Competing with yourself means measuring your progress against your previous performance, not against other people.

Life itself is the ultimate game for self-competition.

If you’re questioning what you’re doing, ask yourself what you could be doing instead.

Games have a binary outcome: victory or defeat.

Some people are born with a competitive chip in their brains, and some aren’t.

This applies to creative individuals too. Creativity can be collaborative, but many creators believe their creativity has to be better than everyone else’s.

People who oppose a system often create something directly related to what they resist.

Truly passionate people cannot not do what they’re doing.

Entrepreneurs have the self-awareness and confidence necessary to confront the marketplace head-on.

An opportunity only becomes one when you recognize it as such.

Resources:

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

The 4 C’s Formula by Dan Sullivan

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®