What separates successful entrepreneurs from the rest? It’s not just having answers—it’s asking the right questions. Dan Sullivan reveals how Strategic Coach® was built on curiosity, resilience, and a relentless focus on the future. Discover why questions drive growth, how to avoid stagnation, and why your next decade could be your most ambitious yet.

Show Notes:

Most people aren’t very good at asking themselves questions—but questions are exponentially more powerful than answers.

Strategic Coach provides value, not by giving answers, but by asking the kinds of questions that transform people’s thoughts and experiences into strategies for growth.

You can only be truly useful to someone if you know what they’re trying to achieve.

In sales and in entrepreneurship, maybes are the enemy. Yeses move you forward, no’s teach you, but maybes drain your energy and resources.

The external approval you seek early in life shapes your identity, but lasting fulfillment comes from measuring your own growth and value.

Resilience isn’t about avoiding setbacks, but about bouncing back stronger.

Teamwork and collaboration are the ultimate multipliers. Your ambition can keep expanding at every stage of life when you build with others.

Resources:

How To Sell Transformation Using This One Question

My Plan For Living To 156 by Dan Sullivan

First 100 Days

The Positive Focus® Exercise

Learn more about Jeffrey Madoff

Learn more about Dan Sullivan and Strategic Coach®

How can you stand out in a crowded marketplace? Think beyond the product or service you’re selling, and make sure you provide customers and clients with an experience they’ll remember. Dan Sullivan and Jeffrey Madoff share the benefits of creating unique memories in “the experience economy.”

Show Notes:

Every purchase is an investment in a future experience. It’s rarely about the product or service itself.

In many cases, what you’re really buying is confirmation of status—a way to signal who you are (or who you aspire to be).

In the experience economy, people talk about how they experience certain products or services.

In essence, what’s being sold isn’t the product—it’s the memory associated with it.

How you feel about a transaction matters more than what you bought.

Nostalgia plays a big role here. We like things that connect us to when we were younger.

Humans are constantly integrating past, present, and future and creating meaning out of their experiences.

Identity is deeply connected to memory.

Resources:

The Experience Economy by B. Joseph Pine II and James H. Gilmore

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Learn more about Dan Sullivan and Strategic Coach®

​Learn more about Jeffrey Madoff

What does true wealth look like beyond bank accounts and net worth? Dan Sullivan and Jeffrey Madoff explore generational wealth, the pitfalls of financial success without purpose, and why relationships, time freedom, and fulfillment matter more than money. Learn how entrepreneurs can build lasting value—without losing themselves in the process.

Show Notes:

Wealth isn’t just net worth—it’s the freedom to focus on what matters most, without financial constraints.

An entrepreneur can pass on the results of their talent, but they can’t pass on their talent itself.

The wealthiest 20% rarely stay in that bracket for long. True sustainability requires reinvention, not just inheritance.

The distance between "rich" and "poor" isn’t a gap—it’s a ladder with multiple rungs, and movement happens in both directions.

Taxes don’t just redistribute wealth; they reveal how fragile financial success can be without strategy.

Generational wealth often persists due to lawyers and accountants, not the achievements of descendants.

Once you’ve maxed out what your efforts can bring you, you have to multiply your income by working less.

It might seem counterintuitive, but you can spend your time doing only what you love doing and find people who love doing the rest.

True confidence in business comes from pricing boldly—charge what scares you, plus 20%—and eliminating "maybes."

Wealth without relationships, purpose, or peace is poverty in disguise

Resources:

The Psychology of Money by Morgan Housel

You Are Not A Computer by Dan Sullivan

Learn more about Jeffrey Madoff

Learn more about Dan Sullivan and Strategic Coach®