Do today’s kids miss out on the lessons learned from early work experiences? Dan Sullivan and Jeffrey Madoff reflect on how childhood roles, from farm chores to paper routes, shaped their entrepreneurial instincts. Discover why hands-on work mattered, what’s changed, and how modern entrepreneurs can cultivate resilience, responsibility, and adaptability in a screen-driven world.

Show Notes:

Children today are rarely seen as contributors in the present moment; the focus is on their future potential.

Many traditional childhood jobs no longer exist.

Big social centers, like soda bars and department store lunch counters have disappeared.

Dining out was once reserved for special occasions.

Shared family meals at home were a cornerstone of daily life.

Private transportation isn’t just convenient; it communicates status.

We’re more isolated than ever before, except for those who prioritize relationships.

The true impact of change often reveals itself years later.

Today’s entrepreneurs achieve success earlier than past generations did.

In the past, your first job could easily become your lifelong career.

The competition for your attention has never been more intense.

Resources:

Learn about Strategic Coach®

Learn about Jeffrey Madoff

Bill Of Rights Economy by Dan Sullivan

The Bottomless Well: The Twilight of Fuel, the Virtue of Waste, and Why We Will Never Run Out of Energy by Peter W. Huber and Mark P. Mills

Do you ever wonder why some entrepreneurs constantly innovate while others stay stuck in the past? Jeffrey Madoff and Dan Sullivan explore how childhood experiences, fear of consequences, and the need for control will either shape or stifle your creativity. Learn how to foster a culture of innovation and why true freedom in business starts with letting go.

Show Notes:

Creativity isn’t something you’re born with. It grows from encouragement, challenges, or even resistance.

Some people are creative because they were supported early on, while others became creative because they weren’t.

Strict childhood rules can create lifelong hesitation about taking risks.

Whether it’s parents, teachers, or bosses, too much control shuts down creativity.

Creative thinkers don’t fear consequences. Everything is feedback.

The best businesses welcome all ideas, knowing not every one needs to be used.

You don’t have to act on every creative idea to benefit from the process.

Great ideas start with simple curiosity and a willingness to explore.

Harsh criticism early in life can make people afraid to share their ideas.

The desire to control has more to do with quashing creativity and innovation than anything else.

The world wasn't created with you in mind. So you're going to have to negotiate.

Resources:

Learn about Jeffrey Madoff

Learn about Strategic Coach®

Do You Know What’s Keeping Your Clients Awake At 3 A.M.?

The 4 C’s Formula by Dan Sullivan

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

My Plan For Living To 156 by Dan Sullivan

Do you ever wonder why some entrepreneurs constantly innovate while others stay stuck in the past? Jeffrey Madoff and Dan Sullivan explore how childhood experiences, fear of consequences, and the need for control will either shape or stifle your creativity. Learn how to foster a culture of innovation and why true freedom in business starts with letting go.

Show Notes:

Creativity isn’t something you’re born with. It grows from encouragement, challenges, or even resistance.

Some people are creative because they were supported early on, while others became creative because they weren’t.

Strict childhood rules can create lifelong hesitation about taking risks.

Whether it’s parents, teachers, or bosses, too much control shuts down creativity.

Creative thinkers don’t fear consequences. Everything is feedback.

The best businesses welcome all ideas, knowing not every one needs to be used.

You don’t have to act on every creative idea to benefit from the process.

Great ideas start with simple curiosity and a willingness to explore.

Harsh criticism early in life can make people afraid to share their ideas.

The desire to control has more to do with quashing creativity and innovation than anything else.

The world wasn't created with you in mind. So you're going to have to negotiate.

Resources:

Learn about Jeffrey Madoff

Learn about Strategic Coach®

Do You Know What’s Keeping Your Clients Awake At 3 A.M.?

The 4 C’s Formula  by Dan Sullivan

Casting Not Hiring  by Dan Sullivan and Jeffrey Madoff

My Plan For Living To 156  by Dan Sullivan

What truly drives entrepreneurs beyond profits? Jeffrey Madoff and Dan Sullivan explore the deep connection between personal identity, core values, and business success. Discover how authenticity, risk-taking, and integrity shape entrepreneurial journeys, and why staying true to your values can lead to lasting impact.

Show Notes:

Your business often reflects who you strive to become in life.

Choosing entrepreneurship narrows your business possibilities but gives you control over your direction.

Dan Sullivan was coaching entrepreneurs before the term “business coach” even existed.

In the past, entrepreneurs could only scale by becoming corporations. The personal computer changed that, allowing entrepreneurs to grow while maintaining ownership and vision.

If you want to be in control of your own life, you need to be an entrepreneur.

Great coaching is about focusing on the aspirations of the person you’re helping, not on yourself.

Having enough money means you don’t have to compromise your values for a paycheck.

Financial debt can be overcome; moral debt is much harder to escape.

Resources:

Learn more about Strategic Coach®

Learn more about Jeffrey Madoff

Visit the Strategic Podcast Network

The Gap And The Gain by Dan Sullivan with Dr. Benjamin Hardy

The 4 C’s Formula by Dan Sullivan

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

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®

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:

​Learn more about Jeffrey Madoff

Learn more about Strategic Coach®

The Impact Filter™

Thinking, Fast and Slow by Daniel Kahneman

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

Learn more about Dan Sullivan and Strategic Coach®