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®

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®

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®

In a tech-driven world, can businesses stay human? Dan Sullivan and Jeffrey Madoff explore how to balance automation with genuine connection. From Chaplin to Spartacus, they explore resisting dehumanization, celebrating the human touch in business, and reclaiming creativity. They also reveal how to ensure technology elevates—rather than diminishes—your entrepreneurial spirit.

Show Notes:

Tech can empower or dehumanize. Confidence and human connection are crucial.

Customers crave real conversations, not automated prompts.

Knowing how to ask the right questions is an art form.

Real solutions that address people’s pain points require empathy and personal connection.

Layoffs aren't a sustainable path to success (or profitability).

Inflating profits by slashing costs is a short-sighted strategy that executives often resort to when preparing a company for sale.

The most interesting people are always the ones who defy conformity.        

The U.S. founders aimed to create a society where individuals could thrive.

Prioritizing quality, service, and the human touch is a smart business plan.

Resources:

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

Perplexity

Charlatan: America's Most Dangerous Huckster, the Man Who Pursued Him, and the Age of Flimflam by Pope Brock

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

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

Are the people on your team ready to step into any role if needed? If not, why not? Dan Sullivan and Jeffrey Madoff explore the "swing cast" concept, explaining how adaptable, cross-trained teams—like actors ready for any role—drive entrepreneurial success. Learn why prioritizing ample time off for team members and focusing on results builds a high-performing business.

Show Notes:

If you try to work continuously without taking time off to recharge, your overall productivity and performance will decline.

Most Strategic Coach team leaders have experience in multiple roles.

Team members can grow by volunteering for responsibilities beyond their initial job description.

People accustomed to working within large corporate structures may struggle in smaller, more agile entrepreneurial environments, which have fewer support systems in place.

Entrepreneurism is a “Results Economy,” not a “Time and Effort Economy.”

Selling is about getting a sale, not the time and effort you put in to get the sale.

Most entrepreneurial companies begin with the founder acting as the primary salesperson.

We can expect to see more people returning to the office, driven by our innate need for social interaction and connection.

If you want to build a great company culture, you need team members in the office.

Resources:

Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

What Free Days™ Are And How To Know When You Need Them

Give and Take by Adam Grant

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

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

Paying your team is a given, but the way you think about it can make a huge difference—for both them and you. If you see your team as just a cost, that mindset won’t get you far. But when you view your team as an investment, everything changes. Dan Sullivan and Jeffrey Madoff dive into why this shift in perspective will be transformative for your entire company.

Show Notes:

If you think of someone as a cost, you’ll communicate that to them.

If someone feels that they’re seen as a cost, they’re deprived of all their creativity.

Creative people compete with other creative people for attention.

If you’re on the receiving end of indifference, you feel taken for granted.

If you’re an owner and founder, your team members are always paying attention to what you say and how you behave.

If you let someone know you see them as a cost, you’ve lost most of their value as an investment.

Just because someone’s successful doesn’t mean working with them is a positive experience.

The top entrepreneurs are collaborative, not competitive.

Every entrepreneur is motivated by either status or growth.

Power is the ability to either produce change or prevent it.

Resources:

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

The 4 Freedoms That Motivate Successful Entrepreneurs

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

The 4 C’s Formula by Dan Sullivan

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

Entrepreneurs come in all types. Just like in TV, movies, and theater, there are character archetypes in the entrepreneurial world. Jeffrey Madoff and Dan Sullivan discuss the ways entrepreneurs can differ from one another, what all of them have in common, and some of the traits they need for success.

Show Notes:

The earliest definition that fits entrepreneurs of today is: an entrepreneur is someone who takes a resource from a lower level of productivity to a higher level of productivity.

Society is generally pretty forgiving of entrepreneurs because they move things forward that benefit a lot of other people.

There are entrepreneurs who raise the value of something, but it only benefits themselves.

Some entrepreneurs’ work robs and endangers people.

The basis of entrepreneurism is someone who has a conception of the future where they can be better off if they take certain actions that would be daunting or even dangerous for other people.

With entrepreneurs, as with fictional characters, it's about the individual decisions and actions that they take and the consequences of them.

To achieve their goals, both entrepreneurs and story heroes have to make sacrifices.

The founders of the U.S. were basically all involved in entrepreneurial activities.

Wanting to have more power isn’t necessarily bad.

As you become more successful, you need to reinvent yourself.

Resources:

Welcome to Cloudlandia podcast

The Power of Film by Howard Suber

Deep D.O.S. Innovation by Dan Sullivan

Unique Ability®

The 4 C’s Formula by Dan Sullivan

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®