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®

Do you see yourself as normal, or do you embrace your weirdness? Dan Sullivan and Jeffrey Madoff explore the nature of normality and weirdness, reflecting on their personal experiences. They discuss the importance of self-consistency, the impact of external perceptions, and how curiosity fuels personal growth and authenticity.

Show Notes:

Most people consider themselves normal and view anyone who perceives them as weird as weird in turn.

You don’t have to take it personally if someone calls you weird.

As an entrepreneur, you’ll likely find that other entrepreneurs share your understanding of what’s considered normal, more so than those outside your field.

You can remain true to yourself across a variety of activities and experiences.

Some people view significant life events as opportunities to reinvent themselves.

If you’re consistent, people who reinvent themselves might mystify you.

Reinventing oneself often involves distancing from people from the past.

A good story is better than a good statistic.

If what you’re doing works for you, that’s a solid reason to remain consistent in your approach.

A person behaving inconsistently might be trying to please others rather than please themselves.

Resources:

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

Perplexity

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®

What is it about creative people that sets them apart? Why can some people consistently create new things while others can’t? Dan Sullivan and Jeffrey Madoff discuss the individuals who bring new value into the world and the best ways someone in business can use their creativity.

Show Notes:

• Quality is the foundation of every successful business plan.
• Never say no to yourself; there are plenty of others who will do that for you.
• Instead of wasting time pondering your ideas, you often just need to take action.
• No one has ever spent any time in the future or in the past. All we have is the present.
• Many people dismiss ideas prematurely without knowing how they might turn out.
• The majority of people struggle to engage directly with the marketplace.
• Creativity isn’t only about having a unique vision. It’s also about taking that vision and being able to replicate it.
• You can replicate a creation, but not its creator.
• To build a thriving business, focus on faithfully replicating what has been successful in the past.
• Every new creation has a limited lifespan; innovation is the key to longevity.
• Balancing creativity with consistency is crucial. Too much focus on expansion can dilute the original experience.
• Your customers are 50% of your creative team. Their feedback and insights matter.
• Beware of letting greed influence your creative process. Passion should come before profit.

Resources:

Personality: The Lloyd Price Musical

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®

We all have the ability to create. So why do some people feel they need permission in order to move forward with their ideas? Dan Sullivan and Jeffrey Madoff discuss how to cast off the need for permission and create value like you were meant to do.

Show Notes:

Permission means that you can’t move forward unless someone else says you can.

If you're asking permission, you're giving someone power to exercise over you in certain situations.

Some people’s first consideration when they have a new idea is to prepare a proposal and get permission to move forward.

Some parents give their children free rein to do whatever they want to do.

If you have a lot of children, you have to manage, not just parent.

Being a parent is like being a business owner in that you’re always being watched.

If you ignore your surroundings and you aren't tuned in, you can get old without having any wisdom.

When you go for the easiest, fastest solution, you’re usually going for the worst one.

Resources:

Creative Careers: Making a Living With Your Ideas by B. Jeffrey Madoff

Charlatan by Pope Brock

Empire of Deception by Dean Jobb

“The Junkification of American Life” by David Brooks

Thinking About Your Thinking by Dan Sullivan

Learn more about Jeffrey Madoff

Dan Sullivan and Strategic Coach®