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 Coac...
Jul 08, 2025•1 hr
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...
Jun 24, 2025•1 hr 2 min
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 re...
Jun 10, 2025•54 min
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 creativit...
May 20, 2025•54 min
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...
May 13, 2025•52 min
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 hollo...
May 06, 2025•55 min
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...
Apr 22, 2025•1 hr 5 min
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 questio...
Apr 08, 2025•50 min
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 conversatio...
Apr 01, 2025•59 min
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 ...
Mar 18, 2025•1 hr 1 min
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 d...
Mar 11, 2025•45 min
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. Societ...
Feb 25, 2025•1 hr 7 min
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 ...
Feb 18, 2025•1 hr 9 min
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 t...
Feb 04, 2025•52 min
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 ide...
Jan 22, 2025•56 min
When a friend asks for your opinion on a new idea, you want to be helpful, but how should you respond when you don’t think their idea will succeed? Dan Sullivan and Jeffrey Madoff discuss ways to be supportive and helpful without lying or making a commitment. Show Notes: You can decide to help someone in a way that won’t involve you beyond a conversation. In the business of coaching small businesses, you discover quickly that there’s a reason why small businesses are small. People who can afford...
Jan 14, 2025•44 min
Do you recognize the unique strengths of your team, or do you overlook them? Jeffrey Madoff and Dan Sullivan explore the art of "casting" in business and life, revealing how self-awareness and understanding can lead to greater success. Discover how knowing oneself can transform team dynamics and drive long-term achievement. Show Notes: There are a lot of talented people out there who are compelled to do what they’re doing. When someone’s auditioning for a role, you get a gut feeling if they’re n...
Dec 30, 2024•1 hr 5 min
Jeffrey and Dan discuss the intricate relationship between humans and technology as they seek to understand how our thoughts and intentions shape technological advancements. Join them as they explore the historical context of technology, the importance of mindset, and how necessity drives innovation—and discover how our human nature fuels continual improvement. Show Notes: Technology is a human-driven process. As long as there have been humans, there have been humans creating technology. The evo...
Dec 17, 2024•59 min
Will AI be a burden on human creativity, or will it free us up to innovate in ways we never thought possible? Jeffrey Madoff and Dan Sullivan predict how artificial intelligence will reshape work, culture, and the economy. Explore the balance between tech advancements and human connection, and discover the surprising ways AI might redefine fulfillment in our lives. Show Notes: AI is set to transform many job sectors, especially those repetitive tasks that don’t bring joy. This isn’t just a chall...
Dec 02, 2024•1 hr 10 min
We live in a world saturated with technology. It can be difficult to tell how much you’re using technology and how much technology is using you. But you can avoid distraction and stick to your purpose by focusing on the basics. Dan Sullivan and Jeffrey Madoff discuss who we are, and who we’re right for, in a world of technology. Show Notes: Regardless of technology, what matters is what you actually have to say that’s interesting and valuable to other people. Technology is a tool, so all you nee...
Nov 06, 2024•59 min
About 50 years ago, the microchip had people making predictions about how the technology would influence all areas of human life. Now, advancements in artificial intelligence are generating the same sorts of predictions. Dan and Jeffrey discuss the psychological effect of AI’s potential, the very different mindsets with which people are approaching it, and who is set to benefit the most. Show Notes: New technologies can force people to rethink their relationship to work and to everything else in...
Oct 23, 2024•58 min
Are you casting your team like a theatrical production or just going through the motions with your hiring? Jeffrey and Dan explore how theater principles can revolutionize entrepreneurship. Discover how casting roles can improve creativity, productivity, teamwork, and engagement. Learn about their new book, Casting Not Hiring, and gain insights into innovative tools for defining roles in your business. Show Notes: The key to building a successful entrepreneurial team is to cast people for roles ...
Oct 10, 2024•36 min
Do you understand the true potential of AI for your business? Jeffrey and Dan explore the practical applications of AI for entrepreneurs and discuss how it can streamline operations, improve productivity, and solve complex problems across various industries. Learn to navigate the current AI hype and discover how to leverage this technology as a powerful tool for driving business growth and innovation. Show Notes: AI is primarily a complexity solver, excelling in areas involving multiple interwov...
Sep 30, 2024•1 hr 2 min
Jeffrey Madoff and Dan Sullivan explore the evolving concept of retirement. They discuss its historical origins, the unique challenges entrepreneurs face, and the impact of longevity on financial planning. The conversation offers valuable insights for any entrepreneur hoping to redefine success and navigate the modern economic landscape. Show Notes: The concept of retirement is relatively new, emerging in the late 19th and 20th centuries. The word "retire" comes from the French word repérer, mea...
Sep 12, 2024•1 hr
Jeffrey Madoff and Dan Sullivan explore the limitations of AI, debunking the myth of technological singularity. They discuss Gödel’s incompleteness theorem, Apple's controversial iPad ad, and the evolving global economy. The conversation challenges common assumptions about AI's potential to surpass human intelligence, offering valuable insights for any entrepreneur navigating the tech landscape. Show Notes Gödel's incompleteness theorem suggests that technology, as a subset of humanity, cannot s...
Aug 27, 2024•59 min
If you run a business, are you sure that every detail is being handled? When the little things aren’t being taken care of, it can be an indication that the big things aren’t going well. In this episode, Dan Sullivan and Jeffrey Madoff share the enormously important things companies have to do now to make sure customers keep coming back. Show Notes: In businesses, one of the first things to go is customer service. The only reason to shop in person rather than online is because it becomes a social...
Aug 07, 2024•59 min
Jeffrey and Dan discuss Dan’s latest book and explore how technological advancements like AI are often perceived as revolutionary, yet are actually extensions of historical innovations. This episode challenges conventional wisdom about creativity and offers a fresh perspective on how we can harness our past experiences to fuel future success. In This Episode: Although we perceive every new technological advancement, like AI, as a game changer, innovations are merely continuations of humanity's l...
Jul 16, 2024•1 hr 1 min
In this episode, Jeffrey and Dan explore the world of thinking tools and the framework that helps entrepreneurs think strategically. Dan shares the origin story of his first tool and how it evolved into over 240 trademarks. He also touches on the concept of Unique Ability® and its role in his company's success. In This Episode: Self-examination and curiosity play a crucial role in achieving success, but most people don’t make the time for it. So, what are thinking tools? Dan provides a definitio...
Jun 25, 2024•47 min
How can entrepreneurs build a high-performing team that operates like a well-cast theatrical production? Evaluate candidates not just for skills, but for their ability to work seamlessly with your existing team. Put together a cohesive group where each member complements the others. By approaching team-building through a theatrical lens, you create a harmonious company culture that delivers a captivating performance for your clients. In This Episode: In theater, casting is about creating an ense...
May 28, 2024•46 min
Jeffrey and Dan dive deep into creativity, innovation, and the intricate dance between good business and exciting innovation. Inspired by Dan's quarterly book, Everything Is Created Backward, they discuss how integrating existing technologies and ideas to create something entirely new can completely disrupt the market and lead to record-breaking profit. In This Episode: There’s a permanent tension between creative people and organizational people (business executives). Most creative people are n...
May 14, 2024•56 min
