Anything And Everything

Curious questions change everything, especially when hiring and building teams. Dan Sullivan and Jeffrey Madoff swap stories about how great conversations reveal true fit and why creating space for engagement and originality beats chasing predictability every time. Discover why the best teams are cast for creativity and growth, not just to fill a role. Show Notes: What makes a good conversationalist is what makes a good salesperson—curiosity that invites a real exchange. The best salespeople don’t pitch; they ask questions that spark new thinking. If candidates show up knowing the company and armed with questions, they instantly set themselves apart. When people engage with you and the moment, they tend to show up fully in everything they do. Seeing an owner enjoying their work is the best advertisement for joining a team. If you’re hiring for predictability, you’re going to structure things in such a way that unpredictability can’t happen. The best test for any team member: Would you hire them again, knowing everything you know now? Context matters—people shine brightest when the environment is right for their talents. Leadership happens where new capabilities are created, not from job titles or louder voices. Resources: Learn about Strategic Coach® Learn about Jeffrey Madoff Casting Not Hiring by Dan Sullivan and Jeffrey Madoff Always Be The Buyer by Dan Sullivan The Talent Delusion by Tomas Chamorro-Premuzic Growing Great Leadership by Dan Sullivan The Impact Filter™

How much does your reputation influence your business outcomes? Jeffrey Madoff and Dan Sullivan explore why your reputation shapes every opportunity, why context matters most, and why the right feedback can uncover hidden talent. Discover essential strategies for building trust, setting your team up for success, and making every interaction count. Show Notes: Your reputation outlasts any project and shapes new opportunities across your entrepreneurial journey. Being easy to deal with and having high standards are not mutually exclusive. Your brand is not your logo or website; your brand is the reputation people share after working with you. Context lets you know exactly how to perform in specific circumstances. There's nothing more dangerous than winning with the wrong approach. Positive word of mouth is the greatest conversion to scale. We often confuse confidence with competence. Talent is the right person placed in the right context where their unique skills can shine. When people feel secure and informed, their best talents emerge and they perform at their highest level. Transparent communication and clear plans make talented people feel valued and reduce the chance of problems down the line. People like to know what’s expected of them. Life is a continuous negotiation, and progress is made by aligning your reasons with others. Resources: Casting Not Hiring by Dan Sullivan and Jeffrey Madoff Learn about Dan Sullivan and Strategic Coach® Learn about Jeffrey Madoff    

Do you believe your business has an inherent value? Dan Sullivan and Jeffrey Madoff dismantle this common illusion to reveal the true nature of value. Learn why it’s determined solely by a buyer’s motivation and how building a Self-Managing Company® is your ultimate path to greater freedom, growth, and engagement. Show Notes: The concept of inherent value is a subjective belief, not an economic fact. True value is determined solely by the agreement between a buyer and a seller at a specific moment. A buyer’s perception of value is entirely dependent on their unique motivations and goals. The ultimate purpose of your entrepreneurial journey is to achieve greater freedom of time, money, relationship, and purpose. Selling your company often means sacrificing your freedom and becoming an employee. Growing your business can create its own kind of prison, depending on how you build it and what you do. Your personal engagement in the creative process is the core fuel for a fulfilling entrepreneurial life. Money is not the game itself but merely the scoreboard tracking your progress and freedom. Building a Self-Managing Company is the strategic vehicle that grants you the freedom to focus on what you love. Life and business are a constant negotiation requiring you to understand the other party’s perspective above all else. Resources: What Is A Self-Managing Company®? The 4 Freedoms That Motivate Successful Entrepreneurs Casting Not Hiring by Dan Sullivan and Jeffrey Madoff “Scary Times” Success Manual: How To Be A Leader When Times Get Tough Never Split The Difference by Chris Voss Freakonomics by Stephen J. Dubner and Steven Levitt Judgment Under Uncertainty: Heuristics and Biases by Daniel Kahneman, Paul Slovic, and Amos Tversky The 4 C’s Formula by Dan Sullivan

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

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®

Discover how to make your sales stand out by focusing on unforgettable customer experiences. Learn why what we truly buy is often wrapped in the memory and emotional connection rather than the product itself. The conversation touches on nostalgia, identity, and personal stories that shape our purchasing decisions. Explore the paradox of technological connection alongside rising isolation and its impact on social skills. Finally, gain insights into fostering engagement as a key driver for sustainable business growth.

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 MadoffLearn more about Strategic Coach®The Impact Filter™ Thinking, Fast and Slow by Daniel Kahneman