Anything And Everything

Dan Sullivan and Jeffrey Madoff
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  • ENTREPRENEURSHIP

Dan Sullivan, Founder and President of Strategic Coach®, and Jeffrey Madoff, Founder and CEO of Madoff Productions, find it really easy to talk about anything and everything. In their conversations, whether they agree or not, there’s a mutual respect, a love of exploration, and a shared belief in the importance of context. Dan and Jeff’s shared interest in entrepreneurship, value creation, technology, and branding will undoubtedly lead to fascinating discussions on all of these topics and more.

  1. 4 DAYS AGO

    What Young Entrepreneurs Miss About Timing

    Are successful entrepreneurs always young prodigies? Dan Sullivan and Jeffrey Madoff dismantle the myth by showing why most real breakthroughs happen in midlife, after years of sorting out direction, taking financial responsibility, and learning directly from the marketplace—especially from rejection, rough patches, and so-called late starts.   Show Notes:   Despite the hype about young founders, the average age of successful entrepreneurs is somewhere between 40 and 45.   More young people are trying entrepreneurship than ever, but many are still using their twenties and thirties to sort out who they are and what game they want to play.​   The moment that you first have to create the money to pay for yourself is the true starting line of your entrepreneurial life.​   Entrepreneurs don’t hunt for “good jobs”; they look for a compelling opportunity, create value, and build jobs around that opportunity.​   Many entrepreneurs initially measure success by reaching a specific financial benchmark, only to discover that progress and impact matter even more.​   Younger entrepreneurs often hesitate to take on overhead because they don’t yet feel financially safe enough to make bigger commitments.​   The pandemic pushed many people to experiment with entrepreneurship, but that surge in attempts didn’t change the typical age at which real success shows up.​   Every successful entrepreneur has weathered rough periods where cash was tight, models weren’t working, or personal setbacks tested their confidence.​   Most people avoid a direct relationship with the marketplace because it involves uncertainty, visible performance, and constant feedback.​   For entrepreneurs, rejection is essential market data; if you treat it as failure instead of learning, you’ll do everything you can to avoid it.​   Resources:   Casting Not Hiring by Dan Sullivan and Jeffrey Madoff   Your Life As A Strategy Circle by Dan Sullivan

    48 min

  2. 22/12/2025

    Standing Out In A World Of Sameness

    Are you letting data define your story or are you doubling down on what makes you truly exceptional? Dan Sullivan and Jeffrey Madoff challenge the idea that AI and metrics are enough, and show why entrepreneurs who cast instead of hire, elevate standout performances, and compete on impact, not price, build the most memorable and valuable companies.   Show Notes:   Casting the right person for a role starts with the story of what they actually do, how their team creates value, and how that supports the company’s bigger narrative.​   Data can describe performance, but it can’t replace the human story that gives work meaning, direction, and context.​   Computers and AI are designed to find what’s the same, which makes them great at patterns but weak at capturing what’s truly exceptional.​   Storytelling focuses on the one person, one result, or one moment that stands out from everything else.​   When organizations cut costs by standardizing everything, they usually strip out the exceptional people, offers, and experiences that make them memorable.​   Entrepreneurs are at their best when they continually differentiate themselves, their offers, and their clients instead of trying to fit into industry averages.​   The real question around AI isn’t, “Is it good or bad” but rather, “In what context am I using it, and does it amplify or erase what’s unique about us?”​   If your company looks and sounds like everyone else, the only thing you can compete on is price.​   Impact is what makes an experience unforgettable, and that memorability is what sets you apart in a crowded market.​   Nothing changes in your business story until you take action and create new experiences worth talking about.​   When you operate from your exceptional strengths, competitors become background noise instead of a threat.​   Many entrepreneurs don’t fully step into their unique story until midlife, when experience and clarity finally catch up with ambition.​   Resources:   Casting Not Hiring by Dan Sullivan and Jeffrey Madoff   Always More Ambitious by Dan Sullivan   Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage   Unique Ability®

    49 min

  3. 02/12/2025

    Your Past Beliefs Are Still Running The Show

    How much does your upbringing still shape you? Dan Sullivan and Jeffrey Madoff explore how childhood worldviews, even those you barely remember, set the foundation for your decisions and relationships. Learn why combining old perspectives with new insights helps entrepreneurs understand themselves, connect with others, and identify opportunities in a world that keeps on changing. Show Notes:   The beliefs you formed as a child still shape how you approach life and business today.​   Kids once had the freedom to explore, play, and learn without constant supervision.​   School is often a miniature version of society, full of social experiments and life lessons.   Asking older generations about their youth is a great way to deepen connection and spark fresh insight.   History reminds us that opportunities and limitations were shaped by things like gender and culture.​   The strongest relationships fill gaps in our lives, giving us things we needed but didn’t have.​   A narrow worldview can make it hard to accept new ideas or be open to others.​   Everyone wants to feel seen, valued, and understood.   Parents often struggle with self-reflection because busy lives leave little room for introspection.​   Resources:   Learn about Strategic Coach®   Learn about Jeffrey Madoff   Casting Not Hiring by Dan Sullivan and Jeffrey Madoff   Who Not How by Dan Sullivan with Dr. Benjamin Hardy   Unique Ability®

    58 min

  4. 11/11/2025

    Why Bigger Isn’t Always Better In Business

    Is growth always the goal, or is there wisdom in slowing down? Dan Sullivan and Jeffrey Madoff share how real breakthroughs happen when you pause, build new capabilities, and stop chasing cookie-cutter success. True progress as an entrepreneur means playing your own game and having the freedom to shape your life, not just your business.   Show Notes:   Growth comes in two forms: expanding outward and building new capabilities internally.   It's difficult to maximize your existing capabilities and create new capabilities at the same time.   Lasting breakthroughs often start when entrepreneurs get bored and look for new challenges.   Every capability, even the ones learned under pressure, adds to your entrepreneurial tool kit.   Treating your capabilities as unique assets, rather than just checking off boxes, leads to bigger, better opportunities.   Strategic Coach® draws inspiration from the entertainment industry, not the corporate world.   Not every business needs to scale endlessly; staying small can give you more freedom and satisfaction.   A tightly scheduled entrepreneur can’t transform themselves.   Most people want to retire because they need time off, but entrepreneurial growth happens when you realize you can take time off now.   If you want your business to support the life you want, be deliberate about choosing both growth and downtime.   Resources:   Learn about Strategic Coach®   Learn about Jeffrey Madoff   The Entrepreneur's Guide To Time Management   Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage   Who Not How by Dan Sullivan with Dr. Benjamin Hardy Always More Ambitious by Dan Sullivan

    1 hr

  5. 21/10/2025

    Entrepreneurial Thinking In A Divided World

    Are you navigating division in your business or community? Dan Sullivan and Jeffrey Madoff explore how entrepreneurial thinking helps bridge the gap between opposing sides, keeps innovation moving, and fosters practical empathy. Learn how to find common ground, how to stay curious during challenging times, and why focusing on what you can control leads to real progress.   Show Notes:   American identity is complex, shaped more by shared beliefs than by politics.​   Deep divisions often go back generations, but most people want similar things: safety, health, and prosperity.​   Entrepreneurial thinking is about agency—owning your choices, not chasing quick money.​   Entrepreneurship is a patriotic act, showing belief in the country you’re in and its future.   The entrepreneurial journey is a lifetime commitment; few ever return to “normal” jobs.​   Genuine curiosity and empathy help bridge gaps between differing viewpoints.​   In many ways, being American feels almost like having a shared faith—it’s deep, personal, and instinctive.​   Americans define themselves by their nationality, while Canadians mostly just know they aren’t American; there’s less focus on a single national identity up north.   Informed, vigorous debate is healthier than shutting out people who disagree with you.​   Find common ground with others; sometimes, a practical approach gets the bills paid and the team moving forward.​   Agency and passion, not money, are what keep entrepreneurs motivated over the long haul.​   Challenging experiences build empathy, resilience, and a shared humanity among entrepreneurs.​   Resources:   Learn about Strategic Coach® Learn about Jeffrey Madoff Casting Not Hiring by Dan Sullivan and Jeffrey Madoff

    59 min

  6. 01/10/2025

    The Questions That Reveal If A New Hire Will Succeed

    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™

    59 min

  7. 16/09/2025

    What People Say About You When You Leave The Room

    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

    55 min

  8. 02/09/2025

    What Your Business Is Really Worth

    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

    1h 1m
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About

Dan Sullivan, Founder and President of Strategic Coach®, and Jeffrey Madoff, Founder and CEO of Madoff Productions, find it really easy to talk about anything and everything. In their conversations, whether they agree or not, there’s a mutual respect, a love of exploration, and a shared belief in the importance of context. Dan and Jeff’s shared interest in entrepreneurship, value creation, technology, and branding will undoubtedly lead to fascinating discussions on all of these topics and more.

Information

  • Creator
    Dan Sullivan and Jeffrey Madoff
  • Years Active
    2021 - 2026
  • Episodes
    89
  • Rating
    Clean
  • Copyright
    TM & © 2024. The Strategic Coach Inc. All rights reserved.
  • Show Website
    Anything And Everything

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