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Anything And Everything

Anything And Everything

Written by: Dan Sullivan and Jeffrey Madoff
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About this listen
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.TM & © 2024. The Strategic Coach Inc. All rights reserved. Economics Leadership Management & Leadership Marketing Marketing & Sales
Episodes
  • Who’s Actually Doing The Thinking In Your Business?
    Nov 3 2026

    Dan Sullivan and Jeffrey Madoff discuss a Fast Company article that asks whether “AI psychosis” is affecting business leaders and draws on a psychiatrist’s experience with a dozen hospitalized patients. They question the comparison, explore how pressure to embrace AI can affect business decisions, and explain why faster answers don’t replace your own judgment.

    Show Notes:

    The Fast Company article makes a big leap from 12 patients’ experiences to claims about millions of business leaders.

    Before accepting a claim, ask who’s being studied, what context is missing, and how key terms are being used.

    Creating something new often starts with believing in an idea before there’s proof it will work.

    Pressure to appear up to date can lead companies to exaggerate how much they’re using AI.

    For some people, joining the AI conversation is more about fitting in than using the technology, or a fear of missing out.

    An answer from AI shouldn’t go unquestioned just because it sounds confident.

    Good research means asking strategic questions, checking sources, and not stopping as soon as you receive the answer you want to hear.

    AI can help you work faster, but you’re still responsible for checking what you put out into the world.

    Resources:

    Most companies hire to fill jobs. The best leaders cast to build greatness. Casting Not Hiring offers a new way to build a team that thrives together rather than a collection of people who simply function on their own. Order Casting Not Hiring now.

    Learn more about Jeffrey Madoff

    Dan Sullivan and Strategic Coach®

    Show More Show Less
    49 mins
  • Before You Invest, Ask “Who Actually Wants This?”
    Oct 21 2026

    How do you tell a real opportunity from an expensive distraction? Dan Sullivan and Jeffrey Madoff explore why big ideas like Segway and Quibi fell short despite big-name backers and huge budgets, and explain how to look past the hype, ask better questions, and focus on what your customers actually want.

    Show Notes:

    Even in a good year, only a small share of IPOs turn out to be good investments.

    Some investors aren’t betting that an idea will work—they’re betting they can get out before everyone else realizes it won’t.

    Sometimes, the promise of what a product could do is easier to sell than something that already works.

    Quibi had big names and plenty of money behind it, but it was solving a problem people didn’t have.

    If you’re doing something new, there may not be credentials for it yet, but customers who keep paying you are a good sign.

    The entertainment business is all guesses and bets, and past success doesn’t guarantee the next hit.

    For every invention that takes off, there are plenty that don’t.

    Sometimes, people try to sell you on who else has invested rather than on the idea itself.

    A great demo gets people excited, but a lasting business needs customers who keep coming back.

    Before you put your money in, ask who gets paid even if the idea doesn’t work.

    Resources:

    Most companies hire to fill jobs. The best leaders cast to build greatness. Casting Not Hiring offers a new way to build a team that performs together rather than a collection of people who simply function on their own. Order Casting Not Hiring now.

    Learn more about Jeffrey Madoff

    Dan Sullivan and Strategic Coach®

    Show More Show Less
    46 mins
  • We Used To Do This Together
    Oct 6 2026

    Most companies hire to fill jobs. The best leaders cast to build greatness. Drawing on Dan Sullivan’s decades of coaching entrepreneurs and Jeffrey Madoff’s experience as a director, producer, and creative leader, Casting Not Hiring offers a new way to build a team that performs together rather than a collection of people who simply function on their own. Order Casting Not Hiring now.

    Activities that were once inherently social in the 1950s and ’60s have become much more solitary. Dan Sullivan and Jeffrey Madoff discuss the changes, technological and otherwise, that have altered the way we work, play, and socialize.

    Show Notes:

    In the mid-to-late-20th century, you generally had to go somewhere and deal with someone in person if you wanted to do something.

    Over the decades, technological advances didn't just make our lives more efficient. They progressively automated, individualized, and digitized tasks that used to require a community to get done.

    The attitude of the marketplace is: if they’re going to do it, we’re going to make it easier for them to do it.

    TV was called the window on the world and the vast wasteland, and both of those statements were true.

    Thanks to targeted ads and content suggestions, where you used to be the observer and the spectator, you're becoming almost the subject of the activity.

    The difference between how much viewer research is being done now compared to the 1950s is enormous.

    Audiences are so splintered now that TV can't aggregate the kind of viewer numbers they used to be able to.

    The introduction of credit cards allowed people to live beyond their means, which caused other kinds of problems.

    Resources:

    Learn more about Jeffrey Madoff

    Dan Sullivan and Strategic Coach®

    Show More Show Less
    40 mins
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