by Dan Sullivan and Jeffrey Madoff
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.
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7/20/2021
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April 22, 2025
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. Prediction is necessary for survival, which is why we’re always looking for things we can count on in the future. A lot of power comes with the belief that your intelligence is better than someone else's intelligence. Thought is a luxury. Only those freed from survival mode can engage deeply with creativity, innovation, and purpose. Humans aren’t information processors—they’re meaning makers. Purpose is created out of greater and greater freedom of money, time, and relationships. Money is the scorecard, not the game. The greatest contribution you can make to another person is your standards. Teams thrive when they know your standards are non-negotiable, even if it’s uncomfortable. Resources: Same As Ever by Morgan Housel You Are Not A Computer by Dan Sullivan The 4 Freedoms That Motivate Successful Entrepreneurs (https://www.strategiccoach.com/resources/the-multiplier-mindset-blog/the-4-freedoms-that-motivate-successful-entrepreneurs) Casting Not Hiring by Dan Sullivan and Jeffrey Madoff Learn more about Jeffrey Madoff (https://www.acreativecareer.com/) Dan Sullivan (https://www.strategiccoach.com/coach/dan-sullivan) and Strategic Coach®
April 8, 2025
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 (mailto:https://www.strategiccoach.com/resources/the-multiplier-mindset-blog/your-business-is-a-theater-production-your-back-stage-shouldnt-show-on-the-front-stage) The 4 C’s Formula by Dan Sullivan Learn more about Jeffrey Madoff (mailto:https://www.acreativecareer.com/) Dan Sullivan (mailto:https://www.strategiccoach.com/coach/dan-sullivan) and Strategic Coach® (mailto:https://www.strategiccoach.com/)
April 1, 2025
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 (https://www.perplexity.ai/) 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 (https://www.strategiccoach.com/resources/the-multiplier-mindset-blog/your-business-is-a-theater-production-your-back-stage-shouldnt-show-on-the-front-stage) Learn more about Jeffrey Madoff (https://www.acreativecareer.com/)Dan Sullivan (https://www.strategiccoach.com/coach/dan-sullivan) and Strategic Coach®
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