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 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®
March 18, 2025
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 decline. Most Strategic Coach team leaders have experience in multiple roles. Team members can grow by volunteering for responsibilities beyond their initial job description. People accustomed to working within large corporate structures may struggle in smaller, more agile entrepreneurial environments, which have fewer support systems in place. Entrepreneurism is a “Results Economy,” not a “Time and Effort Economy.” Selling is about getting a sale, not the time and effort you put in to get the sale. Most entrepreneurial companies begin with the founder acting as the primary salesperson. We can expect to see more people returning to the office, driven by our innate need for social interaction and connection. If you want to build a great company culture, you need team members in the office. Resources: Casting Not Hiring by Dan Sullivan and Jeffrey Madoff What Free Days™ Are And How To Know When You Need Them (mailto:https://www.strategiccoach.com/resources/the-multiplier-mindset-blog/what-free-days-are-and-how-to-know-when-you-need-them) Give and Take by Adam Grant 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® (https://www.strategiccoach.com/)
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