In a hustle-obsessed world, strategy is your ultimate shortcut. Cris Auditore and Dr. Philip Zimmermann reveal why thinking — not constant busyness — is the most powerful skill for entrepreneurs who want to build a self-managing business and a lasting legacy. Learn the four pillars of strategic thinking, how to shift from operator to strategist, and why slowing down is the fastest way to scale. Some topics covered are: Why high-level thinking matters more than hustleThe power of the bla...

Most business owners dream of selling their company, but the reality is that many small businesses cannot be sold because they're too dependent on the owner. Creating a self-managing business that can operate without you is essential whether you plan to exit or not. In this episode Cris & Philip tackle the crucial concept of "Design for Exit," revealing why every entrepreneur should structure their business as if they might sell it tomorrow, even if they plan to run it forever. Some...

When a clinical psychologist told Cris "being a control freak is a sickness," it hit him like a hammer. For years, Cris had worn his controlling tendencies as a badge of honor, even priding himself on how his team would sit up straighter when he walked into the office. This revelation sparked a profound journey of self-examination that transformed his approach to both business and family life. In this deeply personal episode, Cris & Philip reveal how the need to control every aspect of yo...

What would change in your business decisions if you were thinking 500 years ahead instead of just the next quarter? This thought-provoking question frames our exploration of legacy creation for entrepreneurs and business owners who want more than fleeting success. In this episode we explore the concept of legacy creation through the lens of the Medici family, examining how true legacy transcends financial inheritance and requires intentional focus on values, stewardship, and multiple spheres ...

What separates those who work endlessly from those who work efficiently? Systems. Most business owners remain trapped in operations because they excel at exciting new projects but fail to transform them into repeatable processes. If your business doesn't become boring, you can't scale it and you can't delegate it—a hard truth for adrenaline-seeking entrepreneurs. Systems can transform your business operations and personal life, allowing you to work less while achieving more and enjoying great...

What treasures are hiding in plain sight within your business? Discovering untapped revenue potential doesn't require radical transformation—just a strategic eye for the opportunities you've been overlooking. In this episode, Cris & Philip discuss how significantly increasing your business revenue doesn't require massive changes, but rather finding the hidden potential in what you already have. Just as real estate investors look for untapped spaces in properties, business owners can disco...

Ever wonder why some businesses thrive while others struggle despite having great products? The answer might surprise you: it's all about sales. In this episode we explore why sales is the most critical skill for business success and wealth creation, revealing why even legendary figures like Martin Luther King were masterful salespeople. Some topics covered are: Sales Is Your ResponsibilitySales = Global Survival SkillBuild a Sales-First CultureSales Solves Societal ProblemsMaster Sales...

Ruthless leadership isn't about cruelty—it's about decisiveness, stability, and the courage to make necessary choices that others avoid. Drawing from Machiavellian principles and Renaissance ruler strategies, Philip and Cris explore when and how business leaders must make "bloody decisions" to create thriving organizations. Some topics covered are: Bloody Decisions in LeadershipYour Org’s Health > One EmployeeAct, Don’t OverthinkBe Ruthless With Your TimeProcess Over OutcomeLeadershi...

Could your frugality be sabotaging your success? In this thought-provoking episode, the Medici brothers challenge conventional wisdom with what they call "the hardest truth about money nobody wants to hear" – you must spend money to make money, and you must do it before you think you can afford it. Some topics covered are: Unlimited Budgets for GrowthInvest Before You're ReadyThe Cost of Being CheapThe Power of High-Level RoomsValue Your Time Like MoneyA-Players Are Non-NegotiableFeed Y...

Stop the endless hustle and discover the power of force multipliers in your business. Cris and Philip challenge the pervasive hustle culture that has entrepreneurs working harder but not smarter, burning energy without producing meaningful results. Some topics covered are: The myth of hustle cultureIdentifying and activating force multipliersStrategic relationship building: From gatekeepers to kingmakersDelegation mastery: Playbooks, assistants, and systemic clarityFrom grind to legacy:...

The success of your business depends far less on your products than on the people who represent them. In this episode, Cris and Philip explore why developing your team is the silent multiplier that transforms good companies into great ones. Some topics covered are: The hidden power of staff developmentLeadership by design, not defaultImmediate, intentional feedback loopsPurpose over paychecksLegacy through peopleAnd more...

What would you do if you needed a million dollars tomorrow? For most entrepreneurs, this scenario represents a nightmare. For Cris Auditore, it was simply a matter of making one phone call to a trusted friend who wired the money within 24 hours—with no contract. In this episode Cris and Philip explore how building authentic relationships across different wealth categories creates opportunities and opens doors for entrepreneurs seeking funding and support. They examine the power of proximity a...

Marriage presents a unique challenge for business owners who must balance professional success with personal fulfillment. The Medici brothers share honest insights from their combined decades of marriage experience while discussing practical approaches to strengthen this crucial relationship. Some topics covered are: Marriage is simultaneously the most difficult relationship to maintain and potentially the most joy-bringingBusiness owners should apply the same strategic planning to marr...

Meaningful conversations don't just happen—they're deliberately created through intention, location, and the right people. Drawing from personal experience, we explore how pivotal dialogues shaped our entrepreneurial journeys and life trajectories. Some topics covered are: Location mattersTime transforms dialogueIntentionality amplifies impactMentorship happens through consistent conversationThe Platonic Academy modelCommunity transforms isolationHistorical perspective adds depthAnd mu...

What if the secret to building a beautiful life and legacy wasn’t hidden in a secret strategy—but in the pages of the right book? In this powerful episode of Get Your House in Order, we explore how reading isn’t just a habit—it’s a catalyst. From billionaire libraries to personal breakthroughs, we uncover how the written word can shape the way we lead, grow, and live. Some topics covered are: Discussing the transformative power of reading Sharing personal experiences with literatu...

What if the relentless hustle isn’t the golden ticket to success but a fast track to burnout? That’s the hard lesson Cris Auditore learned in his early 20s. Now, he’s sharing the transformative insights that helped him navigate the often-overlooked realm of self-care for business owners. By dissecting the exhausting demands of hustle culture, he makes a compelling case for integrating disciplined rest into your routine. Understanding personal needs and allowing time for rejuvenation doesn’t j...

Cosimo de’ Medici built an empire on principles that still hold weight today. In this episode, we uncover the business wisdom that made him a force to be reckoned with—his sharp focus on customers, his mastery of selling, and his commitment to systematization. These were not just tactics; they were the foundation of a thriving, resilient enterprise. And here’s the kicker: these lessons are as relevant now as they were in Renaissance Florence. Whether you're scaling a startup or refining a leg...

Influence is the foundation of effective leadership, shaping both personal and societal outcomes. This episode discusses the interplay between business and politics, the importance of ethical influence, making hard decisions, and how entrepreneurs can create meaningful change in their communities. Some topics covered are: • Defining leadership as influence • Historical examples of effective influence in business • The need for entrepreneurs to engage in politics • Ethical co...

What does it take to build relationships so powerful they stand the test of time—even shaping history? In this episode, we uncover the secrets of Cosimo de’ Medici, a master of connection who befriended kings, popes, and the most influential figures of his era. Learn how his approach to business, family, and mentorship can help you cultivate meaningful connections, navigate crises, and create a legacy that lasts a lifetime. Some topics covered are: • Emphasizing relationships over transaction...

Rethinking personal growth through the lens of Cosimo de’ Medici, we uncover the necessity of stepping back to cultivate our minds and lives. With insights from history, the episode emphasizes the importance of finding spaces for personal development that lead to innovation and legacy. • Exploration of Cosimo de’ Medici and his personal development practices • The role of Villa di Carreggi as a retreat for self-improvement • Importance of gathering to debate ideas and foster intellectual gro...