Get Your House in Order

Most founders say they want freedom, but we keep building companies that can’t survive a week without us. That’s why we’re arguing for a move that feels backward at first: fire yourself first. When you stop being the daily operator and start becoming the designer of leaders, systems, and decision-making, the business can finally scale without burning you out. In this episode, we unpack why the most counterintuitive growth move is firing ourselves first and building leaders who can run the business without our daily involvement. Some topics covered are: Work yourself out of a jobFrom hustler to systems designerLetting go of controlSabbaticals and handoversRemove owner dependenceRichard Branson and Medici principlesAnd more...

Your day gets decided fast: one glance at your phone, one “quick” message, and suddenly you’re living inside everyone else’s agenda. In this episode we want to pull you back to the one part of the day you can still truly own, your morning, and show how a protected first hour can change your focus, mood, and long-term results. Some topics covered are: Cris’s travels and insights on global business cultureThe “beyond success” question and deeper reflectionRoutines create freedom, travel disrupts themTravel rules, protect a two-hour morning bufferEarly starts vs protecting sleep qualityFlight mode first hour to avoid distractionJournaling for clarity and alignmentMeeting-free mornings and deep workDesign your life now, not somedayAnd more...

The wins you’re most proud of can vanish faster than you think—not from one colossal blunder, but from small, compounding mistakes. In this episode we dig into a simple yet powerful lens: some parts of life are rubber balls that bounce back, while others are fragile ornaments that shatter once and never look the same. That clarity reshapes how we treat money, marriage, leadership, and reputation, and it guides the guardrails we build before stress tests our character.Some topics covered are: Rubber balls vs ornaments frameworkShifting from entrepreneur to investor without a planTaming drive to avoid overreachPark walks as boundary strategyStopping the second mistakeReflection as a control systemRelationship bank accounts and trust depositsChoosing winnable battlesAnd more...

Your sharpest deals and worst mistakes often start in the same place: your emotional state. We’ve watched brilliant founders sabotage partnerships, torch team trust, and overreach on risk not because they lacked strategy, but because their bodies and minds were running too hot. So in this episode we get honest about emotional health as operational risk—and share the practices that keep our own decisions clean when pressure climbs.Some topics covered are: Emotional health as founder riskConflict as dysregulation signalThe inner justifier of bad choicesNotice the clouds and pause decisionsGrace to rest and resetClear feedback and nonviolent communicationExercise and fewer processed carbs for moodBreathwork, sauna, and cold for regulationIntimacy to lower stressTherapy for core wounds and legacyOngoing emotional monitoringAnd more..

Ever feel “always on” but rarely satisfied with the results? In this episode we take a scalpel to modern busyness and rebuild your week around outcomes, not alerts. From killing inbox addiction to installing clear access protocols, this conversation shows how to trade reactive work for deliberate results—and save at least 10 hours every week.Some topics covered are: Email triage with assistants/AIFilter days by urgent vs. importantBlock interruptions with strict access rulesBatch messages to stay focusedSprint weeks for execution; off weeks for strategyIvy Lee: three outcomes per dayOutcome-first, minutes-long meetingsCapture-to-delegate to keep work movingAnd more...

Happiness is a shaky finish line; it wobbles with every mood swing and market turn. In this episode, we set our sights higher. We challenge the modern obsession with happiness and outline a richer target: a beautiful life shaped by meaning, purpose, sacrifice, and generosity. Through family stories, hard-won lessons, and practical tools, we show how to design a beautiful business and a beautiful day.Some topics covered are: Redefining the goal from happiness to beautyChoosing meaning, purpose, and calling dailyA grandfather’s costly love as a model for devotionDelayed gratification as the engine of growthMarriage as a long-term path to beautyCarrying grief and suffering with dignityBuilding a business that serves life and valuesDefining your ideal workday and structureGoals as milestones that require tradeoffsPracticing generosity as a core habitAnd more...

Ready to turn reflection into a competitive edge? In this episode we unpack a year of wins and misses to show how small systems create outsized results—financially, physically, and strategically. No fluff, just the tools and stories we used to design a life and business that compound. Some topics covered are: A 3-day calendar audit vs. a daily–weekly–monthly review loopAutomating investments for steady wealth buildingGold/silver habits, missed rallies, and better systemsRedefining health around sleep, injuries, and family realitiesExecution frameworks that speed decision-makingDigital boundaries with a “brick” phone and two numbersTurning every experience into value through reflectionDaily story capture to turn life into lessonsAnd more...

Tired of being the smartest person in the room? In this episode we break open a better path: become the conductor who assembles and orchestrates a circle of genius. Drawing on the Renaissance playbook of Lorenzo de Medici and the realities of modern boardrooms, we show how curated, cross‑disciplinary advisors can change the trajectory of a business faster than any internal meeting ever will.Some topics covered are: Why you shouldn't be the smartest person in the roomLessons from a Medici fresco on leadershipCurating cross-disciplinary advisory boardsThe cost (and value) of surrounding yourself with geniusMoving from ego to orchestrationHow intention builds confidenceMaking board meetings energizing, not boringWhen and how to build a mastermind or boardAnd more...

Deals don’t fall apart because of numbers. They fall apart because people feel unheard, cornered, or disrespected. In this episode we pull lessons from a Congo standoff and a mafia sit-down to show how hostage negotiation tactics translate into everyday business. We share practical tools—framing, mirroring, humor, and tone—to keep deals calm, human, and effective.Some topics covered are: Surviving a real-life hostage scenario in the CongoNavigating a tense property deal with mafia connectionsWhy negotiation is more emotional than logicalHow to read the room and de-escalate tensionLessons from Never Split the Difference by Chris VossUsing humor, tone, and body language to shift conversationsWhen to choose Zoom, phone, or in-person for hard talksFraming and anchoring techniques for better outcomesAnd more...

What if the real test of your success isn’t just the health of your company, but the health of your city? In this episode, we challenge business owners to think beyond the balance sheet and take responsibility in the civic arena. From a Medici fresco to modern coalitions, we lay out a practical path to be political in the classical sense: serving the common good with humility and patience.Some topics covered are: Why business owners should be politicalThe original meaning of “politics”Lessons from Lorenzo de' MediciBlending business, faith, and city impact3 key questions to guide civic actionLeading through collaborationHumility and patience in change-makingCivic impact as part of your brandAnd more...

Big ideas don’t move the needle if no one cleans the bathrooms. In this episode we unpack the real difference between leadership and management with candid stories—from a student-run catering company that grew fast and cracked under overmanagement, to a hotel pitch that thrilled U.S. investors with vision and then hit a wall when a German board asked the most practical question: who cleans the toilets?Some topics covered are: Leadership vs. management — knowing the differenceSwinging from spreadsheets to visionThe hotel pitch — why toilets matterPairing bold vision with follow-throughUsing the bite factor to test gritHiring based on your leadership–management mixTurning projects into repeatable processesAdding structure to family life and meetingsSpotting vision misalignment vs. routine gapsCodifying values and reinforcing behaviorsAnd more...Send us an email at [email protected] to get the Leader–Manager Framework and Assessment.

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 black notebook habitWhat a self-managing business really meansHow the 80/20 rule can transform your focusFacing reality with data, not emotionSetting a clear destination you can work towardAsking better questions to find smarter pathsCommitting to massive action and resourcesAdapting quickly as circumstances changeAnd more...Email us at [email protected] and ask for the Strategy Framework

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 topics covered are: Business That Can’t Run Without You = JobShift from Superstar to CoachLegal Docs & Contracts Make Business SellableConsultants Help Prepare for ExitSystematic Marketing & Sales Build Self-Managing BusinessBuild to Sell for Peace of MindTime & Resource Freedom Enables Multiple PursuitsSelf-Managing Business Reduces Stress & Builds LegacyAnd more...

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 your business and life can be destructive, sharing personal stories and practical strategies for effective delegation and team empowerment. Some topics covered are: Control Freak = Clinical IssueDelegate to Grow Beyond StartupFive Levels: Tasks, Playbooks, KPIs, Goals, Projects1-2-1 Rule: Problem, Solutions, RecommendationDelegate with Why, Deadline, Success, FiltersMicromanagement Ruins Relationships80/20 Control: Focus on What MattersGetting Help Shows StrengthAnd more...

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 of influence. This conversation goes beyond typical success metrics to explore how entrepreneurs and business owners can think in terms of centuries rather than quarters.Some topics covered are: Think Beyond Short-TermMedici Model For LegacyLegacy Is In PeopleShift To StewardshipInvest In Art & BeautyWrite Your Own EulogyInheritance vs. StewardshipAnd more...

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 greater freedom. The key is shifting from project-based thinking to developing sustainable processes.Some topics covered are: Systems Drive All ResultsEntrepreneurs Neglect ProcessesPlaybook + Delegation = GrowthSystematized Business = ValueCreate Playbooks, Assign OwnershipProjects vs. ProcessesApply Systems to LifeFreedom Requires Hard WorkAnd more...

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 discover valuable "coins" by optimizing their existing assets.Some topics covered are: Before-During-After framework reveals hidden revenueCompetitor referrals drive commissionsUnused space becomes revenueCross-industry innovation sparks ideasSmall conversions = big growthMaximize existing leadsAnd more...

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 Before You SystemizeThe Sales Training GapVision Casting Is SellingBillionaires Still SellHire Through Sales SkillsAnd more...

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 OutcomeLeadership as Loving BoundariesPerfectionism Kills ProgressAnd more...

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 Your Mind DailyAnd more...

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: Building businesses that outlast youAnd more...

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 and trust that enables million-dollar favors without contracts, while emphasizing that true connection happens when you genuinely value people rather than approaching relationships transactionally.Some topics covered are: Raising €1M in 24 Hours Through One RelationshipStrategic Relationship Tiers by Wealth LevelAuthenticity as the Root of TrustHow to Befriend the WealthyMother Teresa’s Model for Universal ConnectionRelationship-Building in Transactional IndustriesTurning Deals Into Relationship OpportunitiesAnd more...

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 marriage as they do to their companiesCreating intentional systems for communication prevents relationships from defaulting to survival modeDivorce can literally cut a business owner's wealth in half - making marital investment financially prudentHow you handle commitment in marriage often reflects how you'll handle business partnershipsRegular "360-degree feedback" conversations help identify and address relationship blind spotsSuccess in marriage doesn't happen accidentally—it requires vision, strategy and commitmentAnd much more...

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 much more...

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 literature and self-development Highlighting the necessity of implementing knowledge from books Encouraging a structured approach to reading as a strategy for growth Offering insights on how books can inspire hope and resilienceAnd much more...

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 just protect your well-being—it enhances your productivity and long-term success.Some topics covered are:  The hustle culture and its effects Personal experiences of burnoutStories of successful entrepreneurs experiencing burnout Principle of the Sabbath as a restorative tool Connecting with nature for mental health Self-care as a necessity, not a luxuryAnd much more...

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 legacy business, Cosimo’s strategies offer a blueprint for success that’s both fulfilling and sustainable. Some topics covered are: • Understanding Cosimo de' Medici's transformative impact on business • The necessity of prioritizing customer needs over product passion • Insights on developing sales skills for business owners • The importance of systematizing for sustainable operations • Learning to adapt and innovate continually for business success • An invitation to explore deeper involvement in the Medici community

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 considerations in business practices • Navigating employee relations and tough conversations • Using influence for community betterment and education • Encouraging responsible legacy-building through influence

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 transactions • The significance of integrating family in business • Learning from Cosimo de' Medici's life and legacy • Importance of preparing for crises in business relationships • Cultivating connections with influential figures • Leaving a legacy through mentorship and investments in others

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 growth• Need for self-care and creating personal spaces• How diversity within the Medici community promotes cross-learning• Encouragement to develop a continuous learning mindsetGet your free copy of the book at MediciBook.com.

Unlock the secrets of the Medici dynasty and transform your approach to success and legacy! Join us as my brother Cris Auditore and I, Dr. Philip Zimmerman, embark on an enlightening exploration of the Medici family's unparalleled influence on art, politics, and business during the Renaissance. Cris shares his unexpected journey from a mere fascination with Italian culture to writing an entire book about Cosimo de' Medici, the mastermind behind the family's legendary bank. Discover how their pioneering spirit and strategic brilliance can guide modern entrepreneurs in crafting not only profitable ventures but also meaningful lives.Our conversation goes beyond history, touching on the timeless lessons in legacy and relationships taught by Cosimo de' Medici. We reflect on the challenge of balancing personal ambitions with family life, drawing from our own experiences in parenthood. These stories highlight the importance of crafting a legacy that harmonizes influence, integrity, and family involvement. We set the stage for our upcoming episode, where we'll further explore the concept of "Get Your House in Order" and introduce you to the four houses that comprise it. Prepare to be inspired and challenged to organize every facet of your life in pursuit of true fulfillment.