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 loop
• Automating investments for steady wealth building
• Gold/silver habits, missed rallies, and better systems
• Redefining health around sleep, injuries, and family realities
• Execution frameworks that speed decision-making
• Digital boundaries with a “brick” phone and two numbers
• Turning every experience into value through reflection
• Daily story capture to turn life into lessons
• And 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 room
• Lessons from a Medici fresco on leadership
• Curating cross-disciplinary advisory boards
• The cost (and value) of surrounding yourself with genius
• Moving from ego to orchestration
• How intention builds confidence
• Making board meetings energizing, not boring
• When and how to build a mastermind or board
• And 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 Congo
• Navigating a tense property deal with mafia connections
• Why negotiation is more emotional than logical
• How to read the room and de-escalate tension
• Lessons from Never Split the Difference by Chris Voss
• Using humor, tone, and body language to shift conversations
• When to choose Zoom, phone, or in-person for hard talks
• Framing and anchoring techniques for better outcomes
• And 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 political
• The original meaning of “politics”
• Lessons from Lorenzo de' Medici
• Blending business, faith, and city impact
• 3 key questions to guide civic action
• Leading through collaboration
• Humility and patience in change-making
• Civic impact as part of your brand
• And 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 difference
• Swinging from spreadsheets to vision
• The hotel pitch — why toilets matter
• Pairing bold vision with follow-through
• Using the bite factor to test grit
• Hiring based on your leadership–management mix
• Turning projects into repeatable processes
• Adding structure to family life and meetings
• Spotting vision misalignment vs. routine gaps
• Codifying values and reinforcing behaviors
• And more...

Send us an email at coaching@medicilegacy.com 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 hustle
• The power of the black notebook habit
• What a self-managing business really means
• How the 80/20 rule can transform your focus
• Facing reality with data, not emotion
• Setting a clear destination you can work toward
• Asking better questions to find smarter paths
• Committing to massive action and resources
• Adapting quickly as circumstances change
• And more...

Email us at coaching@medicilegacy.com 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 = Job
• Shift from Superstar to Coach
• Legal Docs & Contracts Make Business Sellable
• Consultants Help Prepare for Exit
• Systematic Marketing & Sales Build Self-Managing Business
• Build to Sell for Peace of Mind
• Time & Resource Freedom Enables Multiple Pursuits
• Self-Managing Business Reduces Stress & Builds Legacy
• And 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 Issue
• Delegate to Grow Beyond Startup
• Five Levels: Tasks, Playbooks, KPIs, Goals, Projects
• 1-2-1 Rule: Problem, Solutions, Recommendation
• Delegate with Why, Deadline, Success, Filters
• Micromanagement Ruins Relationships
• 80/20 Control: Focus on What Matters
• Getting Help Shows Strength
• And more...