The Learning Leader Show With Ryan Hawk

Ryan Hawk
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12 snips
Sep 28, 2025 • 57min

655: Morgan Housel - The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to Hear

Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk Morgan Housel is the New York Times Bestselling author of The Psychology of Money, Same As Ever, and The Art of Spending Money. His books have sold over 10million copies and have been translated into more than 60 languages. This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Notes: Morgan dedicated The Art of Spending Money to "Kellie the Unicorn" (his sister Kellie) after she was diagnosed with colon cancer and asked him to fulfill her long-running joke request. Sometimes book dedications "mean nothing to the reader, but they can mean everything to the author." People Who Bet on You - Brian Richards (Motley Fool boss) bet on Morgan when he didn't have to, providing unconditional support for a mediocre college writer. Craig Shapiro (Collaborative Fund) pursued Morgan for months to join his tiny VC firm as a full-time blogger when it wasn't a business necessity. What money can’t buy - Morgan once heard a story from a priest that he'll never forget… It’s from a priest who delivers the last rites in hospitals. He described the difference between what kids say to their parents when they’re about to die. The priest tells them to tell their parents what they’re most grateful for… In families with lots of problems, the kids usually talk about something that costs money. In the best families, the ones with solid relationships, the kids say the same thing every time. “Thank you for believing in me.” Making vs. Spending Money - "There are literally tens of thousands of books written on how to make money... There are virtually no books written about how to spend money." Most people assume spending needs no guidance, but wealthy people often demonstrate this isn't true. The Internal vs. External Scoreboard - Donald Crowhurst (fake sailor who killed himself seeking external validation) vs. Bernard Moitessier (expert sailor who quit before winning to avoid attention and live authentically). Modern society pushes us toward Crowhurst's external validation while we actually want Moitessier's internal satisfaction. The simplest formula for a pretty nice life: independence plus purpose. The independence to do what you want, and the wisdom to want to do meaningful things. Chuck Feeney's Wealth Example - The duty-free store billionaire first lived the stereotypical rich lifestyle, realized he didn't like it, then chose to live modestly and give away $10 billion. "I was happy when I was giving money away, and I was not happy when I wasn't giving money away." Every Dollar of Debt - "Every dollar of debt that you have is a piece of your future that someone else owns." Debt narrows the range of outcomes you can endure in an unknowable future. Money and Happiness Research - Recent studies show that earning more money only helps if you're already happy, joyful, and content. For depressed, anxious people, more money doesn't improve well-being. "It leverages whoever you are in either direction." What Money Can't Buy - The book is "40% about how to spend money to make yourself happier and 60% about realizing what money cannot do for you." Relationships, health, and personal fulfillment must come first. “Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart.” "Nobody gives a shit about anything other than how you make them feel." Vacation - Morgan realized while building sandcastles with his kids on the beach in Maui (10/10 experience) that building Legos at home with them was almost as good (9/10). The real value was "uninterrupted time with my family," which required travel to avoid daily distractions but pointed to what actually mattered. Ambition - Morgan's career drive crystallized while kayaking past $25 million mansions on Lake Washington in 2010: "I need to work harder. I want one of those one day." This wasn't envy but ambition - though he notes the line between inspiration and envy is thin, especially once you know the person. A high savings rate is not "saving" but is "purchasing independence." Each saved dollar buys freedom to handle life's unknowable future without someone else's schedule dictating his choices. Why Spending Is Complicated People try to fill emotional holes with material purchases Society tells us what we should like, which may not align with our actual preferences We chase peer comparison rather than personal satisfaction We overestimate the social rewards of nice possessions The Independence Framework Save money not for retirement but for freedom to handle uncertainty Debt narrows your options when life throws curveballs Independence means being able to do what you want, with whom you want, for as long as you want The Internal Scorecard "No one's watching. No one's thinking about you." When people notice your possessions, they're either imagining themselves having them or envying you for them Neither response gives you the social validation you're seeking Use money to buy independence rather than others' admiration Relationship Investments Focus on what creates "uninterrupted time with people you love" Consider how purchases enable deeper connections (bigger kitchen for family dinners) vs. impressing others Remember that belief and support matter more than material provision Purpose Morgan's purpose became clear the moment he became a father: "There. That's it... I don't matter anymore. That's the only thing that matters right there." Purpose can be parenthood, work, religion, or community, but it needs to be bigger than yourself. "Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart." They deliver profound psychological and social insights while focusing on how they make you feel, not their own status. Regret -- Gerontologist Carl Pillemer interviewed 1,000 Americans aged 90-100. Not a single one said, "I wish I earned more money" or "I wish I worked harder." Nearly all said "I wish I spent more time with my kids" and "I wish I were nicer to my spouse." Inspiration vs. Envy -- Morgan credits James Clear as inspiration for "The Psychology of Money" and describes him as incredibly successful yet humble and kind. This creates pure inspiration without envy, unlike other successful writers whose personalities trigger competitive feelings.
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30 snips
Sep 21, 2025 • 1h 4min

654: Jake Tapper - The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You

Jake Tapper, an award-winning broadcaster and CNN's chief Washington correspondent, shares insights from his remarkable career and writing journey. He emphasizes the importance of hard work and the need to be so good that you can't be ignored. Tapper discusses how to handle criticism and the value of truth-tellers in leadership. He reflects on how curiosity fuels his storytelling and the significance of embracing rejection. Additionally, he shares wisdom on balancing family life with a demanding career and the importance of offering clear value.
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72 snips
Sep 14, 2025 • 58min

653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders

Sukhinder Singh Cassidy, CEO of Xero and seasoned leader from Google, Amazon, and StubHub, shares her insights on navigating the CEO journey. She outlines her four non-negotiables when evaluating leadership roles, emphasizing a customer-centric approach. The conversation highlights her innovative hiring strategy, which involves selling the opportunity first to attract talent. Sukhinder also discusses the importance of strong corporate culture, authentic communication, and aligning personal values with organizational goals for success.
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27 snips
Sep 7, 2025 • 57min

652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy

Arthur Brooks, a Harvard Business School instructor, columnist at The Atlantic, and bestselling author, shares intriguing insights on happiness, leadership, and personal growth. He discusses the 'Mad Scientist' profile of high achievers grappling with intense emotions and offers strategies for managing negative feelings through faith and physical exercise. Brooks emphasizes morning routines for productivity and highlights the pitfalls of the arrival fallacy, encouraging listeners to find joy in the journey rather than just in achievements.
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45 snips
Aug 31, 2025 • 52min

651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)

Shaka Senghor, a New York Times best-selling author and motivational speaker, shares his inspiring journey from spending 19 years in prison to becoming an advocate for personal transformation. He discusses the permanent impact of split-second decisions and how literature became his escape, introducing him to new perspectives. Shaka highlights the pivotal role of mentorship from fellow inmates and emphasizes vulnerability as a strength in leadership. His insights on embracing hardship and mastering mindset inspire listeners to take ownership of their lives.
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8 snips
Aug 24, 2025 • 1h 5min

650: Michelle "Mace" Curran - Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower

Michelle "Mace" Curran, a combat veteran and former fighter pilot, shares her journey as the second woman to lead the Thunderbirds. She discusses how early experiences in male-dominated environments built her confidence and resilience. Curran emphasizes the importance of structured debriefs for fostering trust and effective feedback in teams. She also reveals how vulnerability can cultivate strong community bonds and the necessity of communication during high-pressure situations in aviation. Her insights inspire turning fear into a powerful motivator.
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29 snips
Aug 17, 2025 • 56min

649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons)

Sam Lessin, a Partner at Slow Ventures and former Facebook VP, shares invaluable insights shaped by his father's wisdom. He emphasizes the '4:30 AM Advantage', advocating for early starts to gain a competitive edge. Lessin discusses the significance of joy as a sustainable asset in business, stating that angry people rarely win. He also introduces 'Type Two Fun', highlighting how enduring challenges builds resilience. Plus, he recounts a remarkable investment journey in Solana, underscoring the value of relationships in success.
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44 snips
Aug 10, 2025 • 1h 2min

648: Ed Latimore - Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business

Ed Latimore, a professional heavyweight boxer and best-selling author, shares his inspiring journey from addiction and poverty to personal empowerment. He believes that starting any endeavor, 'going from zero to one,' is the toughest part. Latimore emphasizes the importance of discipline over feelings and reflects on his 13 years of sobriety, calling it his hardest fight. He also discusses the psychological aspects of boxing, the significance of body language, and how overcoming life’s challenges can foster resilience and empathy in future generations.
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77 snips
Aug 3, 2025 • 1h 22min

647: Tim Ferriss - Chasing Your Curiosity, Internal vs External Scoreboards, Effectiveness over Efficiency, Winning Even if You Fail, Fame's Hidden Costs, & The Mount Rushmore of Podcasting

In this engaging discussion, Tim Ferriss, bestselling author and influential podcaster, shares his insights on nurturing curiosity and the profound impact of upbringing. He explores the balance between internal and external success measures and emphasizes the value of viewing failures as learning opportunities. Tim also delves into the creation of his card game, COYOTE, and its role in fostering real-world connections. Additionally, he reflects on the hidden costs of fame and the importance of joy amidst seriousness in life.
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14 snips
Jul 27, 2025 • 49min

646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)

In this engaging conversation, Nick Maggiulli, COO and Data Scientist at Ritholtz Wealth Management, shares his insights on personal finance. He discusses how money enhances life experiences rather than being the solution to happiness. Nick compares life to chess, emphasizing practice and persistence over mere intelligence. He introduces the Wealth Ladder, breaking down financial strategies at different life stages. The discussion also touches on financial dynamics in marriage and the importance of purpose in achieving true happiness.

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