Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

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Guest: Dakota Meyer, a United States Marine Corps veteran and Medal of Honor recipient. At just 21 years old, Dakota's actions during the Battle of Ganjgal in Afghanistan saved many lives when he repeatedly went against his orders and drove into a Taliban ambush zone to rescue trapped soldiers. He became the first living Marine in more than 40 years to receive the Medal of Honor. Today, he's a firefighter, entrepreneur, and New York Times bestselling author. Dakota is dedicated to developing leaders who can handle crisis and complexity. In our conversation, you'll hear why Dakota believes his most heroic day was actually his greatest failure, what he was feeling the day he received the Medal of Honor from President Obama, and his practical blueprint for bringing our divided country together.

Notes:

• The Three-Phase Life Cycle - Dakota's framework for wisdom: "You have an obstacle you face. You have to get through that obstacle and become better from it. And then the third piece is you have to share how you got through that obstacle."
• Leadership vs. Responsibility - "Leaders are just people too. You can lead from anywhere in an organization... Leadership comes in many forms." True leadership means choosing where your loyalty lies - with the people you're responsible for or with protecting your own position.
• September 8th, 2009: Leadership Failure - Dakota frames his Medal of Honor actions as "an absolute story of leadership failure at its best" - multiple levels of leaders avoiding responsibility while he went against orders to save his teammates.
• The Loyalty Question - "Where does their loyalty lie? Is it in the people that trust them to lead them and to protect them? Or is it in the organization in order for themselves to keep getting promoted?" This fundamental choice defines every leader.
• Risk vs. Results - "Organizations and leaders today are so risk-averse that risk comes before results... You can't be successful, do hard things, and stay comfortable and be safe. In no world does that exist."
• Mental Health Reality Check - Dakota challenges current mental health approaches: "We're giving people no hope because we're trying to accommodate their emotions and not bring them back to reality and logic." He distinguishes between trauma that needs addressing and self-induced mental health issues through poor choices.
• Love as Choice, Not Emotion - "Love is not an emotion. Love is a choice... If you love me, you're going to always help me be the best version of me. That doesn't always feel good."
• Accountability and Fatherhood - As a father of two daughters: "I can't be anything that I wouldn't let anybody else be to them... You set the bar for what they're gonna accept and what they're not gonna accept."
• The Civil War Warning - "America doesn't need a Civil War. What we need is to vote, to lead, to speak up in schools, to teach our kids history, truth, kindness with strength, and how to disagree without violence."
• The Ambush  - When his team walked into an ambush, promised support assets (air support, mortars, quick reaction force) weren't available due to rules of engagement restrictions. When Lieutenant Johnson called for artillery support, saying, "If you don't give me these rounds right now, we're going to die," the response was "Try your best."
• The Decision to Act - Dakota requested permission to help multiple times and was denied each time. He finally went against orders with his driver, Staff Sergeant Rodriguez Chavez, making four or five trips into the valley over six hours to evacuate wounded and recover bodies.
• The Human Cost - Dakota describes the helplessness of watching Afghan soldiers get "mowed down" while running toward his vehicle for rescue. He performed basic life-saving measures, loaded wounded in trucks with the dead on the bottom and living on top for triage priority, and ultimately recovered some of his fallen teammates.
• The Immediate Aftermath - Dakota put his teammates in body bags, flew them home, then immediately returned to cleaning his truck and helping Afghan soldiers with their dead. He went back to his base alone - the only survivor of his four-man team.
• Mental Health Crisis - Dakota developed a destructive cycle: daily drinking (depressant), massive caffeine intake to compensate, creating anxiety and amplifying trauma. He was surrounded by people who only wanted to discuss trauma and war stories, preventing healing.
• Suicide Attempt - Dakota reached a breaking point where he held a gun to his head, but it wasn't loaded. This became his turning point - he made a commitment to either "rack it back and go ahead and do it, or go out and find a way to get through this and start living a life worthy of their sacrifices."
• The Path Forward - Recovery came through accountability rather than accommodation. Dakota emphasizes that while trauma needed addressing, he was "amplifying and feeding the problem, not the solution" through his choices.
• Real vs. Perceived Heroism - Dakota challenges the hero narrative: "I am an example of the potential that's in every human being... If they believe in a cause that's bigger than themselves, and they love people so much that they're willing to do whatever it takes to stop the suffering."
• Daily Character Building - "You don't just wake up and do the hard thing. It starts every day. Do you get up when you say you're gonna get up? Do you do what you say?" The Medal of Honor action was simply "upholding my end of the deal to my teammates and to my country."
• Being a Great Dad - Dakota sets an extremely high bar as a dad: "I believe that if your daughters start dating shitty and weak men, it's because you are a shitty and weak man." He sees fatherhood as the ultimate accountability.
• Unity through Truth - His current focus: "I just want to bring people together... I wanna put hope back in the world through truth." He believes in finding common ground with anyone through genuine connection and curiosity.
• Education vs. Knowledge - Dakota distinguishes between theoretical education and practical knowledge: "There's a difference between education and knowledge... those who can't do, they teach. We need more that have done teaching."
• The Power of Love - His core philosophy centers on love as action, not emotion: "Love is limitless... there's no expiration date" compared to hate and negativity, which "there's an expiration date on."
• Practical Application
  • Leadership Loyalty Test - Before making decisions, ask where your primary loyalty lies: with those you lead or with your own advancement
  • Risk-Taking Framework - Understand that meaningful results require accepting risk and discomfort
  • Mental Health Approach - Address trauma while taking responsibility for choices that amplify problems
  • Daily Character Development - Build integrity through small daily commitments before facing major challenges
  • Connection Over Division - Seek common ground through curiosity and questions rather than attacking opposing viewpoints

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.

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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.

Go to www.LearningLeader.com for full show notes

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. www.InsightGlobal.com/LearningLeader

The Learning Leader Show with Ryan Hawk

Guest: Jake Tapper is an award-winning broadcaster and chief Washington correspondent, currently anchoring The Lead with Jake Tapper every day on CNN. He’s also the #1 New York Times best-selling author of 7 books, including The Outpost (which was later made into a movie), Original Sin, and most recently Race Against Terror.

Notes:

• Be So Good They Can’t Ignore You. Jake: I’m in control of how hard I work. It is our responsibility to work so hard that we become the obvious choice for the job or the promotion. Be So Good They Can’t Ignore You. "I had to be so good that even though maybe on a broadcasting level I wouldn't be the number one pick... they had to give it to me."
• The one leadership skill that is massively important to develop… Don’t insulate yourself with “yes” people. You have to have truth tellers in your life. Who are your foxhole friends? Who are the people who are willing and able to tell you the truth? Who are the ones who love you and care about you enough to let you know when you’ve messed up? Those people are gold. We all need them.
• Rejection: Dr. Seuss was rejected by 47 publishers. Rejection is part of life. You have to stay in the game for a chance to win it. Keep going. And nobody will give you a job to be nice. What value do you bring to a company? How will you make your boss's life better? You get hired to solve a problem, not because someone wants to be nice.
• Pinned tweet since 2017 – "To see what is in front of one’s nose needs a constant struggle." -- George Orwell. A reminder to see obvious truths being obscured by spin or wishful thinking.
• "You Can Always Tell Them No" - Ted Koppel's crucial advice to young Jake about maintaining journalistic integrity and not compromising values for opportunities. This became a career-defining principle that Jake still follows 20 years later.
• The Jar Jar Binks Theory of Leadership - Successful leaders often remove critics from their inner circle, creating dangerous echo chambers. "Great people often achieve as much as they can to the point that they are able to remove from their inner circle anyone who tells them they're being an asshole or making a wrong decision."
• Constructive vs. Destructive Criticism - Jake learned to distinguish between useful feedback and personal attacks: "Very few of my critics are people that I actually care what they think... folks who understand I'm just trying to be a good faith operative here."
• Curiosity as Career Driver - Deep curiosity drove Jake from reading microfiche about MASH as a kid to investigating complex stories as an adult: "I find something interesting and I wanna find out everything I can about it."
• Rejection as Constant Reality - Even at his career peak, Jake faces daily rejection: "I get rejected every day... it doesn't matter that I've had New York Times bestsellers before... it's part of life."
• Humility Enables Learning - Accepting expertise gaps allows growth: "Having the humility to accept that I am not an expert on any particular thing... I'm a journalist, which means I try to be an expert on whatever I'm covering at that moment."
• Leadership Lessons From Powerful People
  • The Inner Circle Problem: Leaders systematically remove critics until surrounded only by yes-people, creating dangerous blind spots. Jake witnessed this pattern with Joe Biden (surrounded by aides and family who weren't honest about his declining acuity) and across industries.
  • The Solution: Intentionally maintain truth-tellers in your inner circle who care about you personally but will challenge you professionally.
  • Creating Truth-Telling Environments: Jake encourages healthy disagreement with executive producers, acknowledges power imbalances that make criticism harder for junior staff, and creates indirect channels for feedback ("some people on the staff think...").
  • The Criticism Paradox: Public leaders face constant harsh criticism, making them naturally defensive. Understanding this context helps leaders distinguish between constructive feedback that improves performance versus personal attacks that serve no purpose.
• Following Curiosity Despite Opposition
  • Jake's major works were all advised against by professionals:
    • The Outpost (no military expertise)
    • The Atlantic story of freeing a wrongly imprisoned man
    • Biden book (started the day after the election, despite uncertainty)
  • Key Insight: "Every single one of them, people were telling me not to do it... It's been following my curiosities even when people told me I'm not interested in that."
• The Hard Work Advantage: Jake couldn't compete on appearance or natural broadcasting ability, so he outworked everyone: broke stories constantly, used blogs when he couldn't get on air, and made himself impossible to ignore through sheer output.
• Dealing with Rejection
  • Expect constant rejection even at a career peak
  • Don't take rejection personally unless there's constructive feedback
  • Use rejection as data, not judgment of worth
  • Keep creating regardless of immediate acceptance
• The Wave Metaphor: Like Tom Hanks in Cast Away, timing the waves - "every code can be cracked" if you persist and find the right timing.
• Key Elements for Writers:
  • Strong structure: "Act one, chase your hero up a tree. Act two: throw rocks at your hero. Act three, get your hero out of the tree."
  • Good editor who pushes back - be willing to "kill your darlings"
• Life Philosophy
  • The Acceleration Mindset: At 56, Jake is speeding up output: "I don't know how much longer I have this window where people are paying attention... relevance is ephemeral... when it leaves, it looks fucking brutal."
  • For Young People: "So much of life is rejection... You cannot stop it... don't take it personally." Focus on developing skills and delivering value: "Nobody will give you a job to be nice... They'll do it because you have something they want."
  • Time Sacrifice Awareness: Success requires acknowledging costs: "What I cried about is the stuff I missed that I wasn't there for because I was chasing a story or on assignment."

Time Stamps:

02:46 Jake’s Dedication to Influential Figures

05:05 Hot Mic Moment in Alaska

06:59 Preparing for Big Interviews & When to Follow Up

09:01 Dealing with Criticism

12:07 The Story Behind Jake’s Pinned Tweet

13:48 Race Against Terror: The New Book

18:29 Balancing Multiple Roles

20:47 Chasing Your Own Curiosity 

23:58 Sacrifices for Career Success

29:00 The Importance of Humility in Leadership

31:08 Surrounding Yourself with Truth Tellers

34:18 Healthy Tension in Team Dynamics

37:15 Understanding the Pressure on Public Figures

40:09 Empathy in Leadership

45:17 Balancing Career and Family

49:00 Advice for Aspiring Journalists and Writers

52:01 The Reality of Rejection and Hard Work

57:26 The Importance of Structure and Editing in Writing

01:01:16 End of the Podcast Club

Go to www.LearningLeader.com for full show notes

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Sukhinder Singh Cassidy is the CEO of Xero. Xero is a cloud-based accounting software designed for small businesses. They did $2.1 billion in revenue last year. Over the past 25 years, Sukhinder has had leadership roles at Google, Amazon, and StubHub.

Notes:

Key Learnings

• Strategic CEO Job Search Criteria – Sukhinder had four non-negotiables: macro tailwinds/good market, customer she could be passionate about, strong business model, and a role where she could "learn for miles" for 5-8 years. Only two companies met her criteria in 18 months of searching.
• "Sell, Interview, Sell" Hiring Process – First meeting is 50% selling the opportunity to attract top talent. Only after candidates lean in do you shift to intensive interviewing with leadership team exposure.
• The Virtuous Cycle Framework – Customer at the top, supported by "high purpose, high performance, high people" culture. "It's an 'and,' not an 'or'" - you don't get to choose just one element.
• Back-Channeling is Critical – Reference checking happens throughout the entire interview process, not just at the end. "The most important thing is not just front channel... it's all the back channel."
• Values Alignment Over Pure Qualifications – "Go where my values fit and my strengths are valued." Cultural fit becomes the deciding factor in close hiring calls, not competence.
• The Layoff Leadership Test – Six weeks after joining, Sukhinder laid off 900 people based on McKinsey benchmarking. Showed consistency between the outside-in analysis presented to the board and transparent communication to employees.
• Portfolio of Bets Strategy – Balance growth, profitability, and customer happiness through diversified initiatives ranging from "safe moves" to "flyers," with clear probability assessments.
• Consistency as Culture Foundation – "Culture means consistency of message and what's important." Authenticity through change, not resistance to change.
• The 10-Slide CEO Interview Deck Framework:
  1. Vision statement (destination in 2-3 years)
  2. Outside-in market analysis
  3. Competitive landscape
  4. SWOT analysis of current position
  5. Five key strategic moves
  6. Implementation approach ("the how")
  7. Estimated outcomes with probability ranges
• Practical Application:
  • Job Search Strategy – Define 4-5 non-negotiable criteria upfront. Be willing to wait for roles that truly meet your standards rather than taking "the job before the job."
  • Interview Preparation – Always build a comprehensive thesis deck even if not requested. Use it to clarify your own thinking and demonstrate strategic capability.
  • Hiring Excellence – Spend equal time selling the opportunity and evaluating candidates. Use diverse interview panels and back-channel extensively throughout the process.
  • Cultural Leadership – Be consistent in messaging across all stakeholders (board, investors, employees). Authenticity enables trust during periods of change.
  • Strategic Planning – Frame initiatives as a portfolio of bets with clear probability assessments. Balance growth, profitability, and customer satisfaction rather than optimizing for one.
• Leadership Hiring Process:
  • The CEO interviews top 2-3 levels even without hiring authority
  • Diverse interviewer panels with "bar raisers"
  • Business problem-solving presentations in the final rounds
  • Multiple leadership team interactions before the final decision
• Life Lessons:
  • Patience in Career Progression – Sometimes the right opportunity requires waiting. Sukhinder was frustrated during 18 months of searching but found the perfect fit.
  • Preparation Separates Candidates – The depth of strategic thinking demonstrated in final presentations often determines CEO selections.
  • Culture Survives Through Consistency – Not avoiding change, but maintaining consistent values and communication approach through inevitable changes.
  • Leadership Requires Tough Decisions – Laying off 900 people six weeks into the role, but doing it transparently and based on clear data/analysis.
  • Value Creation Through Alignment – Finding roles where your strengths are valued and values align creates exponentially better outcomes than pure skill matching.
  • Systems Thinking Builds Trust – Sharing appropriate "behind the scenes" context helps teams understand difficult decisions and builds long-term credibility.
  • Early Career Focus – "Do great work for great people." Find talented leaders to apprentice under and work exceptionally hard to maximize learning.
  • Authenticity Enables Performance – Being genuine about challenges and changes builds stronger relationships than trying to maintain artificial stability.
  • Strategic Communication – Frame personal asks in terms of organizational benefits. Make it about solving their problems, not your desires.
• The Xero Transformation:
  • Financial Performance: $2.1B revenue, 21% YoY growth while maintaining profitability
  • Cultural Approach: "High purpose, high performance, high people" - no choosing between them
  • Strategic Moves: Pricing/packaging optimization, sales motion transformation, customer experience reimagining (new dashboard with 3000+ customer inputs)
  • Leadership Philosophy: Provide a "systems view" to employees, share investor-level insights appropriately, and maintain authenticity during difficult decisions

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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. www.InsightGlobal.com/LearningLeader

Notes:

Key Learnings

• The Mad Scientist Emotional Profile – High achievers typically have both high positive and high negative affect. "Hustlers, hard workers, strivers, entrepreneurs, ambitious people, they're in that quadrant of high positive, high negative affect." This creates intensity but requires management of negative emotions.
• Dangerous Negative Affect Management – People try to manage high negative affect through alcohol, excessive internet use/pornography, and workaholism. "The isms, the addictions, they're almost all negative affect management techniques."
• Two Best Ways to Manage Negative Affect:
  1. Faith, Spirituality, Philosophy - "Every day, go deep" into transcendent practices
  2. Physical Exercise - "Go pick up heavy things" - resistance training moderates negative emotions
• Arthur's 4:30 AM Protocol – Wakes at 4:30, works out 4:45-5:45, attends mass 6:30-7:00, then has high-protein breakfast with dark coffee at 7:45 for 4 hours of peak creative focus. "I get four hours of creative concentration with maximum dopamine."
• Exercise Reduces Unhappiness, Doesn't Create Happiness – "Working out hard... moderates negative affect. It makes you less unhappy" rather than directly increasing positive emotions.
• The Failure Journal Method – Write down failures/disappointments, return after 3 weeks to note learnings, return after 2 more months to identify good things that resulted. This installs learning in the prefrontal cortex rather than letting it "float around limbically."
• Early Success Can Be Dangerous – Scholars rejected for early research grants outperformed those with early success. "Much better is when you do the work and build yourself up... be a wholesaler before you become a retailer."
• Management Doesn't Provide Flow – "There's one kind of job where you don't get flow, and that's management... you're getting jerked from thing to thing to thing." Being CEO was "satisfying, but not enjoyable."
• Intelligence Must Serve Others – "Intelligence is just another gift... whether or not it makes you happier depends on whether or not you're using it to make other people happier." Denigrating others for lower intelligence indicates misusing your gift.
• The Arrival Fallacy – Olympic gold medalists often experience depression after winning because positive emotion comes from progress toward goals, not achieving them. "Your positive emotion doesn't exist to give you a permanent good day."
• Two Midlife Crisis Solutions:
  1. Focus on what age gives you rather than takes away
  2. Choose subtraction over addition - appreciate what you no longer have to do
• Making Changes Stick Requires Three Elements:
  1. Understand the science - Know why something works
  2. Change your habits - Actually implement different behaviors
  3. Teach it - Explain it to others to cement learning in the prefrontal cortex
• The Happiness Formula – "Use things, love people, worship the divine" instead of the natural impulses to "love things, use people, and worship yourself."

Multi-generational Living Benefits – Arthur lives with adult children and grandchildren: "The research is clear that the closer you are to your grandchildren... the better it is for everybody."

Quotes:

• "I get four hours of creative concentration with maximum dopamine in my prefrontal cortex... ordinarily I would get an hour and a half, two hours of real clarity."
• "The isms, the addictions, they're almost all negative affect management techniques."
• "Working out hard... makes you less unhappy. The research is very clear."
• "Being the boss isn't that fun. It just isn't."
• "I have carefully accounted for all of my days of happiness. They add up to 14." (Emir of Cordoba)
• "What's first prize in a pie eating contest? The answer is pie. So I hope you like pie."
• "Beware the corner office boys. Beware the corner office."
• "Use things, love people, worship the divine."
• "Watch one, do one, teach one." (Harvard Medical School)
• "Don't trust your impulses. Your impulses are to love things, use people, and worship yourself."

Life Lessons

• Develop Daily Discipline Early - A Consistent morning routine with exercise and spiritual practice creates optimal brain chemistry for peak performance throughout the day.
• Manage High Achievement Personality - If you're a driven person, recognize you likely have high negative affect that needs healthy management through exercise and transcendent practices.
• Reframe Career Setbacks - Early failures often build stronger foundations than early successes. Use disappointments as learning opportunities through systematic reflection.
• Question Management Ambitions - Consider whether you enjoy management or just want the status/money. Management roles inherently provide less flow and enjoyment.
• Use Intelligence to Serve Others - Your cognitive gifts should lift others up, not put them down. Intelligence without service leads to unhappiness.
• Focus on Progress, Not Arrival - Derive satisfaction from forward momentum in meaningful work rather than achieving specific goals that won't provide lasting happiness.
• Embrace What Age Gives - In life transitions, focus on new capabilities and freedoms rather than what you're losing or leaving behind.
• Teach What You Learn - The most effective way to cement new habits and insights is to explain them to others. Teaching accelerates your own learning.
• Choose Subtraction - Happiness often comes from eliminating negative elements (bad meetings, toxic relationships) rather than adding more positive ones.
• Build Multi-Generational Relationships - Prioritize time with family across generations. The research strongly supports benefits for all parties.
• Exercise for Mental Health - View physical training as medication for negative emotions rather than just physical fitness.
• Cultivate Transcendent Practices - Whether religious, philosophical, or spiritual, daily engagement with something larger than yourself moderates negative emotions and provides meaning.

Time Stamps:

00:10 Arthur's Fitness and Health Routine

02:01 Link Between Fitness and Happiness

04:03 Managing Negative Emotions

06:23 Morning Routines

13:24 The Importance of Failure

22:26 The Reality of Promotions and Leadership

27:56 The Power of Intelligence: A Double-Edged Sword

28:28 Using Gifts to Spread Happiness

29:20 The Impact of Helping Others

33:28 Avoiding the Arrival Fallacy

36:36 Redefining Retirement and Midlife

47:39 The Importance of Teaching and Learning

51:28 Life Advice

53:01 EOPC (End of the Podcast Club)

Go to www.LearningLeader.com for full show notes

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. www.InsightGlobal.com/LearningLeader

Shaka Sengor spent 19 years in prison for killing a man. He’s transformed his life through not making excuses and taking full ownership of his decisions. Now, he’s a New York Times best-selling author who has been called a “soul igniter” by Oprah. His latest book is called How to Be Free.

Notes:

• • The Permanence of Split-Second Decisions – At 17, shot three times on a Detroit corner. At 19, he killed a man in a conflict after creating a narrative that he would "shoot first." Sentenced to 17-40 years for second-degree murder. "I try to teach young people about understanding the permanence of a 30-second decision."
  • Books as Portals to Freedom – Read over 1,500 books during 19-year incarceration, starting with street literature (Pimp, Black Gangster) as a gateway to philosophy (Plato, Marcus Aurelius). "Books allowed me to escape in the most literal sense... a portal into other worlds."
  • Prison Mentors Changed Everything – Lifers became his guides: "These are men serving life sentences who came equipped with wisdom about what's on the other side... they guided me to books that shattered old narratives and opened possibilities."
  • Reading Creates Writing Excellence – Speed-reading skill from age 8 (learned during punishments with encyclopedias) combined with voracious prison reading, led to becoming a NY Times bestselling author. "You have to be a practitioner of the craft every day."
  • Journaling as Transformation Tool – "It was the most healing experience I've ever had to speak to my truth, speak to the pain points." Uses 20 different journals, writes everywhere - planes, shower thoughts on phone, margins of books.
  • Hidden Prisons We All Carry – "The most powerful prisons aren't the ones made of concrete and steel. They're the ones we carry with us, built from grief, anger, shame, trauma." Everyone has internal prisons that can be opened.
  • Vulnerability as Strength, Not Manipulation – Authentic vulnerability vs. weaponized oversharing. "Human beings have this innate ability to suss out the truth. Authenticity and vulnerability is the super unlock... being true to your center."
  • Community Through Shared Truth – Prison taught extreme friendship criteria: "Are they willing to serve a life sentence for you or die for you?" Now applies accountability standards: showing up consistently, being loyal to family first.
  • Violence Born from Fear – "Reactionary violence is typically born out of fear, being afraid." Prison taught him to see "the child in people" who are acting out, leading to empathy instead of escalation.
  • Voluntary Hardship Builds Resilience – Monthly 3-day fasts in solitary confinement prepared him for food deprivation punishment. "None of us get through life without suffering... that extra hour a week can change your life's outcomes."
  • Composure Through Self-Awareness – Developed through journaling about times he wasn't composed. "Once you've written it down, you own it. When you own it, you can control it. When you can control it, it's easy to become composed."
  • Remove All Excuses – Florence Nightingale quote: "I never gave or took any excuse." Despite a felony record, a violent crime conviction, and 20 years in prison, he chose to "lead a great life" by removing every excuse.
  • The Ben Horowitz Friendship – Unlikely brotherhood with VC billionaire, starting from Oprah's introduction, bonding over music and culture until 3 AM conversations. Shows authentic relationships transcend backgrounds.
• Quotes:
  • "I try to teach young people about understanding the permanence of a 30-second decision."
  • "I was in prison before I stepped foot in a cell, and I was free before they ever let me out."
  • "The most powerful prisons aren't the ones made of concrete and steel. They're the ones we carry with us."
  • "Books allowed me to escape... a portal into other worlds."
  • "Once you've written it down, you own it. When you own it, you can control it."
  • "I never gave or took any excuse." (Florence Nightingale)
  • "Master your thinking, master your destiny."
  • "Violence is typically born out of fear, being afraid."
  • "If you can see the child in the person that's acting out... it equips you to have more empathy."
  • "None of us gets through life without suffering. At some point, we're all gonna go through adversity."
  • "I chose to lead a great life... I removed every excuse."
• Life Lessons:
  • Face Your Internal Prisons – Identify the shame, anger, grief, and trauma that create mental prisons. Recognize that these have doors that can be opened through conscious work
  • Use Reading as Escape and Growth – Books provide mental freedom regardless of physical circumstances. Start with what interests you, then expand to broader learning.
  • Practice Voluntary Hardship – Choose difficult challenges (fasting, extra work, taking stairs) to build resilience for inevitable adversity you don't choose.
  • Journal for Self-Awareness – Write down thoughts, patterns, and reactions to own and control them. Use various methods - handwritten, voice memos, and margins of books.
  • Build Authentic Community – Surround yourself with people who will hold you accountable and tell you the truth. Apply the highest standards to friendship selection.
  • Transform Fear into Empathy – When facing conflict, look for the "child" in the other person. Understanding their fear reduces your reactionary responses.
  • Develop Composure Through Practice – Review past moments of losing control to build awareness. Use this knowledge to respond rather than react in future situations.
  • Remove All Excuses – Whatever your circumstances, choose to pursue greatness rather than accepting limitations. The past doesn't define the future unless you let it.
  • Share Your Truth Vulnerably – Authentic storytelling about pain and growth helps others escape their own prisons. Vulnerability is strength when used to serve others.
  • Create Evidence of Resilience – Completing self-imposed challenges builds confidence for handling external adversities. Each victory creates proof you can handle hard things.
  • Choose Your Narrative – You can change the story handed down to you. Reject limiting beliefs about what's possible based on background or circumstances.
• Apply to be part of my Learning Leader Circle

Go to www.LearningLeader.com for full show notes

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.

My guest: Michelle “Mace” Curran is a combat veteran, former fighter pilot, and only the second woman in history to fly as the Lead Solo for the Thunderbirds, the U.S. Air Force’s elite demonstration squadron. Now on a new mission, she’s using her story to inspire others. She is the best-selling author of The Flipside: How to Invert Your Perspective and Turn Fear Into Your Superpower.

• How to run "debrief" so that giving and getting feedback becomes embedded in your culture.
• The biggest mistake Michelle made when she became a new fighter pilot, and what you can learn from it.
  • Early Exposure to Male-Dominated Environments – Michelle's dad took her hunting with guys starting at age 7, teaching her she "belonged in any room" she wanted to pursue. This early experience prepared her for being 1 of only 2% female fighter pilots.
  • Parents Who Believed in Wild Dreams – Parents worked multiple jobs to afford camps (criminal justice, archaeology) whenever Michelle showed interest in something new. Taught her that opportunities weren't just possibilities - "I could go after it."
  • The Lone Wolf Trap – When struggling in her first squadron, Michelle was afraid to ask questions because she thought it would show she didn't belong. "I wouldn't even ask questions because I felt like asking a question was just so uncomfortable."
  • Three Years of Struggling in Silence – Despite performing well in the air, Michelle spent three years "belly crawling, pulling myself by my fingernails" because she felt pressure to represent all women perfectly.
  • The Fresh Start Power – Moving from Japan to Texas gave her a reset: "No one here knows about my divorce. No one here knows all these struggles I've been going through." Sometimes you need a clean slate to rebuild.
  • Curiosity + Vulnerability = Community – The breakthrough came when fellow pilots asked pointed questions beyond platitudes: "How are you actually doing?" Real curiosity that goes deeper than "let me know if you need anything."
  • The Near Head-On Collision Story – Flying inverted at 500 mph, passing within 80 feet of another jet using only eyeballs for distance measurement. When her student pilot aimed straight at her, she had 2.5 seconds to decide whether to move or hold position.
  • Learning from Mistakes, Not Punishing Them – After the near-collision, Michelle chose teaching over berating: "What is the most productive way we can respond to get the most learning from that?" The student learned faster because he found the boundary.
  • The Debrief Culture Framework – Start with objectives, go through segments systematically, ask "why" five times to find root causes, create specific lesson learned, and share with the entire organization so others don't repeat mistakes.
  • Rank Comes Off in Debriefs – Even generals sit in debriefs led by mid-level captains who are the real tactical experts. "Status comes off" - expertise matters more than hierarchy when analyzing performance.
  • The Teaching-Learning Loop – Moving from student (year 1) to instructor (year 2) creates exponential learning: "Your students will teach you more than you probably learned when you were a student."
  • Time Distortion Under Extreme Stress – During the near-collision, Michelle experienced "the craziest temporal distortion" where "time slows down" but "you can't do anything faster than you normally can."
• Build Competence First, Then Serve Others – Advice for young people: Spend 6-8 years building skills and confidence, then "reach a hand back" to mentor others. Both phases are essential for maximum impact.
• Quotes:
  • "They endlessly believed in every wild dream I set my sights on."
  • "I learned my vocabulary of profanity expanded greatly... but I also learned I could hang in that environment."
  • "I went into it naively thinking that it didn't matter at all... and it's a little bit different as you get into the military."
  • "There's no fear when you're present. Fear is a future thing."
  • "Curiosity plus vulnerability equals community."
  • "What is the most productive way we can respond at this point to get the most learning from that?"
  • "More learning happens in the debrief than actually does during the flight itself."
  • "The egos that people see in Hollywood around fighter pilots... what they don't show is the humility that has to happen behind the scenes."
  • "It's not self-centered to spend that first six to eight years focused on learning and honing skills."
  • "You get to reach a hand back... and it becomes one of the most fulfilling things for you as well."
• Life Lessons:
  • • Expose Children to Challenging Environments Early – Like Michelle's hunting trips, give kids experience in situations where they're the minority or outsider to build confidence.
    • Support Wild Dreams with Action – Don't just say you believe in someone's goals - invest time and money in giving them exposure to those fields.
    • Ask for Help Before You're Drowning – The biggest mistake is thinking asking questions shows weakness. Everyone expects beginners to have questions.
    • Create Psychological Safety for Mistakes – Focus on learning from errors rather than punishing them. The response to mistakes determines future trust and performance.
    • Build Debrief Culture in Your Organization – Set clear objectives, analyze systematically, find root causes, create specific action items, and share lessons broadly.
    • Use Fresh Starts Strategically – Sometimes changing environments gives you the reset needed to implement new behaviors and shed old baggage.
    • Go Beyond Surface-Level Check-ins – Real community comes from curiosity that goes deeper than "how are you?" Be willing to ask uncomfortable follow-up questions.
    • Practice Temporal Awareness Under Stress – In high-stakes situations, your brain may speed up while time seems to slow down. Prepare for this distortion through practice.
    • Separate Expertise from Hierarchy – The most knowledgeable person should lead analysis sessions, regardless of their position in the org chart.
    • Balance Self-Development with Service – Early career should focus on building competence; mid-career should emphasize mentoring others.
    • Accept That High Performance Requires High Standards – Like the Thunderbirds' 70-foot separation at 500 mph, excellence often means operating with minimal margin for error.
• Apply to be part of my Learning Leader Circle

Go to www.LearningLeader.com for full show notes

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. www.InsightGlobal.com/LearningLeader

My guest: Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. His career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital.

Notes:

• Key Learnings
  • The 4:30 AM Advantage – Sam's father would be at his desk by 4:30 AM every day, saying, "It's easy to look smart if you have a several-hour head start on everyone else." Early work creates compounding advantages over time.
  • Either Be Early or Be Late, Don't Be On Time – Father's wisdom about timing and seasons. Start your career super early to get ahead, or strategically wait and come in later. Timing matters more than perfect preparation.
  • Joy as the Ultimate Competitive Advantage – "I just don't think that in the long run, angry people win." Look for joyful people in hiring and partnerships because joy is sustainable while anger burns out.
  • Type Two Fun Builds Resilience – Type 1 fun is enjoyable while doing it (rollercoaster). Type 2 fun "completely sucks while you're doing it, but there's joy on the other side" (climbing mountains, marathons). Entrepreneurs need Type 2 fun experiences.
  • Practice Voluntary Hardship – Sam ran a sub-3-hour marathon and got a pilot's license not for love of activities, but for "practice moments" of perseverance. Creates evidence that you can handle business adversity.
  • Right Person, Right Opportunity, Right Time – Don't ask "is this a great person?" Ask, "Is it the right person at the right moment?" Success requires all three elements to align, not just talent.
  • Write Publicly for Intellectual Receipts – "If you can't write the check, write me the thesis and timestamp it." Writing creates accountability, proves thinking ability, and builds reputation over time.
  • Nobody Knows What They're Doing – Working at Bain taught Sam that even prestigious companies "have no idea what you're doing." This is liberating—you can figure it out too.
  • Big Things Take Time (Slow Ventures Philosophy) – Most success isn't quick wins. Venmo took "so many turns of the crank." Be patient finding the right wind, then sail fast when you catch it.
  • Embrace Being Wrong Most of the Time – Seed investing means "you're mostly wrong, you mostly lose money." Success comes from being very right occasionally, not being right consistently.
  • The Solana 2000x Return Story – Put in $400K, returned 2000x to LPs. Success came from the intersection of thesis (looking for "Ethereum killer") and relationships (following Raj Gokal through multiple startups).
  • Use Humor and Authenticity as Filters – Slow Ventures website looks like a law firm in tuxedos "on purpose." If you don't think it's funny, "you're not who we want to invest in."
  • Writing Pushes Away Wrong People – "I really like to be not liked by the people I don't want to work with." Authentic writing attracts the right people and repels the wrong ones.
  • Manufacturing Hardship for Privileged Kids – "Tiger Dad" sports culture might be a misguided attempt to create necessary adversity for wealthy children who lack natural hardships.
• I loved the throughline of this whole conversation being about his dad, working exceptionally hard, and having joy and excitement for the journey. Maybe it was the near-death experiences that his dad had that led to that mindset. Regardless, it’s something we can all learn from. We want to be around optimistic people who have joy and love for what they’re doing…
• Nobody knows what they’re doing. We’re all figuring it out as we go. You’ll never learn unless you go out and do the thing. Figure it out as you go. Just get started. And iterate. Learn. Try again. And keep going.
• Advice from Sam – Write publicly. You don’t know what you think until you get your thoughts out of your head onto the page. And if you publish them, you have a record of the journey. Also, you might attract someone to work with. That is how Jack Raines (guest on episode #539) caught Sam’s attention, and now they work together.
• Useful Quotes:
  • "It's easy to look smart if you have a several-hour head start on everyone else."
  • "I just don't think that in the long run, angry people win."
  • "Either be early or be late, don't be on time."
  • "The right question is, is it the right person at the right moment?"
  • "Writing is thinking. If you can't write, you can't think."
  • "I feel like a tenured professor of capitalism—responsible to make a lot of money over the long term by being very right every once in a while with permission to be wrong all the time."
  • "One of the most insulting things you can call someone is a market participant."
  • "The beauty of the internet is so big. The right people find you."
  • "Big things take time."
  • "Life's short. Is this really what you're spending your time on?"
• Apply to be part of my next Learning Leader Circle.

• Time Stamps:

  00:11 Sam’s Dad's Unique Career Path

  00:39 Life Lessons from My Dad

  04:35 The Trade-offs of Hard Work

  06:57 Betting on the Right People

  07:23 The Importance of Joy in Success

  10:39 Overcoming Hardships and Building Resilience

  20:40 My Journey: From Harvard to Bain

  26:06 Joining Facebook and Learning from Mark Zuckerberg

  29:36 Balancing Joy and Competitive Spirit

  30:15 The Story of Rippling and Parker

  31:48 The Solana Investment Journey

  34:33 The Importance of Writing and Public Thought

  41:07 The Philosophy Behind Slow Ventures

  52:54 Advice for Aspiring Venture Capitalists

  55:46 Future Plans

Go to www.LearningLeader.com for full show notes

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. www.InsightGlobal.com/LearningLeader

My Guest: Ed Latimore is a professional heavyweight boxer, best-selling author, and veteran of the U.S. Army National Guard. He earned a degree in Physics from Duquesne University. Ed has gained recognition for overcoming personal struggles with addiction and poverty. We recorded this at our 2025 Learning Leader Growth Summit in Scottsdale, Arizona. He's the author of Hard Lessons From The Hurt Business. 

Notes:

• Key Learnings
  • • The Heaviest Weight at the Gym is the Front Door – Starting is often the hardest part. "Zero to one is the hardest part" in any endeavor. Once you begin, momentum builds, but that first step requires the most effort.
    • How You Feel is Irrelevant – "How you feel about doing something is irrelevant. If it is vital to your success, you've gotta bump to the wall a bunch of times." Discipline isn't about motivation—it's about doing what's necessary regardless of feelings.
    • Sobriety: The Hardest Fight – 13+ years sober, describing it as "the hardest fight I've ever had." The turning point came during basic training when he built an identity completely free of alcohol for the first time in his adult life.
    • From Being Liked to Being Respected – "When people like you, they want to party with you... When people respect you, you start getting invited back to family events." Shifted focus from seeking approval through partying to earning respect through character.
    • The Baby Shower Revelation – Breakthrough moment when friends showed up with gifts for his unborn child, "all because he is my human." Realized people genuinely cared about him, which became the foundation for believing he mattered.
    • Taking Ownership vs. Playing Victim – "A judge and a jury do not care about my terrible upbringing if I commit a crime." Despite growing up next to a crack house with family addiction issues, I chose accountability over excuses.
    • Net Positive Impact Philosophy – Goal with raising children: "Make sure they are a net positive, they make things better. At the very least, let's make sure they don't mess anything up." Everyone has an impact on the world for better or worse.
    • Practice Until You Can't Forget – Boxing taught the overlearning principle: going beyond basic competency to automatic response. "We practice until we can't forget... Either you get it or you'll make a mistake, and you probably won't make the mistake more than twice."
    • Tolerance for Boredom Builds Excellence – "If you can be bored, you can go really far because a lot of it is just repetition of really basic things." Elite performers master fundamentals through unglamorous repetition.
    • Body Language Shapes Internal State – "You smile, you feel happy... puff up your chest and the testosterone flows." Physical presentation affects how you feel internally and influences others around you.
    • Fear vs. Responsibility Evolution – Early motivation came from fear of embarrassment; current motivation comes from a sense of responsibility to others. Shift from avoiding personal failure to ensuring others are taken care of.
    • Redefining "At Your Best" – Past definition: having enough money, time, and no worries. Current definition: "Everyone in the house is taken care of." Evolution from internal satisfaction to external impact.
    • Strategic Hardship Introduction – For teaching children without trauma: "Introduce hardships strategically and with awareness." Like weight training—incremental challenges build strength; too much too soon causes injury.
• Useful Quotes:
  • "How you feel about doing something is irrelevant. If it is vital to your success, you've gotta bump to the wall a bunch of times."
  • "The heaviest weight at the gym is the front door."
  • "When people like you, they want to party with you... When people respect you, you start getting invited back to family events."
  • "You have an impact on the world, for better or worse, that makes a huge difference in allowing a person to not destroy themselves."
  • "We practice until we can't forget."
  • "If you can be bored, you can go really far."
  • "I've had my ego dragged through the mud a lot."
  • "What do you want your obituary to say? I didn't just dabble."
  • "When you're completely selfless, then you're fearless. It's the 'what's gonna happen to me' that creates the fear."
  • "Everyone's always either walking in love or fear."
  • "I hope my kid remembers that I was a present happy dude."

• Life Lessons:
  • • Discipline Over Mood – Make decisions based on necessity, not feelings. Success comes from identifying what must be done and executing consistently.
    • Identity Building Without Vices – Spend time in environments completely free from your struggles to build new neural pathways and self-concept.
    • Overlearning for Mastery – Practice skills beyond basic competency until they become automatic responses under pressure.
    • Authentic Accountability – Find mentors who "live what they're yelling at you about." Real influence comes from demonstrated behavior, not just words.
    • Incremental Challenge Builds Resilience – Introduce difficulties gradually to build strength rather than overwhelming with too much too soon.
    • Present Moment Parenting – Model calm behavior during stressful situations because children mirror your emotional energy.
    • External Focus Creates Fulfillment – Shift from personal satisfaction to ensuring others are taken care of for a deeper sense of purpose.
    • Childhood Dreams Reveal True Interests – "What did you want to do when you were 10-12?" Often reveals authentic passions before social conditioning.
    • Breaking Generational Cycles – Consciously choose different patterns than your upbringing to create better outcomes for the next generation.
    • Humility Through Struggle – Getting "ego dragged through the mud" builds character and perspective that success alone cannot provide.
    • Luck Recognition Builds Gratitude – "The only difference between you and me is that I was lucky." Understanding the role of circumstances builds empathy.
  •  
• Apply to be part of my next Learning Leader Circle.

Go to www.LearningLeader.com for full show notes

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. www.InsightGlobal.com/LearningLeader

My Guest: Tim Ferriss is the author of five #1 New York Times bestsellers (including The 4-Hour Work Week, Tools of Titans, and Tribe of Mentors). His podcast, The Tim Ferriss Show, has been listened to more than a billion times. Tim was an early investor in Uber, Shopify, Twitter, Alibaba, and many others. He’s the creator of a new card game called COYOTE.

• Decision making - How can I win even if I lose? He viewed angel investing like his personal MBA. Instead of paying for business school, he invested in companies and learned about business by working with actual businesses. He didn’t expect to make money on those investments. That was just a bonus. Think, “How can I win even if I lose?” Tim won with those investments, regardless of whether he made money or not on them.
• Key Takeaways and Learnings:
  • Parents Who Foster Curiosity – Tim's mother created a "books are always in budget" policy despite tight finances. Used remainder tables at bookstores to expose him to random, off-menu knowledge that sparked lifelong curiosity about unconventional topics.
  • Curiosity-Driven Exploration – When Tim showed interest in marine biology, his mom found Frank Mundus (inspiration for Jaws character), arranged a meeting, and created low-cost adventures like crab fishing with chicken bones to fuel his interests.
  • The Mask You Wear Becomes You – "Be very careful what you pretend to be" - spent years presenting as overly serious to be taken seriously, which created a recursive feedback loop. Now embraces more play and laughter to avoid burnout. 
  • Fiction and Poetry as Life Teachers – Shifted from non-fiction purist to reading more fiction/poetry. Recommends "Ozymandias" as a monthly reminder that all achievements fade: "My name is Ozymandias, king of kings. Look on my works, ye mighty and despair. Nothing beside remains."
  • Internal vs External Scorecards – Money and fame amplify whatever's underneath, like alcohol or power. "If you have certain insecurities or paranoia, all of those are going to be amplified. If you're generous, that's also gonna be the case."
  • Effectiveness Over Efficiency – "Effectiveness is doing the right things, efficiency is doing things well, but doing something well does not make it important." Focus on choosing the right targets rather than optimizing everything.
  • Strategic Slack in Systems – Moved away from filling every 10 minutes. Takes 10 minutes each morning with coffee to read fiction/poetry/meditate to prove "you do not have to front flip out of bed and land in a full sprint."
  • How to Win Even If You Fail – Project selection framework: "How can I win even if I fail?" Focus on relationships built and skills acquired that transfer beyond the project if external metrics don't pan out.
  • The COYOTE Game Philosophy – Created a card game to address the social isolation epidemic. "People don't have a shortage of productivity advice... It's taking some steam out of the system and actually enjoying what you have worked so hard for."
  • Social Bonds as Foundation – "It's the relationships, stupid." Countries rated happiest fundamentally come down to social ties. In-person social interactions are down 70% in certain age groups over the last 10 years.
  • Podcasting as Relationship Building – "My goal is not to have 100% of my audience like any episode... but I do want 10% of my audience to love each episode." The personal is the most universal.
  • Fame's Hidden Costs – With the audience size of major cities comes proportional number of unstable people. "If you have a small village, you're gonna have one village idiot... "How many crazy people are there in New York City?"
  • "Be suspicious of what you want."

•  
• Tim read me the poem by Ozymandias by Percy Bysshe Shelley
• "If more information were the answer, we'd all be billionaires with six-pack abs."
• Be a talent scout - You don’t need a huge network. A+ players in one area know A+ players in others. Seek out people who are great at what they do, regardless of what they do. Study what makes them great at that thing. Then you’ll probably meet other A+ players. Also, it’s on us to strive to be an A+ player at what we do. Be so good at whatever your thing is that other A+ players want to meet you. Tim has been very good at that.
• Quotes:
  • "Be very careful what you pretend to be... the mask you wear often becomes the person you are."
  • "Be suspicious of what you want." (Rumi)
  • "My name is Ozymandias, king of kings. Look on my works, ye mighty and despair. Nothing beside remains."
  • "Effectiveness is doing the right things, efficiency is doing things well, but doing something well does not make it important."
  • "How can I win even if I fail?"
  • "The personal is the most universal."
  • "It's the relationships, stupid."
  • "If more information were the answer, then we'd all be billionaires with six-pack abs."
  • "Follow your curiosity and obsessions with great rigor. Do that and I like your chances."
  • "The superheroes you have in your mind are nearly all walking flaws who've maximized one or two strengths."
  • "You don't need a huge network... the super A+ players tend to know other A+ players."
• Life Lessons:
  • • Cultivate Childhood Curiosity – Create "always yes" policies for learning and exploration. Use constraints (like remainder tables) to discover unexpected interests.
    • Embrace Strategic Experimentation – View life as a series of 6-12-month projects with 2-4 week experiments. Design studies to get feedback, not just chase outcomes.
    • Balance Seriousness with Play – Taking yourself too seriously leads to burnout. Build in recovery phases and "deloading" periods across all life areas.
    • Choose Projects for Learning – Select opportunities based on relationships you'll build and skills you'll acquire, not just potential external rewards.
    • Start With Personal Pain Points – Best opportunities often come from solving problems you personally understand deeply, then expanding adjacent.
    • Build Safety Nets First – Like Arnold's real estate, before acting, create financial/emotional cushions that allow you to say no and wait for right opportunities.
    • Quality Over Quantity in Relationships – Better to have deep connections with fewer people than surface-level networks with many.
    • Morning Rituals Create Calm – Prove to your nervous system you don't have to be frantic by taking 10 minutes each morning for something peaceful.
    • Scratch Your Own Itch – Whether in podcasting, investing, or any pursuit, follow genuine personal interest for sustainable energy and authentic results.
    • Prepare for Success Taxes – Fame and wealth amplify existing traits. Address insecurities and develop strong boundaries before scaling.
    • Value Present Experience – Focus on daily energy in/out rather than constantly deferring happiness to future achievements.
• Apply to be part of my next Learning Leader Circle.

Time Stamps

00:38 Tim's Childhood and Parental Influence

01:15 Curiosity and Lifelong Learning

02:56 Marine Biology and Childhood Adventures

07:06 Influence of Mentors and Teaching Aspirations

08:45 Thoughts on Parenthood and Relationships

12:11 Balancing Seriousness and Humor

25:15 Effectiveness vs. Efficiency

30:50 Creating Slack and Self-Care

34:41 The Importance of Social Bonds and Play

41:07 Meeting a Game-Changing Partner

42:13 The Importance of Analog Social Interaction

42:55 Podcasting: A Platform for Deep Connections

43:30 The Evolution and Challenges of Podcasting

43:47 The Art of Interviewing

49:18 Navigating Fame and Public Exposure

01:04:26 The Philosophy of Risk and Experimentation

01:10:27 Spotting Talent and Following Curiosity

01:20:37 Closing Thoughts and Future Endeavors