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

Apply to be in my next Learning Leader Circle - https://learningleader.com/leadership-circles/

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)