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The Learning Leader Show With Ryan Hawk

The Learning Leader Show With Ryan Hawk

De: Ryan Hawk
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As Kobe Bryant once said, “There is power in understanding the journey of others to help create your own.” That’s why the Learning Leader Show exists—to understand the journeys of other leaders so that we can better understand our own. This show is full of learnings taught by world-class leaders—personal stories of successes, failures, and lessons learned along the way. Our guests come from diverse backgrounds—CEOs of multi-billion dollar companies, best-selling authors, Navy SEALs, and professional athletes. My role in this endeavor is to talk to the most thoughtful, accomplished, and intentional leaders in the world so that we can learn from them as we each create our own journeys.Learning Leader LLC 062554 Economía Exito Profesional Gestión Gestión y Liderazgo
Episodios
  • 655: Morgan Housel - The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to Hear

    655: Morgan Housel - The Simple Formula For Happiness, Betting on Others, Gaining Independence & Purpose, Family Vacation Secrets, The Art of Spending Money, & The Death Bed Lesson Every Leader Needs to Hear
    Sep 28 2025
    Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk Morgan Housel is the New York Times Bestselling author of The Psychology of Money, Same As Ever, and The Art of Spending Money. His books have sold over 10million copies and have been translated into more than 60 languages. This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Notes: Morgan dedicated The Art of Spending Money to "Kellie the Unicorn" (his sister Kellie) after she was diagnosed with colon cancer and asked him to fulfill her long-running joke request. Sometimes book dedications "mean nothing to the reader, but they can mean everything to the author."People Who Bet on You - Brian Richards (Motley Fool boss) bet on Morgan when he didn't have to, providing unconditional support for a mediocre college writer. Craig Shapiro (Collaborative Fund) pursued Morgan for months to join his tiny VC firm as a full-time blogger when it wasn't a business necessity.What money can’t buy - Morgan once heard a story from a priest that he'll never forget… It’s from a priest who delivers the last rites in hospitals. He described the difference between what kids say to their parents when they’re about to die. The priest tells them to tell their parents what they’re most grateful for… In families with lots of problems, the kids usually talk about something that costs money. In the best families, the ones with solid relationships, the kids say the same thing every time. “Thank you for believing in me.”Making vs. Spending Money - "There are literally tens of thousands of books written on how to make money... There are virtually no books written about how to spend money." Most people assume spending needs no guidance, but wealthy people often demonstrate this isn't true.The Internal vs. External Scoreboard - Donald Crowhurst (fake sailor who killed himself seeking external validation) vs. Bernard Moitessier (expert sailor who quit before winning to avoid attention and live authentically). Modern society pushes us toward Crowhurst's external validation while we actually want Moitessier's internal satisfaction.The simplest formula for a pretty nice life: independence plus purpose. The independence to do what you want, and the wisdom to want to do meaningful things.Chuck Feeney's Wealth Example - The duty-free store billionaire first lived the stereotypical rich lifestyle, realized he didn't like it, then chose to live modestly and give away $10 billion. "I was happy when I was giving money away, and I was not happy when I wasn't giving money away."Every Dollar of Debt - "Every dollar of debt that you have is a piece of your future that someone else owns." Debt narrows the range of outcomes you can endure in an unknowable future.Money and Happiness Research - Recent studies show that earning more money only helps if you're already happy, joyful, and content. For depressed, anxious people, more money doesn't improve well-being. "It leverages whoever you are in either direction."What Money Can't Buy - The book is "40% about how to spend money to make yourself happier and 60% about realizing what money cannot do for you." Relationships, health, and personal fulfillment must come first.“Comedians are the best thought leaders because they understand how the world works, but they want to make you laugh rather than making themselves feel smart.”"Nobody gives a shit about anything other than how you make them feel."Vacation - Morgan realized while building sandcastles with his kids on the beach in Maui (10/10 experience) that building Legos at home with them was almost as good (9/10). The real value was "uninterrupted time with my family," which required travel to avoid daily distractions but pointed to what actually mattered.Ambition - Morgan's career drive crystallized while kayaking past $25 million mansions on Lake Washington in 2010: "I need to work harder. I want one of those one day." This wasn't envy but ambition - though he notes the line between inspiration and envy is thin, especially once you know the person.A high savings rate is not "saving" but is "purchasing independence." Each saved dollar buys freedom to handle life's unknowable future without someone else's schedule dictating his choices.Why Spending Is Complicated People try to fill emotional holes with material purchasesSociety tells us what we should like, which may not align with our actual preferencesWe chase peer comparison rather than personal satisfactionWe overestimate the social rewards of nice possessions The Independence Framework Save money not for retirement but for freedom to handle uncertaintyDebt narrows your options when life throws curveballsIndependence means being able to do what you want, with whom you want, for as long as you ...
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    57 m
  • 654: Jake Tapper - The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You

    654: Jake Tapper - The Most Important Leadership Skill, Handling Criticism, Chasing Your Curiosity, Understanding Tradeoffs, Responding to Rejection, and Being So Good They Can't Ignore You
    Sep 21 2025
    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 manBiden 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 ...
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    1 h y 4 m
  • 653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders

    653: Sukhinder Singh Cassidy - Becoming a CEO, Transforming a Company, Earning the Promotion, Knowing Your Non-Negotiables, & Hiring Excellent Leaders
    Sep 14 2025
    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. 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: Vision statement (destination in 2-3 years)Outside-in market analysisCompetitive landscapeSWOT analysis of current positionFive key strategic movesImplementation approach ("the how")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 authorityDiverse interviewer panels with "bar raisers"Business problem-solving presentations in the final roundsMultiple 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 ...
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    58 m
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This is the best podcast. Regardless of who you are or where you’re at in life, you’ll absolutely find incredible value. Literally every episode shared ways to just be a better person overall. And Ryan asks meaningful, impactful questions that drive to tactical approaches that we can actually use. Very grateful for him and this show.

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