The Learning Leader Show With Ryan Hawk

Ryan Hawk
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Leaders are learners. The best leaders never stop working to make themselves better. The Learning Leader Show Is series of conversations with the world's most thoughtful leaders. Entrepreneurs, CEO's, World-Class Athletes, Coaches, Best-Selling Authors, and much more.

  1. HACE 5 DÍAS

    657: Helen Lewis - Why Genius Is a Myth, Edison Needed Teams, Self-Promoters Are Overrated, Conspiracy Theories, Shakespeare Needed Luck, and How To Build an Excellent Career

    Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire one 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 has the hustle and grit to deliver. My Guest: Helen Lewis is a staff writer at The Atlantic and author of The Genius Myth: Great Ideas Don't Come from Lone Geniuses.  Notes: Shakespeare: Talent + Luck + Timing - William Shakespeare died in 1616 at age 52, celebrated but not yet immortal. His icon status required massive luck: friends published the First Folio (saving King Lear), then 50 years later, Charles II reopened England's theaters after Puritan closures and needed content. Companies turned to Shakespeare's IP, adapting his work (including changing tragedies to happy endings). Helen: "If anyone deserves to be called a genius, it's him. But he died as a successful man of his age. Scenius Over Genius - Brian Eno coined "scenius" - places that are unusually productive and creative. Shakespeare moved from Warwickshire to London for the theaters and playwrights. Helen: "You don't just have to be Leonardo, you also need Florence... Where do you find the coolest, most interesting bleeding edge of your field?" Modern example: Joe Rogan's Comedy Mothership in Austin created an alternative to LA/NYC for comedians like Shane Gillis and Tony Hinchcliffe. Ryan: "Put yourself in rooms where you feel like the dumbest person... force you to rise up, think differently, work harder." Tim Berners-Lee vs. Elon Musk - Tim Berners-Lee invented the World Wide Web. Has knighthood, lives an ordinary life, kids named Alice and Ben. Most people have never heard of him. Elon Musk has a lot of children, talks about his genes needing to live on, and lives a very public life. Helen: "We overrate the self-promoters, the narcissists. We demand oddness and specialness... We don't call modest people geniuses because they're too normal." Elizabeth Holmes (Theranos) and Sam Bankman-Fried (FTX) exploited this - looked like a genius (Steve Jobs cosplay, messy math prodigy) but stood on houses of cards. Trauma and the "I'll Show You" Engine - Matthew Parris wrote Fracture after noticing how many "great lives" had traumatic childhoods - loss of parents, being unloved, bullied. Helen: "I don't think that's necessarily genius in objective achievement. It's more like a hunger for recognition or fame... a kind of 'I'll show all of you' engine." Stephen Hawking on IQ - Stephen Hawking: "I have no idea. People who boast about their IQ are losers." The Flynn Effect shows average IQ rose over the 20th century through better nutrition, schooling, and living conditions. Higher IQ correlates with better outcomes. But at the top end, every IQ point ≠ is one success point. Christopher Langan (the highest IQ guy) thinks he has a theory to overturn Einstein, and that Bush did 9/11 to cover it up. No history of achievement. Helen: "Smart people don't always prosper. You need the gears that connect the engine to the wheels on the road." Conspiracy Theories: Narcissism as Driver - Narcissism is the most correlated personality trait with conspiracy thinking. Helen: "The sheeple, the NPCs think this, but I alone have seen the truth. It positions you as the protagonist of reality." The Internet is a "confirmation bias engine." But conspiracies are sometimes true (Epstein's corrupt plea deal), which is why conspiracy thinking persists. Researcher Karen Stenner's solution: Get back to depoliticized conspiracies like Bigfoot, crop circles, Area 51 - harmless things that got people outside instead of "shoot up a pizza restaurant." The Beatles: Finiteness Creates Legend - Psychologist Han Isaac said geniuses should either die before 30 or live past 80. Middle is "eh." The Beatles had both: a short career that ended definitively, then John Lennon was shot at 40, frozen in time. Paul McCartney lives on, performs at Glastonbury with John's vocals. Craig Brown: "The Rolling Stones just go on and on, but there's never as much of the Beatles as you want." Quality Over Quantity - Helen: "Incentive now is producing constantly for algorithms... That's neither fun nor produces the best work." Early career: say YES. Later career: "The most important thing you can say is no." Her metric: "Can I say honestly, that was the best I could do? I didn't cut corners. That's the metric." Podcast: advised to do 2-3 episodes weekly for rankings, has been doing weekly for 10.5 years. Shows that went daily? He stopped listening. "I'm gonna increase the quality bar, not the quantity." Robert Greene: "Do not speak unless you can improve upon the silence." Improving the Silence - "My dad's not the loudest at family gatherings, doesn't have the most words, but when he speaks, we all stop and listen. That's who you want to be." Applies to meetings: people vomit garbage to show how smart they are instead of waiting for something valuable. When you speak, people should want to listen. Thomas Edison: Execution Over Ideas - The Light bulb wasn't Edison's conceptual innovation - the idea dated to Humphrey Davy. What was incredible: Edison made it work (vacuum seal, filament) and created the New York power grid. Helen: "Lots of people can have the idea that a man should be an ant. Not everybody can write the Ant-Man screenplay and have it produced." His Menlo Park lab lasted because he worked with brilliant people on problems they cared about. Logbook shows assistants' names on breakthroughs - collaborative. We underrate logistics and execution. Most "light bulb moments" are actually slow, incremental, contested creations. Why Helen Chooses Teams Over Independence - Could go independent on Substack for more money. Works at The Atlantic for: resources, legal support, editorial integrity, and colleagues she doesn't want to let down. Helen: "You must have people in your life, you think, I wanna do work that they like. Finding those people who make you your best version of yourself." Ryan connects to athletics: "Being surrounded by people better than me forces me to raise my game. That's why we want to be part of a great team." Sample First, Specialize Later - High achievers have "hot streak" later, but sample early - trying different things, learning transferable skills. Helen: "Take the first job at a publication you could learn from. Even if not wildly interested, if it's good and they'll hold you to high standards, do it. Your second job is infinitely easier to get than your first." Work Around People Who Care - Helen: "If you work somewhere where no one cares, it's very hard. You can't care on your own. You'll become infected by the apathy around you." Nothing is more boring than a job you don't care about. Don't Wait to Live - Some devote long hours to something for money, promising they'll retire at 30 and then live. Helen: "What if you spent all that time chasing something and then you get hit by a truck? Don't wait for it. Just try and enjoy what you're doing right now." Quotes: "You don't just have to be Leonardo, you also need Florence."  "We overrate the self-promoters and underrate the humble achievers."  "Smart people don't always prosper. You need the gears that connect the engine to the wheels."  "The most important thing you can say is no."  "Do not speak unless you can improve upon the silence." - Robert Greene "You can't care on your own. You'll become infected by the apathy around you."  It’s funny that we have come to use the phrase ‘lightbulb moment’ to describe a momentary flash of inspiration, because the birth of the lightbulb was slow, incremental, and highly contested.

    58 min

  2. 5 OCT

    656: Dakota Meyer - Medal of Honor, The Battle of Ganjgal, Leadership Under Fire, The Loyalty Question, and What America Needs Right Now

    Go to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk 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 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 s****y 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

    1 h y 4 min

  3. 28 SEP

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

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

    57 min

  4. 21 SEP

    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

    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

    1 h y 4 min

  5. 14 SEP

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

    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 analysis Competitive landscape SWOT analysis of current position Five key strategic moves Implementation 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 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

    58 min

  6. 7 SEP

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

    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: Faith, Spirituality, Philosophy - "Every day, go deep" into transcendent practices 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: Focus on what age gives you rather than takes away Choose subtraction over addition - appreciate what you no longer have to do Making Changes Stick Requires Three Elements: Understand the science - Know why something works Change your habits - Actually implement different behaviors 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)

    57 min

  7. 31 AGO

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

    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

    52 min

  8. 24 AGO

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

    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

    1 h y 5 min
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