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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)

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

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

Notes:

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

Go to www.LearningLeader.com for full show notes

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

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

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

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

Notes:

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

• Time Stamps:

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

  00:39 Life Lessons from My Dad

  04:35 The Trade-offs of Hard Work

  06:57 Betting on the Right People

  07:23 The Importance of Joy in Success

  10:39 Overcoming Hardships and Building Resilience

  20:40 My Journey: From Harvard to Bain

  26:06 Joining Facebook and Learning from Mark Zuckerberg

  29:36 Balancing Joy and Competitive Spirit

  30:15 The Story of Rippling and Parker

  31:48 The Solana Investment Journey

  34:33 The Importance of Writing and Public Thought

  41:07 The Philosophy Behind Slow Ventures

  52:54 Advice for Aspiring Venture Capitalists

  55:46 Future Plans

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

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

Notes:

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

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

Go to www.LearningLeader.com for full show notes

This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader

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

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

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

Time Stamps

00:38 Tim's Childhood and Parental Influence

01:15 Curiosity and Lifelong Learning

02:56 Marine Biology and Childhood Adventures

07:06 Influence of Mentors and Teaching Aspirations

08:45 Thoughts on Parenthood and Relationships

12:11 Balancing Seriousness and Humor

25:15 Effectiveness vs. Efficiency

30:50 Creating Slack and Self-Care

34:41 The Importance of Social Bonds and Play

41:07 Meeting a Game-Changing Partner

42:13 The Importance of Analog Social Interaction

42:55 Podcasting: A Platform for Deep Connections

43:30 The Evolution and Challenges of Podcasting

43:47 The Art of Interviewing

49:18 Navigating Fame and Public Exposure

01:04:26 The Philosophy of Risk and Experimentation

01:10:27 Spotting Talent and Following Curiosity

01:20:37 Closing Thoughts and Future Endeavors

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

Guest: Nick Maggiulli is the Chief Operating Officer and Data Scientist at Ritholtz Wealth Management. He is the best-selling author of Just Keep Buying: Proven Ways to Save Money and Build Your Wealth, and his latest book is called The Wealth Ladder. Nick is also the author of OfDollarsAndData.com, a blog focused on the intersection of data and personal finance.

Notes:

• Money works as an enhancer, not a solution: Like salt enhances food flavors, money amplifies existing life experiences but has little value by itself without relationships, health, and purpose. "Money by itself is useless... without friends, family, without your health, it doesn't add much... it enhances all the other parts of life."
• Nick beat his dad’s friends at chess when he was 5 years old because he practiced more than they did. He got more reps. He did the work. It’s not that he was a chess prodigy. He just worked harder than his opponents did. And he still does that today.
  • Practice creates expertise beyond intelligence: At five years old, Maggiulli could beat adults at chess not because he was smarter, but because he had more practice. Consistent effort over time can outcompete raw talent. "I could beat them, not because I was smarter than them, only because I had practiced something... In this very specific realm, I could beat them."
• Consistent writing builds compound advantages: Writing 10 hours every weekend for nine years created opportunities including book deals and career advancement. The discipline of regular practice compounds over time. "I've been writing for nine years... I spend 10 hours a week every single week for almost a decade now, and that helps over time."
• The most expensive thing people own is their ego.
• How do you add value when you're in a job that doesn't have a clear scoreboard (like sales)?
  • Think... What gets accomplished that otherwise wouldn't have without you?
  • Add value through time savings and efficiency: In roles where impact isn't immediately measurable, focus on how much time and effort you save others. Create systems that make your colleagues more efficient. "How do I save our operations team time? How do I save our compliance team time... I'm designing better oars that'll give us 10% more efficiency."
• Money amplifies existing happiness: Research shows that if you're already happy, more money will make you happier. But if you're unhappy and not poor, more money won't solve your problems. "If you're happy already, more money will make you happier... but if you aren't poor and you aren't happy, more money's not gonna do a thing."
• Ego is the most expensive thing people own: Trying to appear wealthier than you are prevents actual wealth building. Focus on substance over status symbols. "People in level three that wanna look like people in level four end up spending so much money to keep up with the Joneses."
• Follow your interests for long-term success: Passion sustains you through inevitable obstacles and rejection. Maggiulli wrote for three years without earning money because he genuinely enjoyed it. "Follow your interest because when you follow your interest, you're more likely to keep going when you face obstacles."
• The "Die with Zero" philosophy, advocated by Bill Perkins, encourages people to prioritize experiences and fulfillment over accumulating maximum wealth, suggesting spending money strategically to maximize lifetime enjoyment.
• Nick defines six levels of wealth based on net worth, ranging from $0 to over $100 million. These levels are: Level 1: $0-$10,000 (paycheck-to-paycheck), Level 2: $10,000-$100,000 (grocery freedom), Level 3: $100,000-$1 million (restaurant freedom), Level 4: $1 million-$10 million (travel freedom), Level 5: $10 million-$100 million (house freedom), and Level 6: $100 million+ (philanthropic freedom). 
  • Nick also notes a shift in asset allocation as one progresses through the levels. In the lower levels, a larger portion of wealth is tied up in non-income-producing assets like cars, while higher levels see a greater emphasis on income-producing assets like stocks and real estate.
  • Wealth strategies must evolve by level: The approach that gets you to level four ($1M-$10M) won't get you to level five ($10M-$100M). Higher wealth levels typically require entrepreneurship or equity ownership. "The strategy that you use to get into level four is not going to be the strategy that gets you out."
  • Know when "enough" is enough: Level four wealth ($1M-$10M) may be sufficient for most people. The sacrifices required to reach higher levels often aren't worth the marginal benefits. "The rational response for an American household once they get into level four is... maybe I take my foot off the gas and just enjoy life more."
• As a data scientist, Nick leverages data to provide business intelligence insights at Ritholtz Wealth Management, where he also serves as Chief Operating Officer. His work involves analyzing data to answer business questions, identify trends, and build predictive models. For example, he might analyze lead conversion rates, client attrition, or investment patterns to inform business decisions.
• Financial independence requires separate identities: Maintain individual financial accounts within marriage for independence and easier asset division. Pool resources for shared expenses while preserving autonomy. "Everyone needs to have their own accounts. They need to have their own money... especially important for women."
• Nick and his wife have a joint + separate bank account(s).
  • Here's how it works:
    • All of your income and your partner’s income flows into this joint account.
    • That income is used to pay for all shared expenses.
    • Any excess left in the account (above a certain threshold) can either be left in the account or distributed equally between you and your partner (to your separate accounts).
• Apply to be part of my Learning Leader Circle
•  

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

Ryan Petersen is the founder and CEO of Flexport, a technology-driven global logistics company. He’s a leading voice in supply chain innovation and has been at the forefront of solving major trade and shipping challenges worldwide.

Notes:

• “Arrogance is its own form of stupidity.”
• The Tweetstorm That Saved Christmas: Ryan shares the now-legendary story of how he rented a boat, brought tacos, and took another high-powered CEO with him to tour the Port of Long Beach during the supply chain crisis. His viral Twitter thread sparked immediate action, California Governor Gavin Newsom called within hours, and the policy changed shortly after. A masterclass in “doing the thing.”
• Frontline Obsession & Gemba Walks: Why Ryan frequently travels the world (visiting 19 countries last year) to meet employees and customers. He explains the power of Gemba walks, being physically present on the frontlines, and how it shapes his leadership.
• How He Runs Flexport: Ryan’s leadership playbook includes:
  • Managing through writing. Every one of his 26 teams writes a six-page memo monthly, followed by deep conversations.
  • Daily conversations with 30-40 employees to stay connected.
  • Living Flexport’s values: Empower Clients, Play the Long Game, Act Like an Entrepreneur, Commit to the Vision, Ask Why 5 Times.
• Leadership & Decision-Making: He shares his “must-haves” for hiring leaders:
  • Relentless Work Ethic
  • Intellectual Curiosity
  • Humility (“Even wise people are wrong 30% of the time.”)
  • Reliability
  • Charisma
• Lessons from Mentors: Ryan talks about advice from Paul Graham (Y Combinator) and Brian Chesky (Airbnb), including how gathering your top leaders in person sparks innovation and alignment.
• Hard Decisions & Mistakes: He candidly discusses Flexport’s CEO transition gone wrong, hiring Dave Clark from Amazon, and what he learned from that difficult chapter.
• Personal Growth & Life Philosophy: Ryan shares his approach to lifelong learning, inspired by Charlie Munger and René Girard. He emphasizes reading widely, asking questions, and choosing role models wisely.
  • "We’re all imitative people. Choose your role models wisely."
• “We’re making global trade as simple and reliable as flipping a light switch.”
• “Even wise people are wrong 30% of the time. You must stay humble.”

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. Go to www.InsightGlobal.com/LearningLeader

Guest: Blaine Anderson is a dating coach and matchmaker. She’s helped more than 3,000 happy clients attract and build long-term relationships. Her work has been featured in the New York Times, the Wall Street Journal, Forbes, and she earned a deal with Mark Cuban on Shark Tank.

Notes:

• Someone asked Charlie Munger… How do I get a great wife? Deserve one. The best way to find a good spouse is to deserve one, he often said. In business, this translates to working hard and behaving with integrity consistently over time. “To get what you want, you have to deserve what you want.”
• What is the #1 reason you don’t get a second date? You talk about yourself too much. 
  • When you go out to eat with someone, what percentage of the time are you talking? Aim to talk 30% and listen 70%. The reason we don’t get the second date or the follow-up meeting with the prospect is because we are talking too much.
  • Pull conversational threads: Avoid rapid-fire questioning by following up on answers with related questions. Share brief personal connections to create dialogue rather than interrogation. "You want to pull the conversational thread... ask a follow-up question about that same thing. That's where you can start having a conversation."
• Marketing your trajectory matters: People want to know you're going places. Share your goals, dreams, and aspirations authentically to demonstrate upward momentum. "You want to find the balance of sharing things about yourself that indicate you are on an upward trajectory... from a place of getting to know one another."
• Nice guys need boundaries: Being overly accommodating to people you barely know signals weakness. Hold boundaries and don't put others before yourself too quickly. "The general problem with the nice guy is he's putting other people before himself, including people he doesn't know very well."
• Confidence must be genuine: Authentic confidence comes from actually becoming confident through mastery, not just faking body language. Get genuinely good at something. "You have to become that... get really good at something... picking something in your life and getting really good at it is gonna help you build confidence."
• Don't rush to the close: Whether in dating or sales, focus on building connection and trust before asking for commitment. The close is the period at the end of a long sentence. "If you approach a woman or you approach a deal and you're just trying to get to the final step... you're going to rush through a lot of the important and essential steps."
• High-value people are in demand: Present yourself as someone others want to be around. People are naturally drawn to those who appear sought-after by others. "We want the thing that's in demand. We want the thing that other humans recognize as high value."
• Genuine curiosity creates connection: Being authentically interested in others' experiences is a powerful form of respect and love. Ask questions that take conversations deeper. "Your underlying emotion is important... becoming a genuinely curious person who is interested in meeting another human."
• Physical fitness affects confidence: Looking and feeling good about yourself impacts how you show up in every interaction. Invest in your physical health. "You gotta feel good about how you look... who wants to partner up with a slug? Nobody."
• "You should always be dating your partner, whether it's your first date, your 40th date, or you've been married for 40 years."'
• "The close is the period at the end of a very long sentence."
• "Deserve one." - Charlie Munger's advice on getting a great spouse
• Women want 3 things - social status, to be desired, flirty/fun… They want an optimist.
• If things aren’t going well, look in the mirror. Take accountability.
• Her Twitter profile picture. Show the whites of your eyes. Smile. She has two tattoos. Omega is her middle name. Cactus for Tucson, AZ.
• How to build genuine confidence? Get good at something. Become an expert. Work really really hard. Be in great physical shape. It’s hard to be confident if you don’t like how you look. Sounds harsh, but it’s true. Confidence comes from evidence. Create some evidence for youself by consistently working hard and getting great at something. That confidence will ooze out of you wherever you go.
• Shark Tank. Scary, anxious, nervous. Did a deal with Mark Cuban.
• Advice - If you’re building a business, listen to what your customers want. What does your ideal client want? Build that.