The Learning Leader Show With Ryan Hawk

Latest Episodes:

650: Michelle "Mace" Curran - Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower Aug 24, 2025

Show notes

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

649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons) Aug 17, 2025

Show notes

Go to www.LearningLeader.com for full show notes

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

648: Ed Latimore - Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business Aug 10, 2025

Show notes

Go to www.LearningLeader.com for full show notes

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.

647: Tim Ferriss - Chasing Your Curiosity, Internal vs External Scoreboards, Effectiveness over Efficiency, Winning Even if You Fail, Fame's Hidden Costs, & The Mount Rushmore of Podcasting Aug 03, 2025

Show notes

Go to www.LearningLeader.com for full show notes

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

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

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

Time Stamps

00:38 Tim's Childhood and Parental Influence

01:15 Curiosity and Lifelong Learning

02:56 Marine Biology and Childhood Adventures

07:06 Influence of Mentors and Teaching Aspirations

08:45 Thoughts on Parenthood and Relationships

12:11 Balancing Seriousness and Humor

25:15 Effectiveness vs. Efficiency

30:50 Creating Slack and Self-Care

34:41 The Importance of Social Bonds and Play

41:07 Meeting a Game-Changing Partner

42:13 The Importance of Analog Social Interaction

42:55 Podcasting: A Platform for Deep Connections

43:30 The Evolution and Challenges of Podcasting

43:47 The Art of Interviewing

49:18 Navigating Fame and Public Exposure

01:04:26 The Philosophy of Risk and Experimentation

01:10:27 Spotting Talent and Following Curiosity

01:20:37 Closing Thoughts and Future Endeavors

646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder) Jul 27, 2025

Show notes

Go to www.LearningLeader.com for full show notes

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

645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity Jul 20, 2025

Show notes

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

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."

644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People Jul 13, 2025

Show notes

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

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.

643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower Jul 06, 2025

Show notes

Go to www.LearningLeader.com for all show notes

Anthony Scaramucci served as the White House Director of Communications for President Donald Trump from July 21 to July 31, 2017. He was at Harvard Law School with President Barack Obama and First Lady Michelle Obama. He's the founder and managing partner of SkyBridge Capital. And he's the founder and Chairman of the SALT conference.

Leadership through service: True leadership isn't about personal glory but about making others better and helping them succeed in their roles. Derek Jeter exemplified this by never caring about personal statistics, only team success. "If you're on the team, it's not about me, right? It's about you. How am I gonna make you better? Or how am I gonna make you feel good about your role? How am I gonna get you to think that I'm here to help you?"
Flexibility and decision-making under pressure: Football taught Scaramucci the importance of reading situations quickly and making audibles at the line of scrimmage - skills that translate directly to business and life leadership. "You can't just say, okay, here's the game plan, right? Because that's what Mike Tyson says, right? You have the plan until you get punched in the face, or all battle plans go by the wayside with contact with the enemy."
Resilience through adversity: Getting "your ass kicked" early in life builds the resilience needed for future challenges in business and politics. Early defeats teach you how to bounce back from failure. "That's called resilience, right? You gotta get over that... That's how you gotta get your ass kicked. Here I was... and I just remember feeling so puny... So how you gotta get over that."
The confidence battle starts within: The first fight in life is with yourself - believing you're good enough and worthy to compete. Henry Ford's principle applies: "If you think you can or you can't, you are right." "The first fight is with yourself. Am I good enough? Am I worthy? Can I get to the game? Can I believe in myself enough so that I'm standing next to someone else who believes in themselves that I compete?"
Accountability in relationships: When Scaramucci's marriage was in crisis, taking full accountability for his mistakes rather than deflecting blame was crucial to rebuilding the relationship. "I owe my wife Deirdre, a debt of gratitude for actually really loving me because I was off the rails on a few things... she's like, Hey, I'm not having this, so if you love me, get your shit together."
Life coaching vs. therapy approach: Life coaching focuses on progression and future action ("What are we doing today to be better?") rather than regression into past issues. "I feel that therapy is a regression. Life coaching is a progression... forget about the past. What the hell are you gonna do? What are we doing today to make yourself a better person?"
Forgiveness as liberation: Choosing to forgive both others and yourself removes the "millstone of regret" that weighs you down and prevents forward progress. "I can take that millstone of regret and leave it behind me, take it off of my neck and leave it behind me... human frailty and not judging it is not just you judging others, but also yourself."
The comfortable outsider advantage: Being comfortable with your outsider status while still being able to operate in elite circles provides authentic confidence and relatability across all social levels. "I am a comfortable outsider. I'm not an insider... but I'm comfortable with it. You know, like guys like Trump or Rudy, they're uncomfortable. Outsiders... But I'm a comfortable outsider. I don't need to do that."
Intellectual curiosity + neuroplasticity: Combining genuine curiosity about others with the ability to adapt and change allows you to move successfully between different social and professional circles. "Find your superpower... I think your superpower is very similar to my superpower... intellectual curiosity. And so if you can blend intellectual curiosity with neuroplasticity, meaning you can adopt and change... then you can move in various circles."

Pivot for survival: Successful businesses and careers require constant reinvention. SkyBridge's conference business and pivot to Bitcoin were survival strategies that became major successes. "We were going outta business... This was an accidental survivor strategy. This was a pivot that we were making in order to stay in business. This was not some mastermind plan."

642: Jim Murphy - Inner Excellence, AJ Brown, Presence, Managing Fear, Daily Goals, & Understanding Our Greatest Needs Jun 29, 2025

Show notes

Go to www.LearningLeader.com for full show notes

The Learning Leader Show with Ryan Hawk

Jim Murphy is a mental performance coach for some of the most accomplished professional athletes in the world. Formerly a professional baseball player, he now focuses on helping others. You may have heard of him if you were watching the Philadelphia Eagles' playoff run last season, and star wide receiver AJ Brown was reading Jim's book Inner Excellence on the sideline between offensive series.

Notes:

The first 11 days of 2025, Inner Excellence (originally published 16 years ago) sold about 25 copies… What happened on January 12? AJ Brown was shown on TV reading it in between offensive series. It then sold 200,000 copies in 20 days.
Fear is a concern about the future.
Give the best of what you have today. Be present.
Heart, will, spirit = the deepest part of you
When we're at our best, there's no thought of self.
5 greatest needs
- That we have value
- Love and acceptance
- Integrity
- Purpose beyond self
- Growth
Dick Vermiel's coaching style - Coach the person first. Then the sport (or the thing you're doing). The same is true for any leadership role. People won't care what you think unless they know you actually care about them.
4 Daily Goals
- Give the best of what you have today
- Be present. Fear is a future thing.
- Be grateful
- Focus on what you can control
Anxiety is a mind with too many thoughts and concerns. Need to face our fears.
3 Key Areas:
- Belief - expand what you think is possible.
- Freedom - play like a kid (let it rip).
- Focus - Be fully present
Status vs amazing experiences. Love is the most powerful force in the universe. Joy comes from love. Love can come from weaknesses.
Ego - Always comparing, creates a fear of screwing up
Rory McIlroy – Didn't care if he made the cut at the US Open. Played free and made a few birdies at the end of the second round and made the cut.
Jim's Dedication: "My father, Donald C. Murphy. The one who greatly influenced me to think deeply about what to love and what to let go of. I love you. See you soon." His dad worked on the Apollo 11 mission. The first lunar landing.
Grade yourself on presence. 4 daily goals. Rate them 1-10. Anxiety is a sign that someone isn't present.
Jim has always struggled with being self-centered.
Be non-judgmental. Share unconditional love.
Ricky Scruggs - Former teammate and roommate in pro baseball. He invited me to the desert in 2003. Led me to take the risk to leave the safety of family and friends to pursue a meaningful life.
What about for those people who say your stuff is "woo-woo?" "I get paid to help people perform better. And that's what happens when you work with me."
"My whole life, I obsessed about being a superstar, being rich and famous. What I now realize is what I've always wanted was to feel fully alive. I've realized since that what I always really wanted was to feel fully alive. That's what Inner Excellence is about. Pursuing a full life and letting everything else be added. We're created for relationships."
Among Jim's strengths is that he listens and doesn't judge. That's what many people want. "I have this one client, a pro athlete. He said, 'Jim, I smoke, I gamble, I drink. I do all these things, but I don't think you do all those things. Do you think we can work together?' I said, 'If you don't judge me for not doing those things, I won't judge you for doing those things.' We became great friends."
Resonance Key #3 - Love Your Opponent. "The opponent is not the enemy– they're our partner in the dance." – Phil Jackson

641: Larry Connor - The Big 6 Leadership Attributes, Building a Values-Based Culture, Becoming a Billionaire, Working on Saturdays, Flying Into Space, Diving To The Mariana Trench, & Existing To Be The Best Jun 22, 2025

Show notes

The Learning Leader Show with Ryan Hawk

Go to www.LearningLeader.com for full show notes

www.InsightGlobal.com/LearningLeader

Larry Connor is an entrepreneur, non-profit activist investor, and adventurist. In business, he is best known for founding The Connor Group, a real estate investment firm, and growing it from $0 to $5 billion in assets. Outside of work, Larry lives an adventurous life. Within a 12 month period Larry did something that had never been done before. He completed 3 dives to the deepest part of the ocean (the Mariana Trench) AND traveled to the International Space Station as an astronaut. In addition to that, Larry is a private pilot and was part of a Le Mans racing team that has won championships.

"At The Connor Group, we don't have, and never will have, a mission statement. We have culture. When you have the latter, the former is not necessary."
The culture is built on 5 core values, on which we don't compromise:
- Do the right thing
- People count
- Live the Circle of Success
- Think long-term, not short-term
- Relentless pursuit of excellence
"We exist, quite simply, to be the best."
"We don't hire for experience. We don't hire for knowledge. We don't care where you went to school. We hire for personality traits. Especially in leadership roles. You have to have the big 6. You have to have all 6. They are:
- 1. Be able to motivate and inspire others.
- 2. Self-accountability and ability to hold others accountable in an honest, direct manner.
- 3. Organizational multi-tasking. The speed of the game is fast.
- 4. Cultural fit.
- 5. Grit. Doing the thing that others say are impossible.
- 6. Work orientation. If you want to come in at 8:30, take a 90-minute lunch, and leave at 4:30, The Connor Group is not for you.
"People never outperform their own self-image. So aim high!"
"Mediocre people don't like high achievers and high achievers don't like mediocre people."
"By definition, if you want to be exceptional, you have to be different. If you're like everybody else, you're going to end up like everybody else."
In 2008, Larry said, "We simply decided we weren't going to participate in the global recession."
3 P's - People, Plan, Process
People's performances are measured through daily, weekly, and monthly IAMs (Individual Accountability Meetings). Clear expectations and clear management.
When I asked him about becoming a billionaire, Larry immediately jumped to the impact he's having on others. "There are far more important standards than money. How well have you treated your associates? Have you made them better people? How much have you done to help other people? Have you made a difference?" All of that is available to all of us regardless of us being a billionaire or not.
The company headquarters are next door to a hangar that houses a working model of the "Wright B Flyer" - The Wright Brothers' first production airplane.

Our TOPPODCAST Picks

Follow Us

Stay Connected

The Learning Leader Show With Ryan Hawk

Related Podcasts

Links

Stay Connected