The Learning Leader Show With Ryan Hawk Podcast By Ryan Hawk cover art

The Learning Leader Show With Ryan Hawk

The Learning Leader Show With Ryan Hawk

By: Ryan Hawk
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As Kobe Bryant once said, “There is power in understanding the journey of others to help create your own.” That’s why the Learning Leader Show exists—to understand the journeys of other leaders so that we can better understand our own. This show is full of learnings taught by world-class leaders—personal stories of successes, failures, and lessons learned along the way. Our guests come from diverse backgrounds—CEOs of multi-billion dollar companies, best-selling authors, Navy SEALs, and professional athletes. My role in this endeavor is to talk to the most thoughtful, accomplished, and intentional leaders in the world so that we can learn from them as we each create our own journeys.Learning Leader LLC 062554 Career Success Economics Management Management & Leadership
Episodes
  • 646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)

    646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)
    Jul 27 2025
    Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader 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 ...
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    49 mins
  • 645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity

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

    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.”
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    58 mins
  • 644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People

    644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People
    Jul 13 2025
    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 spouseWomen 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.
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    54 mins
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This is the best podcast. Regardless of who you are or where you’re at in life, you’ll absolutely find incredible value. Literally every episode shared ways to just be a better person overall. And Ryan asks meaningful, impactful questions that drive to tactical approaches that we can actually use. Very grateful for him and this show.

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