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The Learning Leader Show With Ryan Hawk

Ryan Hawk
The Learning Leader Show With Ryan Hawk
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  • 646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)
    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  
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  • 645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity
    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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  • 644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People
    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.
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  • 643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower
    Go to www.LearningLeader.com for all 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. Go to www.InsightGlobal.com/LearningLeader 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."
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  • 642: Jim Murphy - Inner Excellence, AJ Brown, Presence, Managing Fear, Daily Goals, & Understanding Our Greatest Needs
    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 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
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About The Learning Leader Show With Ryan Hawk

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