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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
  • 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.
    Show More Show Less
    54 mins
  • 643: Anthony Scaramucci - Getting Fired by President Trump, Working With a Life Coach, Playing Quarterback, Building Confidence + Charisma, Telling The Truth, & Finding Your Superpower

    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 6 2025
    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."
    Show More Show Less
    55 mins

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