Synopsis
As Kobe Bryant once said, There is power in understanding the journey of others to help create your own.Thats why the Learning Leader Show existsto get together and understand the journeys of successful leaders, so that we can better understand our own.This show is full of stories told by world-class leaders. Personal stories of successes, failures, and lessons learned along the way. Our guests come from diverse backgroundssome are best-selling authors, others are genius entrepreneurs, and one even made a million dollars wearing t-shirts for a year. My role in this endeavor is to talk to the smartest, most creative, always-learning leaders in the world so that we can learn from them as we each create our own journeys.
Episodes
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652: Arthur Brooks - The Power of Teaching, The Arrival Fallacy, The Mad Scientist Profile, Lifting Heavy Weights, & The Two Best Practices To Be Happy
07/09/2025 Duration: 56minApply to be in my next Learning Leader Circle - https://learningleader.com/leadership-circles/ This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Notes: Key Learnings The Mad Scientist Emotional Profile – High achievers typically have both high positive and high negative affect. "Hustlers, hard workers, strivers, entrepreneurs, ambitious people, they're in that quadrant of high positive, high negative affect." This creates intensity but requires management of negative emotions. Dangerous Negative Affect Management – People try to manage high negative affect through alcohol, excessive internet use/pornography, and workaholism. "The isms, the addictions, they're almost all negative affect management techniques." Two Best Ways to Manage Negative Affect: Faith, Spirituality, P
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651: Shaka Senghor - From Prison to Purpose: Breaking Mental Barriers, Working with Mentors, and Leading Through Vulnerability (How To Be Free)
31/08/2025 Duration: 51minGo to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader Shaka Sengor spent 19 years in prison for killing a man. He’s transformed his life through not making excuses and taking full ownership of his decisions. Now, he’s a New York Times best-selling author who has been called a “soul igniter” by Oprah. His latest book is called How to Be Free. Notes: The Permanence of Split-Second Decisions – At 17, shot three times on a Detroit corner. At 19, he killed a man in a conflict after creating a narrative that he would "shoot first." Sentenced to 17-40 years for second-degree murder. "I try to teach young people about understanding the permanence of a 30-second decision." Books as Portals to Freedom – Read over 1,500 books during 19-y
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650: Michelle "Mace" Curran - Building a World-Class Team, Running an Excellent Debrief, Rebuilding Trust, Feedback Loops, & How To Turn Fear Into Your Superpower
24/08/2025 Duration: 01h05minGo 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
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649: Sam Lessin - Type 2 Fun, Voluntary Hardship, Joy as a Competitive Advantage, Long-Term Thinking, & Life Lessons From Dad (Lessin's Lessons)
17/08/2025 Duration: 56minGo to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My guest: Sam Lessin is a Partner at Slow Ventures, with prior experience as Vice President of Product Management at Facebook and CEO of Drop.io. His career highlights include serving as a key executive at Facebook, leading product management efforts, and successfully co-founding Fin. His current role at Slow Ventures involves investing in innovative startups across various sectors, showcasing his expertise in entrepreneurship and venture capital. Notes: Key Learnings The 4:30 AM Advantage – Sam's father would be at his desk by 4:30 AM every day, saying, "It's easy to look smart if you have a several-hour head start on everyone else." Early work creates compounding advantage
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648: Ed Latimore - Going From Zero to One, Taking Ownership, Positive Body Language, Strategic Hardship, & Hard Earned Lessons From The Hurt Business
10/08/2025 Duration: 01h02minGo to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My Guest: Ed Latimore is a professional heavyweight boxer, best-selling author, and veteran of the U.S. Army National Guard. He earned a degree in Physics from Duquesne University. Ed has gained recognition for overcoming personal struggles with addiction and poverty. We recorded this at our 2025 Learning Leader Growth Summit in Scottsdale, Arizona. He's the author of Hard Lessons From The Hurt Business. Notes: Key Learnings The Heaviest Weight at the Gym is the Front Door – Starting is often the hardest part. "Zero to one is the hardest part" in any endeavor. Once you begin, momentum builds, but that first step requires the most effort. How You Feel is Irrelevant – "How
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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
03/08/2025 Duration: 01h21minGo to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire 1 person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. www.InsightGlobal.com/LearningLeader My Guest: Tim Ferriss is the author of five #1 New York Times bestsellers (including The 4-Hour Work Week, Tools of Titans, and Tribe of Mentors). His podcast, The Tim Ferriss Show, has been listened to more than a billion times. Tim was an early investor in Uber, Shopify, Twitter, Alibaba, and many others. He’s the creator of a new card game called COYOTE. Decision making - How can I win even if I lose? He viewed angel investing like his personal MBA. Instead of paying for business school, he invested in companies and learned about business by working with actual businesses. He didn’t expect to make money on those investments. That was just a bonus. Think, “How can I win eve
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646: Nick Maggiulli - Proven Strategies for Every Step of Your Financial Life (The Wealth Ladder)
27/07/2025 Duration: 48minGo 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 t
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645: Ryan Petersen (Flexport CEO) - Front Line Obsession, Gemba Walks, Relentless Work-Ethic, CEO Mastermind Groups, & Valuing Simplicity
20/07/2025 Duration: 58minGo 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
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644: Blaine Anderson - The #1 Dating Coach In The World Teaches You How To Genuinely Connect With People
13/07/2025 Duration: 54minGo 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 ta
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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
06/07/2025 Duration: 55minGo 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
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642: Jim Murphy - Inner Excellence, AJ Brown, Presence, Managing Fear, Daily Goals, & Understanding Our Greatest Needs
29/06/2025 Duration: 51minGo 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
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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
22/06/2025 Duration: 01h04minThe Learning Leader Show with Ryan Hawk 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 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 nev
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640: Tony Reno (Yale University Head Football Coach) - Writing a Team Creed, Leaving it Better Than You Found It, Going to Gettysburg, Leadership Retreats, & Winning Championships
15/06/2025 Duration: 55minGo to www.LearningLeader.com for full show notes The Learning Leader Show with Ryan Hawk The Arena gives you direct access to some of the most respected coaching minds in the world. Led by HOFer Sherri Coale, Brook Cupps, Geron Stokes, and Eli Leiker. Leaders who have built winning programs, led at the highest levels, and shaped the next generation of elite performers. The Arena is a Learning Leader Circle for Coaches only. We are opening applications now for our first cohort. If you'd like to be part of it, CLICK HERE to apply. Once the cohort is full, we will be pausing applications. 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 In Patient Pursuit of Greatness – In the spring of 2012, General McChrystal was teaching a leadership class at Yale. That’s when he me
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639: Katie Gatti Tassin (Money with Katie) - Building A Media Business, The Morning Brew Acquisition, Knowing Your Retirement Number, & Living Up To High Expectations
08/06/2025 Duration: 55minThe Learning Leader Show with Ryan Hawk 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 Katie Gatti Tassin is the author of the "Money with Katie" newsletter and podcast, both acquired by Morning Brew in 2022. Katie provides fresh personal finance advice with a unique outlook, coupled with deep, self-taught knowledge. Before founding Money with Katie in 2020, she worked professionally in marketing and user experience design for Southwest Airlines, Dell Technologies, and Meta. She’s the author of Rich Girl Nation: Taking Charge of Our Financial Futures. Notes: If you’re not curious about it, you’re not going to give it your all. But if you are, you can become relentless. Chase your curiosity and obsessions with great rigo
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638: Kirk Herbstreit - The Most Prepared Broadcaster In The World, Responding To Adversity, Faith, Elk Pride, High School Sports, NIL Deals, Lee Corso, & The Emotional Moment When The Buckeyes Won The Title
01/06/2025 Duration: 01h16minGo 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 Kirk Herbstreit is the voice of college football. A former Centerville High School and Ohio State University Quarterback, Kirk has been the lead Analyst for ESPN’s College Gameday since 1996. He calls the biggest games in college football on Saturday nights, and he broadcasts the college National Championship. Beyond college football, Kirk is also the lead analyst for Thursday Night Football on Amazon Prime Video. Kirk has been nominated for 19 Sports Emmy Awards and has won 5 times. This conversation was recorded in front of about 300 people in Centerville, Ohio. Kirk’s dog Peter was with us on stage when he wasn’t wandering around in the audience. Kirk's emotional moment af
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637: Tom Ryan (Ohio State Wrestling Coach) - Chosen Suffering, Emotional Control, Responding to Tragedy, Success Pillars, and Learning from Dan Gable
25/05/2025 Duration: 01h15minThe Learning Leader Show with Ryan Hawk 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 Tom Ryan is the head wrestling coach at Ohio State University. In college, he wrestled for perhaps the greatest wrestling coach of all time, Dan Gable, at Iowa, where he was a two-time Big Ten champion and a two-time NCAA All-American. As a coach at Ohio State, he’s won numerous national coach of the year honors, has coached more than 75 All-Americans, and led the Buckeyes to a national championship in 2015. We filmed this in his office in Columbus, OH, after spending the morning watching some of his championship wrestlers practice. It was one of the coolest days I’ve had in a long time. Notes: “My first workout after driving from Syrac
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636: William Von Hippel - Why We Need Both Autonomy and Connection to Find Happiness (The Social Paradox)
18/05/2025 Duration: 01h48sGo 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. Go to www.InsightGlobal.com/LearningLeader William von Hippel grew up in Alaska, got his B.A. at Yale and his PhD at the University of Michigan, and taught for a dozen years at Ohio State University before finding his way to Australia, where he is a professor of psychology at the University of Queensland. He’s the author of multiple books. A few months ago, he published The Social Paradox: Autonomy, Connection, and Why We Need Both to Find Happiness. Notes Why do people who have comfortable lives filled with freedom and abundance still feel unhappy? Need two things… Connection and autonomy. Are leaders born or made? Yes. Like most things, it’s not a black and white answer. The key is to use your unique strengt
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635: Rich Gotham (President of The Boston Celtics) - How To Build a Championship Organization
14/05/2025 Duration: 56minGo 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. Go to www.InsightGlobal.com/LearningLeader Rich Gotham is the President of the Boston Celtics. He is responsible for all aspects of the Celtics' business operations. In addition, he works closely with Celtics ownership, basketball operations staff, and the NBA on basketball-related matters, as well as team and league initiatives. He succeeds “Red” Auerbach as Celtics team President and serves on the NBA Board of Governors. Since joining the Celtics in 2003, he’s helped grow team revenues by over 300%, and they’ve won two NBA championships. Notes: Must-haves when making hiring decisions for a leadership role: Work ethic, self-awareness, a catalyst for positive energy, purpose-driven, and care ("give a shit"). At
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634: Tom Nolan (CEO of Kendra Scott) - 2% Moments, Setting Big Goals, Being Unbalanced, Moving Fast, Coaching High Performers, & Going Through Hard Things Together
11/05/2025 Duration: 57minThe Learning Leader Show with Ryan Hawk 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. Go to www.InsightGlobal.com/LearningLeader Notes "Average players want to be left alone. Good players want some coaching. Great players want the truth." It is not a company’s job to give work-life balance to someone. And he is not balanced. He’s on 24/7. It was refreshing to hear the real story from someone who is running a company. As Dr. Julie Gurner said on episode #538, “People will tell you in books that you have to live a 'balanced life,' but if we are completely honest, almost all great things are born from periods of imbalance.” Make the most of your 2% moments. 98% of the time, life is just happening… But every once in a while, you’ll have the 2% opportunities.
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633: General Stanley McChrystal - In Pursuit of Greatness, High Standards, The Ranger Effect, Self-Discipline, White-Water Rafting, Obsession, & Making Choices That Define Your Life (On Character)
04/05/2025 Duration: 01h02minThe Learning Leader Show with Ryan Hawk 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. Go to www.InsightGlobal.com/LearningLeader Stanley McChrystal is a retired four-star general. Stan is the former commander of the nation’s premier military counter-terrorism force, Joint Special Operations Command (also known as JSOC). His command included more than 150,000 troops from 45 allied countries. Since he retired from the Army, Stan has written multiple best-selling books including, Team of Teams, and most recently, On Character. The most crucial discipline is to think for yourself. To a sad degree, we’re lazy. People comment on things they haven’t watched or read, but have seen comments by others who align with their political party. They aren’t thinking for the