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
  • 699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money

    699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money
    Aug 2 2026
    The Learning Leader Show with Ryan Hawk www.LearningLeader.com This is brought to you by Insight Global. If you need to hire one 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 has the hustle and grit to deliver. My Guest: Jack Raines is a writer and investor. At 24, he quit his corporate finance job at UPS, bought a one-way ticket to Barcelona, and spent the next year traveling through 25 countries while writing a newsletter that grew to hundreds of thousands of readers. He went on to earn an MBA from Columbia, help build Sherwood News at Robinhood, and join the venture capital firm Slow Ventures, where he invests in creators. His first book, Young Money: A Field Guide to Finding Wealth and Purpose in Your Twenties, is out now. Key Learnings Jack's Grandma Ruth took him to Africa when he was 11. She was in her late 60s. She had the money. She said: "I can spend it on you now or leave it to you when I'm dead. This is better." Money has no value until you exchange it for something. We need to decide what we want that to be. Every year of your 20s is worth $10 million. (Nikita Bier) You'll never have this window of flexibility again. Say yes to interesting experiences in your 20s. Your income is going to climb exponentially anyway. Don't save $500 at the cost of a memory. Move to where the action is. Jack moved to New York for business school. Then San Francisco for a job. Then back to New York. High slope of learning. High slope of contact with good people. Network amplifies ability. It doesn't create it. A million times zero is still zero. A million times two is two million. The only real risk is not doing anything. Every opportunity in life comes through a person. The best networking tool is doing great work. How did Gracie Abrams open for Taylor Swift on the Eras Tour? She wrote great music. Taylor noticed. Taylor called. In your 20s, potential is valued at a premium. In your 30s and beyond, proof of work matters more. Experimenting when you are young speed-runs the learning curve. You develop the skill of taking shots. That skill compounds. It's much harder to start being risk-on at 35 if you weren't risk-on at 25. Personal finance is simple. Spend less than you make. Build a six-month emergency fund. Take the 401(k) match. Contribute to your IRA. Don't gamble on individual stocks. Stay invested. Stay employed. Don't go into credit card debt. Don't get divorced. User error interrupts compounding more than anything else. Set up the boring foundation. Then stop touching it. Most retirees never touch the principal. (Nick Maggiulli) They stack money out of fear, then die with more than they started with. Daniel Kahneman on loss aversion: the pain of losing $100 is twice as strong as the joy of gaining $100. That's why people over-save. Your burn rate at 70 is way lower than at 45. No kids at home. No tuition. Less energy to do stuff. Plan accordingly. Bill Perkins' Die with Zero philosophy... A useful insight was in the first chapter: his best friend took a payday loan at 23 to backpack Europe for three months. Same career trajectory as Bill. Just way more fun at 24. People don't want to think about their mortality. So they focus on making the number go up. If you actually internalized that you're going to die, you'd be more intentional about your time and money. Jack's champagne moment a year from now: He sells a ton of copies of it. And it's still relevant. Reflection Questions Where are you spending your best years earning money you'll never actually enjoy? What would change if you accepted that your peak-energy window is closing?Where are you standing still because the risk of moving feels bigger than the risk of staying? What does the only real risk (not doing anything) look like in your life right now?What is the great work you could do that would make the right person notice you? More Learning #539: Jack Raines - Playing Infinite Games, Living Life Backwards & Building Your Platform #548: Nick Maggiulli - The Power of Compounding #373: Bill Perkins - How To Get All You Can From Your Money & Your Life Podcast Chapters 00:00 The Price of Becoming - Pre-Order Now! 01:38 Meet Jack Raines 03:27 Grandma Ruth Took Him to Africa When He Was 11 08:04 Why Every Year of Your 20s Is Worth $10 Million 12:12 Quitting UPS at 24 for a One-Way Ticket to Barcelona 15:10 How to Increase Your Surface Area for Luck 20:00 Where You Live Is Who You Become 22:00 Why Memories Compound Faster Than Money 26:23 The Financial Stability Basics Nobody Wants to Hear 29:00 Get the Boring Stuff on Autopilot 31:15 Why Retirees Never Touch the Principal 34:02 The Bad Trade of Saving During Your Best Years 37:36 The Bill Perkins Die With Zero Debate 39:15 Experimentation, Agency, and the Only Real Risk 42:53 The Best Networking Tool in the World: Do Great Work 44:10 The Champagne Question: Making...
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    49 mins
  • 698: Joanna Stern - How to Think for Yourself in the Age of AI, Why Deep Work Still Matters, Making Career Decisions With ChatGPT, and How to Stay Human on Purpose

    698: Joanna Stern - How to Think for Yourself in the Age of AI, Why Deep Work Still Matters, Making Career Decisions With ChatGPT, and How to Stay Human on Purpose
    Jul 26 2026
    The Learning Leader Show with Ryan Hawk www.LearningLeader.com New Book - The Price of Becoming - www.LearningLeader.com/Becoming This is brought to you by Insight Global. If you need to hire one 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 has the hustle and grit to deliver. My Guest: Joanna Stern is an Emmy Award-winning technology journalist, chief technology analyst for NBC News, and founder of the independent media company, "New Things." She is best known for her 12-year tenure at The Wall Street Journal, and for authoring the New York Times bestseller I Am Not a Robot. Key Learnings Joanna dedicated her book to her parents "who taught me to think for myself, and the AIs, robots, and machines that made me wonder if I really was." In an age when AI can do the thinking for us, the most valuable thing we can teach our kids is to think for themselves. Walt Mossberg invented tech journalism for humans. His first column: "Computers are too hard to use, and it's not your fault." Without Walt, we don't have a category where technology built for humans is reviewed by humans. AI won't replace the radiologist. It'll make them better. Joanna sat with her doctor while AI scanned her mammogram. The AI flagged three suspicious spots. Two the doctor had already dismissed as benign. But one was something the doctor hadn't caught. She marked it for follow-up. Then the doctor pointed to other cases where SHE had caught things the AI missed. It's not a replacement. It's a partnership. The same technology that finds cancer is the same technology that can autonomously send missiles. That's the great tension of our time. Every powerful technology has good and bad uses. AI colleagues are coming. Joanna has two employees and one AI agent. She predicts that within a year, she'll have full AI employees. Great management books haven't been written yet about how to lead a mixed team of humans and agents. Someone is going to write them. Concert ticket prices tell you everything about human connection right now. Every artist is selling out football stadiums. People are craving in-person interaction more than ever. Bot Girl Summer. Joanna tried to have an emotional relationship with a chatbot boyfriend named Evan for 48 hours. She didn't fall in love. But she noticed how easy it was to talk to something that only wanted to hear about her problems and told her she was great at everything. That's the danger. The AI therapist shut itself down when it realized there was a real therapist in the room. Joanna brought her AI therapist "Ash" into her actual therapy session. Halfway through, Ash said, "I'm sorry, I can't continue this conversation. It sounds like there are multiple people in the room." AI won't replace therapists. It'll help with the shortage and the stigma. Some people don't want to walk into a therapist's office. But they'll open their phones. That's a bridge to real help for people who wouldn't otherwise get it. Kara Swisher's career advice to Joanna: "Leave your fucking job." That was the shortest, cleanest advice Joanna got when deciding whether to leave the Wall Street Journal after 12 years. Joanna used AI as a co-founder for the biggest decision of her career. She uploaded 12 years of notes into ChatGPT and asked it to help her decide whether to leave the Journal. It didn't decide for her. But it structured the risk analysis, laid out the escape hatches, and helped her see the shape of the decision. The muscles atrophy if you don't use them. Writing is meant to be hard. Thinking is meant to be hard. If you outsource the hard work, you stop getting stronger at the hard work. Research is where you learn the most. If you have AI pull the memo for you and you get up and read it, you don't know what you're really talking about. You have to do the reps to know the material. AEI: Already Enough Intelligence. Sam Altman is obsessed with building superintelligence. Joanna proposes we already have enough intelligence to work with. Maybe the goal isn't to build smarter models. Maybe it's to figure out what to do with what we already have. The AI on-ramp for leaders: Take one document you make all the time (a memo, a PowerPoint, an email template). Upload it. Ask AI to make a template out of it. Next time you need it, you're twice as fast. Push yourself to do the harder work. Joanna's analogy: marathon runners are insane. They just want to run. Nobody wants to do the harder work. But that's where the growth is. Joanna's champagne moment a year from now: milestones for her new company. She's already hit 100,000 YouTube subscribers three months after her first video. But she also just wants a nap. Reflection Questions Where in your work are you outsourcing the thinking to AI? Are the muscles you actually need atrophying because you're skipping the reps?If you accepted that you already have enough intelligence to ...
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    55 mins
  • 697: The Price of Becoming - The Compounding Practices of High Performance (My New Book is Now Available!). "Have a Plan. Work the Plan. Plan for the Unexpected."

    697: The Price of Becoming - The Compounding Practices of High Performance (My New Book is Now Available!). "Have a Plan. Work the Plan. Plan for the Unexpected."
    Jul 19 2026
    Go to www.LearningLeader.com The Learning Leader Show with Ryan Hawk Buy my new book, The Price of Becoming www.LearningLeader.com/Becoming This is brought to you by Insight Global. If you need to hire one 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 has the hustle and grit to deliver. Get The Price of Becoming: The Price of Becoming is available now wherever books are sold. "Have a plan, work the plan, plan for the unexpected." From my old Miami football coach, Terry Hoeppner. It was posted in the locker room. He said it every day. I still think about it all the time. There is no hack. There is no one thing. At many keynote Q&As, someone asks me for a quick fix. The only answer is the power of compounding. Consistency, dependability, and reliability are the least sexy words of all time. And they're the whole game. Take your work seriously. Don't take yourself seriously. The best leaders go hard at the work but laugh at themselves. It's important to be able to laugh with your team. Optionality is overrated. "I'm trying to beef up my obituary. I'm not going to dabble." - Ed Latimore (Ep. 648) Live like a hawk. Hawks have eyesight eight times better than humans. They glide and observe constantly. But once they see what they want, they commit with everything they have. Be a professional noticer. Then commit fully. Talk to your people before big decisions. My dad. Miranda. And the wide network of high-caliber people I've built over 700 podcast episodes. Be specific. Off the record. Long conversations. Then trust your gut. Take bits and pieces from the best. Then find your own voice. As a brand new sales rep at LexisNexis, Rex Caswell had me interview and sit with the ten best reps in the company. I took a piece from each, mashed it together with my own personality, and eventually found my own voice. I still use that formula today. Use social media to create in-person moments. Organize dinners, meetups, coffees. Get in the room with people. Concert ticket prices and The World Cup tell you everything you need to know about how much people are craving in-person connection right now. Don't outsource your thinking to AI. You can't walk into the weight room, look around, and expect to build muscle. You have to move the weights. Use AI as a tool. Don't let it do the thinking for you. Your job is to add value to other people's lives. Coach Hoeppner sat 19-year-old me down with the other quarterback and pointed at both of us: "He adds more value to our team than you do. He gives us a better chance to win. That's why he's going to play." It was brutal. It was a very lucky moment for me to experience that in my formative years. I fell into the AI trap. The Be a Pro section originally started as a LinkedIn post that was heavily influenced by Claude. It went well on Twitter too. People DM'd me praising it. It felt great. And it scared me. I was getting the rewards without doing the work. The good old days are right now. I try to work hard when my family is asleep or at school. Between those hours, I go as hard as I can. Outside those hours, I try not to work too much. I've talked with so many dads who are older now, and their kids are out of the house. They miss the time when they were with their kids so much. I try to think of that daily. Making positive dents in the world. Leave people, places, and things better than you found them. That's how you make a positive dent, one person at a time. My philosophy on keynotes and writing: story, science, and practical application. Great storytelling to move people to the edge of their seat. Empirical evidence to make it true. Practical application to answer, "So what? Why should I care?" You have to have all 3. Our edge in coaching leadership teams: my coaches actively live what they teach. They didn't attend a seminar and get certified. They're still active coaches themselves, still leading teams in real time. That's what separates authentic teaching from performance. Push your edges. Find your Goldilocks zone. James Clear told me you don't get better at tennis by playing Roger Federer. He'll destroy you. But you also don't get better by playing a five-year-old. You need to be uncomfortable, but not so uncomfortable that you break. Shane Gillis walked off stage looking exhausted. Dan saw him live in Cincinnati. On stage, effortless. The second he stepped behind the curtain, his shoulders slumped like he was ready to fall asleep. That's what the great ones do. They make it look easy because of the price they paid to get there. My productive paranoia. Our team has to earn it every session. It creates a productive paranoia knowing that continuous improvement is necessary. The reward is bigger than the cost. It's the greatest gig in the world. I bet on myself and the team every single day because if we keep adding value, I like our chances. Reflection Questions Where...
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    1 hr and 14 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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