702 episodes
702: Blake Mycoskie (Founder of TOMS) - Hitting Every Goal & Still Feeling Worthless... Gratitude, Mantras, and Hiring Like a Champion
23/08/2026 | 55 mins.The Learning Leader Show with Ryan Hawk
www.LearningLeader.com
The Price of Becoming is a USA Today, LA Times, and Publishers Weekly Best-Seller!
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.
Blake Mycoskie founded TOMS Shoes in 2006 after a trip to Argentina, where he saw children without shoes and built a company around giving away a pair for every pair sold. TOMS went on to donate more than 100 million pairs of shoes and became one of the most copied business models in the world. What most people don't know is what happened after he sold it, and I'm grateful that he was open to talking about that on this episode of The Learning Leader Show.
Key Learnings
Make your gratitude specific. Not "I'm grateful for my family." Name the exact thing. Blake's example from that morning: the photos the camp posted of his daughter laughing in the lake, and knowing his stoic kid does not smile like that unless she is genuinely happy.
He kept the practice going for five years when he couldn't feel any of it. Blake could not name five things he was grateful for, and he had all the same things in his life he has now. He did it anyway. He credits it as one of the things that kept him going.
Surfing is a great thinking practice. Surfing is mostly just sitting on the board. Three hours in the water, ten waves, maybe five minutes standing. The rest is paddling and sitting. That's why it works as a thinking practice.
Capture the idea in the moment or lose it. Blake programmed the side button on his Apple Watch to open a voice memo. Every idea he has sitting on the board, he records. They're all waiting when he gets out.
He hit every marker and still felt worthless. "I did everything, and I still, deep down in my soul, had this feeling like I'm not worthy, I'm not enough, and I never will be."
The external validation was the drug. Selling TOMS cut off the supply. The thing that had been holding up his sense of self was suddenly gone.
If you get there and it's empty, don't panic. Panicking is what Blake did, and having money meant he could make expensive mistakes fast. Build the dream house. Get divorced. One thing after another.
The emptiness may be the point. Blake's read on it: if achievement delivered what society promises, you'd never go inward. Feeling hollow at the summit is what forces the inner work.
He re-patterned the sentence he'd been telling himself since childhood. The old one was "you're not enough." He replaced it with "I am enough. I've always been enough." Twenty minutes every morning and every evening. Forty straight days. It worked, and he no longer needs to do it daily.
Sometimes you just need a physical cue to catch the loop. That's the whole idea behind the bracelet he wears. Not magic. A reminder on your wrist that interrupts the thought.
Give the second one away. Blake found the bracelet's real power was handing one to a friend. Now you're both wearing it, you're both in on it, and there's an unspoken agreement that neither of you has to have a bad day alone. Men are worse at building that than women are.
Tell your kids they're enough, and keep telling them. They're going to get the opposite message from everywhere else, which is exactly why it has to come from you repeatedly. Blake says the relaxation you'll see in them is immediate.
Be brutally honest about how hard the job is. Try to talk them out of it. Blake is the last interview in the process now. If he can lay out every negative and they still desperately want it, the commitment is real.
"How many people did you convince not to take the role before you got the right person?" Most leaders slip into sales mode, talk the candidate into it, and end up talking themselves into the candidate.
What he screens for during the interview process:
Integrity first. If it isn't there, it surfaces fast now.
Attitude second. The person who never says "that's not my job."
Whether they're building a resume or joining a movement.
Find the people who cover what you're bad at. Blake is a storyteller, a vision-sharer, and high energy. He is not a supply chain guy, not a finance guy, and he has trouble saying no. So he hired around it. That's what let him actually be the chief shoe giver instead of pretending to be a CEO.
Don't wait for permission. Most people stand in line at the front door. Blake looks for side doors. In Argentina he had no investors and no plan, just an idea and the words One For One. Ryan's version for his kids: everyone can apply online. Drive to the restaurant and go talk to the manager instead.
Having no experience was the advantage. He'd never made a shoe, so he didn't know which rules he was breaking. Same with outdoor advertising. Same with driver's ed. He learned it from Richard Branson: ask forgiveness, not permission.
Nashville wouldn't allow advertising, so he sold art instead. Blake spent two years with the city council and got there by removing the ad from the ad. No price, no call to action. Just album covers on the sides of buildings, called country music art. Once one artist had one, they all wanted one. He sold the company to Clear Channel.
You don't attract what you want. You attract what you are. Want honest friends, be honest. Want peace at home, bring peace. Want trust, practice it when nobody's watching. Blake applies it to customers too: sloppy companies attract sloppy customers, and that's usually the real reason the business fails.
Charlie Munger got asked how to get a great wife. He said: deserve one.
Be known for doing what you said you'd do. Early on Blake didn't have the skills, so he built the reputation on execution instead. Move fast, keep it simple, do it with integrity. Momentum is a form of trust.
The other half of that is not overpromising. Blake's own failure mode is getting excited, feeling falsely confident, promising something big, and missing. When it happens, own it fast and be honest, and the relationship usually survives.
Be careful using a general-purpose chatbot as a therapist. Blake's warning, and the reason the founders of Sonia built a purpose-built tool instead: the big consumer models are designed to make you feel good about yourself. If you need to hear something hard, that's the last thing you want.
He went from skeptic to advisor in six months. Blake met the Sonia founders at a mental health conference, tried the app to be polite, and by the third session was getting insights he hadn't gotten elsewhere. He now spends five to ten hours a week helping them. His reason for loving the work: "Now I get to be the coach instead of the athlete."
Stop chasing balance. Design for harmony. Blake picked this up from an executive at Cannes who said she'd given up on balance. He goes hard in phases. Full dad mode with the office waiting on emails. Then all in on a launch and missing things at home. The measure isn't evenly split day to day. It's whether, over a year, everyone in his life feels like they got what they needed to thrive. Including him.
Reflection Questions
What did you actually feel grateful for today? Not the category. The specific moment.
What is the sentence you've been repeating to yourself since childhood, and is it true?
In your last hire, how hard did you try to talk them out of it? Or did you spend the interview selling them, and then sell yourself?
More Learning
#598: Sam Parr - Bold. Fast. Fun. Living by a Mantra & Building a Media Company
#547: Dr. Michael Gervais - Stop Worrying About What Other People Think of You
#676: Jesse Cole - Built for The Fans (The Owner of the Savannah Bananas)
Episode Chapters
00:00 Meet Blake Mycoskie
01:38 Surfing is Great for Deep Thinking
03:41 Make Your Gratitude Specific
05:39 Blake Sold TOMS and Fell Apart
11:20 Advice for Those to "Make It" and Feel Nothing
13:23 "I Am Enough" and the Bracelet on His Wrist
17:35 The No Magic Pill
19:41 The Risk of Chatbot Therapy
22:42 A Surgeon Dad, a Bestselling Mom, and the Pressure Nobody Said Out Loud
25:13 Telling Your Kids They're Enough
31:31 How He Got Country Music Art on the Side of Buildings
35:15 Learning to Be Proud of TOMS Again
38:49 Hiring Around Your Weaknesses
41:25 Try to Talk Them Out of the Job
45:07 You Don't Attract What You Want. You Attract What You Are.
46:54 Don't Wait for Permission
48:34 Be Known for Doing What You Said You'd Do
50:02 The Champagne Question: Harmony, Not Balance
52:28 EOPC701: Mark Pincus (Founder of Zynga) - Why We All Need a Coach, Maintaining High Standards, The Book of Life, Aggressive Ambition, and Why Your Instincts Are Almost Always Right
16/08/2026 | 52 mins.The Learning Leader Show with Ryan Hawk
www.LearningLeader.com
The Price of Becoming is a USA Today, LA Times, and Publishers Weekly Bestseller!
www.LearningLeader.com/Becoming
My guest - Mark Pincus is the founder of Zynga, the social gaming company he built from zero to $12.7 billion, pioneering a category that generated over a billion app installs and introduced hundreds of millions of people to online play. He's a serial founder who has started ten companies, taught product development at Stanford, and made early seed investments in Facebook and Twitter. His new book is Life at the Speed of Play.
Key Learnings
Coaches are cheat codes. Mark has hired a surfing coach, a tennis coach, a chess coach, a life coach, and the legendary Bill Campbell. None of them were assigned to him. He went and found them.
"You throw to where you swing. You don't swing to where you throw." His tennis coach, Jorge, on learning how to serve. Commit to the natural swing first. You'll miss. You'll look stupid. Eventually your brain realizes you're serious and puts the ball where it belongs.
You play to get better. You don't play to win. Not this point. Not this match. What am I doing right now that makes me better in the next game?
Kill the ego so it gets out of the way of you being humble and curious.
Don't contort the organization around one talented jerk. Colleen McCreary, Zynga's chief people officer, kept a sign on her wall: "No jerks allowed." She once vetoed an acquisition because she believed the founder was toxic. When the organization sees you refuse to bend just to win one point, they build muscle and confidence too.
You'll have periods out of alignment. That's okay. Sometimes the person is in a crucial seat and you can't swap them tomorrow. What matters is that you're aligned with the philosophy.
Bill Campbell's two lessons: intellectual honesty and courage. Be committed to the deep truths above everything else, and say them to your team even when it hurts. Then have the courage to stand up to your own team, your own board, and your own investors.
A well-run company is a democratic dictatorship. Campbell leaned heavily on the dictatorship half. Unapologetically.
The flip side of ambition is sacrifice. Everyone says they're a ten out of ten on ambition.
Mark's test: would you toil in obscurity for the next ten years, nobody respecting what you're doing, for an 80 or 90 percent chance at something bigger than your wildest dreams? Or take the 80 percent chance at a respectable single and a pat on the back?
Nobody believes in us as much as we do. That's why we become founders. At 41, VCs who had already backed Mark twice told him he was too old, too rich, and too settled to go all in on Zynga.
Mark isn't all in until he is. He calls it a lazy on-ramp to curiosity. Lots of projects. Looking for signals in a lot of places. Processing. Then it flips. "When the fish are running, we're up all night throwing nets until they're done running, not until we're tired."
The chess lesson: play boring. His chess coach told him if you want to beat a player rated much higher than you, play boring and conservative and let them make the mistake. He started doing it. He started winning.
Your kids don't follow what you say. They follow what you do. Mark set out to be a different kind of dad than his own, who measured people by their résumé. Then he watched his 15-year-old daughter spend every waking minute with math tutors before leaving on a service trip. "How did we get here? Oh, I know how we got here. They're not listening to what Dad says. They're following what Dad does."
Happiness comes from feeling useful to a community you care about. Not from being useful. From feeling it. That's Alfred Adler, by way of The Courage to Be Disliked.
There are two levels of success. A life well lived is a life in alignment with what only you can bring to the world. You don't have to build Google to feel like you went for it. The ultimate success is the greatest instantiation of your talents.
Use money as freedom, not lifestyle. When Freeloader sold and 28-year-old Mark had more money than he'd ever imagined, he made a list of everything he was going to buy. It totaled about $9,000. He put leather interior in his Pathfinder. He still has the vehicle.
He set a $500 million goal that had nothing to do with buying things. At a net worth around $15 million, working with a life coach, he wrote it down because that's the capital required to run a studio of teams chasing many ideas without going to anyone else with hat in hand. "Creatively, that's freedom."
Retirement is spiritual death. The stretches between building things are what Mark calls the abyss. Once you've felt the high of building with a great team and shipping something into users' hands every week, it ruins you. You can't be happy with less.
Over-fund the things that matter. Not every day is the same. Not every life moment is the same. When one of those moments comes, put all your best players on the ice.
The Allen & Company investor tour. They told Mark it was a dog and pony show. Just shake some hands. He told his team: this is our IPO, this is our roadshow, and we are going to use every minute of it the way we want. He gave the biggest public market investors a full presentation, handed them his numbers, and told them to judge him against those numbers in a year. He met with them a year later and had crushed them.
King for a day. Carol Bartz brought Mark in to talk to Yahoo's entire senior management. He spent two weeks building a presentation on how he'd run Yahoo if he were king for a day, stood up, and took over the room for an hour. They got a deal done and one person in that room came to work for him. He ran the same play on the CEO of AMEX with a credit card that competed on fun. Amex spent $75 million with them.
Seven minutes with Obama became 45. Mark was told the President would ask about his kids and then the meeting would be over. He walked in with a PowerPoint on the ten bold objectives he'd run on if he were president. Obama went through the entire thing and then asked what else he had.
Prepare as hard for everything going right as you do for everything going wrong. Mark had under-prepared for the version of where Obama said, "Yeah, I'm buying. What else you got?"
We sleepwalk through our own biggest moments. The question isn't what's the agenda or why they want to meet with you. It's: I have five minutes with the king. What is theoretically possible here?
The Book of Life. Every year during the Jewish New Year, Mark writes in the same book. Only during that window. It isn't a journal. It's a spiritual board meeting with himself. He reads back through every previous year first, then writes.
Partner with your future self. "What will Mark 2030 thank me for doing right now?"
It started with quitting smoking. October 19, 1994. "I pulled my own power back. If I can quit smoking and really commit to it, what else can I do?" A year later he quit his job and did something bigger.
Even if you missed the big goal, ask what you actually did toward it. Did you talk about it? Did you do real things? Did you turn the boat toward it? If not, maybe you don't believe in the goal.
When Mark is at his lowest, he's humbled, he picks achievable goals, and he finds the most grit. When he's winning, he picks stratospheric goals and does the worst. After his biggest successes, he isn't humble enough to succeed again, and he has to go through failure to reel himself back in.
Mark's champagne moment a year from now: that the book connects for hundreds of thousands of people, and that he's built a product people find real meaning in.
Reflection Questions
If you went and hired a coach, who is the person who could most change your life right now?
What is your next high-stakes moment, and are you treating it like the dog and pony show or like your IPO?
What is the one habit your future self would most thank you for making this year? What would it unlock if you actually committed to it?
More Learning
#688: Dr. Henry Cloud - Your Desired Future: 5 Steps to Take You Where You Want to Go
#689: Eric Ries - Why Good Companies Go Bad, and How Great Companies Stay Great
#687: Jim Collins - What to Make of a Life & The 3 Types of Luck
Episode Chapters
00:00 Meet Mark Pincus
01:40 Why Mark Hires So Many Coaches
02:25 Lessons From Tennis In Leading People
04:56 Refusing to Bend the Culture for One Great Player
07:03 Lessons From Bill Campbell
09:17 On Being Called a Control Freak
13:38 The Ambition Question Mark Asks Founders
14:53 What High Standards Do to Your Kids
20:55 How Mark Defines Success
23:26 Money as Freedom, Not Lifestyle
29:45 Why High Achievers Can't Retire
32:39 Over-Fund the Things That Matter
34:35 Treating a Handshake Tour Like an IPO Roadshow
35:36 King for a Day at Yahoo and Amex
38:14 Seven Minutes With Obama That Became 45
41:39 The Book of Life
45:21 Why Mark Does His Best Thinking at His Lowest
46:48 The Champagne Question
48:40 EOPC700: Keith Hawk & AJ Hawk - Conscious Competence, Delusional Confidence, Stacking Days, After-Action Reviews, Taking Big Risks, The Power of Compounding, and Modeling High-Standards
09/08/2026 | 1h 29 mins.The Learning Leader Show with Ryan Hawk
www.LearningLeader.com
The Price of Becoming is a USA Today, LA Times, and Publishers Weekly Bestseller!
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 Guests:
My dad, Keith Hawk (also known as Pistol), spent decades leading sales teams at LexisNexis and has taught leadership and public speaking to audiences all over the country. He's the author of multiple books including Get Real Selling. Pistol has that rare ability to be both universally liked and 100% respected by all who know him.
My brother AJ Hawk was an All-American linebacker at Ohio State, where he won a national championship. He played 11 years in the NFL, won a Super Bowl with the Green Bay Packers, and retired as the franchise's all-time leading tackler. Now you'll see him every weekday on ESPN as a co-host of the Pat McAfee Show
Notes:
Key Learnings
Be a consciously competent leader. Pistol's framework: you have to understand the processes of the work you're asking people to do, not just the end result. First-line leaders have to know the work at a great level of detail.
One tactical way to get there: do after-action reviews on both wins and losses. Know why you win. Know why you lose. Describe both in detail. That's how you earn vivid clarity.
Give people vivid clarity. Don't tell your team to "go get the ball carrier." Tell them precisely how to handle each situation. Great leaders are great because they give vivid clarity to the people they're leading on how to do the thing.
Stack days. If I can't win by being brilliant, I can win by being able to endure. Just get up and do the thing day after day. Growing up, AJ and I had an unwritten rule: no matter what we did the night before, we were going to the first available lift. You don't have to go to bed early. But you're going to work no matter how you feel.
When AJ knew he could do it. Freshman year at Ohio State. A tunnel screen play in camp. He read it perfectly, took off, and delivered a textbook hit on the receiver. That was the moment: "Football's football. These guys are all monsters. But I think I can find a way to make some plays."
How to write a book: get up an extra hour early for 200 days in a row and never miss a day. Anybody can do it. You just have to be willing to make the decision, and then follow through, and then follow through again.
My scout team Super Bowl. As a scout team QB at Ohio, I picked the Florida game to prepare like it was the real thing. I wore Rex Grossman's number and arm sleeve. Spatted my cleats. I rewrote the practice cards based on real Florida plays. We ended up being in a tight ball game against a national powerhouse. My teammates came back after the game and said practice that week was harder than the actual game. This is when I learned what is possible when prepared for the moment.
The Mike Nolan $10 bill story. When AJ was in college, the 49ers head coach Mike Nolan needed to tip a valet and asked if he had any cash. AJ gave him $10. Weeks later, a handwritten note showed up at AJ's college house with a $10 bill inside and a thank-you note from Mike Nolan. Follow-through. Attention to detail. Paying people back. AJ never forgot it.
AJ's delusional confidence in Tahoe. AJ had an unlucky drive that left him 254 yards from the pin, in the first cut. Jack Wagner was still on the green in front of us. AJ pulled out a four iron. I told him to wait. He said, "I'm just gonna go, and hit it on the green." He flushed it. Landed on the green 25 feet from Jack. There's power in belief, speaking things into existence, and then doing them.
Irrational self-confidence isn't irrational. Pistol quoted Bill Simmons: "As long as you believe it's possible, it's possible." Regardless of what it is.
My biggest risk: leaving corporate at the end of 2017. I had a VP of sales job, and I left it all to bet on this podcast. Miranda believed in it maybe even more than I did. That combination made it possible.
Pistol's biggest risk: August 1st, 1999. He left LexisNexis after 14 years to go be a public speaker. Two years later, on August 1st, 2001, he came back. Both times on his birthday. His career jumped five notches on his return. Sometimes you have to leave to come back better.
AJ's biggest risk: hiding a broken wrist during a Super Bowl run. AJ refused an X-ray or MRI so they couldn't shut him down. The trainer taped and casted it. He played the whole season, won the Super Bowl, and made the Pro Bowl. He had surgery to repair it days after the Super Bowl.
The best players are consistent. When I'd talk to AJ's teammates in Green Bay about him, they used the unsexy words: "Most consistent guy on the team. First guy in the weight room. Will be where he's supposed to be on every play." He did that for eleven years.
Show up. Every single day. Pistol said it: "Anybody that's been great at something didn't get great on the first day, but they did the right types of things along the way."
Don't grade your kid's games. Grade the effort. "Did you play hard? That's all I care about." AJ said his family doesn't have good or bad games. There's only one question after the game: did you play hard or did you not?
Show them what "hard" actually looks like. Sometimes kids think they're playing as hard as they possibly can when they're not. AJ's brother-in-law Jack Johnson reminded him of this. You can't just say "play hard." You have to describe it. You have to show them. Otherwise they don't know what the standard is.
Model it. Don't tell. Leadership is caught more than it's taught. My primary role as a dad and a husband is to be the model. If I have low standards, my kids will have low standards. If I show up every day, they'll learn what showing up looks like.
Do all the work. Then trust your instincts. AJ's approach to football. Reinstall the defense from scratch every year. Take fresh notes. So when it's game time, you don't have to think. You just play.
The Dinner Guest Draft: Every hundredth episode, we do a draft. This one: pick five living dinner guests.
AJ's table:
Michael Jordan
Charles Barkley
Arnold Schwarzenegger
Palmer Luckey
Denzel Washington
My table: (All dream guests for The Learning Leader Show)
Dave Chappelle
Dave Matthews
Mike Rowe
Doris Kearns Goodwin
Michael Lewis
Pistol's table: (All former guests of the show)
Admiral William McRaven
Dan Patrick
Nikki Glaser
Stephen M.R. Covey
Oz Pearlman
Champagne Moments a Year From Now
My dad: Celebrating his 71st birthday dinner with all of us.
AJ: To keep being present with his kids while they're still young. To slow down and enjoy it.
Me: A good year of college for the older girls in our family.
Reflection Questions
Where in your work are you giving people vivid clarity? Or are you handing them broad general directives and hoping they figure it out?
What is your version of the Mike Nolan $10 bill story? What small act of follow-through could you do this week that someone will remember for years?
Where are you being performative right now, doing something for the audience instead of doing it because you want to be great? What would change if you only did it when nobody was watching?
More Learning
#600 - AJ, Pistol & Ryan Hawk - Setting the Standard
#500 - AJ, Pistol, Ryan & Pat McAfee - Live Your Life as a Movie
#400 - AJ, Pistol & Ryan Hawk - The Life Experiences That Shape Our Character
Podcast Chapters
00:00 The Arena Invite
01:30 Meet Keith "Pistol" Hawk and AJ Hawk
03:34 What Everyone's Been Up To For the Past Two Years
05:09 What We Learned From Robert Saleh (head coach, Tennessee Titans) and Mike Macdonal (head coach of the defending Super Bowl Champion, Seattle Seahawks) About Tackling
08:50 Be a Consciously Competent Leader. Give People Vivid Clarity.
10:44 Inflection Point Stories: When AJ and Ryan Knew They Could Do It
16:33 How Pistol Spotted the Talent Early
21:32 Why Written Communication Is More Important Than You Think
25:21 The Power of Stacking Days
33:06 The Mike Nolan $10 Bill Story
35:24 Delusional Confidence: The Tahoe Golf Moment
42:51 Irrational Self-Confidence Isn't Irrational
43:15 The Biggest Risks Each of Us Ever Took
47:24 Playing Through a Broken Wrist to Win a Super Bowl
50:38 How to Raise Kids With High Standards
54:28 Regimented vs. Disciplined
59:30 AJ's Hack to Beat a Shellfish Allergy
01:06:00 The Dinner Guest Draft Begins
01:21:21 Draft Recap
01:23:43 The Champagne Question
01:26:33 EOPC699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money
02/08/2026 | 49 mins.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 the Book Matter a Year From Now
45:53 EOPC698: 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
26/07/2026 | 55 mins.The Learning Leader Show with Ryan Hawk
www.LearningLeader.com
New Book - The Price of Becoming - www.LearningLeader.com/Becoming
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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 work with, what would you actually build with what's in front of you right now?
More Learning
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#605: Seth Godin - The Power of Remarkable Ideas
#697: Dan Smith & Ryan Hawk - The Price of Becoming
Podcast Chapters
00:00 The Price of Becoming - Pre-Order Now!
01:44 Meet Joanna Stern
02:31 Teach Your Kids to Think in the Age of AI
03:25 The Parents and Mentors Who Shaped Her Career
04:16 Lessons From Walt Mossberg
05:55 Why Joanna Spent a Year Living With AI
14:47 How AI Can Make You a Better Leader
17:30 Why People Crave Human Connection More Than Ever
21:00 Bot Girl Summer: Dating a Chatbot Named Evan
25:13 The AI Therapist Trial
29:51 Using ChatGPT for a Career Change
33:29 Don't Let Your Thinking Muscles Atrophy
40:20 Sam Altman on Superintelligence, and Joanna's Case for "AEI"
42:51 Joanna's Advice for College Students
45:29 How Joanna Actually Uses AI to Write
47:17 Practical AI for the Fortune 500 VP
50:17 The Champagne Question
52:43 EOPC
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