The Learning Leader Show With Ryan Hawk - 699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money

Duration: 49m
Broadcast on: 02 Aug 2026
Audio Format: other

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 EOPC

For we get to this episode, I want to tell you about something I'm pumped about. It's called the arena. Great coaches want to surround themselves with other high achievers. Great coaches want to be in a group where high standards are the norm. That's exactly what the arena is, a private community of hungry, driven, growth focused coaches led by the Hall of Famer Sherry Cole, Brooke cups, Garin Stokes, and Eli Liker. These are the people I personally go to to become a better leader. Here's what's different this year. We just finished our first full year. It was awesome. Lots of coaches from all over the country at every level, from high school to college to the pros across more than a dozen sports. Mike Powell with the Arizona Diamondback said, "If you are looking for a group to push you out of your comfort zone, give you the tools to become a better human coach." One leader, this is the space, it's not comfortable, but you're going to grow and connect. Applications for the next cohort are open now. The arena might be for you if you are a high caliber, high character coach who is not afraid to be pushed and challenged and work on yourself to be better for the people you are leading. If that's you, go to learningleader.com/arena to apply. That's learningleader.com/arena. Welcome to The Learning Leaders Show presented by InSight Global. I am your host, Ryan Hawke. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. On to tonight's featured leader, 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. Since then, he's earned an NBA from Columbia, helped Robin Hood build its media company and joined the venture capital firm, Slow Ventures, where he invests in creators. His first book is called Young Money, a Field Guide to Finding Wealth and Purpose in Your 20s. During our conversation, we discuss why Jack's grandmother Ruth hooked Jack when he was 11 years old to Africa and how that trip shaped everything he believes about spending money on experiences. Then, how we can all increase our surface area for luck and specifically what Jack does. We also talk about the best networking tool and then he shares what you can learn from studying how retirees spend their money. Super interesting. Ladies and gentlemen, please enjoy my conversation with Jack Raines. I love your book. I love all your writing. You know, it's funny how quickly you became one of the few people who's, every time you publish something, I read it. Blog, obviously your book now, in that kind of Morgan Hausal, Tim Urban, James Clear, realm of, "All right, Jack, just publish something new. I'm going to read it." So do I... Huge pop.

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