
699: Jack Raines - How to Build Your Career, Increase Your Surface Area For Luck, and Find Your Purpose | Why Memories Compound Faster Than Money
Ryan Hawk... · 49:21 · 1,480 plays
From the album The Learning Leader Show With Ryan Hawk
Description
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 mat
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710: Ravi Gupta - The Anti-Dabbler's Guide to Mastering One New Skill Every Year, Why Presence Isn't Enough, Bourdain's Masterclass in Humility, and Pairing Reasonable Goals With Delusional Ones
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693: Tina Seelig - Fortune vs. Luck, The Power of Curiosity, Why Your Words Change Lives, Failure Résumés, Thank You Notes, and Creating Luck Through Relationships, Observation, & Daily Action
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703: Angela Duckworth - Why Grit Isn't Enough, Situation Over Willpower, How Belief Gets Borrowed, John Wooden's Socks, and How the Right People and Places Bring Out Your Best
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690: Austin Kleon - Why Activated Leaders Win, The Analog Desk, Don't Call it Art, Stay Light, Professional Noticers, Lead with Curiosity, and How To Steal Like an Artist
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694: Clark Lea - LIVE! At The 2026 Learning Leader Growth Summit: The Mission Is Winning, Checking the Cabinets, Leading as an Introvert, Alabama Week, Decoupling Worth From Outcomes, and Building a Championship Culture
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701: 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
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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."
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708: Danny Meyer - How You Make People Feel: The Founder of Shake Shack & Union Square Hospitality Group on Culture as Soil, the 49/51 Hiring Formula, and Leading With Generosity
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702: Blake Mycoskie (Founder of TOMS) - Hitting Every Goal & Still Feeling Worthless... Gratitude, Mantras, and Hiring Like a Champion
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