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She's built companies worth over a billion dollars. She's been on the cover of Inc. Magazine. She was the youngest woman ever accepted into Y Combinator. And what she told me in this conversation is something she says most founders at her level are too scared to admit publicly.

Jess Mah has been quietly tracking the happiness scores of high-performing CEOs for over a decade, and the results are devastating. We go deep on why getting your F-U money doesn't actually make you happier, why Silicon Valley rewards founders who lie about how hard it is, how she finds billion-dollar opportunities in boring industries, and why the smartest people she knows are diversifying their happiness the same way they diversify their investments.

If you've ever chased a goal thinking it would finally make you feel enough, this one's for you.

CHAPTERS:
(00:00) The Best Secrets Aren't on YouTube
(02:36) How Jess Finds Billion Dollar Ideas by Talking to People
(04:48) The 5-Hour Brainstorm That Changes Everything
(07:04) Starting a Business at 11 Years Old
(09:14) Why She Builds "Boring" Businesses
(11:09) Getting Calls from Billionaires
(12:13) How Giving Without Expectation Creates Opportunity
(15:03) Finding Ideas in Obscure Industries
(17:18) How to Meet Experts When You Have No Credentials
(19:47) The Happiness Data on CEOs (This Will Shock You)
(23:18) Why Most Successful Founders Score 5-7 Out of 10
(25:40) Richard Branson's Secret to Actually Being Happy
(26:32) Happiness Diversification (Not Just Financial)
(28:51) Why Hustle Culture Is Destroying Founders
(30:38) Silicon Valley Rewards the Act
(33:16) Is This Conversation Work?
(35:27) Focus vs. the Richard Branson Route
(38:53) 50% of the Time Still Feels Like Running Uphill
(39:49) Why Famous Entrepreneurs Won't Be Honest on Podcasts
(42:46) The Purpose Expert Who Needed Help Finding Purpose
(44:10) Why We're Addicted to the Illusion of Enlightenment
(49:16) The Return to Classical Wisdom

🔗 CONNECT WITH JESS:

Instagram: https://instagram.com/jessmahofficial

LinkedIn: https://linkedin.com/in/jessicamah

Twitter/X: https://x.com/jessicamah

Website: https://jessmah.com

Mahway: https://mahway.com

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🧠 More from Jack:
► Website: https://jackwagoner.co
► Instagram: https://www.instagram.com/jack_wagoner_/
► 1:1 Coaching: jackcwagoner@gmail.com
📺 Watch on YouTube: https://www.youtube.com/@Jack_Wagoner

⸻
🎙️ About Jack:
I moved to France alone at 16, started my first business at 17, and launched this podcast because I kept meeting people who had the answers to questions I didn't even know I was asking. My philosophy: you can set massive goals while being deeply fulfilled right now. That's the duality of gratitude and ambition.

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Stay grateful, stay hungry.