The Ambitious Generation

Episode 164 of The Ambitious Generation with Jack WagonerRyan Lang spent years in sports radio working with the Tampa Bay Buccaneers, the New York Yankees and ESPN.Then he helped build an 8-figure company in oil and gas.He had the cars, the money and a beautiful family, and he says he hated who he had become.So I asked him about the moment he decided to bet on himself.His answer was the scariest yes of his life: sitting in his car on the brink of divorce, asking himself if he was willing to try. We get into why we're "meaning making machines," how to stand guard at the gate of your mind, why it's state before strategy, the knowing-doing gap, and what he's grateful for after 20 years of marriage. If you look successful on the outside and feel empty on the inside, this one is for you.⏱️ Chapters:0:00 — When did he decide to bet on himself?0:48 — "I had the money. And I hated myself."1:27 — The scariest yes of his life2:49 — "Could I become somebody different?"4:06 — What Kobe taught Alan Stein Jr. about the basics5:43 — How to turn "what if I fail" into "what if I win"7:40 — Stand guard at the gate of your mind9:06 — State before strategy10:20 — The knowing-doing gap11:09 — Why I started this podcast12:28 — What he's grateful for13:33 — 20 years married to a crazy entrepreneur15:05 — Where to find RyanSubscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏Connect with Ryan:Empire Partners: https://empirepartners.netPath to Mastery podcast: https://www.pathtomasterypod.comLinkedIn: https://www.linkedin.com/in/ryan-lang-b46a545b/Instagram: https://www.instagram.com/realryanlang/📺 Listen on your favorite platform:Apple Podcasts: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061Spotify: https://open.spotify.com/show/5EsTEpQAjU4BxUrDoFyZ6b🧠 InnerVue — a complete self-awareness tool:→ https://yourinnervue.comUse code GRATEFUL20 for 20% off a Tier 1 InnerVue, plus a complimentary coach-led debrief of your report.🧠 More from Jack:► Website: https://jackwagoner.co► Instagram: https://www.instagram.com/jack_wagoner_/► 1:1 Coaching: [email protected]📺 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.Subscribe and turn on notifications so you never miss an episode.Stay grateful, stay hungry.

Episode 163 of The Ambitious Generation with Jack WagonerDr. Richard Weissbourd is a Harvard psychologist and the faculty director of Making Caring Common.His team just surveyed thousands of Gen Zers about meaning and purpose.And he says achievement that isn't meaningful can corrode your friendships and, eventually, your soul.So I went to his office at Harvard and asked him what happens to a kid who achieves every goal and still doesn't feel like enough.We get into the two kinds of achievement, why your friends start to feel like threats, why not wanting to work 70 hours a week is a healthy instinct, why chasing happiness backfires, what happened when his survey offered people double the salary for a job with less meaning, the AI companion problem, and why nobody teaches us how to love. If you've ever hit a goal and felt nothing, this one is for you.⏱️ Chapters:0:00 — Coming up0:15 — Every goal is just another gate1:22 — Two kinds of achievement2:44 — When achievement corrodes your friendships5:01 — Why your friends start to feel like threats7:09 — Don't get all A's and flunk life8:49 — How individualism makes us lonely10:52 — Is Gen Z lazy, or just healthy?11:49 — Why chasing happiness backfires13:09 — We find meaning in mattering to others16:58 — 79% of Gen Z want work that helps people19:24 — Would you take double the salary for less meaning?20:38 — Money identity vs. meaning identity23:38 — AI and disappearing entry-level jobs24:51 — Why young people are so lonely28:35 — The AI companion problem29:56 — What replaces religion?35:38 — Why nobody teaches us how to love39:24 — How do you know you're in love?42:51 — What young people should know about loveSubscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏Connect with Richard:Making Caring Common: https://mcc.gse.harvard.edu/Harvard faculty page: https://www.gse.harvard.edu/directory/faculty/richard-weissbourdGen Z Wants to Do Good (the Gallup study): https://mcc.gse.harvard.edu/reports/gallup-gen-z-wants-to-do-goodTurning the Tide in 2026: https://mcc.gse.harvard.edu/s/Turning-the-Tide-2026-Making-Caring-Common-lejm.pdf📺 Listen on your favorite platform:Apple Podcasts: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061Spotify: https://open.spotify.com/show/5EsTEpQAjU4BxUrDoFyZ6b🧠 InnerVue — a complete self-awareness tool:→ https://yourinnervue.comUse code GRATEFUL20 for 20% off a Tier 1 InnerVue, plus a complimentary coach-led debrief of your report.🧠 More from Jack:► Website: https://jackwagoner.co► Instagram: https://www.instagram.com/jack_wagoner_/► 1:1 Coaching: [email protected]📺 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.Subscribe and turn on notifications so you never miss an episode.Stay grateful, stay hungry.

The Ambitious Generation with Jack WagonerEpisode 162Ryan Cass thought 100 miles was as far as his body and mind could go. Then he ran 150. Then he ran across the entire state of South Carolina. In December he's going for 200 miles, to raise money for families fighting cancer.So I asked him what's actually going on in his head at mile 30.His answer goes way past running. We get into the voices that show up when you want to quit, why tying your effort to something bigger than you is what gets you through, the woman with stage 4 cancer who put his blistered feet in perspective, the one question he asks himself to stay honest, and the promise he made at six years old, the night he answered the door to the police. If you think you've already hit your limit, this one is for you.⏱️ Chapters:0:00 — Meeting in person for the first time1:20 — "Who am I being right now?"2:30 — What running taught him about his limits3:30 — From 100 miles to 150 to across South Carolina4:50 — Training for 200 miles for families fighting cancer5:35 — What your mind does at mile 307:50 — Would you trade your problems?8:45 — The stage 4 cancer story10:25 — Every problem is an opportunity13:10 — The promise he made at 6 years old15:05 — Why his dad is now one of his best friends16:05 — Where to find RyanSubscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏Connect with Ryan:Win Today podcast: https://podcasts.apple.com/us/podcast...LinkedIn: / ryanacass Website: https://ryancass.comUnshakeable Discipline: https://www.unshakeablediscipline.com/📺 Listen on your favorite platform:Apple Podcasts: https://podcasts.apple.com/us/podcast...Spotify: https://open.spotify.com/show/5EsTEpQ...🧠 InnerVue — a complete self-awareness tool:→ https://yourinnervue.comUse code GRATEFUL20 for 20% off a Tier 1 InnerVue, plus a complimentary coach-led debrief of your report.🧠 More from Jack:► Website: https://jackwagoner.co► Instagram: / jack_wagoner_ 📺 Watch on YouTube: / @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.Subscribe and turn on notifications so you never miss an episode.Stay grateful, stay hungry.

The Ambitious Generation with Jack Wagoner Episode 161 Owen Fitzpatrick has spent close to thirty years studying how belief forms, in boardrooms at Google and Coca-Cola, in Olympic training camps, and in NorthKorea, Rwanda, and Afghanistan. He has coached billionaires and world-class athletes. When I asked him what separates them, he did not say ambition. He said ambition is not the variable. What the elite have is ambition that holds its shape across years. He also said something I had not heard anyone say out loud: a lot of the best performers in the world are running on pain. 00:12 What is the voice inside my head 02:18 Where the inner dictator comes from 05:18 Am I my inner voice, or separate from it 08:01 Your brain is a double agent 11:26 Beliefs are functional, not factual 14:49 Hangry, depression, and why feelings feel like facts 16:59 Your brain runs an echo chamber 19:29 How to actually get out of it 25:06 The incentive to question what you already believe 28:58 Picking a school with your gut, justifying it later 31:04 The three gates: feeling, identity, logic 36:17 Rigging your own pros and cons list 41:02 What billionaires and Olympians have in their heads 45:50 Ambition is not the variable 49:01 Procrastinating presence 49:50 Inner Propaganda Owen Fitzpatrick Links: Inner Propaganda Book: https://innerpropaganda.com/ Website: owenfitzpatrick.com LinkedIn: linkedin.com/in/owenfitzp Instagram: https://www.instagram.com/owenf23/?hl=en📺 Listen on your favorite platform:Apple Podcasts: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061Spotify: https://open.spotify.com/show/5EsTEpQAjU4BxUrDoFyZ6b🧠 InnerVue — a complete self-awareness tool:→ https://yourinnervue.comUse code GRATEFUL20 for 20% off a Tier 1 InnerVue, plus a complimentary coach-led debrief of your report.🧠 More from Jack:► Website: https://jackwagoner.co► Instagram: https://www.instagram.com/jack_wagoner_/► 1:1 Coaching: [email protected]📺 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.Subscribe and turn on notifications so you never miss an episode.Stay grateful, stay hungry.

The Ambitious Generation with Jack Wagoner Episode 160 with Trey Roth, founder of Yaystack Most people treat optimism like a personality trait you either got or you didn't. Trey Roth treats it like a decision with a cost attached. He's the founder and CEO of Yaystack, a platinum-selling songwriter and music producer, and a father of four who spent a decade being told his company was a failure before anyone called it anything else. In this conversation he does something almost nobody does: he admits that pessimists are right more often, and then explains exactly why he refuses to be one. We go deep on the line he's used for years to catch his own blessings before they pass, why he gets visibly excited when something goes wrong, the identity sentence a 15-year-old handed him at lunch that he couldn't stop repeating, and the difference between faith and fear that comes down to one word: action. If you've ever been right about something going badly and realized that being right didn't help you at all, this one's for you. Timestamps: 00:00 The question that started it 00:26 "Dad, this is one of those moments" 01:26 The line he uses to catch his own blessings 03:17 The thing on the side of your head 04:12 A bench on the Cape and my mom's hand 05:37 What a 15-year-old said after her first time on stage 07:10 "You get so much wrong on the way to getting it all right" 10:36 Why he gets excited when something goes wrong 12:38 You can be a pessimist and be right more often Connect with Trey Roth:Instagram: https://www.instagram.com/treyroth/LinkedIn: https://www.linkedin.com/in/treyroth/Yaystack: https://www.yaystack.co/📺 Listen on your favorite platform:Apple Podcasts: https://podcasts.apple.com/us/podcast/the-grateful-podcast-with-jack-wagoner/id1725776061Spotify: https://open.spotify.com/show/5EsTEpQAjU4BxUrDoFyZ6b🧠 InnerVue — a complete self-awareness tool:→ https://yourinnervue.comUse code GRATEFUL20 for 20% off a Tier 1 InnerVue, plus a complimentary coach-led debrief of your report.🧠 More from Jack:► Website: https://jackwagoner.co► Instagram: https://www.instagram.com/jack_wagoner_/► 1:1 Coaching: [email protected]📺 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.Subscribe and turn on notifications so you never miss an episode.Stay grateful, stay hungry.