The Ambitious Generation

Episode 165 of The Ambitious Generation with Jack WagonerAt 19, Michelle Jacobik left home for a job at a financial services firm. Then Visa and Mastercard became her "angel investors."By 23 she was buried in credit card debt and payday loans, while she was literally studying money for a living.At 29, she and a partner bought the company she worked for, and grew it to over $12 million a year in sales.So I asked her what to do when you feel behind and you want to achieve so much.We get into the community college shame that fueled her, how she dug out of debt in two and a half years, the $1.25 million number her boss wrote on a napkin, how she actually paid for it, why she sold her share of "the monster" she built, how to pick a mentor, the $50,000 mistake new entrepreneurs make, and the exit she never celebrated. If you feel behind, this one is for you.⏱️ Chapters:0:00 — Coming up0:15 — What do you do when you feel behind?2:05 — "I failed at adulting in a big way"2:47 — Growing up with no money6:27 — The community college shame9:04 — Visa and Mastercard, my angel investors12:35 — What being broke at 23 taught her16:47 — Her first house at 2617:53 — $1.25 million on a napkin18:56 — How she financed buying the company19:39 — Figure out what you want by taking action26:22 — "I built the monster"30:01 — Get paid to learn32:02 — Learning from Ed Mylett39:58 — Do you need to meet your mentor?42:02 — The $50,000 mastermind mistake45:51 — The Third Door47:40 — Advice to her 19-year-old self48:35 — The exit she never celebrated50:04 — Where to find MichelleSubscribe for more deep conversations with thinkers, seekers, and soulful creators. 🙏Connect with Michelle:Website: https://michellejacobik.comThe Path to Profits (book): https://michellejacobik.com/resources/Instagram: https://www.instagram.com/michellejacobikLinkedIn: https://www.linkedin.com/in/michelle-jacobik-267724Facebook: https://www.facebook.com/michellejacobik📺 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 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.

The Ambitious Generation with Jack Wagoner Episode 159I researched Evan Carmichael for two days before this conversation. What I didn't plan for was walking in with the age parallel, him at 19, me at 19 now, and having him turn the interview around on me. This one isn't really about him. It's about the question I've been avoiding answering myself.We get into:0:00 — Cold open
2:16 — The pinnacle of his life happened at the exact age I am right now
4:11 — "Universities train you to get a job, basically"
11:47 — "I never get asked what university I went to. People care, zero."
13:36 — He challenges me to challenge him back, live
16:37 — "So what am I actually building this for?"
23:22 — How he met his wife, and the 90-day, 23-city tour that nearly broke them both
24:27 — He broke his neck mid-tour and finished the tour anyway
38:04 — The year everything actually changed for him: marriage, and getting a coach
45:10 — What ownership really means, and why belief comes first
48:36 — His Big Y, Little Y framework for surviving ambition without losing gratitude
53:35 — The insecurity he still carries about not hitting 1,000 followers
56:37 — "Ask the questions you most need to hear," and why that changed how I interviewIf you've ever wondered whether the safe path is quietly costing you the real one, this one's for you.🔗 Evan's LinksWebsite: https://believe.evancarmichael.com/homepageYouTube:https://www.youtube.com/channel/UCKmkpoEqg1sOMGEiIysP8TwInstagram: https://www.instagram.com/evancarmichael/?hl=enLinkedIn: https://www.linkedin.com/in/evancarmichael/?isSelfProfile=false📺 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.

The Grateful Podcast with Jack Wagoner Episode 158

Guesting Suneet Bhatt, Author of Making Sense of Purpose

Suneet Bhatt has spent twenty five years helping people answer one question: why am I here. He teaches purpose at Rutgers, he wrote the USA Today Bestselling book Making Sense of Purpose, and he has had the conversation thousands of times.

So I asked him something nobody has asked him before. Not what a person with purpose does. What they never do.He stopped. He said he had never been asked that. Then he gave an answer that reframed the entire conversation: people with purpose do not carry guilt.

This one is about what you are holding that is keeping you stuck.

0:00 — The three things every definition of purpose agrees on0:56 — "Who is a person with purpose?"2:22 — The question he has never been asked3:13 — Why people with purpose refuse to carry guilt3:35 — Community, religion, and the third arrow4:44 — Rock bottom, and the two immigrant parents who said no5:36 — Four years, two years, one year6:26 — "It was never about the job. It was the work."6:35 — He had everything and opened with "I don't know why I'm here"8:33 — Shopping for purpose while you're starving9:59 — Satiated is not sustained11:48 — The 700% problem12:41 — Why ikigai starts on step two14:37 — Happiness is a precursor, not a result16:36 — Be grateful on purpose18:11 — Where to find Suneet

🔗 Suneet's Links:

Book: makingsenseofpurpose.com

Website: myauthenticstory.com

LinkedIn: linkedin.com/in/suneetbhatt/📺 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 Grateful Podcast with Jack Wagoner Episode 157 with Michael McLeodMichael McLeod thinks nobody should own a phone before 18. Not 16, not 14. Eighteen, the same way we handle alcohol and driving.He has worked with kids and teens since 2005 and watched valedictorians, athletes, and artists lose interest in everything inside a year of getting one. He also thinks history will look back on the last fifteen years of school and call it the great mistake.Later in the conversation he explains why employers are already skipping people in their early twenties, and what it has to do with a skill nobody ever taught you.I was in the first class handed a Chromebook in elementary school. So this one was personal.Michael's links:Website: https://www.grownowadhd.com/about/Instagram: https://www.instagram.com/grownowadhd/?hl=enYouTube: https://www.youtube.com/@grownowadhd📺 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.1898/5000

The Grateful Podcast with Jack Wagoner Episode 156Nicholas Epley studies why people struggle to connect for a living. He says the reason isn't what you're saying, it's what you're assuming before you even open your mouth.We go deep on why pessimism about how people will respond to you becomes self-fulfilling, the commuter train study that disproves what busy people assume about "wasted" time, and why connection outweighs income for daily happiness by seven times over.If connection has felt harder than it should lately, this one's for you.⏰ TIMESTAMPS00:00 — Are You Coming Across as Creepy?01:19 — Why We're Wired to Avoid What Helps Us02:59 — Socially Pessimistic (And Why That's Dangerous)05:55 — Connection Is a Series of Choices, Not a Feeling18:11 — Why "Being Articulate" Matters Less Than You Think20:11 — How to Not Come Across as Creepy22:49 — The "New York Moment" (Single-Serve Friendships)39:06 — Frequency Beats Duration in Every Relationship40:02 — Even Epley Gets This Wrong at Home43:18 — The Commute Study That Breaks the Productivity Myth45:49 — The 7x Gap Between Money and Connection🔗 NICK'S LINKSWebsite: https://www.nicholasepley.com/Book: A Little More Social — nicholasepley.com/booksLinkedIn: linkedin.com/in/nicholas-epley📺 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.