The Grateful Podcast with Jack Wagoner

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...

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 scaries...

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...

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 v...

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 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 befo...

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 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...

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 las...

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 &q...

The Grateful Podcast with Jack Wagoner Episode 155He runs a company with 250 people. Every Monday morning he plans his workouts and his family time before he plans a single hour of work. Ken Rusk started digging ditches at 15 through a hole in his high school fence, opened franchises across the Midwest before he was 23, and built his own company from six employees to 250. He has never worn the 80...

The Grateful Podcast with Jack Wagoner Episode 154  Two years ago I sent 200 cold emails and got zero replies. This week I turned down offers from two of the biggest podcast networks in the world. The distance between those two things is 150 conversations with founders, psychologists, behavioral researchers, and authors. I went in looking for tactics. I came out with six rules, and they are the on...

The Grateful Podcast with Jack Wagoner Episode 153 Guesting Alex Wieckowski, known online as Alex & Books  @AlexandBooks  Subscribe for more deep conversations with thinkers, seekers, and soulful creators. Alex Wieckowski has read over 750 books and built an audience of more than a millionpeople teaching other people how to read. So I asked him the question everyone isquietly asking right now:...

The Grateful Podcast with Jack Wagoner Episode 152 Richard Moore spent 23 years in sales before anyone knew his name. Ten years in the City of London, standing up, cold calling 100 businesses a day, not allowed to sit down. In this conversation he breaks down the thing nobody explains to you: how you manufacture leverage when you have zero proof, zero network, and zero reason for anyone to say yes...

Episode 151 of The Grateful Podcast with Jack WagonerEvan Carmichael has 4.3 million subscribers, more than 8,000 videos, and a list of interviews that reads like a who's who of the last two decades. Ask him who he still wants to talk to and the answer is nobody. He says he wouldn't know what to ask. Twenty seconds later in this conversation he pulls out a camera, unprompted, and records a pitch o...

Episode 150 of The Grateful Podcast with Jack WagonerScott Clary hosts a Top 10 business podcast with over 100 million downloads. He's interviewed 700 founders. And he wrote publicly that advice is just other people's trauma dressed up as wisdom. So I asked him how he squares that with running an advice show every single week. His answer changed how I think about content, consumption, and the enti...

The Grateful Podcast with Jack Wagoner Episode 149 with John LeeJohn Lee built a property portfolio in London, wrote a bestselling book, and has amassed 6 million followers teaching people how money actually works. He says he was self-made by 27. What he does not usually lead with is how it happened: he sold his car for $15,000, kept $5,000, and handed the other $10,000 to a stranger for two days...

The Grateful Podcast with Jack Wagoner Episode 148 with Bob BurgBob Burg co-wrote The Go-Giver, a parable that's sold over a million copiesand reshaped how a generation thinks about success. But before he wrote it,he spent decades noticing something most people miss: the most sustainablysuccessful people he's ever met all had one trait in common, and it isn'tthe one Hollywood taught yo...

Amberly Lago was T-boned by an SUV on Ventura Boulevard. Thrown thirty feet. Femoral artery severed. Induced coma. She woke up to doctors telling her they had to amputate. She had a 1% chance to save the leg. She took it. 34 surgeries later, they saved it. Today she's a USA Today bestselling author, TED speaker, Today Show and Doctors guest, and host of True Grit and Grace. She wrote 90% of he...

Nat Eliason left a decade of independent building to take his first job in over ten years. He is now running Founder School, a new private high school in New York City that promises every graduate a million dollar business, or the family gets their $600,000 tuition refunded in full. The refund pool is backed by a billionaire's personal capital, not insurance. If the model fails, he writes the...

You don't get to choose what you believe. That's the standard line on confidence, stated as law by the biggest podcast in this space. Markus Kaulius disagrees, and he's got a $170M company to back it up. I sat down with him right after his daughter closed out a room of authors at Book Thinkers 2026. Markus built Magnum Nutraceuticals from nothing and wrote the USA Today bestseller Play a Bigger Ga...

Send us Fan Mail The CEO of the largest positivity community on the internet says you're doing gratitude wrong. I sat down with Kristen Butler at BookThinkers Live. Over 50 million people follow her work, and she'll tell you the gratitude journal on your nightstand is not doing what you think it's doing. Not a list. A somatic practice that regulates your nervous system in three minu...

Send us Fan Mail Most people ask before they get a yes. The best ask after. This weekend I recorded 23 podcast interviews in two days at Book Thinkers Live 2026, including Evan Carmichael, Kristen Butler, Marcus Kaulius, and Amberly Lago. I landed the live podcast at 19 because I broke a rule most people never think to break: I asked for more after the person had already said yes. Nick, the CEO of...

Send us Fan Mail Chester Elton has spent 40 years teaching gratitude to executives. He's sold 1.6 million books. He's coached leaders at American Express, AT&T, the World Bank. But when his designer friend Ayse Birsel asked him "how have you designed time with your family?", his answer was three words: I don't do that. The world's leading gratitude expert wasn&apo...

Send us Fan Mail Savio Joseph, Canada's Got Talent finalist, has built his entire career around one idea. The best hypnotist you know is already in your head. The words you say to yourself, the limits you accept before you ever try, the patterns you run without noticing. In this conversation, he walks me through how he sees that loop in other people, the auditions the world never saw before C...