From selling cars to two decades in SaaS, Nikki Ivey turned a writer’s love of words into a sales career—and a conviction that the people most skilled at moving others should be creating culture, not just complaining about it. A writer first, a LinkedIn Top Voice, and co-founder of SDRDefenders, Nikki joins Jolie to get honest about the parts of sales that don’t make the highlight reel: the wigs she spent years suppressing as the only Black woman in the room, the narratives that walk in before she does, and the extra work it takes to reach the same baseline of confidence a typical seller starts from. Along the way she reframes the meritocracy debate, separates structural exclusion from the interpersonal kind, and offers a way through the DEI backlash that asks nothing of your politics—only that you care how your behavior lands on someone else. Her throughline: you can criticize culture or you can create it, and sellers are built to create.

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Somewhere past 500 podcast episodes, hosting and guesting combined, and nobody had ever asked Richard Harris what talking about his mental health has cost him. Founder of The Harris Consulting Group, creator of N.E.A.T. Selling and author of The Seller’s Journey, Richard joins Jolie to trace it back to one morning in San Francisco when he woke up in the fetal position and physically could not move. What follows: the phone call to his mom, the sentence that kept him from getting on the plane, 20+ years with the same therapist, and imposter syndrome that shows up live on the recording. His throughline: you do you, and don’t be afraid to make the phone call.

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From 15+ years in professional kitchens to two decades in sales, James Buckley has built Say What Sales—a personal brand rooted in one line: if you're a salesperson, we're the same person. Founder of Say What Sales and host of the daily sales show Sell Better, James joins Jolie to get honest about the parts that don't make the highlight reel: an addiction that shifted from hard drugs to food, a 2006 ER visit that had his family relocated from Miami to Tennessee within 48 hours, and the 3 a.m. gym routine that's kept him steady through a recent type 2 diabetes diagnosis. His throughline: resilience isn't a personality trait, it's a choice you make over and over.

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From one-and-done author to accidental evangelist for a better way to work, Freddie Laker has spent a decade building Chameleon Collective, a four-time Inc. 5000 “collective” where everyone gets to be the boss and share the risk instead of one person throwing themselves in the fire. Founder of Chameleon Collective and co-author of the bestselling Collective Capitalism, Freddie joins Jolie to get honest about the parts that don’t make the highlight reel: why he preaches “no one should carry it alone” and still grabs the stressful hot potato himself, what actually scares him about AI, and the on-mic existential crisis when he realized he might be the last person who should talk about work-life balance. His throughline: there’s opportunity in chaos, but only if you stop trying to carry it alone.

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From the number one enterprise rep at Salesforce to a self-described "functioning addict" living a double life at the top of his game, Ian Koniak traces how a 20-year work-hard-play-hard grind nearly cost him his marriage and his family, and what it finally took to get sober. Founder and CEO of Untap Your Sales Potential, Ian joins Jolie to riff on the president's-club culture he lived and loved, why "the pain of staying the same has to be greater than the effort to change," the rock bottom that turned him around, and how honesty, faith, and recovery rebuilt a life he's actually proud of. His message for anyone white-knuckling a secret: pick your poison, there's a 12-step for it, and the opposite of addiction is connection.

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From accidentally landing in addiction counseling with “no life jacket” to building a whole career on one radical idea, that people recover better when treatment isn’t a miserable experience, Master Addiction Counselor Amber Hollingsworth traces how growing up surrounded by addiction shaped her relationship-first approach. Founder of Hope for Families Recovery Center and creator of the YouTube channel Put the Shovel Down, Amber joins Jolie to riff on why calling herself the client’s “defense attorney” instead of their probation officer earns more trust than tough love, why there’s no bad reason to get sober, and why the driven, high-performing execs who can’t turn their brain off so often drink to do it. Her throughline: stop waiting for rock bottom. You can just put the shovel down.

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A 600kg horse landed on Hacia Atherton while she was training for international dressage. What followed: six months in the hospital, 30-plus procedures, and 117 days of work just to stand for ten seconds. She studied for her CPA exams from a hospital bed, went on to earn a master’s in positive psychology, founded an organization fighting for women in the trades, and wrote a book about the billions hiding in plain sight in workplace culture. She and Jolie get into the emotional cage the Industrial Revolution built, why telling men they’re allowed to feel means nothing without the tools to do it, and why belonging, not titles or diversity programs, is what actually moves the needle.

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From layoffs and COVID teaching her what’s actually controllable, to a husband’s truth bomb that finally broke a years-long pattern of “riding it out,” Heather Bell traces the line from people-pleasing grit to self-responsibility at work and at home. She and Jolie riff on why mental health is a revenue metric, not a side quest; what it actually took to land a job with her own list of non-negotiables. And why “they just hire good people” is the only diversity strategy that’s ever worked for her.

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From breaking down the “polished corporate box” to rebuilding identity through faith, community, and self-responsibility, Anthony Morell shares what helped him move from people-pleasing to authenticity: online and off. He and Jolie riff on why healing work is heavy (but worth it), how to catch burnout before it catches you, and what Anthony’s “hard season” operating manual looks like: get fed, get out of the house, move your body, and don’t isolate.

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Rob LoCascio (founder/former CEO of LivePerson) joins Jolie to riff on purpose, grit, and what it really takes to build for the long haul, mentally, emotionally, and spiritually. From sleeping on an Ikea couch during LivePerson’s earliest days (and still keeping the couch as a reminder) to building two new AI startups, Rob shares why “certainty + control” can quietly destroy founders, and how reconnecting with God helps him cut through the noise, lead with humility, and build technology that brings families closer (instead of pulling them apart).

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