Holly Madison On Life At The Playboy Mansion, Early 2000’s Fame, & Finding Herself Again
The Skinny Confidential Him & Her Show
Release Date: 06/12/2025
The Skinny Confidential Him & Her Show
#879: Join Michael Bosstick as he sits down to discuss navigating life throughout different stages of life. In this solo episode, Michael shares practical advice for regaining clarity when life feels overwhelming. He offers practical tools for navigating challenges in career, dating, relationships, health, & parenting, while providing perspective shifts that bring clarity & balance. Drawing from his own experiences, Michael breaks down simple, actionable steps to help you reset and realign when you’re feeling stuck. He also highlights key resources & habits that can support you...
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#878: Join Michael Bosstick as he sits down to share essential personal finance tips & strategies to help you take control of your money today! In this episode, Michael breaks down the key stages of building financial health, sharing advice & practical tips he has learned over the years. From getting out of high-interest debt & using budgeting tools to create clarity, to building an emergency fund & investing for long-term wealth, he covers it all. If you’re looking for practical money advice, smart investing strategies, & ways to avoid common financial traps, this...
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#877: #871: In this raw and unfiltered solo episode, Michael Bosstick breaks down what it actually takes to build, scale, and sustain a business in today’s world. Drawing from 20+ years of firsthand experience as the Founder & CEO of Dear Media, an investor in high-growth startups, and a serial entrepreneur, Michael shares hard-earned lessons from both wins and failures. He dives deep into the biggest mistakes new founders make, how to choose the right business partners, the importance of financial discipline, and how to protect your energy while building something that lasts. Whether...
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#876: Join Michael Bosstick for an exclusive conversation with Mimi Evarts – The Skinny Confidential's powerhouse Director of Branding, the driving force behind every chapter, & most importantly, Michael’s Sister-in-Law. Having been a key mentor throughout Mimi’s stages of life, Michael sits down with her for a candid, real talk about navigating your 20s & lessons learned. In this episode, Michael & Mimi share hard-earned life lessons on investing early, cultivating meaningful relationships, discuss transformative books that shifted their perspective, & reveal the...
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#875: Join us as we sit down with Vani Hari – food activist behind Food Babe, 4x NY Times best-selling author, & founder of the organic food brand Truvani. Vani’s viral testimony before the US Senate ignited a nationwide movement, calling out major food corporations for using harmful ingredients in America that are banned in other countries. In this episode, Vani breaks down how to make smarter choices at the grocery store, exposes what’s really hiding in your food, highlights urgent policy changes that need to happen, & shares how to live a clean, organic lifestyle – even...
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#874: Join us as we sit down with Phoebe Gates & Sophia Kianni – entrepreneurs, advocates, Stanford grads, & hosts of The Burnouts podcast. As co-founders of Phia, a cutting-edge digital fashion platform, Phoebe & Sophia are reshaping how Gen Z shops & builds brand identity in the digital age. From sealing high-stakes deals to navigating late-night TikTok binges, the duo gets candid about the unfiltered reality of startup life. In this episode, The Burnouts open up about business wins & growing pains, what it really takes to pitch top investors, how to embrace...
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#873: Join us as we sit down with Sage Robbins – motivational speaker, wellness advocate, former actress, & the wife of life coach, Tony Robbins. With a blend of grace & strength, Sage has been a transformative force both on stage & behind the scenes at some of the world’s most impactful live seminars. Known for her deep work around emotional well-being, mindfulness, & holistic healing, Sage guides others through personal breakthroughs & relationship blocks in real time. In this episode, Sage opens up about creating emotional safety, self-regulation tools to stay...
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#872: Join Michael Bosstick as he sits down to share six core values designed to help lead you with intention, parent with purpose, & create a more meaningful life. These values – kindness, integrity, personal accountability, discipline, resourcefulness, & independence – serve as a foundation for a grounded & resilient mindset. In this episode, Michael offers practical insights & real-world examples to show how these principles can be applied across every area of life! Whether you're raising kids, building a business, or simply refining your own mindset, this episode...
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#871: Join us as we sit down with Damon West – bestselling author, college professor, & one of America’s most sought-after motivational speakers, whose powerful story of transformation & resilience inspires audiences around the world. As a former college quarterback turned crime boss, Damon now uses his M.S. in Criminal Justice & his personal experience to motivate millions on leadership & the incredible power of positively changing the environment around you. In this episode, Damon gets real about how a life sentence in the Texas prison system became the catalyst for...
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#870: Join us as we sit down with Henry Penix & Laura Widney – the founders of SOAAK. The interconnection of the mind, body, & spirit isn’t just a concept – it’s a powerful key to understanding how our emotional, mental, & physical states continuously shape one another. Known for their innovative work in sound frequency therapy & holistic wellness, SOAAK is redefining how we think about healing. Sound frequencies can influence the nervous system, shift brainwave states, & directly impact how we feel, focus, & function. In this episode, Henry & Laura break...
info_outline#854: Join us as we sit down with Holly Madison – an American television personality, model, author, & entrepreneur best known for her role on the reality hit series The Girls Next Door, which chronicled life inside of the Playboy Mansion. In this episode, Holly opens up about her experience living in the Mansion, the pivotal moments in her upbringing that shaped her path, & the untold stories behind the gates of Playboy! She dives into iconic pop culture moments from the early 2000s, her evolution into a true crime host on The Playboy Murders with Investigation Discovery, & the success of her podcast Girls Next Level – where she & co-host Bridget Marquardt revisit the legendary series & share what really happened off camera.
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This episode is sponsored by BUMPSUIT
To Shop the Lauryn Bosstick x Bumpsuit Collection visit https://bit.ly/BUMPSUITXLB and use code SKINNY for 15% off for a limited time.
This episode is sponsored by Active Skin Repair
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This episode is sponsored by Nutrafol
For a limited time, Nutrafol is offering our listeners $10 off your first month’s subscription and free shipping when you go to http://Nutrafol.com and enter the promo code SKINNYHAIR.
This episode is sponsored by Simply Pop
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This episode is sponsored by Opill
Opill is birth control in your control, and you can use code SKINNY for 25% off your first month of Opill at http://Opill.com.
This episode is sponsored by Spritz Society
Spritz Society is now available everywhere! Head to http://spritzsociety.com to find a store near you, and make sure to follow @spritz on Instagram for all their latest announcements and upcoming events. Spritz Society, Summer Starts Here!
This episode is sponsored by Boulevard
Boulevard is offering new customers 10% off your first year subscription when you go to join http://BLVD.com/SKINNY and book a demo.
Produced by Dear Media