Kirk Myers: DOGPOUND, Rock Bottom, and Rebuilding From Nothing.

Jared Freid: Dating Is Broken. You're Probably Part of the Problem

Jared Freid has built a career telling people the truth they don't want to hear. Through his hit podcasts, sold-out comedy tours, Netflix special, and millions of listeners, he's become the internet's favorite brutally honest dating translator — the guy who can explain exactly why someone left you on read without making you feel worse about it. Now he's putting it all into a book. Jared joins OFFICE OF to talk about Walking Red Flag, his new book that takes on modern dating with the same sharp observations, self-awareness, and humor that have made him one of the most trusted voices in the space. Part comedy, part survival guide, and part reality check, the book tackles everything from dating apps and situationships to commitment, rejection, loneliness, and the stories we tell ourselves while staring at a text message. We talk about how Jared accidentally became "the dating guy," why dating feels harder than ever, the biggest mistakes people make when looking for love, and what he's learned from years of hearing people's relationship disasters. We also get into getting older, confidence, being perpetually single, why some people seem addicted to chaos, and the difference between wanting a relationship and actually being ready for one. Funny, self-aware, and refreshingly honest, this conversation feels less like an interview and more like sitting across from the friend who tells you exactly what you need to hear. IN THIS EPISODE, WE DISCUSS: • The inspiration behind Walking Red Flag • Why modern dating feels more confusing than ever • Dating apps, situationships, and mixed signals • How Jared accidentally became "the dating guy" • Rejection, confidence, and self-worth • The biggest mistakes people make when dating • Why some people are addicted to chaos in relationships • Getting older and being single • What men are actually thinking (according to Jared) • The difference between wanting a relationship and being ready for one • Why honesty is the most underrated dating skill FOLLOW JARED FREID: Instagram [https://www.instagram.com/jaredfreid] TikTok [https://www.tiktok.com/@wizardofha] LISTEN TO: U Up? Podcast [https://www.youtube.com/@uuppodcast] The JTrain Podcast [https://youtube.com/playlist?list=PLDupFMMvZlAIH0isuNr-fn51YfvJoqV-t&si=PVtneheeD7IP525B] GET THE BOOK: Walking Red Flag [https://www.simonandschuster.com/books/Walking-Red-Flag/Jared-Freid/9781668061800] Questions, comments…sharp takes?  Shoot us a note at WhatsUp@officeof.world [WhatsUp@officeof.world] Find out more about the Office Of Podcast [https://www.officeof.world] One more thing!  Not all offices are created equal.  See who else is part of our world and all of the unstructured, messy behind-the-scenes that comes with it on our Instagram [https://www.instagram.com/yalebreslin] , TikTok [https://www.tiktok.com/@officeofworld] & YouTube [https://www.youtube.com/@OfficeOfWorld]. And!  If you particularly enjoyed this episode – or any others – please subscribe and leave a rating and review on  Apple [https://podcasts.apple.com/us/podcast/office-of-podcast/id1812065579] or Spotify  [https://open.spotify.com/episode/2mKJulwRaUq9DdrqIyHIAn?si=c1BxiNseTEq4kDCJcwg6eg]or where ever you get your podcasts. Recorded at The Newsstand Studios [https://www.rockefellercenter.com/newsstand-studios/] at Rockefeller Center [https://www.instagram.com/rockefellercenter/]. Thank you for listening.

Ryan Serhant: How to Become Impossible to Ignore

Ryan Serhant didn't start as a real estate mogul — he started as a struggling actor in New York City with no money, no connections, and no clear plan. Long before Million Dollar Listing, SERHANT., bestselling books, and one of the largest personal brands in business, Ryan was simply trying to survive. What began as a necessity quickly became an obsession. In this episode, Ryan reflects on the early years of his career — running out of money, getting rejected, learning how to sell, and discovering that confidence isn't something you're born with. It's something you build. The conversation explores the mindset that helped Ryan go from broke actor to one of the most recognizable entrepreneurs in America. Ryan opens up about why he views everything as a game, why he's become a professional optimist, and why nobody gets anywhere by going backwards. Ryan also speaks candidly about money, ambition, fear, and success. He shares why he doesn't connect money to self-worth, the pressure that comes with leading a growing company, and the habits that allow him to perform at a high level year after year. From waking up at 4:30 AM to navigating uncertainty, Ryan explains why the only way out is through. Throughout the episode, Ryan returns to one core idea: the opportunities that change your life usually exist on the other side of the thing you're most afraid to do. Join us for an energetic, insightful, and wildly entertaining conversation in Ryan's Office. Don't miss this interview where we discuss: • Growing up and the path that led him to New York City • Running out of money and starting over • Becoming a real estate broker by necessity • Million Dollar Listing and life in the public eye • Building SERHANT. from survival mode to industry leader • Why confidence is difficult to teach • Curiosity as a competitive advantage • Optimism, mindset, and resilience • Sales, communication, and human psychology • Fear, discomfort, and personal growth • Why Ryan treats everything as a game • Money, self-worth, and success • Entrepreneurship, leadership, and scaling a business • Happiness, ambition, and the pursuit of more • Why there has never been a better time to be alive Find Ryan: IG: @ryanserhant [https://www.instagram.com/ryanserhant/] IG: @serhant [https://www.instagram.com/serhant] Questions, comments…sharp takes?  Shoot us a note at WhatsUp@officeof.world [WhatsUp@officeof.world] Find out more about the Office Of Podcast [https://www.officeof.world] One more thing!  Not all offices are created equal.  See who else is part of our world and all of the unstructured, messy behind-the-scenes that comes with it on our Instagram [https://www.instagram.com/yalebreslin] , TikTok [https://www.tiktok.com/@officeofworld] & YouTube [https://www.youtube.com/@OfficeOfWorld]. And!  If you particularly enjoyed this episode – or any others – please subscribe and leave a rating and review on  Apple [https://podcasts.apple.com/us/podcast/office-of-podcast/id1812065579] or Spotify  [https://open.spotify.com/episode/2mKJulwRaUq9DdrqIyHIAn?si=c1BxiNseTEq4kDCJcwg6eg]or where ever you get your podcasts. Recorded at The Newsstand Studios [https://www.rockefellercenter.com/newsstand-studios/] at Rockefeller Center [https://www.instagram.com/rockefellercenter/]. Thank you for listening.

Bruce Bozzi: 30 Years of Friendship with Andy Cohen, Losing The Palm, Vulnerability, and Why 60 Is Hot

Bruce Bozzi has lived many lives — actor, restaurateur, podcast host, husband, father, and one of New York’s great conversationalists. But beneath the charm, humor, and larger-than-life stories is someone who’s spent much of his life trying to understand identity, friendship, vulnerability, and what happens when the thing you thought would last forever suddenly disappears. Born into The Palm restaurant dynasty, Bruce grew up inside one of New York’s most iconic hospitality institutions — surrounded by celebrities, regulars, white tablecloths, and a culture built entirely around human connection. In this episode, Bruce reflects on the emotional impact of losing the family business, the trauma that followed, and the identity crisis that came with separating himself from something that had defined his life for decades. The conversation moves through masculinity, aging, control, reinvention, and male friendship — particularly Bruce’s thirty-year friendship with Andy Cohen, whom he calls “a great love” in his life. Bruce opens up about never fully feeling safe in friendships, learning how to let his walls down, and why vulnerability is still so difficult for so many men. Bruce also discusses marriage, fatherhood, and building a life with Bryan Lourd, while navigating grief, pressure, and the constant question of: “What now?” He reflects on working as an NBC page, trying to become an actor before realizing he was “the worst actor,” getting nervous around Anna Wintour, and learning how to embrace uncertainty instead of trying to control every outcome. Throughout the episode, Bruce returns to one core idea: real confidence has nothing to do with ego — it comes from kindness, presence, and being willing to show people who you actually are. Join us for a funny, emotional, and deeply human conversation in Bruce’s Office. Don’t miss this interview where we discuss: • Growing up inside The Palm restaurant empire • Losing the family business and the grief that followed • Identity, reinvention, and starting over later in life • Bruce’s 30-year friendship with Andy Cohen • Why male friendship and vulnerability matter • Letting go of control and embracing uncertainty • Marriage, fatherhood, and family with Bryan Lourd • The emotional walls men build to protect themselves • Why every kid should work in hospitality • Aging, confidence, and why “60 is hot” • Working as an NBC page in New York City • Trying — and failing — to become an actor • Podcasting, storytelling, and meaningful connection • Jennifer Aniston, celebrity culture, and humanizing fame • Why movement and routine are essential for mental health • Learning how to be vulnerable after years of self-protection • Why kindness is the ultimate form of confidence Find Bruce: IG: @brucebozzi [https://www.instagram.com/brucebozzi] Questions, comments…sharp takes?  Shoot us a note at WhatsUp@officeof.world [WhatsUp@officeof.world] Find out more about the Office Of Podcast [https://www.officeof.world] One more thing!  Not all offices are created equal.  See who else is part of our world and all of the unstructured, messy behind-the-scenes that comes with it on our Instagram [https://www.instagram.com/yalebreslin] , TikTok [https://www.tiktok.com/@officeofworld] & YouTube [https://www.youtube.com/@OfficeOfWorld]. And!  If you particularly enjoyed this episode – or any others – please subscribe and leave a rating and review on  Apple [https://podcasts.apple.com/us/podcast/office-of-podcast/id1812065579] or Spotify  [https://open.spotify.com/episode/2mKJulwRaUq9DdrqIyHIAn?si=c1BxiNseTEq4kDCJcwg6eg]or where ever you get your podcasts. Recorded at The Newsstand Studios [https://www.rockefellercenter.com/newsstand-studios/] at Rockefeller Center [https://www.instagram.com/rockefellercenter/]. Thank you for listening.

Joey Gonzalez: Masculinity, Burnout, Obsession, and Building the Cult of Barry's

Joey Gonzalez didn’t start at Barry’s as an executive — he started as a client. Long before becoming Executive Chairman and helping scale one of the most recognizable fitness brands in the world, Joey was simply someone searching for transformation, connection, and purpose inside the Red Room. What began as an obsession quickly became a life-changing experience. In this episode, Joey reflects on the early days of Barry’s — the immersive energy, the fist bumps, the music, the collective atmosphere — and why the workout became far bigger than fitness. From Barry’s humble beginnings in 1998 to becoming a global phenomenon, Joey shares how the brand tapped into something deeply emotional for people: identity, confidence, belonging, and human connection. The conversation explores the psychology behind the Barry’s experience and why people become so emotionally attached to it. Joey opens up about the “enter-trainers” who lead the classes, the addictive energy of the Red Room, and why Barry’s was always designed to make people feel something — not just sweat. Joey also speaks candidly about masculinity, burnout, pressure, and emotional exhaustion. He reflects on the version of masculinity he grew up around, the expectations placed on men, and the challenge of balancing ambition with emotional wellbeing while operating at a high level. Throughout the episode, Joey returns to one core idea: most people are far more capable than they think they are. Join us for an emotional, insightful, and surprisingly vulnerable conversation in Joey’s Office. Don’t miss this interview where we discuss: • Joey’s journey from Barry’s client to Executive Chairman • The origins and evolution of Barry’s since launching in 1998 • Why the Red Room became a cultural phenomenon • Fitness as entertainment, immersion, and emotional release • The psychology behind community and collective energy • “Enter-trainers” and the power of human connection • Barry Jay, sobriety, and the DNA of the brand • Fear, intimidation, and why people underestimate themselves • Masculinity, vulnerability, and emotional pressure on men • Burnout, obsession, ambition, and identity • Building a global fitness empire without traditional marketing • Why transformation starts long before physical results Find Joey: IG: @joeygonzalez [https://www.instagram.com/joeygonzalez/] IG: @barrys [https://www.instagram.com/barrys] Questions, comments…sharp takes?  Shoot us a note at WhatsUp@officeof.world [WhatsUp@officeof.world] Find out more about the Office Of Podcast [https://www.officeof.world] One more thing!  Not all offices are created equal.  See who else is part of our world and all of the unstructured, messy behind-the-scenes that comes with it on our Instagram [https://www.instagram.com/yalebreslin] , TikTok [https://www.tiktok.com/@officeofworld] & YouTube [https://www.youtube.com/@OfficeOfWorld]. And!  If you particularly enjoyed this episode – or any others – please subscribe and leave a rating and review on  Apple [https://podcasts.apple.com/us/podcast/office-of-podcast/id1812065579] or Spotify  [https://open.spotify.com/episode/2mKJulwRaUq9DdrqIyHIAn?si=c1BxiNseTEq4kDCJcwg6eg]or where ever you get your podcasts. Recorded at The Newsstand Studios [https://www.rockefellercenter.com/newsstand-studios/] at Rockefeller Center [https://www.instagram.com/rockefellercenter/]. Thank you for listening.

Brendan Fallis: Virality, Identity, Fatherhood, and Building a Life Online

Brendan Fallis has worn a lot of hats over the years — professional skier, DJ, creator, entrepreneur, husband, father, and internet personality. But beneath the polished content and public-facing life is someone who’s spent years trying to figure out what it actually means to stay true to yourself while the world watches. Before building a life in New York, Brendan drove to the border from Canada with a letter and fifty bucks, chasing something bigger for himself. What followed became an unconventional career built through reinvention, risk-taking, and an early belief in the power of the internet before most people took creators seriously. In this episode, Brendan opens up about the emotional side of living publicly online — from the dopamine hit of virality to the pressure of relevance and the vulnerability that comes with sharing your life on the internet. He reflects on feeling embarrassed by content creation in its early days, how perceptions around creators have shifted, and why authenticity ultimately became his greatest advantage. The conversation also explores masculinity, community, identity, parenting, and the need for more honest conversations between men. Brendan talks candidly about building a life and family with Hannah Bronfman, the importance of showing up for the people you love, and why “Google is the new dad” for a generation looking for guidance, answers, and connection online. Join us for a funny, self-aware, and unexpectedly thoughtful conversation in Brendan’s Office. Don’t miss this interview where we discuss: • Brendan’s early years as a professional skier in Canada • Moving to New York with almost nothing and building a life from scratch • The evolution of content creation and creator culture • Virality, internet validation, and the psychology of social media • Why authenticity matters more than perfection online • Masculinity, vulnerability, and emotional openness among men • Reddit, community, and the internet as modern-day connection • Fatherhood, marriage, and building a life with Hannah Bronfman • The pressure of public identity versus private self • Why one post can completely change your life Find Brendan: IG [https://www.instagram.com/brendanfallis/] X [https://x.com/brendanfallis] Questions, comments…sharp takes?  Shoot us a note at WhatsUp@officeof.world [WhatsUp@officeof.world] Find out more about the Office Of Podcast [https://www.officeof.world] One more thing!  Not all offices are created equal.  See who else is part of our world and all of the unstructured, messy behind-the-scenes that comes with it on our Instagram [https://www.instagram.com/yalebreslin] , TikTok [https://www.tiktok.com/@officeofworld] & YouTube [https://www.youtube.com/@OfficeOfWorld]. And!  If you particularly enjoyed this episode – or any others – please subscribe and leave a rating and review on  Apple [https://podcasts.apple.com/us/podcast/office-of-podcast/id1812065579] or Spotify  [https://open.spotify.com/episode/2mKJulwRaUq9DdrqIyHIAn?si=c1BxiNseTEq4kDCJcwg6eg]or where ever you get your podcasts. Recorded at The Newsstand Studios [https://www.rockefellercenter.com/newsstand-studios/] at Rockefeller Center [https://www.instagram.com/rockefellercenter/]. Thank you for listening.