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Mr Jay Hill is a multi media journalist & influencer from Baltimore, MD. He interviews compelling & interesting people from all around the entertainment industry. Subscribe to enjoy all his content twice a week!! Support this podcast: https://anchor.fm/mrjayhill/support
237 Episodes
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Most people think they’re broke because they don’t make enough money.The truth? Many are losing money before it ever reaches their bank account.In this episode, Jay Hill sits down with Michel “Money Makin’ Mitch”, a Certified Public Accountant (CPA) and tax strategist, to break down why so many people — especially entrepreneurs and creators — are unknowingly overpaying the IRS.This isn’t about shortcuts or “tax hacks.”It’s about understanding how the tax system actually works — and why it was designed to reward people who learn the rules.We cover:• Why taxes are the biggest expense most people ignore• How the “ignorance tax” quietly drains your income• The difference between being broke vs. being uninformed• How entrepreneurs legally reduce what they owe• When you should (and shouldn’t) pay yourself from your business• What “write-offs” really mean (and what they don’t)• How travel, vehicles, and even events can become legitimate deductions• The biggest mistakes people make that cost them thousands every yearJay also asks the real questions most people are afraid to ask — about paying yourself, setting money aside for taxes, and how much grace entrepreneurs actually get when they’re just starting out.If you’ve ever felt like you’re working hard but not getting ahead…This conversation will change how you look at money.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Before acting, before Power Book IV: Force, before the cameras and recognition—Isaac was chasing the NFL. And when that dream ended, he didn’t just lose a career… he lost a sense of who he was.In this powerful conversation, Isaac opens up about what really happens when success is taken from you, how losing football forced him to confront shame, ego, and identity, and how acting ultimately became the unexpected path that saved him. He shares the reality of going from professional sports to rock bottom, navigating faith during moments of doubt, and learning how to rebuild his life without letting bitterness take over.This episode isn’t just about sports or television—it’s about reinvention.Isaac reflects on the emotional toll of starting over, the discipline required to transition from athlete to actor, and why Power Book IV: Force represents more than a role—it represents the birth of a new chapter built on purpose, patience, and self-belief.If you’ve ever had to let go of a version of yourself you thought defined you, this conversation will resonate deeply.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Akea J is one of the rawest, realest voices in comedy today — but the journey behind that honesty has been painful, complicated, and expensive. In this powerful and unfiltered conversation, she sits down with Jay Hill to reveal the truth about what it really takes to survive and succeed as a Black woman in a male-dominated comedy industry.For the first time, Akea opens up about the battles she fought behind the scenes: being silenced, being overlooked, being mistreated, being blamed for things she didn’t do, and even being sexually assaulted in spaces where she was supposed to be protected. She shares the emotional toll of being punished by association, blackballed without explanation, and left to navigate an industry where power, ego, and silence often matter more than skill or integrity.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
From the outside, Baltimore Bella looked like confidence, beauty, and strength — but behind the viral moments and the personality the city thought it knew was a woman fighting battles nobody ever saw. In this powerful and vulnerable episode, Bella sits down with Jay Hill to share the full story behind her childhood, her relationships, the heartbreaks that changed her, and the healing that’s shaping the woman she’s becoming today.Bella opens up about growing up too fast, surviving environments that forced her into responsibility long before she was ready, and the emotional weight she carried as a daughter, sister, partner, and mother. She speaks on love, loyalty, betrayal, and the moments that pushed her to choose herself for the first time in her life.This isn’t just an interview — it’s a story of transformation.A story of a girl who had to be strong just to survive…and a woman who’s finally learning she deserves softness, healing, and peace.Whether you’ve lived through childhood trauma, stayed in the wrong relationship too long, lost yourself trying to love someone else, or are fighting to rebuild your identity — Bella’s journey will speak to you deeply.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
What do you do when your car gets repo’d, your bank account is in the negative, your business fails, and you’re sleeping in bunk beds with your family… after believing you were on the way up?Most people break.Richard Gilbau built a monster.In this emotional and brutally honest interview, Richard opens up about hitting absolute rock bottom — eviction court, repo, losing his job, moving his wife and kids into his in-laws’ home — and how that pressure turned him into the entrepreneur he is today.But this isn’t just a comeback story.This is THE blueprint for any man trying to rebuild his life, his finances, and his family.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
When Hellcat Hot went viral, TMC became one of the fastest-rising young artists in Baltimore. Overnight, he had the attention, the momentum, and the talent to take over the city. But behind the scenes, something else was happening — something he never fully opened up about until now.In this raw and vulnerable conversation, TMC The Don sits down with Jay Hill to share how signing a label deal early in his career changed everything. What looked like a breakthrough became a setback: delays, restrictions, loss of control, and a three-year period where he couldn’t release music at all. For a young artist still trying to understand himself, the silence became heavier than the fame.This episode dives deep into how that experience affected his confidence, personal life, creativity, and mental health — and how it ultimately forced him to grow up, rebuild, and find his voice again. This isn’t just a story about the music industry. It’s a story about timing, self-discovery, and learning how to rise after being broken.Whether you’re an artist, creator, or someone who’s ever felt stuck or misunderstood, TMC’s journey will hit home.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
For years, DJ Flow has been the engine behind some of the biggest stages, the biggest moments, and the biggest movements—yet somehow, one of the most overlooked.In this raw, honest conversation, Flow sits down with Jay Hill to reveal how hate, doubt, and being underestimated didn’t destroy him… it transformed him.From basement parties to touring with major artists, from promoting flyers on the yard to becoming one of the most electrifying DJs of his generation, Flow opens up about the mindset, the pain, and the hunger that turned him into the force he is today.This is the untold story behind his rise—filled with imposter syndrome, being counted out, proving himself in every city, and the moment he realized he didn’t need permission to become great.Whether you’re a DJ, a creator, an artist, or someone fighting to be seen, this episode will hit home.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
When life fell apart, Zoe Spencer didn’t break — she transformed.In this powerful episode, Zoe sits down with Jay Hill to reveal how losing her relationship, losing both her jobs, and hitting rock bottom became the moment that made her fearless, focused, and truly unstoppable.Zoe opens up about the pressure to change who she is for the internet, the labels thrown at her (“loud,” “obnoxious,” “doing too much”), and why she refuses to dim her personality to make people comfortable. From going viral to stepping into acting, from navigating hate comments to finding her lane in streaming, Zoe shares the real story behind staying unapologetically herself in a world that constantly tries to mold you.If you’ve ever reinvented yourself, battled doubt, or felt misunderstood, this episode will speak to you directly.💡 Topics CoveredLosing everything & the moment she “locked in”The breakup, the firings, and her January 1st resetWhy authenticity is her superpowerGoing from Burlington & banking to streaming successThe pressure to be “quiet,” “smaller,” or less “animated”Gender double standards in online spacesHow NYC streaming is rebirthing a cultureThe acting pivot and her Scary Movie reenactmentFinding real friends in the creator worldThe truth about live numbers, view-botting & consistencySupport this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this powerful episode, DJ Quicksilva — one of the most respected voices in radio and nightlife — sits down with Jay Hill to deliver real game about relevance, branding, and longevity in a changing industry.From being mocked when he first came to D.C. to becoming one of the biggest names in radio, Quicksilva opens up about the truth behind gatekeeping, how he built his brand bigger than any station, and what it really takes to stay undeniable when the game keeps changing.He breaks down the difference between value and validation, explains why radio still matters, and shares lessons learned from over 30 years of success, setbacks, and self-belief.Whether you’re a DJ, artist, entrepreneur, or content creator, this episode will shift your mindset forever.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this episode, Prince Ali, a first-generation entrepreneur from Senegal, sits down with Jay Hill to reveal how he turned a 640 credit score into a seven-figure business. Ali breaks down how he went from door-to-door sales to building a funding empire that teaches people to escape the rat race and build generational wealth — all through credit, mentorship, and discipline.From learning Spanish to close more sales, to watching his mom use his credit score so the family could qualify for a home, this conversation is full of real stories, practical lessons, and powerful game that’ll shift how you see credit forever.Ali shares the exact mindset that helped him become financially free, how to get funding for your business, and the one question most people never ask their credit repair company — but should.🎯 Connect with Prince Ali👉 Instagram: @theonlyprinceali👉 Free Workshop + $27 Challenge: Credit2Capital.comSupport this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
They love the chaos—but they never ask what it costs.”In this raw and unfiltered episode of The Jay Hill Podcast, Diamond The Body opens up like never before about the real price of fame, the reality behind Baddies, and the personal battles that came before the cameras ever rolled.From stripping at sixteen to becoming one of the most recognizable faces in reality TV, Diamond reveals how she turned pain into power—while still fighting to be seen beyond the headlines and stereotypes.Jay and Diamond dig deep on everything from fame, faith, and forgiveness to the blurred lines between entertainment and exploitation.💔 The emotional cost of going viral and being misunderstood🔥 The truth about Baddies and how she uses chaos as marketing🎤 Her journey from the strip club to signing a record deal💡 Why she forgave her mother and what healing really looks like🎭 The thin line between influence, entertainment, and accountabilityThis isn’t just a reality star story—it’s a lesson in survival, self-awareness, and staying grounded in a world built to tear you apart.▶️ Watch now for the full conversation behind the headlines—and the woman fighting to be seen beyond the noise.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Everybody wants freedom—but nobody wants the discipline that comes with it.”In this unfiltered episode of The Jay Hill Podcast, Smitty Da Goat sits down with Jay Hill for a brutally honest conversation about money, mindset, mentorship, and the reality of building separation in 2025.Smitty breaks down what financial freedom really looks like—beyond flexing, followers, or fake gurus. He shares how betrayal from mentors taught him to trust his own blueprint, why most people mistake visibility for value, and what it truly takes to separate yourself in a copycat economy.💰 The real path to financial freedom (and why most never reach it)🧠 The mindset shift that separates hustlers from entrepreneurs💔 Learning from betrayal and fake mentorship📉 Why clout chasing kills credibility and long-term growth⚡ How to build systems that create real separation, not social media hypeThis episode isn’t about motivation—it’s a masterclass in clarity, accountability, and ownership.▶️ Watch now to learn the truth about freedom, mentorship, and the mindset that builds legacy.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this powerful episode of The Jay Hill Podcast, Chicago’s own Dreezy opens up like never before. From navigating the pressures of the music industry machine to enduring heartbreak in the public eye, she reveals the hard truths behind stepping away from the spotlight—and the courage it took to return.Dreezy talks candidly about:The reality of being caught in the industry system and why she had to fight for her voiceThe emotional toll of her high-profile breakup and how it shaped her artistryThe importance of rebranding and rediscovering herself on her own termsLosing friends, finding peace, and the power of starting over strongerThis isn’t just a story about music—it’s about resilience, growth, and reclaiming your narrative. Whether you’re a fan of Dreezy’s music or someone chasing your own comeback, this conversation will inspire you to keep fighting for your truth.✨ Watch the full interview now and see how Dreezy turned pain into power.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this powerful episode, Troy Millings and Rashad Bilal of Earn Your Leisure sit down with Jay Hill for a raw, unfiltered conversation about what it really takes to build one of the most influential financial literacy platforms in the world.This is more than a business success story—it’s about sacrifice, setbacks, and the unshakable vision that’s driving a legacy for generations to come.From the early days of recording in small studios to creating a global brand that inspires millions, Troy and Rashad open up about the discipline, trust, and faith that fueled their rise, and the personal costs that came with It.💡 The sacrifices no one sees behind building a movement🤝 How trust and humility keep their partnership strong🌍 Turning a podcast into a worldwide financial education platform🛑 Why they turn down certain deals to protect their brand🏛 The mission to create generational wealth and a legacy that will outlive themIf you’ve ever dreamed of building something that matters—or wondered what it takes to turn vision into impact—this conversation will inspire you to keep going, no matter the obstacles.▶️ Watch now for the untold story of how two men built a movement that will live forever.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In one of his most raw and revealing interviews yet, Algee Smith sits down with Jay Hill to open up about the spiritual toll of Hollywood, the pressure to perform, and what it took to finally reclaim his peace.From breakout roles in Euphoria, Detroit, and The New Edition Story to battling depression behind the scenes, Algee shares the internal war between fame and faith—and why he chose to walk away from the spotlight to find himself again.This isn’t a conversation about the industry—it’s about identity, ego, healing, and the quiet strength it takes to start over.🎭 The dark side of being “successful” but feeling empty🙏🏾 How walking away from L.A. helped him reconnect with God🧠 Therapy, ego death, and the battle for mental health🎵 Why he stopped creating for validation and started creating for healing🚫 What it means to say no to fame and yes to faithIf you’ve ever questioned your purpose, battled with identity, or felt like success still left something missing—this episode is for you.▶️ Tap in for a conversation about growth, God, and the courage to let go of who the world told you to be.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this vulnerable and reflective episode, Corey SSG sits down with Jay Hill to unpack the internal battles so many men never speak about. From ego and isolation to fatherhood and faith, Corey opens up about what it truly takes to outgrow who you were—and intentionally become who you’re meant to be.This isn’t a conversation about perfection. It’s about progress.It’s about choosing peace over performance. Purpose over popularity.🔥 Why “being outside” was a mask for deeper pain🧠 The emotional cost of outgrowing your environment👨👦 How fatherhood and faith shifted his perspective on masculinity💔 The lonely truth about healing and setting boundaries❤️ Why real strength is in vulnerability—not performanceThis episode is a blueprint for any man (or woman) who’s ever felt trapped by the version of themselves they’ve outgrown.It’s a raw look at what healing really feels like—and why it’s worth it.▶️ Watch now for a powerful conversation about manhood, growth, and finally doing the inner work.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
🔥 “I was preparing for my mom to die… and still showing up for work.” 🔥In this raw and powerful episode, media personality and entrepreneur Loren Lorosa joins Jay Hill for an honest conversation about what it really takes to succeed in the spotlight—and what it costs you behind the scenes.From her mother’s stage 4 cancer diagnosis to carving out her place on The Breakfast Club, Loren opens up about how fame, family, and identity collided—forcing her to confront her limits, protect her voice, and reclaim her power.💔 Balancing her mother’s illness while still showing up in the industry🎤 Navigating the transition from producer to on-air talent & the emotional cost of being overlooked🧠 Surviving burnout, learning to say no, and finding softness again after hard seasons🔥 Dealing with tension, miscommunication, and public pressure at The Breakfast Club❤️ Why her success now looks like boundaries, clarity, and doing it on her own termsThis isn’t about going viral. It’s about knowing who you are when the cameras are off—and how to protect that version of yourself at all costs.▶️ Watch now to hear Loren Lorosa like you’ve never heard her before—transparent, powerful, and finally in control of her voice.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
I had everything I ever wanted… and still felt empty.”In this raw and soul-searching episode, international artist Gashi sits down with Jay Hill to share the untold truth behind his success — and the emotional collapse that followed it.Born in Kosovo, raised in Brooklyn, and catapulted to fame through music, Gashi opens up about the emotional toll of chasing acceptance, the identity crisis of being caught between two worlds, and the devastating loss of his father — the man who sacrificed everything for his future.🎭 Why the spotlight left him feeling more alone than ever🏃♂️ The moment he walked away from music — and why he had to do it twice💔 How losing his father forced him to reevaluate his purpose🧘♂️ Why fame, validation, and going viral are no longer his goals🎙️ How his music is now driven by healing, not attentionThis episode isn’t just about the industry — it’s about identity, grief, purpose, and reclaiming your soul when the world has labeled you something you're not.▶️ Watch now for one of the most vulnerable and honest conversations we’ve had on this platform.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this powerful and personal conversation, DDG sits down with Jay Hill to reflect on the journey from being underestimated as a YouTuber to evolving into a respected artist, businessman, and father.This isn’t about flexing success. It’s about the pressure of expectations, the sting of being boxed in, and the constant fight to evolve beyond the internet’s perception.For the first time, DDG opens up about:🎭 Why being underestimated still motivates him—and why it hurts more when it’s about his music🧠 How he built thick skin to survive the internet, but still cares deeply about his craft❤️ The role fatherhood plays in grounding him & redefining what real love and legacy mean🚀 The addictive chase for “more” and how he’s learning to balance ambition with peace🎶 How criticism shaped his career, but his authenticity keeps pushing him forwardThis is DDG beyond the vlogs, beyond the memes, beyond the trolls—a conversation about growth, gratitude, and never letting others define your ceiling.▶️ Watch now for a raw, insightful conversation that shows DDG like you’ve never seen him before.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
In this revealing and introspective episode of The Jay Hill Podcast, K Camp returns to talk candidly about his journey of falling out of favor in the music industry, reclaiming his power as an independent artist, and staying grounded through personal evolution.K Camp shares how, even after creating hit records, the industry made him feel invisible—and how opening his own studio and starting Rare Sound allowed him to finally embrace his worth. He discusses the pressures of being “hot” in a fast-moving industry and what it means to truly feel like "him."The emotional rollercoaster of fame and how artists are often discarded after the spotlight fades.His new partnership with Virgin and how he secured a “Master P-level” deal after years of funding his own career.The power of ownership, spiritual discipline, daily self-improvement, and detaching from external validation.Deep talks about grief, including losing his cousin (like a brother), and how that moment reshaped his mindset on life and death.The business of music—navigating shady contracts, learning to say no, and knowing your value.Finding love, dealing with obsessive fans, and the personal struggles that come with dating while being in the public eye.This episode is a blueprint for artists navigating both the music industry and personal growth. K Camp proves that staying authentic, being informed, and walking in purpose are more powerful than any record deal.Support this podcast at — https://redcircle.com/the-jay-hill-podcast/exclusive-contentAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
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