Won of One: A PLLRS Podcast

Kei Henderson on Life After 21 Savage, Mental Health and Live Nation Deal | Won of One EP 16

Before the Grammy, before the Live Nation deal, before 21 Savage was a household name, there was Kei Henderson, watching closely, betting early, and building differently. In this episode of Won of One: A PLLRS Podcast, the Founder and CEO of Third + Hayden traces a career path that began as a side hustle while she was still in corporate, ran through the underground Atlanta rap scene, and ultimately produced one of the most distinctive artist development companies in the music business today. Henderson talks openly about the risk calculus of entrepreneurship, deal structure, and leverage. With a landmark Live Nation partnership in 2024 and a roster built on ownership from day one, Kei Henderson is rewriting the music industry from within, on her own terms, and with receipts. About Today’s Guest Kei Henderson is the Founder & CEO of Third + Hayden, the Atlanta-based management, label, and publishing company rewriting what independent artist development can look like. You may know her name from the 21 Savage era: she spotted him as a local Atlanta rapper in 2014, built him into a global phenomenon, and earned a Grammy Award in the process. Launched in 2021, Third + Hayden operates on a deceptively radical thesis: that great artists require whole human beings first. That means ownership and masters retained from day one, and perhaps most unusually in this business, a non-recoupable personal development fund for every label signee, directed toward therapy, rehab, or whatever an artist actually needs to thrive. The business world noticed: in 2024, Live Nation announced a landmark artist development partnership with the company, the first time the live entertainment giant has ever partnered with an Atlanta-based management firm. A multiple Billboard Power List honoree, Kei Henderson is one of the most vocal and visionary executives in the industry on the intersection of wellness, ownership, and what a long career in music can actually look like when the incentives are finally aligned. Key Points from this Episode: * 0:00 Welcome Back to Won of One: A PLLRS Podcast with Today’s Guest, Kei Henderson * 2:00 From Corporate Side Hustle to Founding Third + Hayden * 4:30 The Risk of Entrepreneurship and Betting on Yourself Without a Roadmap * 6:45 The Live Nation Partnership and Getting Involved With Artists Earlier * 8:50 Managing 21 Savage From the Underground and What the Drake Co-Sign Changed * 16:00 Helping 21 Savage Secure His Masters, Label Leverage, and Building Ticket History * 22:27 Label Resources vs. Building Independently: How Managers Decide * 28:22 Why Third + Hayden Funds Therapy, Wellness, and Personal Development for Artists * 35:55 Kei Henderson's Advice to Artists on Navigating the Music Industry * 38:53 Is the Era of the Superstar Over? Mentioned on the Show * Connect with Kei Henderson: https://www.instagram.com/keiopensdoors/ [https://www.instagram.com/keiopensdoors/] * Third + Hayden: https://thirdandhayden.com/ [https://thirdandhayden.com/] Join the Conversation:  🏛️ Watch more on YouTube: https://www.youtube.com/@thePLLRS [https://www.youtube.com/@thePLLRS] 🏛️ Follow us on Instagram: https://www.instagram.com/thepllrs/ [https://www.instagram.com/thepllrs/] 🏛️ Follow us on TikTok: https://www.tiktok.com/@thepllrs [https://www.tiktok.com/@thepllrs] 🏛️ Connect with us on X: https://x.com/the_pllrs [https://x.com/the_pllrs] 🏛️ Connect with us on Bluesky: https://bsky.app/profile/thepllrs.bsky.social [https://bsky.app/profile/thepllrs.bsky.social] 🏛️ Connect with us on Threads: https://www.threads.com/@thepllrs [https://www.threads.com/@thepllrs] 🏛️ PLLRS Press and more: https://linktr.ee/ThePLLRS [https://linktr.ee/ThePLLRS] 🏛️ Connect with Won of One Host, Reg Calixte: https://www.instagram.com/LTLENG [https://www.instagram.com/LTLENG] 🏛️ Connect with Keith Nelson, Jr.: https://www.instagram.com/keithnelsonjr [https://www.instagram.com/keithnelsonjr] 🏛️ Connect with Rose Mercado, MA.Ed.: https://www.instagram.com/photo_bombshell [https://www.instagram.com/photo_bombshell] 🏛️ Manhattan Neighborhood Network: https://www.instagram.com/mnnnyc [https://www.instagram.com/mnnnyc] 🔊 Listen on Spotify: https://creators.spotify.com/pod/profile/thepllrs/ [https://creators.spotify.com/pod/profile/thepllrs/] 🔊 Listen on Apple: https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899 [https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899] ✉️ For Business Inquiries, email: rose@photobombshell.media [rose@photobombshell.media]

Jason Lee Goes OFF On Friendship With Drake, Kanye Drama & His Hollywood Empire | Won of One EP 15

From Stockton to the streets of Hollywood to city hall, Jason Lee has never moved in a straight line, and that is precisely what makes him worth watching. In this episode of Won of One: A PLLRS Podcast, the Hollywood Unlocked CEO and newly elected Vice Mayor of Stockton sits down for an unfiltered conversation about building an independent media empire from the ground up, the responsibility that comes with cultural influence, and what it actually means to hold power accountable while holding power yourself. Lee speaks candidly about his relationships with some of the biggest names in entertainment, including Drake, Kanye West, Kevin Hart, and Chris Brown. Equal parts media strategist, crisis observer, and public servant, Jason Lee challenges the long-held dismissal of independent platforms and makes a compelling case that the future of cultural journalism, and maybe even politics, looks a lot more like Hollywood Unlocked than anyone in legacy media wants to admit. About Today’s Guest Multimedia powerhouse, entrepreneur, and now elected public servant, Jason Lee is the CEO and driving force behind the Hollywood Unlocked media empire. After building his television profile on Love & Hip Hop: Hollywood and MTV's Wild 'N Out, Lee leveraged his celebrity relationships and cultural influence to launch Hollywood Unlocked in 2015. In 2023, he expanded his reach with The Jason Lee Show, and in November 2024, he was elected to the Stockton City Council representing District 6, subsequently being appointed Vice Mayor in January 2025. A man who has moved seamlessly from red carpets to city council chambers, Jason Lee brings a perspective on media, entrepreneurship, and the intersection of pop culture and politics that cannot be manufactured. Key Points from this Episode: * 0:00 Welcome Back to Won of One: A PLLRS Podcast with Today’s Guest, Jason Lee * 1:00 BET's Black + Iconic Soirée and Reflecting on the Journey * 4:27 Building Hollywood Unlocked and the Impact Awards * 8:00 How Impact Award Honorees Are Chosen and the State of Black Media Platforms * 11:36 Should Black Award Shows Carry the Same Weight as the Grammys and the Oscars? * 15:49 Kevin Hart, Past Run-Ins, and the Responsibility of Media Integrity * 20:45 Freedom of Speech, the Kevin Hart Roast, and Where the Line Gets Drawn * 29:50 When Boonk Pulled a Gun Mid-Interview, Backlash in the Field, and T.I. * 35:53 Working with Kanye During the White Lives Matter Fallout * 44:40 Crisis Management, PR, and Why Jason Wants to Rebuild Chris Brown's Career * 49:30 Jason Lee on Drake, the Kendrick Beef, and What Comes Next * 52:52 Fighting the Dismissal of Independent Media and What Hollywood Unlocked Proved * 1:01:55 Vice Mayor Jason Lee: Politics, Power, and the Bigger Plan Mentioned on the Show * The Jason Lee Show: https://www.thezeusnetwork.com/the-jason-lee-show [https://www.thezeusnetwork.com/the-jason-lee-show] * The Hollywood Unlocked Impact Awards: https://www.thezeusnetwork.com/the-hollywood-unlocked-impact-awards [https://www.thezeusnetwork.com/the-hollywood-unlocked-impact-awards] * Hollywood Cares Foundation: https://www.hollywoodcaresfoundation.org/ [https://www.hollywoodcaresfoundation.org/] * Hollywood Unlocked: https://hollywoodunlocked.com/ [https://hollywoodunlocked.com/] * Becoming Warren Buffett: https://www.hbomax.com/movies/becoming-warren-buffett/ba67620c-448a-4922-93e6-f397bf98fdb8 [https://www.hbomax.com/movies/becoming-warren-buffett/ba67620c-448a-4922-93e6-f397bf98fdb8] Join the Conversation:  🏛️ Watch more on YouTube: https://www.youtube.com/@thePLLRS [https://www.youtube.com/@thePLLRS] 🏛️ Follow us on Instagram: https://www.instagram.com/thepllrs/ [https://www.instagram.com/thepllrs/] 🏛️ Follow us on TikTok: https://www.tiktok.com/@thepllrs [https://www.tiktok.com/@thepllrs] 🏛️ Connect with us on X: https://x.com/the_pllrs [https://x.com/the_pllrs] 🏛️ Connect with us on Bluesky: https://bsky.app/profile/thepllrs.bsky.social [https://bsky.app/profile/thepllrs.bsky.social] 🏛️ Connect with us on Threads: https://www.threads.com/@thepllrs [https://www.threads.com/@thepllrs] 🏛️ PLLRS Press and more: https://linktr.ee/ThePLLRS [https://linktr.ee/ThePLLRS] 🏛️ Connect with Won of One Host, Reg Calixte: https://www.instagram.com/LTLENG [https://www.instagram.com/LTLENG] 🏛️ Connect with Keith Nelson, Jr.: https://www.instagram.com/keithnelsonjr [https://www.instagram.com/keithnelsonjr] 🏛️ Connect with Rose Mercado, MA.Ed.: https://www.instagram.com/photo_bombshell [https://www.instagram.com/photo_bombshell] 🏛️ Manhattan Neighborhood Network: https://www.instagram.com/mnnnyc [https://www.instagram.com/mnnnyc] ✉️ For Business Inquiries, email: rose@photobombshell.media [rose@photobombshell.media]

Shyne on His 25 Year Transformation, Four New Albums, and Return to Politics | Won of One EP 14

In this episode of Won of One: A PLLRS Podcast, Moses “Shyne” Barrow delivers a powerful, full-circle conversation on transformation and purpose, reflecting on 25 years since his incarceration and how time, faith, and perspective reshaped him. He opens up about using entertainment as a vehicle for inspiration, balancing a global political career with a return to music, and the mindset shift required to re-enter a creative space after years of public service. From headlining King’s Theatre on the 25th anniversary tour to revisiting and re-recording past projects through a healed lens, Shyne unpacks the intersection of artistry, identity, and growth. He also explores hip hop’s historical fixation on the “villain” narrative, the power of social media to build direct community, and his future ambitions, from new music with elite collaborators to book releases and a continued path in politics, with aspirations of becoming Prime Minister of Belize. This episode is a masterclass in evolution, ownership, and redefining legacy on your own terms. About Today’s Guest Shyne is one of hip-hop's most unlikely and undeniable stories. Born in Belize City and raised in Brooklyn's East Flatbush, he fought his way into the inner circle of Sean "Diddy" Combs and Bad Boy Records, only to have his career derailed at its peak by a 1999 nightclub shooting that landed him a 10-year prison sentence. Behind bars, he released the Billboard No. 3 album Godfather Buried Alive, and signed a $3 million deal with Def Jam. After his release and deportation back to Belize, he traded the mic for a seat in the House of Representatives, rising to Leader of the Opposition. His life story is the subject of the documentary The Honorable Shyne, and now, he's bringing it to Won of One. Key Points from this Episode: * 0:00 Welcome back to Won of One: A PLLRS Podcast with today’s guest, Shyne * 3:05 Shyne breaks down how storytelling through entertainment became his vehicle to inspire the world * 9:13 25 years later, Shyne reflects on no longer being in opposition with himself * 16:12 From incarceration to center stage, Shyne headlines King’s Theatre while honoring Godfather Buried Alive * 18:37 Shyne gears up for a global music return, tapping elite producers, Dr. Dre, Hit Boy, Swizz Beats, RZA, Timbaland, and more * 27:58 Transitioning from politics back to music, Shyne reveals the shared discipline behind both worlds * 33:16 Revisiting Gangland, Shyne plans to re-record from a place of healing and evolution * 36:33 Shyne unpacks hip hop’s obsession with the “bad guy” narrative after topping charts while incarcerated * 40:50 With The Honorable Shyne, he balances music, literature, and political aspirations * 46:55 Social media becomes Shyne’s direct line to the people, where fans evolve into extended family * 49:00 From incarceration to influence, Shyne’s evolution defines what it means to reclaim your narrative Mentioned on the Show * Connect with Shyne on Instagram: https://www.instagram.com/shyne_bz/ [https://www.instagram.com/shyne_bz/] Join the Conversation:  🏛️ Watch more on YouTube: https://www.youtube.com/@thePLLRS [https://www.youtube.com/@thePLLRS] 🏛️ Follow us on Instagram: https://www.instagram.com/thepllrs/ [https://www.instagram.com/thepllrs/] 🏛️ Follow us on TikTok: https://www.tiktok.com/@thepllrs [https://www.tiktok.com/@thepllrs] 🏛️ Connect with us on X: https://x.com/the_pllrs [https://x.com/the_pllrs] 🏛️ Connect with us on Bluesky: https://bsky.app/profile/thepllrs.bsky.social [https://bsky.app/profile/thepllrs.bsky.social] 🏛️ Connect with us on Threads: https://www.threads.com/@thepllrs [https://www.threads.com/@thepllrs] 🏛️ PLLRS Press and more: https://linktr.ee/ThePLLRS [https://linktr.ee/ThePLLRS] 🏛️ Connect with Won of One Host, Reg Calixte: https://www.instagram.com/LTLENG [https://www.instagram.com/LTLENG] 🏛️ Connect with Keith Nelson, Jr.: https://www.instagram.com/keithnelsonjr [https://www.instagram.com/keithnelsonjr] 🏛️ Connect with Rose Mercado, MA.Ed.: https://www.instagram.com/photo_bombshell [https://www.instagram.com/photo_bombshell] 🏛️ Manhattan Neighborhood Network: https://www.instagram.com/mnnnyc [https://www.instagram.com/mnnnyc] 🔊 Listen on Spotify: https://creators.spotify.com/pod/profile/thepllrs/ [https://creators.spotify.com/pod/profile/thepllrs/] 🔊 Listen on Apple: https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899 [https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899] ✉️ For Business Inquiries, email: rose@photobombshell.media [rose@photobombshell.media]

Akon on Move to Country Music, Signing Lady Gaga & Why AfroBeats is Just Getting Started | Won of One EP 13

Episode 13 of Won of One: A PLLRS Podcast welcomes Akon for a wide-ranging conversation that traces his evolution from the era of Konvicted to his present-day resurgence, marked by his new project “A Beautiful Day” and a return to touring. Reflecting on two decades in the industry, Akon contrasts his earlier hustle with a more intentional, business-savvy approach, while opening up about experimenting with country music, maintaining a vault of unreleased records, and rediscovering excitement for large-scale creative work. He revisits his role in shaping careers for artists like Lady Gaga and T-Pain, and weighs in on the global rise of Afrobeats and its subgenres, highlighting Tyla’s emergence through Amapiano. The conversation also explores the intersection of music and technology, including AI’s role in artistry, alongside candid insights into entrepreneurship, investing in “un-sexy” businesses, and building sustainable ventures beyond music. Closing with reflections on his diverse influences, from Bob Marley to The Red Hot Chili Peppers, and his criteria for signing new talent, Akon offers a blueprint for longevity, reinvention, and ownership in an ever-evolving industry. About Today’s Guest Akon is a Grammy-nominated Senegalese-American artist, producer, entrepreneur, and actor, known for his impact on the global music scene and the African music movement. His unique style blends Pop, R&B, Hip-Hop, and EDM, earning him a massive online following of over 130 million. With five Grammy nominations, 45 Billboard Hot 100 hits, four Diamond records, and more than 300 collaborations with legends like Michael Jackson, David Guetta, and more, Akon's influence is unmistakable.  Key Points from this Episode: * 0:00 Welcome back to Won of One: A PLLRS Podcast with today’s guest, Akon * 1:03 Akon on releasing “A Beautiful Day,” marking his return to full-length music projects and going on tour with Ne-Yo * 3:08 The 20th anniversary of Konvicted and Akon as an artist then vs. now * 4:37 Akon’s country music conversion and creating original country songs, and being a trailblazer in genre-bending * 7:20 Navigating his return to larger-scale music projects with renewed enthusiasm * 9:50 Akon’s vault full of unreleased music  * 11:40 On scouting and signing Lady Gaga and T-Pain * 14:33 Afrobeats and the growing landscape of afrobeat subgenres, Tyla’s journey in Amapiano * 19:05 Embracing AI in music, using it as a tool, and owning your voice * 22:05 Bridging the gap between music and business as an artist by being educated * 26:56 Akon on getting into “un-sexy” businesses, investing in things that are naturally in his path * 31:25 What Akon looks for in signing new artists, his girl group Simien, and investing in music in new ways that produce products * 35:51 Reflecting on his catalogue and musical influences * 38:30 Working with Wyclef Jean and the artist's role and responsibilities outside of music * 44:38 Akon’s top 5 standout artists right now Mentioned on the Show * Listen to ‘A Beautiful Day’ on Spotify [https://open.spotify.com/album/0beloHUnrqAmH58rSMxDoa?si=Cjftu5NbSsS01VdLodXFwA] * Listen to ‘A Beautiful Day’ on Apple Music [https://music.apple.com/us/album/beautiful-day/1887370593] Join the Conversation:  🏛️ Watch more on YouTube: https://www.youtube.com/@thePLLRS [https://www.youtube.com/@thePLLRS] 🏛️ Follow us on Instagram: https://www.instagram.com/thepllrs/ [https://www.instagram.com/thepllrs/] 🏛️ Follow us on TikTok: https://www.tiktok.com/@thepllrs [https://www.tiktok.com/@thepllrs] 🏛️ Connect with us on X: https://x.com/the_pllrs [https://x.com/the_pllrs] 🏛️ Connect with us on Threads: https://www.threads.com/@thepllrs [https://www.threads.com/@thepllrs] 🏛️ PLLRS Press and more: https://linktr.ee/ThePLLRS [https://linktr.ee/ThePLLRS] 🏛️ Connect with Won of One Host, Reg Calixte: https://www.instagram.com/LTLENG [https://www.instagram.com/LTLENG] 🏛️ Connect with Keith Nelson, Jr.: https://www.instagram.com/keithnelsonjr [https://www.instagram.com/keithnelsonjr] 🏛️ Connect with Rose Mercado, MA.Ed.: https://www.instagram.com/photo_bombshell [https://www.instagram.com/photo_bombshell] 🏛️ Manhattan Neighborhood Network: https://www.instagram.com/mnnnyc [https://www.instagram.com/mnnnyc] 🔊 Listen on Spotify: https://creators.spotify.com/pod/profile/thepllrs/ [https://creators.spotify.com/pod/profile/thepllrs/] 🔊 Listen on Apple: https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899 [https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899] ✉️ For Business Inquiries, email: rose@photobombshell.media [rose@photobombshell.media]

Felton Brown on Friendship with J. Cole, Helping build Dreamville & The Fall-Off | Won of One EP 12

Felton Brown, Vice President of Creative Services at Dreamville Ventures, sits down with Reg Calixte for a conversation that moves fluidly between the boardroom and the booth. In episode 12 of Won of One: A PLLRS Podcast, Felton traces his path from a high school internship at Def Jam that lit the spark to becoming a key architect of Dreamville's visual identity and cultural infrastructure. He breaks down what it really means to be a creative intermediary: the person who speaks both artist and executive without compromising either, and why that skill set is rarer and more necessary than ever. Felton shares candid reflections on the music industry's shifting gatekeeping culture, the entitlement mentality creeping into creative spaces, and why internal checks and balances matter more than people admit. He opens up about developing a friendship with J. Cole through his blog, his role in shaping the aesthetics of The Fall-Off, and a standout record that never made it to the final album, a meditation on how some of the greatest work never leaves the vault. The conversation also goes deep into the declining perceived value of music, why physical media still holds cultural weight, and where Dreamville stands today as an independent platform built by artists, for artists, inside a UMG partnership. About Today’s Guest Felton Brown has spent his career living at the place where artists, brands, and communities actually meet, not in theory, but in practice. At Dreamville, he's been part of building something rare: an independent label that grew into a full cultural platform, spanning albums, live experiences, festivals, merchandise, documentaries, and brand collaborations, where every decision carries both creative and business weight. Key Points from this Episode: * 0:00 Welcome back to Won of One: A PLLRS Podcast with today’s guest, Felton Brown * 0:45 Felton Brown on his role at Dreamville Ventures as a creative intermediary * 2:00 The current state of the music industry, the original intention of gatekeeping as quality control in the space * 16:50 How a high school internship at Def Jam inspired Felton Brown’s career in the music industry * 27:30 The best moments working at Def Jam * 31:00 Entitlement mentality in creative spaces and the importance of checks and balances * 35:08 Developing a friendship with J.Cole * 40:48 Shaping the aesthetics of Dreamville * 43:07 Felton’s role in J. Cole’s The Fall-Off and how some artists' greatest work never makes it out of the vault * 49:00 The changing value of music and the need for creative engagement and physical media * 51:26 Behind the scenes of the J.Cole apology * 57:50 The current state of Dreamville after the UMG deal with artists leading the way Mentioned on the Show * Connect with Felton Brown on LinkedIn: https://www.linkedin.com/in/feltonbrown/ [https://www.linkedin.com/in/feltonbrown/] * Felton Brown: www.FeltonBrown.com [http://www.feltonbrown.com] * The Fall-Off: https://www.thefalloff.com/physical [https://www.thefalloff.com/physical] Join the Conversation:  🏛️ Watch more on YouTube: https://www.youtube.com/@thePLLRS [https://www.youtube.com/@thePLLRS] 🏛️ Follow us on Instagram: https://www.instagram.com/thepllrs/ [https://www.instagram.com/thepllrs/] 🏛️ Follow us on TikTok: https://www.tiktok.com/@thepllrs [https://www.tiktok.com/@thepllrs] 🏛️ Connect with us on X: https://x.com/the_pllrs [https://x.com/the_pllrs] 🏛️ Connect with us on Bluesky: https://bsky.app/profile/thepllrs.bsky.social [https://bsky.app/profile/thepllrs.bsky.social] 🏛️ Connect with us on Threads: https://www.threads.com/@thepllrs [https://www.threads.com/@thepllrs] 🏛️ PLLRS Press and more: https://linktr.ee/ThePLLRS [https://linktr.ee/ThePLLRS] 🏛️ Connect with Won of One Host, Reg Calixte: https://www.instagram.com/LTLENG [https://www.instagram.com/LTLENG] 🏛️ Connect with Keith Nelson, Jr.: https://www.instagram.com/keithnelsonjr [https://www.instagram.com/keithnelsonjr] 🏛️ Connect with Rose Mercado, MA.Ed.: https://www.instagram.com/photo_bombshell [https://www.instagram.com/photo_bombshell] 🏛️ Manhattan Neighborhood Network: https://www.instagram.com/mnnnyc [https://www.instagram.com/mnnnyc] 🔊 Listen on Spotify: https://creators.spotify.com/pod/profile/thepllrs/ [https://creators.spotify.com/pod/profile/thepllrs/] 🔊 Listen on Apple: https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899 [https://podcasts.apple.com/us/podcast/won-of-one-a-pllrs-podcast/id1840643899] ✉️ For Business Inquiries, email: rose@photobombshell.media [rose@photobombshell.media]