You can’t rewrite the past — but you can learn from it. Amber Grimes did exactly that, going from college dropout to Executive Vice President in the entertainment industry with no map, just mistakes and lessons that turned into power moves. If You Knew Better is where Amber shares that wisdom — alongside artists, creatives, and culture-shifters who open up about the missteps they made, the mindsets that changed everything, and the game they wish they knew sooner. Together, they unpack the highs, the lows, and the pivots in life, career, and relationships — so you either don’t have to go through it, or can move smarter when you do. Every episode delivers real talk, hard-won insight, and practical gems to help you grow into the version of yourself that knows better… and does better.

Listen here and subscribe to If You Knew Better with Amber Grimes on the iHeartRadio app or wherever you get your podcasts!

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Today features Wheezy—co-host of Decisions, Decisions (formerly Whoreible Decisions) and an entrepreneur behind Trap Haus Fitness and WTF Media—about sex positivity, public judgment, and the business realities of building a brand. Wheezy explains the name change was driven by missed opportunities and lost ad revenue tied to “Whoreible,” even though the original title fit their message about how liberated women get labeled anyway; the shift brought more money but felt like losing some of the show’s original, kink-centered cultural impact. She shares how online backlash still hurts, why Black kink communities value the safe space she helped create, and how her open relationship can still reflect commitment. She ends with advice for women to communicate what they want sexually, prioritize pleasure, and stop treating desire like something to be ashamed of.

Connect @CariChampion @WeezyWTF

Listen: Decisions Decisions

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Larry Miller, chairman of the advisory board for Nike’s Jordan Brand, shares how he went from being a smart kid in West Philly to joining a gang, killing a teen at 16, and serving time for murder and later armed robberies. In prison, he earned his GED, entered a college program, got an associate’s degree, then finished a Temple University accounting degree and built a decades-long career while keeping his record private after losing a job offer when he disclosed it. Encouraged by his daughter, he finally told his story in a book, which ended his nightmares and migraines, and he received support from Phil Knight and Michael Jordan. He now leads JUMP (Justice and Upward Mobility Project) to reduce recidivism through education, apprenticeships with NBA teams, and partnerships like the Players Coalition, while highlighting second-chance hiring successes at companies such as Lowe’s and JPMorgan Chase.

Connect @CariChampion @LarryMiller_Jump

Learn More: JumpProject.org

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Cari welcomes trailblazer Jane Kennedy, praising her as the first Black woman she saw on TV doing sports and urging listeners to read her memoir, Plain Jayne: A Memoir by trailblazing actress and sports broadcaster Jayne Kennedy. Kennedy explains the title as identifying as “the girl next door”, tracing her early pageant and tomboy roots, and describes how limited roles for Black women in 1970s Hollywood pushed her to adapt across acting, modeling, singing, and sports broadcasting. She recounts breaking into CBS’s The NFL Today, being given only a six-week contract, and earning credibility by securing a Muhammad Ali interview—only to later be fired without being told, rehired, and fired again amid network politics and bias. Kennedy also shares stepping away due to endometriosis, building a stage production with her husband, and how a stolen sex tape derailed her career, leading to years of shame before choosing to tell the full story - owning her narrative, forgiving herself, and relaunching her career.

Connect @CariChampion @JayneKennedyOverton

Read: Plain Jayne

Learn More: JayneKennedy.com

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Cari reflects on Reverend Jesse Jackson’s death (Tuesday, February 17) and what he represented to her growing up; watching family gather around the TV during his 1984 and 1988 presidential runs, hearing “Keep Hope Alive” and “I am somebody,” and learning how much those messages of dignity and possibility mattered to Black communities. Cari speaks on Jackson’s legacy and contribution to the Civil Rights movement, his presence at key moments like Martin Luther King Jr.’s assassination, and argues that even with flaws, his impact can’t be erased, especially in a time of DEI rollbacks, political turmoil, and threats to marginalized communities’ rights.

From there, the episode shifts to NBA All-Star Weekend: why fans keep complaining the game is boring, and how today’s stars feel more focused on social currency and being friends than on real competition, something earlier eras embodied through players like Kobe Bryant (and even stories about Michael Jordan’s mindset).

Cari also recaps a major highlight from the all-star weekend: a “Love & Basketball” 25th anniversary panel sponsored by HBCU First Look, featuring Sanaa Lathan, director Gina Prince-Bythewood, Candace Parker, Jane Kennedy, Cheryl Miller, and hosted by Laura Coates. They talk about how the film was ahead of its time, how it helped shape women’s sports storytelling, the importance of giving elders their flowers, and the way each generation builds on the last, along with behind-the-scenes stories and standout cast memories.

The episode closes by tying it all back to the same message: if you don’t document your history and control your narrative, someone else will.

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In this special edition of Naked Sports, host CarI and her friend/co-host Jemele Hill introduce their new podcast, 'Flagrant and Funny.' Recorded live from the Super Bowl, they discuss the podcast's focus on lively conversations about women's sports, culture, and race, emphasizing the need for honest critiques and praise. They share their hesitations and experiences critiquing athletes, drawing parallels between sports critique and racial discussions. The episode features their first-ever guest, Katie Nolan, who reflects on her career, the Super Bowl, and the importance of reconnecting with fandom. They also play a fun game guessing NFL players' positions based on their anonymous quotes about Bad Bunny performing at the Super Bowl.

Connect @CariChampion @JemeleHill

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Listen: Flagrant & Funny

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Cari kicks off the 'Naked Sports' podcast by taking listeners back to 1977, when New York was a mix of World Series excitement and urban crises. The spotlight shines on Elliot Williams, a former federal prosecutor, as he discusses his book 'Five Bullets,' which tells the story of Bernard Goetz, the so-called subway vigilante. Williams recounts Goetz's controversial 1984 shooting of four black teenagers, an event that highlighted racial tensions and crime fears in a gritty New York City. He touches on the public's reaction, media bias, and how the subjects of safety and vigilantism remain relevant today. The discussion also includes the impact of the crack epidemic on New York's housing projects and the ongoing celebration of vigilantes in American culture. It’s a rich exploration of how past events continue to shape contemporary issues.

Connect @CariChampion @ElliotWilliamsPhotos

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Read: Five Bullets by Elliot Williams

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Today, Cari welcomes Selema Masekela, an influential figure in action sports, music, and storytelling. Selema shares his journey of embracing his unique identity, recounting his transformation from being known as 'Sal' to reclaiming his full name, 'Selema.' They discuss the challenges he faced in predominantly white spaces and the significance of maintaining cultural authenticity. Selema talks about his impactful work in expanding diversity in extreme sports, his experience growing up in a musically rich household, and the importance of standing firm in one's identity. The conversation also touches on personal anecdotes, including Selema's reflections on grief and his father's legacy.

Connect @CariChampion @Selema

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Music: Listen to Alekesam

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