If You Knew Better with Amber Grimes

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.

  1. 1d ago

    Reasonable Doubt’s Emayatzy & McKinley Know Jax & Lewis Love Each Other #HuluPartner

    Amber Grimes sits down with Reasonable Doubt stars Emayatzy Corineal and McKinley Freemandi to unpack the powerful meaning behind Jax and Lewis’ intimate hair scene [00:00] and the emotional stakes of their relationship [00:33]. The actors reveal how playing the couple has shaped their own views on relationships and marriage [01:22], debating forgiveness versus simply moving forward [03:38], loyalty versus love [05:39], and how Lewis can support Jax without losing himself [07:12]. They also explore Jax’s vulnerability after trauma [09:39], what both characters need emotionally [11:58], and the therapy, accountability, listening, and commitment required for them to thrive together [15:05]. McKinley and Emayatzy explain why portraying such a complicated marriage works for them as actors [18:40] and revisit the hair scene as meaningful Black imagery centered on trust, care, and intimacy [20:41]. They break down their preparation and commitment to the roles [22:55], the process of becoming Jax and Lewis [24:14], and the intensity surrounding the courtroom defense in the Reasonable Doubt finale [27:25], while giving credit to creator Raamla Mohamed and the writers for allowing the characters—and their marriage—to remain messy, layered, and real [29:13].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow Emayatzy Corinealdi @emayatzycorinealdi Follow Mckinley Freeman @mckinleyfreeman Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

  2. Sep 29

    Abbott Elementary’s William Stanford Davis Knows You Only Fail If You Quit.

    Amber Grimes sits down with Abbott Elementary star William Stanford Davis, who traces his journey from a childhood vision of seeing himself on TV [00:00] and the myth of overnight success [00:56] to finding inspiration in Black entertainers like Nat King Cole and Sammy Davis Jr. [02:14]. He recalls DJing [04:59], playing in bands [07:07], Upward Bound [08:26], radio success [10:06], and facing racism and setbacks in Texas [11:18] before moving to Los Angeles [13:47]. Comedy classes led to his first commercial [14:34], followed by acting training and early roles [17:05] as he learned to define success through the craft itself [21:05], guided by faith, gratitude, and his grandmother’s mantra: “we don’t quit” [24:43]. Davis reflects on seeing his childhood vision become reality [28:11], the sacrifices behind it [29:35], his grandmother’s influence [31:22], and the mentors who helped shape him [32:12]. He breaks down auditioning during COVID [34:32], the Abbott Elementary broom dance that helped him stand out [36:37], becoming a series regular [39:36], and experiencing global recognition [41:05] alongside Quinta Brunson and the cast [42:47]. Davis closes with lessons on practicing your craft daily [47:18], recognizing young talent [49:12], encouraging dreamers to experience life and never quit [50:42], and remaining grateful for the journey [53:53].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow William Stanford Davis @thewilliamstanforddavis Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

  3. Sep 22

    Olly Sholotan Knows What’s For You Is For You

    In this episode of If You Knew Better, Amber Grimes sits down with Bel-Air actor and musician Olly Sholotan to talk patience, ambition, and learning to focus on what you can control [00:00]. Olly recalls the reality check of having his first All American scenes cut [00:11], meeting the actor who would later play Carlton on Bel-Air [00:41], and navigating patience and pressure while pursuing success [01:59]. He reflects on his ambitious goal of achieving an EGOT by 30 [02:47], lessons from Forbes 30 Under 30 [03:59], and learning that “what’s for you is for you” [06:02] after losing out on another series that never aired while Bel-Air became life-changing [07:29]. That experience helped shift his mindset from chasing excitement to chasing peace [10:03], staying grounded in the work [14:12], and valuing the process over results [15:39]. Amber and Olly also unpack the balance between ambition and burnout [20:16], developing self-awareness around what you can control [22:20], and the value of supportive parents and a strong foundation [24:44]. They discuss choosing work that feeds you [25:15], recognizing when to stop before burnout hits [26:06], treating rest as fuel [27:32], surrendering to creative ideas [28:26], and detaching from other people’s approval [29:32]. Olly explains how focusing on what’s within his control [32:14], pairing ambition with self-care [33:46], and making room for hobbies [36:27] help him stay balanced. He closes with the power of gratitude [38:59], allowing dreams to expand beyond acting [41:19], and practicing specific gratitude to stay grounded [42:24], leaving listeners with encouragement to trust their process and protect their peace [46:45].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow Olly Sholotan @ollysho Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

  4. Sep 15

    Angel McCoughtry Knows It’s About The Journey Not The Destination

    In this episode of If You Knew Better, Amber Grimes sits down with WNBA legend Angel McCoughtry to talk about timing, identity, and having the courage to pursue more than one dream [00:00]. Angel reflects on how women athletes are finally being celebrated as multidimensional [00:24], after facing double standards when she pursued music during her playing career [01:31], and why timing and legacy matter more than outside expectations [02:44]. She opens up about life after basketball [04:06] and her transition into filmmaking, including directing Bygones and developing stories centered on WNBA players [05:36], documentaries, and the untold lives behind professional athletes [07:38]. From remembering the MySpace era [10:22] and rethinking “girl boss” culture [12:48] to resisting social media comparison [17:50], Angel encourages people to chase their actual dreams instead of fame [19:19], trust that purpose can lead to success [22:21], and understand the difference between gifts, passions, and purpose [22:58]. Angel explains why starting before you feel completely ready is essential [24:44] and challenges the idea that only superstars have meaningful potential [26:40], while reflecting on past choices without regret [28:41] and the consequences of rushing life and relationships [30:50]. She also discusses her interest in crime, law, and storytelling [32:37], before revealing how an injury, depression, and the end of her basketball career unexpectedly opened a new creative lane [37:29] and forced her to discover an identity beyond the game [39:08]. Together, Amber and Angel explore finding your true “why” [40:28], accepting that your dream may look different than you originally imagined [43:18], and giving yourself grace with the timing of your journey as you build a life and legacy that extend far beyond one career [44:43].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow Angel McCoughtry: @mccoughtry Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

  5. Sep 12

    If You Knew Better: Lil Durk's Mom LaShawnda Woodard Knows the Hardest Person to Forgive Is Yourself

    The Black Effect Presents... If You Knew Better with Amber Grimes! In this episode of If You Knew Better, Amber Grimes welcomes LaShawnda Woodard aka "Mama Durk" for a deeply personal conversation about teen motherhood, grief, trauma, and healing [00:00]. LaShawnda reflects on becoming a young mother [01:44], lessons she later understood from her own mom [03:51], supporting Lil Durk’s music dreams [05:49], and raising each child according to their individual needs [07:01]. She remembers her oldest son D-Thang [09:00], opens up about living with grief after his death [09:55], and shares her struggles with depression and isolation [13:58]. Amber challenges LaShawnda’s self-blame while discussing the importance of community [19:42], before LaShawnda speaks candidly about surviving sexual assault [21:59], encouraging other survivors to speak up and seek help [28:42] as they explore lingering trauma [30:27] and finding language for painful experiences [30:58]. Amber encourages LaShawnda to give herself grace [32:23], examining parenting through pain [32:58], accountability versus blame [33:40], and faith and forgiveness [36:00]. LaShawnda discusses sharing her story through 7220 [37:05] and surviving an attempted assault as a teenager [38:11], while Amber reinforces that survivors are not responsible for the harm done to them [40:56] and encourages her to release the weight she has carried [41:55]. They reflect on how children remember their upbringing differently [45:19], learning to acknowledge the good alongside the mistakes [48:44], and LaShawnda’s final memories with D-Thang [50:55]. The episode closes with a challenge to rediscover joy [53:11], understand how trauma can freeze us in time [56:13], reconnect with community [57:09], and continue the journey toward healing [58:15].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow LaShawnda Woodard: @real_mswoo Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books   O.P. Date: September 8, 2026 See omnystudio.com/listener for privacy information.

  6. Sep 1

    Justice Baiden Knows Pursuing Your Passion Should Come Before Pursuing Partnership

    In this episode of If You Knew Better, Amber Grimes sits down with Justice Baiden for an honest conversation about relationships, purpose, and the lessons that come from committing before you're truly ready [00:00]. Justice explains why he initially avoided serious commitment [01:05] and reflects on how early success in the music industry changed the dynamics of his relationships [05:24], ultimately teaching him the importance of establishing purpose before partnership [07:49]. He opens up about avoiding difficult conversations in an effort to "keep the peace" [09:59], ignoring red flags while convincing himself everything was working [14:02], and expressing love by trying to fix problems for his partner [16:50]. Justice also examines how unspoken resentment and passive-aggressive communication eventually manifested as stress [18:19], leading him to recognize that healthy relationships require clarity about individual goals [22:24], reconnecting with the passions and interests that once gave you direction [24:34], and creating intentional next steps toward the life you actually want [25:46]. Justice goes deeper into why actions ultimately matter more than promises [27:59] and introduces the importance of defining "yours, mine, and ours" within a partnership [28:37], including honest conversations about sacrifice, expectations, values, and true non-negotiables [30:34]. He reflects on overcoming the fear, guilt, and concern about other people's perceptions that can keep someone trapped in an unhealthy relationship [33:27], while confronting remorse, infidelity, and the responsibility of breaking destructive patterns [35:46]. The conversation also explores how father figures and role models shaped his understanding of manhood and relationships [40:51], the healing that can come from reparenting yourself through honest conversations [42:29], and the biggest lessons he carries from past love [44:12]. Now with a clearer understanding of himself, Justice shares whether he's ready for love today [45:54], before closing with a powerful reminder that lasting relationships begin with transparency, self-awareness, purpose, and the courage to tell the truth—even when that truth is uncomfortable [50:19].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow Justice Baiden: @justicewearscoolpants Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

  7. Aug 25

    Gail Bean Knows Defensive Dating

    In this episode of If You Knew Better, Amber Grimes sits down with actress Gail Bean for an honest conversation about love, loyalty, and learning to date with greater intention [00:00]. Gail reflects on why she stopped leading people on when she knows there’s no romantic interest [01:10], the importance of establishing clear boundaries with platonic male friends [04:18], and how to receive or give compliments without creating confusion [06:45]. She explains how her approach to relationships evolved toward intentional dating [08:18], distinguishing preferences from true non-negotiables while identifying the difference between red flags and undeniable “sirens” [11:17]. After taking a year to reflect on herself and past relationships [16:10], Gail revisits a serious relationship where love was sometimes used to overlook deeper problems, ultimately realizing that love alone isn’t enough without loyalty, character, accountability, and shared values [18:00]. She also discusses accepting responsibility for your role in relationships [19:40] and why healthy love should challenge both partners to evolve [21:30]. Gail then opens up about what changed when she chose a partner capable of leading with intention, consistency, and purpose [22:48], redefining what genuine support looks like beyond money or surface-level gestures [27:03] and sharing communication tools that help strengthen their relationship [29:04]. She takes Amber inside their origin story [31:04] and explains how dating intentionally [32:24] eventually became what she calls “defensive dating”—asking important questions early about monogamy, finances, exes, and other potential complications instead of discovering deal-breakers later [34:14]. Gail also emphasizes listening to trusted friends and family [35:51], creating accountability through honest relationship check-ins [37:39], and how greater stability in her personal life has coincided with elevation in her career, including becoming number one on the call sheet [39:07]. She closes with reflections on choosing relationships that encourage growth, provide emotional security, and prove that who you build with can influence who you ultimately become [40:24].  Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow Gail Bean: @gail_bean Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

  8. Aug 18

    Naomi Sharon Knows Relationship OCD Is Real

    In this episode of If You Knew Better, Amber Grimes sits down with singer-songwriter Naomi Sharon for a vulnerable conversation about childhood trauma, anxiety, rumination, and how unresolved experiences can follow us into adult relationships. Naomi sets the tone by opening up about her mental health journey [00:00] and explains how anxiety can turn into cycles of overthinking and rumination [00:53]. She traces many of those patterns back to her parents’ difficult divorce when she was 12 and the relationship triggers that developed from it [03:11], including fears around secrets, hidden truths, and a desire for radical honesty that can become its own emotional loop [04:49]. Naomi discusses building a greater tolerance for emotional discomfort instead of constantly searching for immediate peace [08:09], discovering relationship OCD and recognizing herself in its patterns [09:41], and learning how safety, self-awareness, and healthier coping mechanisms can interrupt behaviors rooted in childhood survival [13:31]. She also reflects on gratitude and transforming pain into art [20:16], balancing mental health with the demands of her music career [23:28], and how her parents’ divorce continues to shape her private life and family relationships [26:29], including hearing her brother’s perspective and confronting the absence of her father [27:00]. The conversation deepens as Naomi explores therapy and the process of finally meeting the younger version of herself who carried responsibilities far beyond her years [30:25]. She discusses learning to let difficult feelings exist without immediately trying to fix them [30:52], reparenting and comforting her inner child [31:26], and what she would tell her 12-year-old self today [33:07], leading to an emotional breakthrough symbolized by a powerful teddy bear story that Amber shares [33:41] and the release that comes from allowing herself to cry [37:25]. Amber and Naomi also explore choosing partners who create emotional safety, understanding different love languages [40:47], and the importance of centering yourself as you enter a new stage of adulthood [45:09]. Amber reframes ego as something that can be adjusted [46:34], reflects on discovering who she is when she's truly alone [49:22], and considers what real love looks like when two people continue changing and growing [52:38]. She closes by discussing the freedom of sharing her authentic self [54:05] and reflecting on a healing journey built around self-compassion, emotional honesty, and learning to give herself the safety she once searched for in others [55:36]. Ask or Share with Amber: withambergrimes@gmail.com Follow Amber Grimes on Instagram: @ambergrimes Follow Naomi Sharon: @naomisharon Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club Get Amber's Book Club Merch  Read Amber's Favorite Books See omnystudio.com/listener for privacy information.

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Ratings & Reviews

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About

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.

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