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.

If You Knew Better with Amber Grimes is a education podcast hosted by Amber Grimes, with 31 episodes on record and a Required Pod Score of 80.

Amber Grimes hosts If You Knew Better with Amber Grimes, a education show with 31 episodes published.

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  Episode #30

  Olly Sholotan Knows What’s For You Is For You

  Sep 22, 202648 minS1

  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.

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  Episode #29

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

  Sep 15, 202646 minS1

  In this episode of If You Knew Better , Amber Grimes sits down with WNBA legend A ngel 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.

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  Episode #28

  LaShawnda Woodard Knows the Hardest Person to Forgive Is Yourself

  Sep 8, 202659 minS1

  In this episode of I f 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 See omnystudio.com/listener for privacy information.

  ListenShow Notes
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  Episode #27

  Justice Baiden Knows Pursuing Your Passion Should Come Before Pursuing Partnership

  Sep 1, 202651 minS1

  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.

  ListenShow Notes
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  Episode #26

  Gail Bean Knows Defensive Dating

  Aug 25, 202642 minS1

  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.

  ListenShow Notes

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