Advertise on podcast: If You Knew Better with Amber Grimes

What happens when you stop waiting for Hollywood to give you an opportunity and start creating your own? In this episode of If You Knew Better, Amber Grimes welcomes actor, writer, and producer Jean Elie for an inspiring conversation about betting on yourself [00:00] and embracing his "Green Light Yourself" philosophy [00:14]. Jean shares how industry rejection pushed him to create his own opportunities [00:41], why manifestation requires action [03:22], and the leap of faith that brought him to Los Angeles [06:57]. He discusses taking control of his career [09:48], hustling his way into a paid role on Project X [10:22], and how losing his brother shaped his fearless mindset [14:52]. From building opportunities through production [16:24] and overcoming doubts about his acting abilities [18:25] to encouraging creatives to stop waiting for permission [20:41], Jean reflects on finding inspiration through patience [21:18], trusting small wins [23:25], and navigating the unexpected emotions of reuniting with his Insecure castmates [23:56]. Jean also explains the importance of maintaining momentum [24:45], reflecting on his decision to pause Send Help[25:14] and how the 2023 Hollywood strikes disrupted his progress [26:37]. He opens up about prioritizing family [27:43], practicing self-compassion [28:36], embracing the stability of a nine-to-five [29:51], and building communities that financially support independent artists [31:10]. He introduces his Kickstarter campaign for Living Practical, a vertical mockumentary romantic comedy about a couple navigating newly acquired superpowers [32:49], before discussing personal trauma and safety [34:26], communicating needs with grace [39:10], and giving supporters behind-the-scenes access through Patreon [43:27]. The conversation closes with reflections on pride, perseverance, and his canyon metaphor for personal growth [45:16], reinforcing the power of believing in yourself and creating your own opportunities [45:57]. @ambergrimes Follow Jean Elie @jeanelie Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club See omnystudio.com/listener for privacy information.

What happens when the strong Black woman finally gives herself permission to put herself first? On If You Knew Better, Amber Grimes welcomes actress and comedian Tisha Campbell for an honest conversation about unmasking in her late 50s [00:00], therapy, complex PTSD, grief, and embracing her AuDHD diagnosis [01:25]. Tisha recalls an emotional Easter gathering that challenged her lifelong survival mode [07:39], teaching her self-compassion [12:57], healthier boundaries, and how motherhood shaped her need to appear strong [14:54]. She reflects on learning to live in the present [20:32], writing her book The A Word: A Mother and Son's Journey Through Autism and Love [23:38], receiving a diagnosis on set [26:19], and whether Damon would understand her personal transformation [27:49]. Tisha discusses confronting painful memories through journaling [29:57], turning those experiences into a book without a ghostwriter [30:34], and getting her son Zen's approval [34:07]. She shares how writing became therapeutic [35:53], the difficulty of discussing Zen's past suicidal thoughts [36:41], and the boundaries he helped her establish [40:27]. From discovering healing through stand-up comedy [44:30] and embracing creative freedom [46:36] to redefining masking [49:58], understanding autism traits [53:02], and introducing the world to the real Tisha Campbell [55:35], she offers an inspiring perspective on motherhood, mental health, authenticity, and personal growth [56:57].  @ambergrimes Follow Morris Chestnut @tishacampbell Get Amber's Newsletter on Substack Watch This Episode on Youtube Thursday at 6pm ET  Follow Amber's Book Club See omnystudio.com/listener for privacy information.

In this episode of If You Knew Better, Amber Grimes welcomes Morris Chestnut, Taylor Polidore, and Tank for a candid conversation about perseverance [00:00], career lessons, and their characters’ complicated dynamics [00:17]. They examine why talented men sometimes get a pass for bad behavior [00:52], the responsibility of men to protect women in uncomfortable situations [02:03], and the importance of respect and accountability [03:27], especially when women are unfairly labeled difficult [04:38]. The conversation explores portraying characters whose actions conflict with personal values [05:20] and approaching acting with empathy rather than judgment [06:26]. Tank credits Jamie Foxx as a pivotal mentor [07:14], while Taylor shares how memoirs from influential Black actresses helped guide her career [08:20]. They also discuss giving back and maintaining a strong work ethic [10:02]. The trio reflects on the sacrifices behind success [12:00], missing important family moments [13:21], navigating different seasons of life and career [14:14], and balancing ambition with family responsibilities [14:18]. They unpack handling rejection [15:27], including Tank’s humbling onstage experience [17:25] and a disappointing career setback for Taylor [18:53]. From advice to their younger selves about trusting the process and not taking rejection personally [20:38] to rapid-fire lessons inspired by their characters [25:15], Morris, Taylor, and Tank leave listeners with reminders about resilience, accountability, and staying committed to their craft [27:10]. Ask or Share with Amber: [email protected] Follow Amber Grimes on Instagram: @ambergrimes Follow Morris Chestnut @morrischestnutofficial Follow Taylor Polidor @taylorpolidor Follow Tank @therealtank 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.

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: [email protected] 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.

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: [email protected] 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.

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: [email protected] 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.

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: [email protected] 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.

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: [email protected] 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.

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: [email protected] 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.

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: [email protected] 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.

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: [email protected] 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.

In this episode of If You Knew Better, Amber Grimes challenges women to rethink modern dating by throwing away rigid relationship checklists in favor of 5 non-negotiables that prioritize character, compatibility, and emotional safety. Amber opens by inviting listeners to question their dating "type" [00:00] before explaining why it's time to let go of limiting checklists [01:13] and how that mindset shift transformed her own love story [03:14]. She reveals why attraction often grows through emotional connection rather than first impressions [04:56], explores the idea that many people know more about what they don't want than what they truly need [08:44], and introduces a practical framework for building healthier relationships through five intentional relationship buckets [10:33]. Amber then breaks down the first four non-negotiables—safety [12:16], communication and emotional availability [14:18], shared values [17:06], and future lifestyle alignment [19:33]. The conversation concludes by encouraging listeners to identify one authentic deal-breaker instead of an endless list of preferences [22:34], expand their dating pool by casting a wider net [24:22], and approach dating with greater intention through meaningful conversations rather than surface-level attraction [27:00]. Amber also reminds listeners that healthy relationships are built on mutual choice—not chasing someone who doesn't choose you back [30:56]—before leaving the audience with a practical exercise to redefine their approach to love [31:43]. Combining actionable dating advice, self-reflection, and relationship wisdom, this episode offers a refreshing roadmap for anyone ready to build stronger, healthier, and more intentional connections.  Ask or Share with Amber: [email protected] Follow Amber Grimes on Instagram: @ambergrimes 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.

In this episode of If You Knew Better, Amber Grimes sits down with Algee Smith for a thoughtful conversation about identity, purpose, and finding self-worth beyond success. Algee reflects on how social media and career milestones can become unhealthy measures of personal value [00:27], revisiting the breakthrough role that changed his life with The New Edition Story [01:08] and the lessons he learned about detaching his identity from achievements [03:00]. He opens up about career disappointments that once felt devastating [04:58], how faith helped him embrace the belief that delay is not denial [06:55], and the daily practices—including prayer, stretching, meditation, and journaling—that have grounded him through seasons of uncertainty [09:08] [10:31]. Algee also discusses balancing authenticity on social media [12:50] while protecting the parts of life that deserve privacy [15:27]. The conversation deepens as Algee shares how therapy transformed his perspective despite his initial skepticism [16:28], helping him uncover childhood experiences [19:02] that fueled a lifelong search for validation [20:08] and shaped his ambition through unresolved trauma [21:08]. He explains his philosophy of "winning the day" by focusing on daily habits instead of distant outcomes [22:37], embracing the process [24:44], and valuing skill development over raw talent [26:34]. Closing the episode, Algee previews his upcoming EP, television pilot, film projects, and producing ventures [27:57], offers advice to his younger self [29:41], and reflects on the growth that has made him most proud [30:41]. Honest, inspiring, and deeply reflective, this episode offers practical wisdom on healing, discipline, purpose, and defining success from the inside out.  Ask or Share with Amber: [email protected] Follow Amber Grimes on Instagram: @ambergrimes Follow Algee Smith: @itsalgee 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.

In this episode of If You Knew Better, Amber Grimes sits down with sports journalist Jemele Hill for an honest conversation about love, marriage, and building a partnership on your own terms. Jemele shares why she defines marriage as a daily commitment rather than a destination [01:04], reflecting on how years of prioritizing her career [03:03] and lessons from her family [03:23] initially made marriage feel unlikely. She opens up about meeting her husband [07:40], embracing a relationship without rigid expectations [09:05], and how a long-distance romance built on consistency, intention, and clear communication laid the foundation for their future together [11:42]. Jemele also recalls making their relationship public [14:53], explains the importance of "minding your business" instead of letting outside opinions dictate your relationship [17:06], and challenges common misconceptions about dating, marriage, and Black women's desirability. The conversation expands into the role money, ambition, and shared values play in healthy relationships, as Jemele discusses financial compatibility [22:42], redefining standards beyond salary [26:01], and the humorous story behind her "Amex glow up" [26:29]. She explains why unwavering career support from a partner matters [28:00], how marriage has increased accountability and encouraged greater vulnerability [29:44] [34:35], and why true emotional safety allows her to embrace a softer side of herself [37:07]. Closing the conversation, Jemele offers practical dating advice [41:49], shares her perspective on choosing marriage without feeling pressured by timelines around children [46:04], reflects on navigating a new season of professional transition [49:45], and wraps by discussing her latest book and what's next [53:16]. Thoughtful, empowering, and deeply personal, this episode offers a refreshing perspective on relationships, success, and defining happiness on your own terms.  Ask or Share with Amber: [email protected] Follow Amber Grimes on Instagram: @ambergrimes Follow Jemele Hilll: @jemelehill 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.

In this episode of If You Knew Better, Amber Grimes sits down with Lil Rel Howery for an inspiring conversation about building a lasting career in entertainment through persistence, purpose, and creative evolution. Rel reflects on the moment he realized he'd truly "made it" in film and television [00:46], then looks back to the high school performance that first showed him he could win over even the toughest audiences [02:04]. He shares how directing became part of his journey after encouragement from Bobcat Goldthwait [03:29], the lessons he learned making his directorial debut [06:19], why collaborating closely with every department shaped the experience, and how casting friends and fellow comedians—including support from Tiffany Haddish—helped bring his vision to life [07:56]. The conversation also explores his love of horror-comedy [11:00], how comedy continues to evolve alongside audiences [13:46], and the way grief and personal experiences have informed both his work and perspective [16:47]. Rel also discusses the importance of inspiring the next generation to understand the many career paths available in entertainment [19:10], the values instilled by his parents through community service and mentorship [22:46], and the filmmakers who inspired his own creative ambitions, from Steven Spielberg [27:08] to the lessons he drew from Sylvester Stallone and Rocky [29:04]. He explains why studying the business has been just as important as mastering the craft [30:37], the unique challenge of acting while directing [32:34], and how he now defines success through personal milestones like Get Out and his Chicago Theatre special [33:54] [36:36]. Closing on a reflective note, Rel shares how he stays grounded and present [43:53], the wisdom and healing that have shaped this stage of his life [47:07], and previews his new horror-comedy Haunted Heist, arriving in theaters on July 24 [50:50].  Ask or Share with Amber: [email protected] Follow Amber Grimes on Instagram: @ambergrimes Follow Lil Rel Howell: @comedianlilrel 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.