Lil Rel Howery Knows You Have To Define Your Own Success.

Lil Rel Howery Knows You Have To Define Your Own Success.

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].  Follow Amber Grimes on Instagram: @ambergrimes [https://www.instagram.com/ambergrimes] Follow Lil Rel Howell: @comedianlilrel [https://www.instagram.com/comedianlilrel/] Get Amber's Newsletter on Substack [https://substack.com/@withambergrimes] Watch This Episode on Youtube Thursday at 6pm ET  [https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0] Follow Amber's Book Club [https://www.instagram.com/ambersbookclub/] Get Amber's Book Club Merch  [https://ambersbookclub.com/collections/hats] Read Amber's Favorite Books [https://a.co/d/01GreLFP] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Amber Knows She's Pregnant

In this special episode of If You Knew Better, Amber Grimes shares the biggest personal announcement of her life—she's expecting her first child. Amber opens the episode with her exciting pregnancy reveal [00:00], explains why she waited to share the news publicly [01:59], and reflects on manifesting the space to embrace motherhood through maternity leave [03:52]. She also recounts the encouraging conversation in Las Vegas that shifted her mindset [05:22], the emotional moment she took the pregnancy test [06:41], and the unforgettable surprise of telling Conor they were expecting [08:59]. Amber candidly discusses keeping the pregnancy private [11:16], navigating first-trimester exhaustion [11:50], and adjusting to new routines centered around nutrition, hydration, and prenatal care [14:04]. As the journey continues, Amber shares the emotional experience of telling family at 12 weeks [17:32], explains why she chose to skip a traditional gender reveal [19:13], and instead joyfully reveals the gender on the show [19:54]. Looking ahead, she invites listeners to be part of this next chapter [21:02], laughs about baby names and maternity fashion [23:17], and closes with heartfelt reflections on gratitude, growth, and the life-changing adventure of becoming a mother [24:02]. Filled with vulnerability, excitement, and optimism, this episode marks the beginning of a deeply personal new season and celebrates the power of embracing life's biggest milestones. Ask or share with Amber: withambergrimes@gmail.com [withambergrimes@gmail.com]  Follow Amber Grimes on Instagram: @ambergrimes [https://www.instagram.com/ambergrimes] Get Amber's Newsletter on Substack [https://substack.com/@withambergrimes] Watch This Episode on Youtube Thursday at 6pm ET  [https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0] Follow Amber's Book Club [https://www.instagram.com/ambersbookclub/] Get Amber's Book Club Merch  [https://ambersbookclub.com/collections/hats] Read Amber's Favorite Books [https://a.co/d/01GreLFP] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Candiace Dillard Bassett Knows IVF and Family Planning

In this episode of If You Knew Better, Amber Grimes sits down with Candiace Dillard Bassett for a candid conversation about fertility, IVF, and the deeply personal journey to intentional motherhood. Candiace shares why family planning became a priority [00:00], walks through the beginning of her IVF experience [03:00], and breaks down the importance of genetic testing [06:10] and understanding the IVF process [09:09]. She opens up about navigating hormonal treatments [12:01], overcoming physical and emotional challenges throughout the process [14:54], the realities of egg retrieval [18:11], and processing gender expectations and disappointment [21:01] while learning to trust her own path. Candiace also reflects on the emotional highs and lows of IVF [23:49] and how the experience ultimately reshaped her perspective on motherhood [27:12]. The conversation continues with an honest look at emotional resilience during fertility treatments [32:32], why Candiace chose to publicly share her story to help others [35:54], and the importance of thoroughly researching fertility options [37:50]. Amber and Candiace also discuss the unique healthcare challenges Black women face [40:37], advocating for yourself in medical settings and interracial relationships [43:44], the invaluable role of doulas during childbirth [47:34], and Candiace's labor and delivery experience [50:29]. The episode closes with reflections on balancing music and personal growth [53:34] and how motherhood has transformed her life, purpose, and identity [56:59]. Blending vulnerability, education, and empowerment, this episode offers an insightful guide for anyone navigating fertility, reproductive health, and the evolving journey of motherhood. Follow Amber Grimes on Instagram: @ambergrimes [https://www.instagram.com/ambergrimes] Follow Candiace Dillard Bassett: @therealcandiace [https://www.instagram.com/therealcandiace/] Get Amber's Newsletter on Substack [https://substack.com/@withambergrimes] Watch This Episode on Youtube Thursday at 6pm ET  [https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0] Follow Amber's Book Club [https://www.instagram.com/ambersbookclub/] Get Amber's Book Club Merch  [https://ambersbookclub.com/collections/hats] Read Amber's Favorite Books [https://a.co/d/01GreLFP] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Shayla Cowan Knows How To Land The Plane

In this episode of If You Knew Better, Amber Grimes sits down with award-winning producer and Collective Edge President Shayla Cowan for an insightful conversation about leadership, career evolution, and building a lasting legacy in entertainment. At (00:30), Shayla is introduced, followed by a look at how she and Amber first connected at (01:12). By 04:15, Shayla shares why she made the move from Los Angeles to New York, and at 06:18, she reflects on her 15-year journey in the industry. At (09:02), she breaks down her rise from executive assistant to manager, including a memorable “sunglasses interview” story at (14:03) that highlights her boldness and work ethic (17:00). The conversation continues with insights on leading as the boss (21:11), balancing comfort and creativity (23:48), and planning major career moves (25:33), all while navigating imposter syndrome (28:16). The episode also dives into the leadership skills that define successful executives, including setting boundaries and leading with empathy. Shayla shares how she manages stress through baking (30:10), self-talk and music (30:34), and offers strategies for handling difficult people (31:36), including her “24-hour rule” (34:50) and approach to disarming tense situations (36:57). She recounts powerful industry moments like the Pulled Up Agency story (38:47), explores the balance between ego and leadership (43:42), and walks through a high-pressure concert contract crunch (46:58). The conversation wraps with lessons on maintaining boundaries and off-hours (49:05), leaving your light on for opportunity (50:55), and putting actionable steps together (52:24), before closing with key takeaways and gratitude at (54:27). Through candid storytelling and practical advice, Shayla offers invaluable lessons on executive leadership, personal growth, resilience, and building influence without sacrificing authenticity. Follow Amber Grimes on Instagram: @ambergrimes [https://www.instagram.com/ambergrimes] Follow Shayla Cowman: @shayla_pc [https://www.instagram.com/shayla_pc/] Get Amber's Newsletter on Substack [https://substack.com/@withambergrimes] Watch This Episode on Youtube Thursday at 6pm ET  [https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0] Follow Amber's Book Club [https://www.instagram.com/ambersbookclub/] Get Amber's Book Club Merch  [https://ambersbookclub.com/collections/hats] Read Amber's Favorite Books [https://a.co/d/01GreLFP] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Justin Tranter Knows It’s Never Too Late To Pivot

In this episode of If You Knew Better, Amber Grimes sits down with Justin Tranter for a candid conversation about career reinvention, creativity, and finding success on your own terms. Justin reflects on the journey from rock star to hit songwriter [00:00], sharing how understanding the balance between artistry and industry structure [11:20] ultimately led to a major career pivot [20:47]. Justin opens up about recognizing when change is necessary, embracing new opportunities, and discovering the joy of writing songs for other artists [25:52]. The conversation offers valuable insight into navigating the music business while remaining authentic, adaptable, and committed to personal growth. Amber and Justin also explore the realities of sustaining a creative career, discussing the songwriter's journey [27:51], setting meaningful and achievable goals [31:53], and the importance of self-awareness in identifying strengths and limitations [36:25]. Justin shares lessons on pivoting throughout different stages of life and career [39:49], challenges common misconceptions about fame and success [45:01], and explains why embracing both strengths and weaknesses is essential for long-term fulfillment [51:06]. Packed with wisdom for creatives, entrepreneurs, and anyone facing a crossroads, this episode is a masterclass in evolution, resilience, and trusting the path forward.  Follow Amber Grimes on Instagram: @ambergrimes [https://www.instagram.com/ambergrimes] Follow Justin Tranter: @tranterjustin [https://www.instagram.com/tranterjustin/] Get Amber's Newsletter on Substack [https://substack.com/@withambergrimes] Watch This Episode on Youtube Thursday at 6pm ET  [https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0] Follow Amber's Book Club [https://www.instagram.com/ambersbookclub/] Get Amber's Book Club Merch  [https://ambersbookclub.com/collections/hats] Read Amber's Favorite Books [https://a.co/d/01GreLFP] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.