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:withambergrimes@gmail.com

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

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&mdash;including support from Tiffany Haddish&mdash;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].&nbsp;
Ask or Share with Amber: <a href="mailto:withambergrimes@gmail.com" data-ogsc="">withambergrimes@gmail.com</a>
Follow Amber Grimes on Instagram:
<a href="https://www.instagram.com/ambergrimes">@ambergrimes</a>
Follow Lil Rel Howell:
<a href="https://www.instagram.com/comedianlilrel/">@comedianlilrel</a>
<a href="https://substack.com/@withambergrimes">Get Amber's Newsletter on Substack</a>
<a href="https://youtube.com/@iykbetter?si=WMEDSWNJOsxlRkD0">Watch This Episode on Youtube Thursday at 6pm ET&nbsp;</a>
<a href="https://www.instagram.com/ambersbookclub/">Follow Amber's Book Club </a>
<a href="https://ambersbookclub.com/collections/hats">Get Amber's Book Club Merch&nbsp;</a>
<a href="https://a.co/d/01GreLFP">Read Amber's Favorite Books</a>

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.

You can&rsquo;t rewrite the past &mdash; 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.
&nbsp;
If You Knew Better is where Amber shares that wisdom &mdash; 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.
&nbsp;
Together, they unpack the highs, the lows, and the pivots in life, career, and relationships &mdash; so you either don&rsquo;t have to go through it, or can move smarter when you do.
&nbsp;
Every episode delivers real talk, hard-won insight, and practical gems to help you grow into the version of yourself that knows better&hellip; and does better.

If You Knew Better with Amber Grimes

Lil Rel Howery Knows You Have To Define Your Own Success

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/c6790623-bdfe-4431-85b5-b48e001b2fb3/transcript