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

Follow Shayla Cowman:

@shayla_pc

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 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).&nbsp;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 &ldquo;sunglasses interview&rdquo; 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 &ldquo;24-hour rule&rdquo; (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:
<a href="https://www.instagram.com/ambergrimes">@ambergrimes</a>
Follow Shayla Cowman:
<a href="https://www.instagram.com/shayla_pc/">@shayla_pc</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

Shayla Cowan Knows How To Land The Plane

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/817fa9db-ef2a-4813-8f4b-b47900558e4b/transcript