The making of a fashion powerhouse—how does a designer go from starting out to dressing Hollywood’s biggest stars?

Brandon Gray has built a brand that commands attention on the red carpet—from the NAACP Image Awards to the Oscars and the Met Gala. But behind those moments is a story of persistence, strategy, and learning how to build in an industry that rarely gives you a clear path.

In this episode of NAACP+ Inside the Industry, Brandon Gray breaks down how he turned House of Gray into a sought-after fashion brand, how he broke into the industry without connections, and what it really takes to build something that lasts in fashion.

We'll also cover:
- What it takes to dress high-profile clients
- How to turn talent into a real business
- How designers can stay relevant as fashion evolves

If you’re a designer, creative, or entrepreneur trying to build something of your own, this conversation gives you a real look at what it takes to go from starting out to becoming a recognized name.

About Brandon Gray:
Brandon Gray is the founder of House of Gray, a fashion brand known for dressing top talent at major events, including Colman Domingo, Tyler Perry, and Niecy Nash.

Subscribe to NAACP+ Inside the Industry for weekly conversations with leaders across film, television, fashion, and digital media.

Follow NAACP+ ITI: @naacpinsidetheindustry
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Facebook: @naacp

• (00:00:00) - Sneak Peek at Brandon Gray
• (00:01:14) - Episode Start
• (00:01:35) - Designing for The Met Gala
• (00:03:15) - How Brandon Defines Fashion
• (00:05:26) - His Responsibility as a Black Designer
• (00:06:27) - How Fashion Became his Profession
• (00:09:04) - What Influences his Style
• (00:10:14) - Moving from Inglewood to Paris
• (00:14:52) - Gaining Confidence in Your Abilities
• (00:16:31) - How he Overcome Imposter Syndrome
• (00:16:50) - Navigating Access and Opportunity as you Elevate
• (00:18:17) - Stay Ready so you Don't Have to Get Ready
• (00:19:24) - Making it Through the Pandemic
• (00:25:46) - Why it's Important to Travel and Network
• (00:27:03) - Your Network is your Net-worth
• (00:29:39) - Connecting to your Audience through Social Media
• (00:31:21) - Mistakes to Avoid
• (00:33:10) - Originality vs Following Trends
• (00:36:26) - The Next Era of Fashion
• (00:37:59) - Habits you Need to Succeed in Fashion
• (00:39:36) - What Aspiring Designers Should Focus on Now
• (00:40:59) - What his Legacy Will Be
• (00:44:38) - 3 Tips to Break into Fashion
• (00:44:40) - Who you Dress Matters
• (00:45:38) - Nothing Changes Overnight
• (00:46:08) - Originality is Still a Thing
• (00:46:49) - Exposure doesn't Always Pay the Bills
• (00:48:30) - Realizing I didn't Want to be a Lawyer

How do you break into Hollywood without connections?

For most people, the biggest barrier to entering the entertainment industry isn’t talent—it’s access. So how do careers actually get started when you don’t know anyone?

In this episode of NAACP+ Inside the Industry, James Swoope—Partner at M88—breaks down how aspiring creatives can break into Hollywood, how talent managers identify potential, and how opportunities are built behind the scenes.

From building relationships to creating leverage without traditional access, this conversation reveals how careers gain traction in today’s entertainment industry.

We cover:

• How to break into Hollywood without connections
• How talent managers discover and develop talent
• How opportunities and deals get made
• How relationships create long-term leverage
• What aspiring creatives should focus on right now

If you’re trying to get into the entertainment industry—or build a career from the ground up—this is your starting point.

About James Swoope:

James Swoope is a Partner at M88, where he helps guide talent strategy, package projects, and build opportunities for clients across entertainment and sports.

Subscribe to NAACP+ Inside the Industry for weekly conversations with leaders across film, television, music, and digital media.

Follow NAACP+ ITI: @naacpinsidetheindustry
Instagram: @naacp
Facebook: @naacp

• (00:00:00) - Intro to James Swoope
• (00:00:42) - Episode Start
• (00:05:28) - The Moment He Knew Management Was His Path
• (00:12:30) - The Hardest Part Of Breaking Into This Industry
• (00:13:31) - How He Overcame Imposter Syndrome
• (00:15:20) - First Step to Becoming a Manager
• (00:18:16) - Defining What a Manager Does
• (00:20:36) - Misconceptions about What Managers Do
• (00:22:51) - One Mistake that Aspiring Managers Make
• (00:25:13) - A Hard Lesson James Swoope Learned
• (00:26:21) - Mental Health and Overcoming Burnout
• (00:29:35) - How to Stay Competitive Today in the Industry
• (00:32:25) - What James Swoope Looks for in a Client
• (00:34:55) - Tips on Breaking Into Entertainment Without Connections
• (00:37:32) - Game: Real Talk or Industry Cap
• (00:40:31) - One Decision That Changed Everything For James Swoope
• (00:42:54) - James Shares a Question for the Next Guest

Welcome to the vertical storytelling era.

But how do you actually break into vertical storytelling and short-form content right now?
Short-form content is reshaping the entertainment industry—and creating new opportunities for writers, producers, and creators looking to build in vertical storytelling.

In this episode of NAACP+ Inside the Industry, Wendy Calhoun—writer, showrunner, and co-executive producer behind Empire—shares how she built a powerhouse career across traditional television and the rapidly growing world of micro dramas.

We cover:

• Why vertical storytelling is growing across platforms
• How short-form content is changing audience behavior
• What makes micro dramas successful
• How to approach writing and producing for vertical content
• Where creators can find real opportunities right now

If you’re a writer, producer, or creative trying to understand how to get into vertical storytelling and short-form content, this conversation gives you a clear look at where the industry might be headed.

About Wendy Calhoun:
Wendy Calhoun is a writer, showrunner, and executive producer known for her work on Empire, and is now building projects in vertical storytelling and micro drama formats.

This episode explores vertical storytelling, short-form content, and micro dramas, and how these formats are changing the entertainment industry. If you’re interested in TV writing, digital storytelling, or building a career in film and television, this conversation breaks down how the industry is evolving.

Subscribe to NAACP+ Inside The Industry for weekly conversations with industry leaders across film, television, and digital media.

Follow NAACP+ ITI: @naacpinsidetheindustry
Instagram: @naacp
Facebook: @naacp

#InsideTheIndustry #WendyCalhoun #VerticalStorytelling #MicroDramas #ShortFormContent #DigitalStorytelling #HollywoodCareers #EntertainmentIndustry #TVWriting #ContentCreation

• (00:00:00) - Inside the Industry: Introductions
• (00:01:06) - Intro to Wendy Calhoun
• (00:07:44) - How Wendy got into storytelling
• (00:09:45) - Wendy on breaking through in her career
• (00:14:25) - Wendy on overcoming microaggressions
• (00:17:21) - Defining Micro Dramas and a Vertical Dramas
• (00:18:47) - How dopamine keeps us watching this content
• (00:20:22) - How Microdramas have changed the way we consume stories
• (00:23:23) - Shocking Microdrama statistics
• (00:25:29) - How you can get into Verticals now
• (00:30:39) - Why it's important to own your content
• (00:31:30) - The importance of authentic voices and representation
• (00:35:20) - How KPop Demon Hunters changed the game
• (00:38:34) - Why emerging creators today have the advantage
• (00:39:51) - Will AI change the way stories are made?
• (00:44:09) - Hollywood is trying to play catch up to YouTube
• (00:45:36) - What Creators should be doing right now to get into Verticals
• (00:48:39) - 3 tips for producing a Micro Drama or Vertical

What does it take to build a career in entertainment today?

NAACP+ Inside The Industry is a new original series exploring how film, television, music, fashion, and digital culture actually operate—through conversations with the professionals shaping the business.

Hosted by Ariana Drummond, a publicist with over 15 years of experience across multiple areas of the industry, the series connects the dots between creative work and the business behind it.

Each episode features real stories, practical insight, and the decisions that define long-term success across entertainment careers.

Guests include producers, executives, designers, and creatives working at the highest levels of the industry.

- New episodes drop weekly on NAACP+.
- Subscribe for more conversations on film, television, music, fashion, and creative careers.

• (00:00:01) - Inside the Industry: How to Get Your Job