In this episode of Creators Inc with Matt Sandler, rapper Symba and his manager and business partner Caston "Cas" Grigsby trace the through-line from a teenage party promoter charging five dollars at the door in Northern California to landing a role in a major Hollywood film and closing equity deals with Series B startups. From the moment Cas saw Symba on a Santa Monica stage, to the nine months they spent in the studio talking more about business than recording music, the two map out a partnership built on radical honesty and a refusal to be anything but authentic. Together they unpack what it really means to be a multi-hyphenate in today's entertainment landscape: why music is a marketing tool, how a calculated bet on an NFL freestyle turned into Monster Energy and Mitchell & Ness partnerships, and why knowing what you're giving—not just what you're selling—is the anchor of their business philosophy. This is a conversation about building something real when the old rules no longer apply.

Chapters:

00:00:00 - Intro

00:00:17 - Getting Space Jam 2

00:02:30 - Growing Up In the Bay Area

00:04:55 - From Basketball to Rap

00:07:54 - How Cas Met Symba

00:11:35 - Initial Disagreement Between Symba and Cas

00:13:20 - Discipline In the Studio / Honest Exchange

00:16:22 - Shift In How to Sell Music

00:22:49 - Ability to Connect / Building Business from Authenticity

00:30:18 - Business of Symba Today

00:32:02 - Viral NFL Freestyles & Partnerships

00:34:36 - Breaking Into Acting

00:37:26 - Making a Million Dollars Outside of Music

00:43:10 - How to Align With the Right Brands

00:45:11 - What Symba Wants to do with Amazon

00:48:55 - What Nipsey Hustle Taught Symba

00:50:38 - What Clarence Avant Taught Cas

00:53:22 - Most Important Check

00:58:04 - Outro

In this first episode of Creators Inc. with Matt Sandler, Nick Cannon and his longtime manager, Michael Goldman, run through their three decades together building Nick's career into one of the most durable and savvy in all of entertainment. From sneaking up to LA as a fifteen-year-old to warm up crowds at The Comedy Store and the Improv, to walking away from the biggest paychecks in network television on pure principle, Nick and Michael trace the through-line of a career built on the idea that ownership and honing instincts are non-negotiables. Together they talk about what it really means to incubate a brand from the inside out: the Wild 'N Out empire, the Masked Singer gamble that everyone said would end his career, and why watching Dave Chappelle say no to $50 million was the most important business lesson Nick ever received. Candid, hilarious and real, this is a conversation about what happens when you stop following others' playbooks and bet on your own.

Chapters:

00:00:00 - Intro

00:00:16 - LA Comedy Scene In the 90s

00:03:43 - How Nick and Michael Start Working Together

00:07:00 - Nick's Detour Into Rapping

00:09:00 - Getting Drumline Audition

00:12:44 - Developing Wild 'N Out

00:15:58 - Goldman on Importance of Wild 'N Out

00:21:23 - Getting Creative with Revenue Streams

00:28:54 - The Masked Singer Gamble

00:40:44 - Standing on Principal

00:41:47 - Creating with Amazon

00:45:57 - Dream Collabs, Jealousy & Best Advice

00:47:50 - Outro