Symba and Cas Grigsby on Space Jam, NFL Freestyles and Making A Million In A Year Without Dropping Music

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