How Google, God and $500 made this Supermom into a viral money maker! (with Trina Smalls)

We’re kicking off season three of How I Got Here with Dreena Whitfield with Trina Small, founder, and CEO of Supermom Culture.

Trina dreamed up the idea for Supermom Culture when clothing brands didn’t speak to moms of all kinds — single, divorced, of all ages and abilities. So her brand celebrates the moms who get it all done, even when sh*t hits the fan.

When she got a call from Good Morning America to appear on the show and sell 10,000 units, she was still producing each shirt from the guest bedroom in her house. The pandemic dried up the t-shirt supply chain, and she’d never scaled her business to that production level. Still, Trina knew she was going to figure it out. 

Listen as Trina tells us how her previous career path helped her navigate her apparel business, why social media has been key to the success of Supermom Culture, and how the community of Supermoms has been key to bringing the brand to the next level.

Connect with Trina on…

Instagram: https://www.instagram.com/heytrinasmall

Follow Supermom Culture on Instagram: https://www.instagram.com/supermomculture/?hl=en 

Get your Supermom on: https://supermomculture.com/ 

About the Host:

Dreena Whitfield has a proven ability to create tangible outcomes that help clients exceed expectations. Her diverse career has led her to spearhead the communications and marketing efforts for leaders in the nonprofit, corporate, and political sectors and small businesses internationally.

With more than a decade of experience, Dreena and the WhitPR team have a proven ability to spot opportunities for our clients to grow their brand recognition in saturated markets that align with their overall objectives. The Huffington Post named Dreena as one of their “Top 25 African American Millennials in PR to Watch.”

Follow Dreena, WhitPR, and the show on all the socials:

@dreenawhitpr, @whitpr & @howigothere_

Join The WhitPR Collective: www.whitprcollective.com

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit howigotherewdreenaw.substack.com

Creators and Guests

Host

Dreena Whitfield

Dreena Whitfield-Brown is the Founder and CEO of WhitPR, an integrated strategic communications agency with 15+ years serving clients in the nonprofit, corporate, and political sectors. Recognized as one of PRWeek's 40 Under 40, a PR News Top Woman in PR, and named to Inc.'s 2025 Female Founders 500 List. She created How I Got Here to have the raw, honest conversations about entrepreneurship that nobody has on the record.

Producer

Keena Williams

Keena Williams is the founder of Struxa and the Executive Producer, Writer, and Creative Director of How I Got Here.

What is How I Got Here with Dreena Whitfield?

How I Got Here with Dreena Whitfield goes beyond the highlight reel with Black women founders, executives, and leaders. Real conversations about the pivots, the setbacks, and the purpose behind the work. From bootstrapping a beauty brand with $500 to leading a professional sports franchise, each episode explores the moments that shaped who they became and the cost of building something meaningful.
For women navigating leadership, business ownership, career reinvention, and the cost of ambition.

New episodes biweekly on Wednesdays.

Host: Dreena Whitfield
Executive Producer, Writer & Creative Director: Keena Williams / Struxa
howigotherewdreenaw.substack.com