# Outsmarting the Big Guys: Building a Challenger Brand Agency from Scratch

An episode of [Do Small Business Like a Big Boss Podcast](https://invisiblenetwork.ai/podcast/1860975420), 9 Jul 2026, 37 min.

Audio: https://api.riverside.com/hosting-analytics/media/b309dc0b2c6e1e6108133e8efda98fa27e7e367177665ee75ce7689c478a369c/eyJlcGlzb2RlSWQiOiJlNzE0ODc3OS0wYjVjLTQzMzgtYjU1NS05Y2QwNjUxZDc1NzkiLCJwb2RjYXN0SWQiOiIwN2NhY2I0Mi03YzBmLTQ0ZDQtODg0ZC04YmUyMzA0MzEyNGUiLCJhY2NvdW50SWQiOiI2ODdhZjZjNWY1MjhmYzVlMDY2ZTc2ZmQiLCJwYXRoIjoibWVkaWEvY2xpcHMvNmE0Zjk5NTg4ODI1NWRhYWJjM2Y0MmQ2L2Fpc2hhLW1hc3NlbmdpbGxzLXN0dWRpby1jb21wb3Nlci0yMDI2LTctOV9fMTQtNTEtMzYubXAzIn0=.mp3

In this episode of Do Small Business Like a Big Boss, host Aisha Jorge Massengill sits down with Justin Bajan, Co-Founder and Creative Director of Familiar Creatures, to talk about leaving a six-figure career to build an award-winning independent advertising agency from the ground up. Justin shares how his team helps challenger brands outsmart larger competitors, the realities of entrepreneurship, and the lessons that helped Familiar Creatures become one of Adweek’s fastest-growing agencies. 🎧 What You’ll Learn in This Episode: • How Justin transitioned from corporate life to launching his own agency • The realities of pricing professional services and avoiding undervaluing your work • How Familiar Creatures evaluates potential clients using its “Smiley Face System” • Why saying no to the wrong opportunities can accelerate long-term growth • How small, agile teams can outperform much larger competitors ⏱️ Episode Timestamps: • 00:03 – Introduction • 01:10 – Leaving a six-figure salary • 02:56 – Moving his family to start over • 03:26 – Why Richmond became home for the business • 07:09 – Landing the first anchor client • 09:20 – The financial realities of early entrepreneurship • 11:58 – Learning while building the business • 13:52 – Pricing professional services • 17:22 – Building a reputation over time • 18:33 – Making decisions as business partners • 21:47 – The creative process behind successful campaigns • 26:06 – Scaling the agency from 2 to 10 people • 29:30 – Choosing the right clients • 30:23 – The “Smiley Face System” explained • 33:23 – Why saying no can be the best business decision • 37:57 – How small teams outperform big agencies • 41:08 – What “Do Small Business Like a Big Boss” means to Justin • 43:06 – Where to connect with Justin and Familiar Creatures 👤 About the Guest: Justin Bajan is the Co-Founder and Creative Director of Familiar Creatures, an independent advertising agency based in Richmond, Virginia. Since launching in 2018, the agency has been recognized as one of Adweek’s 25 fastest-growing agencies and has helped challenger brands like Duke’s Mayonnaise, Crunch Fitness, and Bubba Burger achieve remarkable growth through strategic creative marketing. Website: familiarcreatures.com Instagram: @familiarcreatures Want to see how your business stacks up? Download this business self-assessment: www.smallbizzlegalguide.com Stay Connected with Sedgwick Andrews: 👉 https://linktr.ee/Sedgwick_Andrews_LC Build the dream messy, build it scared, just don't build it small. If this episode helped you, don't forget to subscribe, download, and share with another boss who needs to hear it. 🎧

## Transcript

Aisha Massengill: Me it to me it means owning. It. Owning what you do, having a sense of who you are, and going with it. It's not about asking for permission, it's asking for forgiveness. It's not about being reluctant, it's about taking shots and big swings and somehow balancing all of that with empathy on top of that. Welcome to Do Small Business Like a Big Boss, where we explore the real stories, hard-earned lessons, and game-changing strategies of entrepreneurs who've moved beyond the side. Hustle and build businesses that scale with confidence. This show is proudly sponsored by Project Icon. I'm your host, Aisha Jorge Massingil, your small business legal guide. Let's dive in. What up, bosses? Welcome to the latest episode of Do Small Business Like a Big Boss. I am your host, Aisha Jorge Massingil, your small business legal guide. And today we are pumped to have Justin Bajin. Justin is the co-founder and creative director of Familiar Creatures, an independent advertising agency based out of Richmond, Virginia. In 2018, he walked away from a six-figure salary, packed up his wife and three daughters, and drove a minivan from Boston to Richmond to bet on himself. Starting his agency with just one client, a local brewery, and a big idea about how Challenger brands could punch above their weight. Today, Familiar Creatures has been named one of Ad Week's 25. fastest growing agencies in the world. Their clients include Dukes Mayonnaise, Crunch Fitness, Bubba Burger, amongst others. This is my favorite part. They've become known for helping smaller brands outsmart, not outspend the big guys. And this is why he's a perfect guest for this show. Welcome Justin. Hey thanks for having me. So let's start at the beginning. You had a six-fig figure salary. I'm imagining a family with a comfortable life in Boston. What was that actual moment or feeling that made you say, I'm gonna blow this thing up and I'm gonna start from scratch? Yeah. It was ⁓ staying in conversation with, you know, my future

Shows are listed from Apple Podcasts' charts and directory, and Podcast Index where it is used. Every show and episode belongs to its publisher and plays from the publisher's own feed; this site hosts none of them.