Culprit Underwear: From Viral Marketing to Sales Tax Success with Numeral

About

Culprit Underwear

Culprit Underwear, a brand built on bold creativity and even bolder marketing, didn’t think they’d ever scale to become a multi-million dollar brand.

Industry

Fashion & Apparel

Migrating From

TaxJar

Culprit Underwear's website
It was started in 2017 as a side hustle by filmmakers David and Dylan, who crafted small batches of underwear for friends and family. Then came 2020, and with it, the global pandemic that brought the film industry to a grinding halt.

Suddenly faced with the uncertainty, David and Dylan saw an opportunity.

They had a product, filmmaking expertise, and a burning desire to break free from the constraints of commercial filmmaking. They poured their creative energy into crafting a commercial for their underwear, launched it on YouTube and Facebook, and watched in awe as it took the internet by storm.

“David and Dylan, being kind of wild entrepreneurs, were like, this is a good opportunity because we’ve always loved making commercials because that’s what they do for a living, but they were always tired of making commercials for other people because they got put in a creative box. No one ever took their ideas seriously when they had big, bold, wild ideas.”

Tim Fox, a stage actor and waiter, received a life-changing call from Dylan amidst the chaos.

“It’s blowing up, and I need help,” Dylan declared, referring to their burgeoning underwear business. And with that, Tim found himself thrust headfirst into the whirlwind world of Culprit Underwear, quickly rising to the position of COO. “I literally didn’t know anything,” Tim admits. “When they gave me the head of operations role, I was looking at an email, and I was like, Dylan, what’s a pallet?”

Their journey with Culprit Underwear was a crash course in entrepreneurship, filled with challenges that tested their resilience and forced them to learn on the go. They experienced the difficulties of working with multiple fulfillment centers, including one particularly distressing experience where Tim had to “break into this facility and get $4 million worth of underwear out of there in six hours” after their fulfillment center went bankrupt.

But little did they know there was a much bigger threat to their business—tax compliance.

Challenge

As Culprit Underwear’s popularity exploded and orders poured in from across the country, a stack of envelopes began piling up at Dylan’s doorstep—their temporary company headquarters. These were official notices from various state governments, each bearing the dreaded words “sales tax.”

“We started getting these letters on the side… from all of these states, and we were like, what’s going on here? What are all these letters from South Dakota, Washington, Florida, California?”

Initially, they ignored the letters, hoping the problem would magically disappear. But as the stack grew taller, reality began to set in. A quick investigation revealed a harsh truth – they hadn’t been collecting sales tax on their Shopify store.

“We looked at it, and we didn’t know what to do,” Tim recalls. “Shopify doesn’t make that automatic. Like it’s a button you have to turn on when you start your store, which I was absolutely thunderstruck by because I think that’s not only unfair, but just kind of shocking.”

Panic set in. Untangling years of unfiled sales tax felt impossible.

Solution Needed

Their first attempt at tackling the sales tax beast led them to OmniTax Solutions, a company recommended by a fellow entrepreneur. While OmniTax proved helpful with payment plans and mitigating penalties, they didn’t offer filing services, leaving Culprit to handle submitting their returns manually.

Hoping for a more comprehensive solution, they found TaxJar, a well-known name in sales tax automation. What followed was an experience that can only be described as a masterclass in frustration.

“TaxJar is terrible,” Tim said. “Their platform was really confusing… I tried reaching out to TaxJar to merge those accounts… and not being able to get them to actually do anything.”

Instead of easing their burden, TaxJar added another layer of complexity. The platform’s confusing interface, coupled with nonexistent customer service, brings them back to square one, but with the added weight of wasted time and mounting anxiety.

Solution

Just as their sales tax situation felt unmanageable, an email from Numeral landed in Tim's inbox. It was a simple message inquiring about their sales tax setup and offering assistance.

"It was perfect timing," Tim recalls. "Just moments before, I was wrestling with this exact issue, feeling completely overwhelmed."

Right from the initial meeting with Kevin and Sam from Numeral, Tim sensed a different energy. This wasn't just another sales pitch—it was a genuine connection. They understood Culprit's brand, their entrepreneurial journey, and their anxieties. This wasn't about closing a deal; it was about building a partnership fueled by trust and a shared drive to see Culprit succeed.

_“We immediately clicked with Kevin and Sam,