How an Iraq War Veteran Launched an $8 Million Ecommerce Empire from Prison & Whipped Depression

How an Iraq War Veteran Launched an $8 Million Ecommerce Empire from Prison & Whipped Depression

The first sketch was made in a gang-infested federal prison.

So was the second, third, and the dozens that followed.

“I just started sketching out t-shirt ideas and making notes,” says Shawn Wylde, a Marine convicted of defrauding the country he once proudly served in Iraq.

Wylde’s past may have cost him his freedom for a time, but not his creativity.

I mailed myself hundreds of pages of notes from prison. That way I’d be sure to have all of my designs and social media strategies when I got out.

Wylde’s path is littered with controversy, war, and suicidal thoughts.

But believe it or not …

Those are also the very things that would ultimately help him build a multimillion dollar ecommerce enterprise now impacting the world in humorous, patriotic, and charitable ways no one but Wylde likely ever imagined possible at the time.

It’s probably a bit cliche’ to argue prison saves lives.

In Wylde’s case it may have.

Because for a time, he certainly didn’t seem interested in saving his own.

A Rebel’s Rebel

It’s the bathroom break heard ‘round the military world.

The security officer tasked with escorting a then 21-year old Wylde from the Virginia Military Institute campus from which he had been expelled let down his guard for just a moment and unknowingly ushered in two weeks of alumni weekend chaos that would reverberate across campus for years to come.

“The officer had to use the bathroom and left me alone for just a moment,” Wylde recalls of what was supposed to be his last day on VMI’s campus.

Instead, Wylde made a break for it, hid out for weeks, and continued to secretly organize protests like the one that got him expelled. The protests aimed to embarrass school administrators for what Wylde describes as a mishandling of VMI cadet discipline procedures.

With a laugh about eluding campus authorities, Wylde recalls:

“They were chasing me all over campus as I was jumping out windows to escape I was just standing up for what was right and later learned from high ranking military alumni that I was seen as a sort of cult hero for challenging the poor leadership.”

But that cult hero status would soon fade.

Following a tour of duty in Iraq, a bout of post-traumatic stress disorder and a traumatic brain injury, and no plan to return to school like his peers were all doing since his VMI experience, Wylde did the only thing that felt natural; he joined the Marine reserves and was once again placed on active duty. But as that stint ended, and Wylde once again had no plan for the future or way to deal with the depression and anxiety that accompanied the death of several friends in Iraq, Wylde began to self-destruct.

"I lost faith in the country's approach to sending people to war. I lost friends and Marines and blamed the military. I wasn't thinking clearly and I was spiraling downward fast"

Wylde needed a pick me up.

The Department of Veterans Affairs owed him over $100,000 so he rationalized he could get what he deserved through defrauding the military:

It was a natural high. It was exhilarating and I started to enjoy getting away with it. It’s how I got my thrills.

As you might expect from a guy who changed his last name from Joyce to Wylde, the thrill of not getting caught eventually lost its oomph.

Wylde needed a bigger rush.

So he began taunting military auditors, hinting at the fraud, and daring them to catch him if they could.

They did.

Not only did auditors uncover more than $90,000 in false lodging receipts and Veterans Affairs benefits he earned but wasn’t supposed to receive while on active duty, the case was turned over to the Department of Justice for prosecution. The Marines declined to pursue the case.

It’s almost incomprehensible, isn’t it?

In Wylde, the United States had a Marine Corp Captain who had implemented logistics software which saved the military millions of dollars and prevented service members from dangerously entering battle short staffed. In fact, the most senior officers rated Wylde as an exceptional Marine and summed up his value this way on his performance reports:

  • “He is the biggest long ball hitter on the staff and is the one person that absolutely makes the subordinate battalions successful here and in combat."
  • “Dynamic, remarkably gifted; clearly cut above. Midas touch; everything turns to gold.”
  • “The best I have seen."

So what was the world missing about Wylde?

He didn’t even need the money he was stealing from Uncle Sam as evidenced by the fact he paid it all back in one check the day he was sentenced to four months in a federal prison.

He had over $100,000 the VA owed him.

In fact, he had his own savings, more than $100,000, and he had secretly been using it to pay for private mental health counseling rather than ask military doctors for help and risk being stigmatized. 

So what did we all miss with Wylde?

The secret was revealed for everyone the night Wylde drank too much, popped too many pills, and woke up in an ambulance to learn he had tried to kill himself.

I was going to die or get over it. It was prison or death.

Prison it was.

But before being locked up Wylde, who was now broke, would have to come up with $4,000 he owed his lawyer. Wylde was tired of borrowing from his family and for some reason recalled a Facebook page he ran while in the Marines; one that humorously poked fun at life in the Marine Corps.

“I kept the page a secret from superiors and never took the page seriously but realized it had more than 20,000 fans.” 

What might appeal to 20,000 Marines?

Wylde, who by now you know has a knack for designing t-shirts, created his first ever that read “American As F*ck”, threw up an image on the Facebook page, and made $5,000 in one week; plenty to pay his lawyer and pocket a profit.

Wylde had proof of concept.

But he also had four months to serve in prison.

Launching on House Arrest

Eighteen hour days every day. 

That’s how Wylde describes life after serving his prison sentence, taking a bus cross country to live with family, and creating American AF, a collection of humorous and patriotic clothing, from the piles of notes he had mailed himself from prison.

“I was on house arrest,” Wylde says with a laugh. “What else was I going to do but work?”

American As F*ck, or AAF, launched on Shopify and a few months after being released from prison had sold $1.2 million of apparel. “Shopify made it super easy and I created the site from scratch,” Wylde says. “This was my second chance and Shopify allowed me to pour everything I had into making it successful.”

Wylde had been in the service for eight years and thought he’d have to painstakingly hard code an ecommerce site himself. “To discover an out of the box solution that helped me ramp up so quickly is unbelievable,” Wylde says.

But this is Wylde we’re talking about.

Cue the controversy!

“Oh, jeez,” Wylde laughs when asked about any bumps in the ecommerce road. “I move at the speed of light which means I hire fast and fire even faster.”

Wylde cites an instance in which he was growing so quickly the t-shirt printer he had partnered with couldn’t keep up with demand. Instead of owning up to a growing backlog, though, Wylde says the printer lied and wasn’t shipping the apparel he promised he was.

“I had to send a lot of apology emails to customers. There were a lot of delays and definitely some bumps in the road.”

But customers weren’t deterred.

They continued buying from AAF and the company continued its torrid triple digit growth rate.

“Everyone recommended Shopify to me and they were right,” Wylde says of his ecommerce mentors.

I never would’ve gotten to $1.2 million in sales so quickly without Shopify.

In 2016, with growth accelerating, AAF upgraded to Shopify Plus, an enterprise ecommerce solution for high volume merchants. It was just before July 4th, one of AAF’s busiest times of year, and Wylde suddenly noticed a problem that could cost him dearly; the brand new AAF site he had created for Plus was loading extremely slow.

Wylde’s Plus account manager noticed and showed the site to a Shopify engineer who identified the problem and outlined a fix just in time for the Independence Day holiday. “I never expected the level of service I got from Shopify,” Wylde says.

The results:

  • The site’s conversion rate doubled
  • Profit margins doubled

Subsequently, AAF also leveraged Plus’ ability to customize the checkout experience to further increase conversions and earn customer trust. “The people at Shopify are awesome,” Wylde says. “It was an immediate bump in profits and there’s no way AAF would be where it is today without the people at Shopify.”

As of this writing, AAF has done more than $8 million in sales in just fifteen months. What started as a company that sold almost exclusively to Marines now counts 98-percent of its customers as civilians who purchase shirts to display their patriotism or as a way to evoke laughter at a party.

“The secret is we make fun of everyone,” Wylde says of the Democrat and Republicans often featured on AAF’s apparel. “Everyone told me I had to choose a side in the beginning but we’ve proven you can poke fun at both sides and still be successful.”

Wylde, who admits he didn’t even know what a SKU was in the beginning, credits Shopify’s simplicity with allowing him to focus on what’s really important; building the business and a strong team that can grow it.

The success isn’t something Wylde hoards.

In fact, Wylde shares AAF’s profits with the small team he has built. “They seem to like me,” he says of his employees with a laugh. “I give them a cut of the profit at the end of every month so there’s no waiting for yearly bonuses. I reward them immediately because it’s so fast paced.”

That team Wylde has built, which can now run the business even if Wylde steps away, is what he’s most proud of at AAF.

“It was immediately profitable, but it wasn’t sustainable,” Wylde says of the early days. “It’s my baby, but it can make money without me now which is why I’m so proud of the team we have.”

The Secret Sauce: Obsession

“The real secret to success is obsession,” Wylde says. “Entrepreneurship is my obsession and gives me so much that’s why I work 18-hour days.”

Wylde’s obsession is growing.

Besides being involved with four other ecommerce stores, Wylde has also taken over ecommerce operations for the military brand OAF Nation increasing their online sales exponentially:

“There’s definitely a similarity between the military and entrepreneurship when it comes to life and death. Obviously, the repercussions aren’t as severe in entrepreneurship, but the threat of failure is real and motivates you to give it your all.”

Wylde’s all has certainly paid off in a variety of ways.

Case in point Wylde now credits his business success and the Marine Corps, with allowing him to help others in need. The Marines gave Wylde a Honorable discharge, despite his conviction and prison sentence. To date, Wylde has donated more than $103,000 to various military and police charities including $36,500 after five officers were killed in an ambush in Dallas.

“I’m really happy doing ecommerce. And the military was good to me. Getting second chances in the land of opportunity is American As F*ck. Especially after making a mistake and being labeled by some as a bad person, it feels fantastic to be able to give money away and help people who really need it.”

In helping others heal… turns out Wylde has also healed himself.

I’m the happiest I’ve ever been but not because of my financial success. I broke out of depression and anxiety, I beat it. I’m just me now and it’s great.

About the Author

Nick Winkler is a contributor to the Shopify Plus blog and founder of The Winkler Group, a strategic communications firm that provides content marketing services to the world's best-known brands, businesses, and marketers. Get more from Nick here.