From Prison to $40M in Sales: An Iraq War Vet's Multi-Store Ecommerce Strategy

Launched from a federal prison cell, Shawn Wylde's ecommerce empire employs a distinctive multi-store approach that utilizes customized checkout experiences:

Wylde's first store, American AF, went from zero to $8M in 15 months

Days before their busiest holiday, Shopify Plus helped AAF improve its load time, doubling conversion rates and profit margins

Today, Wylde operates five stores set to gross more than $40M in 2018


"There's definitely a similarity between the military and entrepreneurship when it comes to life and death," says Shawn Wylde, CEO of American AF. "Obviously, the repercussions aren't as severe in entrepreneurship, but the threat of failure is real and motivates you to give it your all."

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 , 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 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.

"They were chasing me all over campus as I was jumping out windows to escape," Wylde says with a laugh about eluding campus authorities. "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, 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.

As that stint ended, Wylde once again had no plan for the future. Nor did he know how 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"

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," Wylde admits. "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."

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 everyone miss about Wylde?

Pain, Prison, and (NSFW) Patriotism

The secret was revealed 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," Wylde says matter of factly. "It was prison or death."

Prison it was. Dead broke ... but not dead.

Before being locked up, Wylde had to come up with $4,000 he owed his lawyer. Tired of borrowing from his family, Wylde 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"

From $1.2 Million to $8 Million and Beyond

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:

  • Conversion rates doubled, as did profit margins.

Subsequently, AAF also leverages Shopify Scripts to customize the checkout experience and further increase conversions and earn customer trust.

AAF's customized checkout includes (1) real-time stock availability on product pages, (2) trust seals throughout, (3) upsells within the cart, and (4) mobile-optimized payment options like PayPal, AmazonPay, and Shopify Pay's one-screen, two-factor authentication for returning customers

"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."

In just its first fifteen months in operation, AAF generated more than $8 million in sales. What started as a company that sold almost exclusively to Marines now counts 98% 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."

Multi-Store Ecommerce: Breaking $40 Million in Sales through 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."

Today, Wylde has much more to be obsessed about.

With others taking notice of the speed at which AAF has scaled, Wylde has been approached with new opportunities and now has a unique multi-store strategy.

While multi-store generally evokes images of cloned stores serving multiple geographies or countries as part of a multi-channel global growth strategy, Wylde is applying his logistics and supply chain expertise to scale multiple unrelated stores simultaneously.

In all, Wylde now operates five Shopify Plus stores that will combine to generate more than $40 million in sales in 2018.

While Wylde isn't interested in naming these other stores just yet, he says each was in need of business expertise he gained building AAF.

Today, each is a multimillion dollar property Wylde suggests are primed for accelerated future growth.

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

Importantly, Wylde also credits Print Brains, a new application he helped create that offers fulfillment services for on-demand printed products, with helping him lift sales and conversions across the various properties he operates:

"It connects shops with on-demand printers so brands can focus only on growth. We wanted to make it really easy so everyone can achieve what AAF has."

The Freedom to Give

The Marines gave Wylde an 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," Wylde says. "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.

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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.