Bowling Green native creates online business empire

Tyler Webster founded the website in 2011, selling t-shirts and other merchandise. The site took off in 2016, selling Trump and right-wing apparel.

Drake Kizer

Nashville entrepreneur and former WKU student Tyler Webster, 25, has faced quite a bit of controversy, but after a lot trial and error, he feels like he has found his niche.

Webster was born in Bowling Green, and after moving around during his middle school years, he settled into the district for Greenwood High School. During his freshman year, Webster, 14 years old at the time, began doing graphic design on MySpace.

“I started out making MySpace layouts,” Webster said. “I had some MySpace layout websites, and I have always been making websites and doing design since then.”

Today, Webster still finds himself working in the realm of design, and he’s had rather large, commercial success.

While at WKU, Webster changed courses of study on multiple occasions, starting out with graphic design and marketing before switching to criminology. Though his majors changed, his passion for creating did not. During his third semester of college in 2012, he started what is now his largest company, It was just a political Twitter page then, but eventually it expanded into selling clothing that capitalized on the popularity of now President Donald Trump and right-wing ideologies.

“I started doing shirts through a company called Teespring a few years ago,” Webster said. “The actual store really got established and took off in September 2016.”

You can trace Webster’s design roots back to his time at Greenwood. He took on design assignments that would have been challenging for seasoned designers, much less a completely self-taught young person. Around that point, he began to feel like he had stumbled upon a skill he could utilize in the future.

“The T-shirt company Gildan gave out around 100,000 shirts I designed at Panama City Spring Break in 2011,” Webster said. “It was around then that I realized I could probably just do this for a living.”

Webster graduated from high school in 2011 and planned on attending WKU that fall. However, just before the start of his freshman year, he was prohibited from setting foot on university grounds. According to an August 2011 Herald article, Webster was “banned from WKU for planking and promoting his website with stickers around campus.” Webster was in the news quite frequently for a while, but he was eventually allowed to re-enroll in classes.

“I remember NewsChannel 5 came up to Bowling Green and interviewed me, and I was their top story,” Webster said. “It was one of my first websites that started to kind of take off. We started selling shirts and having users sign up and post pictures. After all that happened to me, it fell off and planking died out.”

Dustin Meherg, a WKU graduate and lifelong friend of Webster, said he never knew how much Drunk America was going to blow up when it first started. He is not surprised though, since he said Webster has always been skilled in graphic design and marketing.

“I helped him with different things, whatever he asked me to honestly,” Meherg said. “I majored in marketing so we swapped ideas with how to market his company. We were going to try and market it to local businesses, but he decided it would be best to hit the social media platform, and it worked out for him.”

Drunk America has gotten a lot of publicity since its inception for being very Trump-centric, but Webster said he is trying to expand into a broader direction that includes more than just that, at least until the next presidential election. Funny shirts are what is popular, and in trying to come up with clever ideas, he has gotten into trouble with copyright a few different times.

“Usually you just get a cease and desist or they will send a notification by email, and you just work it out that way,” Webster said when asked about his legal issues.

For example, he said he had a Tom Brady shirt with him wearing a “Make America Great Again” hat when the New England Patriots won the Super Bowl in 2017, and a company that handles copyright for the NFL got his ad account taken down on Facebook and banned.

Since exploding in popularity during late 2016, Drunk America’s store has expanded to include hats, tumblers and other items. Webster said he is extremely careful not to post or sell anything he does not personally believe or agree with. However, some of the ideas promoted on Drunk America’s items have been deemed offensive by certain groups, which has caused him to receive a lot of backlash.

“I get hate messages all the time,” Webster said. “All day, every day.”

WKU sophomore Logan Trimmer doesn’t think it’s right Webster gets rude remarks just for trying to make a living selling products online. He said he believes the general public has become too easily offended by controversial thoughts and ideas.

“It is pretty sad to send someone hate mail over a product,” Trimmer said.

He said people don’t have to buy Webster’s merchandise and if they don’t agree with the messages Drunk America puts forth “they should just ignore them and not send equally offensive messages.”

Despite negativity, Webster has not become discouraged. He runs numerous websites in addition to Drunk America, and he said he recently launched another company called He is excited about the project’s prospects since he enlisted internet sensation Billy Buck Roscoe as one of his business partners in the endeavor. He said he believes Raging Patriots will end up being big too, likely as big as Drunk America.

However, he said he anticipates the new website being different from Drunk America.

“We are going to make it more college-oriented,” he said. “It will be like Old Row or Barstool Sports but for patriotism.”

Though he stopped attending school when his business became successful, he said he will likely end up getting his criminology degree online since he does not have much left to finish. However, his current focus is on coming up with new ideas that can grow his businesses and keep him ahead of the curve.

“The good thing about being a graphic designer is I do not have to pay somebody to do the designs; I can go make them right when I think of them,” Webster said about what he believes continues to set him apart from his competition. “Sometimes coming up with ideas is the hardest part, but that is pretty much how I have gotten to where I am in this business, just staying on top of [current events] and whatever is hot at the time.”

Features reporter Drake Kizer can be reached at 270-745-2653 and [email protected] Follow Drake on Twitter at @drakekizer_.