When a new meme explodes, the race to transform it into merchandise is fierce. Within hours of the laurel vs. yanny controversy, for instance, Instagram meme pages were attempting to cash in by selling yanny-and-laurel-themed T-shirts, aprons, and more.

But there was a time, from around 2008 to 2012, when seeing memes out in the world, plastered on books, merchandise, and T-shirts, was still novel. Social media was just catching hold, and memes began to seep out of forums and corners of the internet like Reddit into broader culture.

The literary agent Kate McKean, who has sold several meme-based books, refers to this time in history as the “OH! The Internet Is a Thing!” stage. It was a time when almost anyone could slap a meme onto a T-shirt, mug, plate, book, or poster and cash in. Meme-focused Tumblrs began to get book deals, FunnyJunk.com started carrying “rage face” merchandise, and Urban Outfitters ordered boatloads of T-shirts emblazoned with an image of “Scumbag Steve.”

Just five years later, the landscape has transformed dramatically. Competition is intense, and according to those who make a living selling meme-based products online, it’s harder than ever to make money on a meme.

The biggest threat to meme-focused e-commerce businesses, according to those in the field, is the rate at which people today consume memes.

“One of the biggest factors in a meme dying is if a meme gets overused,” says Jason Wong, the founder and CEO of a meme-focused e-commerce business called Dank Tank that sells merchandise like Tide Pod socks. “People today are consuming more memes than ever. The expiration date for them has shortened more since even last year. Memes used to last for two to three weeks, but recently we’ve noticed they die after just a few days.”

“It feels like the internet is all moving a lot quicker,” says Samantha Fishbein, the co-founder and COO of Betches Media.

Brad Kim, the editor in chief of Know Your Meme, has observed this phenomenon firsthand. “In the early days of meme culture, so, late 2008 to early 2012, memes used to go on for months on end,” he says. Memes like the advice dog, for instance, first broke out in 2008 but remained in steady use until mid-2012. More recently, memes like Doge and Harambe stayed popular for nearly a year. “These are memes that would have way shorter shelf life now because they would get mutated into something different or cycled out by the community entirely,” Kim says.

The 24-7 nature of today’s meme cycle has posed problems for businesses that design custom merchandise based on memes. Time is needed to pull together a design, coordinate supply chains, and work with retailers. By the time things all come together, the moment has passed.

“A few years ago, we’d see a phrase and that phrase had a longer shelf life because memes came and went at a lower pace,” Fishbein says.

Today, memes come and go sometimes faster than T-shirts can be printed, and there’s nothing more mortifying than donning a T-shirt with a dated phrase. The Instagram star Tank Sinatra says this is the reason he’s shied away from selling meme-focused merch like other Instagrammers.

“By the time the merch is ready to go, by the time the design is even approved by a shop, it’s not even worth the effort because it’s old,” he says. “You’re going to look out of touch.” The few times he has produced meme-focused items, such as pillows featuring the crying Jordan face and “Hide the Pain Harold,” they have underperformed.

Because timeliness is key, most big meme accounts and websites now use third-party services like Shopify to handle the back end of their stores. This allows them to get products up quickly. Consumers can also create their own custom meme merchandise (often for cheaper) by using sites like Redbubble, Spreadshirt, or Zazzle, which allow you to upload any image and have it printed on a variety of products.

“Those sites are really good at what they do,” says Sinatra. “But even as quickly as they work, you’re still not getting your stuff for three days or five days. By then, the boat has sailed.”

“The shorter lifespan has ... been a big challenge in our company,” says Wong.

It’s also almost impossible for sellers to monetize entire swaths of memes featuring trademarked characters like SpongeBob or Kermit the Frog.

On top of everything, the nature of what constitutes a meme itself is shifting. While early memes followed standardized formats, like white block font plastered on top of a funny photo, today’s memes are more esoteric.

Edward Stockwell who has managed meme-based social-media accounts for sites like theCHIVE and Rooster Teeth says that memes today relative to a few years ago are wildly different, and that makes them more difficult to commoditize.

“A lot of memes today are much more niche and rely on specific reference points to understand, so they’re less marketable to a wider audience,” he says. “Not that long ago there were maybe a handful of memes that everyone knew: Grumpy Cat, Scumbag Steve, etc. They were characters that stuck around.” Today’s memes, he explains, are more nebulous.

Social media and photo-editing apps have also affected the way people interact with memes. “We don’t just look at memes, laugh, and pass them on,” says McKean. “Now we want to incorporate their language into our daily speech, we want to manipulate them for our own meaning on Twitter.”

When most people see the “distracted boyfriend” meme, for instance, their first inclination is not to run out and buy a mug with it. Its humor lies in the endless, real-time, personalized manipulations of the image. Even the photographer who took the photo and Shutterstock, which owns it, weren’t able to make any meaningful revenue off the meme’s virality.

If a meme is niche enough, it can generate some revenue. Lee Ayers, who runs the popular Instagram meme pages @middleclassfancy and @friendofbae, says that he’s been able to successfully sell some meme-themed products with memes that are specific to his page. He has created his own recurring inside jokes such as referring to cold beers as “crispy boys” and summer as “grilling szn,” and has monetized by selling merchandise with those phrases.

While some meme retailers like DankMemeMerch.com have stayed true to their mission, most others have begun to pivot wholly away from memes and into broader novelty merchandise.

Wong says that over the last year Dank Tank has started to sell fewer meme-based products and more generally humorous items. “We’re shifting away from products based on specific memes and focusing on internet culture as a whole,” he says. “Like we sell candles now with phrases like ‘the smell of my bed sheeting when I cry myself to sleep at night.’ It’s not a meme, but sort of just general teen mood and mentality.”

Other sellers have begun hawking the type of humor tees that would look right at home on a New Jersey boardwalk. Reid, a man who runs 15 popular Instagram meme accounts including @shitheadsteve and @drunkpeopledoingthings via his company Steve Media, now sells shirts with phrases like “I’d rather be with my dog” and “I don’t need life, I’m high on drugs.” “I think we see ourselves as being the next Spencer’s, online,” he says. “Novelty products are a good fit for our audience.”

Fishbein says that some of the most popular products at Betches have been been based on throwback lines from Sex and the City or puns. “We want to make something that our audience feels attached to so that even if the trend fades it doesn’t feel completely outdated,” she says.

“The idea of producing products to sell specific memes to people has become very unfavorable and seen as cringe-y among the communities I frequent,” says Ryan Davis (known online as Kmorae), who owns and operates Meme.Shopping. “So the ‘novelty’ route is a much safer bet and works much better in the long run.”

And while meme merchandise itself may never completely disappear, Fishbein predicts that customers in the future will become more discerning. “How much room do you have in your budget or closet or life for T-shirts of various memes that came and went?” she says.