It’s fair to say that Jayson Koss knows his city as well as any Delray “old timer.” Though only 39, Koss has “been in every house in Delray,” as he likes to say.
He’s not exaggerating much. As the founder of Delivery Dudes, Koss was literally the driving force behind one of the city’s most beloved startups, navigating its byways in his moped while ferrying food from Delray restaurants in the brand’s once-ubiquitous double-“D” insulated bags.
In the first few years of the delivery service, circa 2009 to 2012, Koss recalls thinking “this thing’s fun, but it’s never going to become anything.” The native Floridian had just returned from several years in the New York City fashion industry, wholesaling clothes from brands such as John Lennon, Marc Ecko and Tommy Hilfiger. Delivery Dudes—its name harkening to Koss’ easygoing, hippie ethos—seemed like a change of pace from the hurly-burly of New York. Until it blew up.
Aided by improved point-of-sale payment systems and the advent of Google Maps (Koss remembers having to print MapQuest directions for every order), Delivery Dudes, which predated DoorDash and Uber Eats, would ultimately expand to more than 50 cities nationwide. In March 2021, Koss made the “bittersweet” decision to sell Delivery Dudes to Louisiana-based online restaurant delivery platform Waitr Holdings—for some $24 million. By late 2022, the big “DD” was no more.
“Chapters end, and new things are born, and everything must die,” says Koss, with characteristic Zen. “But I wish, at minimum, the brand was still around a little bit, even locally. It was a really good service, and the people we sold it to ran it into the ground. [Waitr, which rebranded as ASAP in 2022, filed for bankruptcy in 2024.—Ed.] … It was such an integrated part of little Delray that I loved. It was sad to see it not only disappear, but get worse and then disappear.”
Though elevated to the ranks of the multimillionaire class, Koss isn’t the type to invest in megayachts and private chefs; in his downtime, he enjoys sipping tea in a yurt he erected in his backyard. “I live in the same house, I drive the same moped,” he says. “But I bought a Volkswagen van I’ve always wanted, and I bought a really cool gong and some singing bowls. Other than that, more so than monetarily, my life changed because of the space that was created, of not being the CEO of such a large company anymore. … It bought me some years to breathe and figure out what I wanted to do next.”
That turned out to be Eightfold Ventures, a bespoke venture capital firm Koss started with another entrepreneur, Ed Mileto, 38, whom he met through a friend. Mileto had recently exited his own company, Perfect Practice, a putting mat for golfers that, at its zenith, was endorsed by Masters champion Dustin Johnson and appeared in more than 4,000 brick-and-mortars in addition to its ecommerce origins.
Koss and Mileto bonded over their shared love of tea and their similar business backstories. “We were feeling each other out, and what each other’s superpowers are,” Koss recalls. “Little by little, he got me off the bench and put me back to work.”
Launched in 2023, and based out of a nondescript office near The Bunny Hive and Captain Clay’s, Eightfold Ventures funnels its founders’ expertise into assisting mostly ecommerce brands toward greater prosperity. Its portfolio includes brands such as DADFUEL, a superfood supplement; NBT clothing, an apparel brand for the motorcycle set; Catori Life, a woman-owned philanthropic jewelry business; and Urban Abundance, which installs and maintains home gardens.
Koss and Mileto limit their active portfolio to eight companies, of which they are an integral part of their teams, from participating in weekly meetings to assisting in their long-term budgeting. “We constantly surprise ourselves with how quickly Eightfold has grown,” Koss says. “All the brands have grown from a million to $4 million to $7 million, and now onto eight figures.”
Naming their firm after the Buddhist concept of the Noble Eightfold Path, Koss and Mileto opted not to seek outside funding for their venture, launching Eightfold with their own capital and enjoying the freedom of running the company their way. “We don’t wear suits by any means, and we show up to meetings and have them in Jayson’s yurt, and drink tea, and do things pretty casual,” Mileto says.
Sixteen years after the launch of Delivery Dudes, Koss’ leonine locks are greyer, his bankroll is fatter, and his stomach, he believes, is happier. “I had Delivery Dudes at a very amazing discount for years,” he says. “I would order DD five times a day. Now, since DD ended, I’m cooking again. I have vegan meals made, and I’m growing a bunch of food, and making salads. I feel like if I had DD at a 70% discount, I wouldn’t be as healthy as I am now. It’s probably a good thing.”
This story is from the Summer 2025 issue of Delray magazine.
