Delivering The Food and Being The Good

by Darien Davies

Photos: Ben Hicks

If you haven’t heard about Delivery Dudes, you’re either living under a rock (where they can still deliver to, by the way) or are starving. Delivery Dudes is the local, and now non-local, restaurant delivery service that brings your favorite foods directly to your pie hole, and is the delicious brainchild of Jayson Koss.

Jayson, founder and owner of Delivery Dudes, started the company in 2009. He doesn’t even credit a super mind-blowing realization, either. He just realized there was a need for it and, whamo, here we are.

“It was just as simple as we knew that food delivery was happening elsewhere and, at that time, the only food you could get was Rotelli or Papa John’s. I don’t even think the Chinese restaurant was delivering,” Jayson said. “So we said, ‘wow, this makes a lot of sense to do,’ and [a buddy of mine and I] started it.”

He traveled around a bit during that time period, at which time the company was more of a side project. But, when he returned to Delray in 2012, he went full steam ahead. The company started out small, with only about five to fifteen deliveries per day, but with determination, persistence and sheer personal necessity, the numbers improved.

“I didn’t realize that it was going to be what I was going to do. I ran deliveries because I needed money to eat,” Jayson said. “My girlfriend and I, and our little dog, were living above Deck84. We had no money and were just running deliveries. I learned that I actually enjoyed it, it made me happy, and it was easy. A lot of it was because I could be honest with my work. I wasn’t trying to pull a fast one on the restaurant owners. I realized that I could create transparent win-wins.”

And win-wins is what it’s all about. As business grew, he started needing more drivers and more people. He saw that the drivers were having a good time and were having the same type of experience he had. So, they had the great idea to grow the business by growing the team, and giving the drivers the opportunity to work toward earning their own franchise. “It’s another amazing aspect of the business. Five years later and it’s been non-stop,” Jayson said. “If you want to grow and want to do more business, you just need to solve problems. If you solve problems, you get bigger. Then, the bigger you are, the more problems you have. It’s a cycle that consumes your life.”

But, with all of that, he’s still enjoying it and realizes that stress is a choice. Their mantra is “be good, do good, have fun,” and in that order. He knows that you have to take care of yourself to do good, and makes sure that everyone knows they need to put their own oxygen mask on first.

“You want to do something that makes you happy. Sometimes I get lost and don’t remember that,” Jayson said. “I didn’t mean to start [the business], which is so weird. But it was a platform for making people happy, growing the local business, and making customers happy. I wanted the drivers to have the same opportunity I did. At the end of the day, if I go back to that, that’s what we’re making happen every day.”

Let’s revise that. That’s what they’re seriously making happen every day. The company is now comprised of a couple thousand people including employees and drivers, and spans across more than 40 cities in four states. On average, they make around a couple hundred thousand deliveries per month. “It’s really wild. It’s so stupid to even say it,” Jayson said. “To do 100 deliveries a day is so easy. To do a couple thousand is such a different game. Every step along the way has been so painful. There is so much shit that breaks.”

But, there’s a plan to make sure it doesn’t keep breaking. He said that a really awesome CEO gave him some great advice, which he values because he has since realized that being a CEO is not for him. First, you need to set the vision. Second, make sure the vision is funded and that there’s money in the bank to make the vision possible. Third, make sure the right key members of the team are there in order to fulfill that vision. In order to pass the threshold from a small business into an enterprise, he realized that he needed to enable his people and not to micromanage them.

“We are constantly setting goals, hitting them, missing them, reevaluating them and resetting them. Goals for us never had to be accurate, as ridiculous as that sounds. You just have
to be working toward something,” Jayson said. “Do we have three to five wet dreams? For sure. But what we try to do is have three to six-month strategies where we know
what we need to get done, and why. Then we reevaluate basically every quarter. It might have made sense two months ago and it might not now.”

As far as advice for an aspiring business owner? “Get a job!” (Just kidding.) “It always comes down to two choices for me. It’s either give up or keep going,” Jayson said. “If you strip it all back it comes down to those two things. You’re only playing against yourself and you just need to keep playing every day and you’ll be better.”

Right now, the company is focusing on stabilizing and protecting what they have on their home turf. They are working on making their franchise program more efficient and easy to open throughout the country, as well as continuing to provide a better service for their customers.

He says they had a lot of growing pains because they grew so fast for such a long time, so now they want to make the company better, stronger and more stable.

“A part of me thinks that if I’m not hard on myself, then I’m not going to be good,” Jayson said. “If it was to ever be over, and it ended somewhat okay, I hope that I would be able to say, ‘Wow, amazing ride, I crushed it.’”

Until then, he’s doing one delivery at a time, helping one new Dude at a time, and crushing it one day at a time.


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