These Grandparents Make $10,000 a Month on Their Delivery Side Hustle, With Free Workcations — 'We Hit a Hotel With a Pool' These seniors started driving for Instacart and Doordash, then added apps from there. Within a few months, the "Gigging Grandparents" had turned a part-time delivery gig into a comfortable living.
By Frances Dodds Edited by Mark Klekas
Key Takeaways
- How to earn a substantial income through driver delivery apps by starting with small deliveries and scaling up strategically.
In their late 50s, Day and Al Stefanelli found themselves in a tough financial spot. They needed to make some money — and fast. So they looked around at what they could use and saw one unairconditioned Jeep. It was not ideal in Atlanta, but it was something.
So the Stefanellis downloaded the basic driver delivery apps, and hopped behind the wheel. Fast forward to today, and the couple has gone from making a couple hundred bucks here or there on deliveries, to $10,000 a month. Fortunately, for anyone else interested in driving their way to a six-figure annual income, the Stefanellis are sharing their strategies.
But first, a bit of backstory. This all started when Day and Al did something most people only dream of. "We dropped off the planet for four years," Day says. They moved out of their house in Atlanta, and flew to Panama with nothing but a few suitcases and their little dog. In the previous years, Day's mother had been living with them while battling dementia. When she moved into a home, they were tired and needed to hit pause. "We were like, 'Oh my God, all of our kids are doing really well right now. Do you want to run away? That sounds like an adventure,'" Day says. "We took hikes, there were waterfalls, mountains, gorgeous, everything was affordable. It was just magical."
But eventually, the grandchildren started coming along, and it seemed like time to come home. Unfortunately, the logistics of easing back into the U.S. workforce proved more complicated than they hoped, and they needed a quick source of income. One of their daughters suggested picking up shopping jobs on Instacart, and that's how their delivery saga began. "We had a car, and we both had licenses," Day says. "As seniors, we get better insurance rates because we've been driving longer and we're more careful. So you've gotta use what you have! We call ourselves the 'gigging grandparents.'" They even came up with a hashtag: #GigNGrandparents.
They knew they didn't want to give people rides, since their Jeep wasn't air conditioned — plus, people can be kind of a pain. According to a survey of 10,000 drivers by Roadie, a crowdsourced delivery platform owned by UPS, only 7% of drivers on the apps prefer ride-sharing. By comparison, 78% of drivers favored "delivery of goods." The Stefanellis were in that camp.
So they started with the small stuff: food and grocery deliveries, shopping errands. "On the weekend nights, we'd pull in a hundred dollars in five hours doing all the little food ones," Day says. "Then Uber started offering some package services, like 'go to Walgreens and shop for me', or 'go to the Apple store,' and those paid better. The shopping ones take longer, you're actually walking the store a hundred times, so they paid better. I could hit $150 a day with those if I picked up a good four jobs."
From there they moved onto Amazon routes, which start at $90 for a five-hour route — although, Day says, "If they get into a pinch, like the driver threw it back and you've got to be there within the hour, I've seen them raise it as high as $160." Day's pro-tip is to go to the parking lots of their fulfillment centers in the morning, and snag a last-minute job at a higher rate. There are typically about 30 to 35 stops on an Amazon route, "And you'll need every bit of the five hours," Day says, "unless there's one apartment building where you drop off 10 packages or something." She adds that the worst part of delivering for Amazon is trying to get into people's buildings and developments. "There was a lot of arguing with security guards at a gate because nobody gives you their gate code. We would waste an hour and a half and have our route marked late because we didn't have access codes."
As the months went by, the Stefanellis kept adding apps on apps, and they worked out a system. Al drove, while Day navigated, scanning the apps for jobs with routes that lined up. "Eventually we noticed, hey, the bigger stuff makes bigger money," Day says. "And we saw how many people were like, well, if you could take a pallet, I would use you." So they decided to invest in a cargo van, and started driving more for Roadie, which offers bigger jobs like delivering food for a catering job, or moving a basketball hoop, or transferring trees between landscaping nurseries. "Instead of running 10 little gigs, you can run five bigger ones," Day says.
But as they soon discovered, there's always a bigger job just around the bend, and as soon as they were running heavier jobs in their cargo van, "Roadie kept popping up with trailer stuff," Day says. "So we were like, we need to invest in a trailer, so we can take even bigger loads."
They got themselves a trailer, and pretty soon the Stefanellis were averaging $500 to $750 a day — and $1,000 on their best ever day. "It was a long day," Stefanelli says, "but it was profitable. We moved ten 500-pound, 20 foot long trees." One perk of a long day like that, she says, is that driving laws mandate for the client to pay for the driver's lodging. "If it's over ten hours of driving, they have to give us a per diem to stay overnight somewhere," Day says. "So we always try to hit a hotel with a pool or something cool like that. We call them workcations."
These days, their biggest client is private — a large landscaping nursery that needs products moved between locations. She guesses that she and Al started making $10,000 a month back in April, and they already have their sights on their next vehicle upgrade: a truck with a stake bed. That way, they can work up to all their deliveries being "No Touch Freight."
"No touch freight means they load us, they unload us," she explains. "You need really big vehicles for those jobs, because it's giant heavy stuff. Those can pay $500 or $1,000 a pop because they go by weight. So at that point, we'll double our income. But also, we want to save our backs! That's important at our age."
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For anyone who doesn't mind being on the road, Day says there's a lot going for the delivery life. She and Al have spent countless hours riding around together, and sure, it's no waterfall in Panama, but they're still having fun. "Give it a shot," she says. "You get a little time running around, meeting new people. It's an adventure."
