FleetUp and Truckers for the Homeless: Checking in with David Wolkow

For the last two and a half years, FleetUp has supported the work of Truckers for the Homeless. It’s a charity founded by David Wolkow, a driver who has been running routes in 48 states for the last 25 years.

Truckers for the Homeless is a charity that supports homeless in cities and rural areas. As David said in our first interview, “Truckers see homeless everywhere.”

A lot has happened since the last time we talked with David – a pandemic, a growing homeless crisis, and a booming post-COVID economy. We wanted to check back in and see how Truckers for the Homeless is doing. Our interview is below, with some light edits for style.


FleetUp: Tell me about Truckers for the Homeless in 2021.

David: The charity is exploding. Last time we spoke, only about three drivers were handing out bags on the highway. Now, thanks to FleetUp, we’re doing monthly events in Louisville and Owensboro, Kentucky. Every two weeks, these events feed up to 140 people.

Even amidst COVID, it’s exciting. We’ve got a lot of irons in the fire!


FleetUp: Tell me about the two monthly events in Kentucky.

David: We have a team of about 10 people in both Louisville and Owensboro. In Louisville, we work out of a church called the Voice of Truth. The pastor has a heart to help people.

At the events, we have a flat top barbecue grill. We have clothing that we’re giving out. We’ve also made connections with a couple recovery centers. Their case workers attend our events and have one-on-one counseling with the homeless. They’re able to help them with IDs, get them set up with benefits, and more.

We also go out to homeless camps that are in the general vicinity. We explain who we are, where our events are happening, and give them rides to the events.

This Saturday, we’re having a kid’s fun day. We want to get the community involved. We’ll have a bouncy house and face painting and other things for the kids. It’s free, we’re just asking the families to bring some kind of donation, whether that’s a food or a case of water. We wouldn’t have been able to put this together without FleetUp’s donations.


FleetUp: Tell me about the people who come to your events.

David: Two months ago, a guy named JJ showed up. He helped set up and hung out all day. We had people who were giving free haircuts, so he got his haircut.

He played cornhole with our volunteers and listened to the music, then helped us tear everything down and put it in the trailer. He just glowed all day.

He said, “I really appreciate everything you guys are doing. I’ve been on the streets for 10 years. It’s a blessing to have clean clothes, brand new socks, food, a blanket.” It always makes us feel better to hear this kind of reaction from the people we reach out to.


FleetUp: Has the pandemic presented any challenges?

David: We tried to feed a hot meal last Thanksgiving and the city wouldn’t let us set up and cook the food, so we cooked it and placed it in containers. Instead of having a dinner for 100 or so, we made up 65 bags and took them out to 3 tent cities around the Louisville area.

This year, we have the thumbs up from the city. We’re putting a full Thanksgiving dinner together for 200 people.


FleetUp: Why do you think it’s especially important for truckers and logistics professional to fight homelessness?

David: America is one of the richest countries in the world. In the trucking industry, we move the country’s goods and we see a lot of waste.

I’ve made deliveries and had a pallet of frozen chicken refused because one of the cardboard boxes was hit with a forklift that didn’t puncture the bag. That was 42 fifty-pound cases of chicken quarters that I took to four different charities. I couldn’t even tell you how many people we fed.

But it’s not just the food. It’s personal hygiene items and clothing and socks. There’s just a lot of waste.

Truckers are the pawns on the big chess board of life. We’re put out first. If people were more proactive, maybe some hate and discontent would go away.


FleetUp: What are your plans for the future?

David: We’re planning on bringing mobile showers to the events. I’ve reached out to a company in North Carolina about a donation.

We’re also looking for a facility where we can house the homeless, give them thirty days to six months to help them in the process of getting back on their feet.

If it wasn’t for FleetUp we wouldn’t be planning any of this. Before you stepped in, there were zero donations. If the money didn’t come out of my wife and I’s pocket, it didn’t come in at all. The money we get from FleetUp, I don’t believe we would even be around if it wasn’t for that.


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