A millionaire picks up four hitchhikers on the side of the road in rural Ohio. It already sounds like the beginning of a bad joke. But when one hitchhiker, a guy named Woncho — yes, rhymes with Poncho — tells the story, it’s not leading to a punchline. “That was one of the best rides ever,” Woncho says. “We told him to drive around in circles so we could listen to him talk more.” The millionaire driver had been a hitchhiker in the ’70s. Back then it was just another mode of transportation. Safety wasn’t on the radar. Getting rides was easy.

Today, it’s a bit of a different story for the modern hitchhiker. Technology can step in when a thumbs-up on the side of the road fails. Woncho — whose real name is Hoang-Chau Nguyen — has tried just about everything to go his own way. By the age of 21 Woncho had already hitchhiked across the 48 continental United States. “I’m kind of crazy,” says Woncho, who’s now 27. “It was uncharted territory. I was younger.”

Sometimes the thumbs-up fails. That’s why hitchhiker Woncho brings a cardboard sign with him to show his intended destination.

Sometimes the thumbs-up fails. That’s why hitchhiker Woncho brings a cardboard sign with him to show his intended destination.

But instead of disappearing into the wild after the cross-country trip, Woncho embarked on a second hitchhiking adventure, this time in the Midwest, in 2013. He liked how the cities were unpretentious, the people a little friendlier. He liked the laid-back hospitality he encountered everywhere, from an industrial neighborhood in Chicago to gas stations in Nebraska. He launched a Kickstarter fund for this second trip. He, two friends, and a cameraman started in Woncho’s hometown of Dallas, hitchhiked up through Little Rock and Louisville; made their way to Detroit and Kalamazoo, Michigan; caught a train to Chicago; headed to Madison; and finally found a ride all the way back to Dallas. It took 17 days. And he got it on camera, planning to produce an online docuseries about the trip.

While traversing the Midwest, Woncho has shared rides with everyone from farmers to soccer moms. Here, the expert hitchhiker lets us in on his five tips for success.

1. Being friendly = more rides

Never underestimate the power of being friendly, Woncho says. And in the Midwest, drivers tend to return the favor. “Accept everything a driver wants to give you as a gift: food, money, parting gifts,” he says. “Personally, I don’t beg. But if drivers offer you something, don’t say, ‘No, thanks.’ Out of courtesy just say, ‘Thanks, I’d love some.’”

Woncho stays in one place for only two or three days, usually with a stranger willing to offer up a couch. If he’s lucky, the favors keep coming. After crashing with a particularly friendly squatter in Detroit, Woncho scored a ride with him to Kalamazoo, Michigan, to check out one of his favorite breweries, Bell’s Brewery.

2. Innovate

The old-fashioned thumbs-up is tried and true. But Woncho says that’s not always enough. He also relies on a cardboard sign displaying his intended destination and word of mouth. He asks everyone he meets where they’re going. If it gets him closer to his destination, he hops in.

3. Pack smart

Woncho encourages being prepared — but only to a point. His golden rule: “Pack what you’re willing to carry. You can overpack. Just realize that you’re going to have to lug all that shit around as you go across the country.”

His packing priority? Clean clothes. Woncho can’t overstate the necessity of dressing the part — as in being clean. Woncho typically packs a pair of shoes, boots, an extra pair of pants, and more socks and underwear than he thinks he’ll need. He suggests dressing like someone you’d be willing to pick up.

A key to hitchhiking is being friendly. If you’re nice to drivers, chances are they will offer you help.

A key to hitchhiking is being friendly. If you’re nice to drivers, chances are they will offer you help.

4. Use technology to your advantage

Finding shelter is always the hardest part of the game. This is where technology comes in. Woncho uses Couchsurfing.com — essentially Craigslist for the low-maintenance, carefree traveler willing to sleep on anything. And he uses Craigslist Rideshare. Woncho has posted requests such as: “Hitchhiking to the Midwest. Don’t have much money to offer but will provide entertainment and travel stories.” Anything to get from Point A to Point B.

To stay on top of local laws, Woncho relies on Digihitch.com. Hitchhiking is illegal in some states, such as Wyoming, Utah, and Colorado, but that’s never been a problem for Woncho. “In places that are illegal to hitchhike, it’s really not enforced. Many of my rides come from police officers dropping you off at the county line just so you can get out of their jurisdiction,” Woncho says. “If a cop stops you, just be friendly and transparent about your plans of adventure and where you came from and where you’re trying to get to.”

5. Don’t get discouraged (too easily)

There’s no guarantee with hitchhiking: Sometimes rides will come within five minutes. Other times, you’ll still be stuck for hours. That’s what happened in Fargo, North Dakota, on his first hitchhiking trip. Woncho got stranded. For two days. At a gas station. “I remember trying to approach people in the area and they would just ignore me,” Woncho says. “I ended up checking Couchsurfing, and someone happened to be going to Sioux Falls. So I lucked out in that way.” He won’t be going back to Fargo anytime soon.

But part of hitchhiking is making the best of situations, dealing with a bad hand. For Woncho, the key has always been to keep looking ahead. “Having an open mind is important because hitchhiking can be frustrating,” Woncho says. “You have to find ways to entertain yourself and keep on going. It’s being able to enjoy the stuff that’s going on around you instead of stressing out about not getting a ride. It’s definitely made me more open minded.”

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Hitchhiking can be frustrating. Woncho says you have to make the best of every situation you’re in and use innovative methods to find rides.