San Mateo driving instructor Kenneth Dupree teaches all his students patience, humor and understanding

Kenneth Dupree has had an affinity for transportation his entire life.

He first learned how to drive at age 12 growing up in the South, he said, reflecting on navigating a car for the first time on his family’s 40-acre property, occasionally driving into town to the store.

Later in life, he’d become a conductor, and after that an engineer, for the Class One Kansas City Southern Railway for 13 years.

Now, he teaches Bay Area students of all kinds to drive as a co-owner at Push Start Driving School in San Mateo — a job he really, truly loves.

“When I talk about this, I feel like I don’t even have a job. I’ve never gone to bed thinking, ‘Oh, I have to do this again? I’m just getting this out of the way so I can shoot pool,’” he said. “There are times when it gets hectic … but I like problem-solving, too. I truly feel like I don’t have a job.”

The Push Start Driving School has been a full-time job for Dupree and his business partner Anna Nyguen since 2021, when he went full time. He now has six full-time, licensed driving instructors on staff who can help students master driving skills and provide the necessary paperwork for under-18 students to fulfill their testing requirements.

Driving school is often associated with teenagers and high schoolers getting licensed because only students under the age of 18 must complete a mandatory six hours of training with an accredited school before taking the Department of Motor Vehicles licensing exam.

Although those clients make up 60%-70% of Dupree’s business, he meets people of all different ages, from all over the world, in his line of work who want to practice or learn how to drive for the first time.

“I take all the special projects,” he said. “When we have people who are not just your normal, ‘I need to pass [the test].’”

One of his clients, Janet, was in a car crash at age 19.

“It was a bad one, but something she could walk away from,” he said.

Six months later, she got in another accident — although she wasn’t behind the wheel, it was so traumatizing she didn’t get in a car again for 15 years. Living in London, with excellent public transportation, it wasn’t a necessity, he said. But after moving to the area, she needed to learn how to drive.

“We started with opening the door and getting in the car, allowing me to drive her,” Dupree said. “She had a mouth like a sailor. When she got excited, she cursed — the first time, she said ‘I can’t f— believe I’m driving,’ in that British accent.”

Four months later, she passed her driving test with only three deductions, a rarity for the DMV, he said, and afterward when she told him they both started crying.

Dupree recently saw Janet, serendipitously, driving behind him on the street.

“I jumped out and gave her a big hug,” he said. “We’re still good friends. Still on the Christmas card list.”

Because of the diversity of the Bay Area, combined with a booming influx of technology jobs that draw in a global array of employees, Dupree said he meets people from all over the world.

“The joke is, ‘You’re a software engineer, just like everyone else?’” He said of getting to know his clients. “Or we have people getting their Ph.D. at Stanford, trying to cure cancer — they’re smart enough to know, let’s take a lesson. Or sometimes it’s people who’ve just never driven.”

He’s gotten to meet students from Mumbai, Tahiti, Nepal, Pakistan and North and South America, among other areas — even suggesting the installation of an interactive map to track where everyone’s from. For these individuals, who already have full-time jobs and careers, getting successfully licensed can be a real weight off their chest.

“For a student that goes to Aragon, they’re just getting their license. This person, now they don’t have to walk,” he said. “My older students from foreign countries, they just need to get it off their plate. And when they do, you can see the relief on their face. Like OK, now you can go cure cancer.”

Of course, Dupree loves getting to know his teenage clients as well.

“I like to build a rapport with them. I’m going to find some way to connect with them,” he said. “I’m a sports guy too, I was on the student council, too.”

One major tool Dupree uses to get to know his students? Music.

“Hey, what kind of music do you listen to?” is a great conversation starter, he said, even if teenagers will usually say simply “all kinds.”

But once Dupree gets them to offer up one song or artist — “Now I’m designing your playlist, what you’re listening to in the car,” he said, noting he often puts teenage students on to one or two of his own favorites.

The first skill he teaches students, teenage or not, is defensive driving; a skill where drivers are prepared for the actions of other drivers or situations on the road.

“I’m generally pointing everything out, we’re scanning constantly. That’s the first step to defensive driving. I see things coming a long way away,” he said.

It’s also important to impress the responsibility of driving on students.

“That first time they don’t clear the bike lane, or they’re about to pull out, I say, ‘Stop, look to your left.’ I say — and this is a little abrasive — ‘look, if you pull out in front of somebody, and they hit you at 30 mph, you’re going to the hospital. Any faster than that, it might not be something you’re walking away from,’” Dupree said. “That’s about as abrasive as it gets.”

But he also keeps it lighthearted, reminding students of the cost of even a minor collision or advising them with more obvious tidbits.

“When I ride around with students, I say this — half-heartedly, but I’m very serious about it — we’re cruising down the road to a red light, I say ‘Don’t hit this guy!’” Dupree said.

To learn from typical first-time errors, Dupree has a saying.

“Forget the mistake, remember the lesson,” he said.

And of course, the Push Start Driving School Honda Civics are all equipped with accelerators and gas pedals on the passenger side of the cars, in case errors need to be remedied.

For Dupree, teaching students to drive is a deeply fulfilling aspect of his life.

“When that light comes on, when people start to get it, when they start to get it, and they get that smile, we’re making progress,” he said. “Things are changing in their life drastically.”