The Device Detangler

Barry Chertov, the founder of WaccoBB, is helping local elders fix their tech problems

Barry Chertov in his native environments - at his home by the Laguna and with assorted Apple products. (Photo by Laura Hagar Rush)

Wondering how to get text messages on your Apple computer, how to organize your email, or just wish your myriad devices did a better job of talking with each other?

Barry Chertov can help.

Chertov was the founder of WaccoBB, the beloved west county bulletin board service, which he ran for more than 15 years before closing it in 2020. (Ad income had dwindled due to competition from newer platforms like Nextdoor, and handling too many obstreperous posters had gotten tedious.)

Chertov tried retirement. He wasn’t bored, but he found it lacking in purpose. The question was “How to be useful?” he said.

He had been acting as an unofficial tech support person for family and friends for years. After helping his mom and some of her friends at her retirement home with their devices, he realized, “You know, I bet there are all sorts of seniors out there who are needing a whole bunch of tech support,” he said. “It seemed like a cool thing to do. It seemed like it was a need. And I'm interested in fulfilling a need.”

Chertov jokingly calls himself a “tech support hero.”

One Sebastopol resident, Amy Van Leeuwen, suggested an alternative title on Nextdoor: “My husband called him an ‘IT shaman’ and I would add a marriage counselor,” she wrote.

She continued, “Besides curing baldness, it looks like Barry can do almost anything…He solved tech problems from 2023, 2022—all the way back to the 90s, it seems. Now, we can both operate the TV and play music with the ‘good speakers’ in the living room. And that was on top of patiently and respectfully problem solving and explaining a long list of email/calendar/Zoom problems.”

One of Chertov’s favorite queries from a potential client was this one: “What are all these cables and do I need them?”

Chertov is an Apple guy. “I don’t do Windows, as it were,” he quips. “I do iPhones, iPads, Smart TVs, Bluetooth speakers and Smart Home stuff.”

And sometimes, he helps with really, really simple things.

“I’ve taught a few people how to cut and paste,” he said. “That's always a fun way to rock their world.”

Chertov has a calm, gentle manner, and no matter how simple the job, he said it’s important to treat elders with respect. “I just treat them with respect and patience, and sometimes playfulness,” he said.

Like many techies, Chertov’s home overlooking the Laguna is full of cool devices, but his favorite device of the moment is his Apple Watch.

“I'm surprised how much I like it,” he said. “My sister bought one, so I figured I’d get one and check it out, so I would know how to help her with it, right? And I was surprised how useful it is!” (He uses it for alerts, as a remote control for his sound system, and as a kitchen timer.)

He also loves his iPhone 12 ProMax, which he uses, well, like the rest of us, for everything, but also to control the irrigation in his yard.

And he’s enjoying his new gig as a tech guru.

‘It’s creative, and it's intriguing, and I love it,” he said. “People have been so thankful when I untwist whatever is going on with them and make something work that hasn't worked for awhile. That’s a kick each time.”

Barry Chertov can be reached at barry.chertov@gmail.com.