The primary tip for life online: The Internet is a lot like Vegas.

“What happens on the Internet stays on the Internet,” says Dave Hamilton. “I tell my kids all the time, anything you write or tell someone online lives forever.”

This bit of insight from Dave the Nerd, founder of one of the oldest and largest Mac-news websites around, the Mac Observer, was borne not just of fatherly protectiveness, but a history of talking and writing through computers that dates back to the Reagan years. Those old bulletin board systems back in the 1980s were the grandparents of what became sites like Facebook, and as we’ve been discovering, courtesy of certain recent chats on Capitol Hill, information online is a volatile commodity.

For Hamilton, who grew up on those bulletin boards, computer-driven information and how to deliver it the right way is of core importance. Every so often he drops by the Princeton Mac Users Group, or PMUG, to inform the crowd about what’s happening in the Mac/Apple universe. Sometimes it’s informational, but mostly his visits are centered around things like tips and tricks for Apple and Mac users.

Hamilton is the guest speaker at PMUG’s May meeting on Tuesday, May 8, at 7:30 p.m. at the Princeton Theological Seminary. The meeting is free and open to everyone. Visit

Hamilton will be giving out tips and tricks this round because, he says, that’s what people really want to know most, how to actually do stuff. But he has a caveat about himself.

“I’m an expensive guy to know,” he says. “I end up recommending things people want to buy.”

It’s not a sales or commission thing, Hamilton is just one of those guys who’s really into Mac gadgets and apps. And because Apple is not a free-stuff company, things might get pricey from time to time. But Apple users have their share of issues with their devices, so they always appreciate a good tip.

A sampling of what Hamilton will be talking about includes ways to set your iPhone to auto-quit apps you’re not actively using (“You can make it so apps aren’t chewing up your CPU without your knowledge”), ways to find programs and updates that are taking up a lot of real estate in your phone’s or computer’s memory (“The big secret to cleaning your Mac”), and ways to remove unwanted apps in bulk.

These are no small thing, Hamilton says. Like most Mac fans, he loves Apple products, but he admits they can get a little overzealous with the apps and updates. So he likes to help people be less frustrated with their gadgets, but being able to convey information the right way can be tricky. Hamilton likes to keep in mind that while he knows what he’s doing with computer tech, a lot of people don’t. They just want to be able to use their phones and laptops while the machines continually update in an effort to make their lives easier.

Hamilton learned his lessons over a long time. A natural-born tech nerd, the 46-year-old Hamilton says he grew up in Connecticut, essentially a Millennial in a Gen-X body. His father is “an electrical engineer by education, and mostly a QA engineer by trade,” he says. “My mom was a social worker at the Department of Child Services in Connecticut.”

Back in the mid-1980s, Hamilton took to Apple machines, Apple being “the underdog” despite having probably the most famous Super Bowl commercial in history in 1984. He used the Macintosh machines to communicate with other people, much like people do through texting and social media apps now.

His non-computer passion being the drums, Hamilton studied music and computer engineering at the University of Connecticut. “But, really, what I learned while I was there was how to write and communicate,” he says. “That was an odd time to be learning computer engineering given that the school didn’t even let undergrads access the Internet. Seriously.”

He left school because he was neither enjoying it nor getting enough out of it, he says. “And I was earning more from my own businesses and ventures in the summers than friends were earning in the year after they graduated, so I took a break. I’m still on that break.”

His first and only “real” job was as a member of the home access team at Citibank, where he was involved with the rollout of the first banking screen phone and their (dial-up) online banking system. It was a good job, he says, but he didn’t like the pace of things in corporate life. “Too much red tape and too many people involved in every little decision.”

In 1995 Hamilton and a friend, Lee Robin, started a computer consulting business called Computer NERDZ!, exclamation point included.

By 1998 Hamilton and Robin decided to follow different career paths, and Hamilton paired up with Bryan Chaffin to start the Mac Observer. Hamilton modestly refers to it as “the best Mac-news site on the web.” They hired a single ad rep, which Hamilton says was greeted with a flurry of Mac-based websites asking if the Mac Observer crew could put together better websites that got people’s attention through content.

Hamilton, who lives in New Hampshire, didn’t really want to be the content guy on the site. He was the guy with all the tech skills, able to build site infrastructure in the days before there were user-friendly programs like DreamWeaver or SquareSpace. But, he says, “Brian always pushed me to write columns.” He ended up answering the tech questions people (inevitably) had, and that has not stopped yet.

As he was with text-based communication, Hamilton was an early adopter in the podcast sphere. Part of the draw was because Hamilton is an audiophile and musician (he still plays the drums), part was because he foresaw that podcasts would be a thing. In 2005 he started iPodObserver, a news site that “focuses and comments on the life-changing revolution brought about by portable music players, portable audio, podcasting, and iPod-related stuff in general,” according to Hamilton’s website.

The Mac Observer is still the bread-and-butter site, though Hamilton does still do some computer consulting on the side. At the Mac Observer the questions just keep coming all these years later, Hamilton says. And by now he is used to being a content generator, because the questions never seem to slow down. What the years of tips, tricks, and answers has taught him, though, is that communicating is never one thing; there’s no one right way to do it. And answering questions makes him think in ways he hadn’t anticipated. Take, for example this question Hamilton regularly asks himself: “How often do we revisit the same topic?”

Less an answer than a direction is what Hamilton tries to keep in mind: “Not everyone knows what I said five years ago.” There’s always a new Mac owner and always a frustrated user who can’t figure out how to shut off the damn updates already, so Hamilton says he from time to time goes back over lessons that might sound old to some, but are diamond-studded new solutions to others.

Hamilton does a lot of talks in a lot of places, too. Despite being nearly born inside the cocoon of technology-based communication, he typically prefers the in-person events. Like all writers, Hamilton doesn’t typically get to see people reacting to things he has written; he never knows how someone is using or understanding what he’s put into print. He has a similar issue when he talks on his podcast.

“You have to really think about explaining something technical to someone in audio only,” he says. “I learned very early on that you never say the thing you’re going to type. Even if you know what it is, you can’t follow it.”

In other words, if the answer to how to do something is “Hold down Ctrl then hit F2, up arrow, down arrow, 5, +, Page Down” or something, you’re going to lose whoever is hearing that out loud. That kind of command series (which, by the way is total gibberish) would be fine to write down, but not to say. So how to communicate in different ways has become a major driver for the guy who has been communicating in so many different ways longer than most people alive today.

Despite that Apple is now big business (when only a decade or so ago it was a barely surviving also-ran), Hamilton says he is still happy with the community he finds among Mac fans. Being an Apple person is a lot more hip and mainstream these days, but, pardon the pun, the core is still in tact.

“There’s still a camaraderie in Apple users,” he says. “But it’s not like it was 30 years ago.”

But then, technology isn’t either, is it?

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