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I did this in the mid 90s. It was really fun to see inside a lot of rich people's houses, the sort that have libraries so big they need those ladders with wheels on to scoot around.

I was hit on by several bored housewives, including one that answered the door in her open robe.

One American woman had brought her inkjet from the USA and I hooked it up to a decent convertor, but it wasn't one that converted the frequency, and the inkjet released its entire content of magic smoke, which incidentally was enough to fill a very large penthouse apartment. I ran her out of the apartment, then I remembered it was still plugged in, so I had to stagger totally blind through the apartment to find the damned thing and unplug it lol

That job put me in contact with a criminal gang who went on to supply with me dozens of GBs of stolen hard drives that I used to create what was probably the largest warez FTP in the world and a dump site for most of the top pirate groups like Razor 1911.

Just a PSA (not trying to harp on parent commenter, just taking their comment as an opportunity to soapbox) but never, ever, every go into a room or building that is getting smokey from something burning. It's how you N+1 the casualty/death count in a fire. Unlike the heroes in films and movies, you don't have Plot Armor.

It is incredibly common that people think they can just go back in holding their breath or stay low or cover their mouth with their clothing like in hollywood...but they take a bit of a breath, cough, and suck in lungfuls of the smoke, and are almost immediately incapacitated.

A lot of things, like PVC for example, release chlorine gas when they burn, which immediately turns your lung mucus into hydrochloric acid. All the other things in the smoke is incredibly bad for you both short and long-term, too.

The smoke is also flammable. Opening a door lets in oxygen, and oxygen + fuel + heat = a fuckton of heat, very suddenly.

I really wish that writers would suffer legal liability for shit like showing people entering a building with their shirt over their mouth - it's where people get the idea that they can so that sort of stuff.

I did window cleaning in the 2000s and went inside many rich folks homes. It was my favorite part of the job.

But I had a much different experience. They were kind, more humanizing than middle class housewives, and very proud of their homes which were often fully custom to their spec. Most had built a successful business. Perhaps my curiosity went a long way to flatter them, or they saw themselves in me - young and hustling.

> That job put me in contact with a criminal gang who went on to supply with me dozens of GBs of stolen hard drives that I used to create what was probably the largest warez FTP

Statements like this seem to agree with the anti-piracy groups' narrative about piracy being closely related to organized crime, a claim that initially seemed questionable to me.

I also did this in the 2000s and while it was fun to peer into their lives, the amount of porn I was forced to see on elderly people's machines was... not great. Especially during those rare occurrences where they wanted to watch what I was doing to "learn how to use the computer." Just awkward all around.
I specialized for a while in NYC as someone who get a network of Macs connected to the internet with an ISDN line.

I know exactly what you are talking about.

In the late 1980s I had a friend who was a bit of a thug who ran a BBS that you could download any pirate software you wanted if you paid a monthly membership fee and also worked in some kind of computer warehouse where he would occasionally nick a hard drive and sell it for much less than retail. His apartment was saturated with tobacco smoke and he always had a copy of Atlas Shrugged around.
>I was hit on by several bored housewives, including one that answered the door in her open robe.

When you applied for the job did they list this under the benefits?

> I was hit on by several bored housewives, including one that answered the door in her open robe.

Not sure I believe that.

Wild read!
I love this. It's written for the hell of it. Not to get likes, or people to subscribe, or buy a product or show off technical prowess. It's just writing to share - Oldschool Internet content.

[Not that there's anything wrong with the things I mentioned - I just mean it's refreshing to see something not written with an obvious motive. Gah. I still sound like a wanker.]

One of the things I miss by reading this post is how empowered CSRs were back in those days. Today, everything is scripted and highly metricized. Going through the customer service line today will get you the run around and lot of toothless solutions. No one can do anything and even "escalation" mostly means handing you off to another powerless CSR to continue the runaround.

This post reminds me of my youth. I had a Mac and the motherboard died. AppleCare told me it was out of warranty. But I had the receipt of the extended warranty we bought from Sears. They wanted me to pay for the repair and send them the invoice. I told the Sears CSR "this is my schoolwork computer and we don't have money like that. Which is why we bought this warranty. Because you told us it would take care of any problem with our Mac." That CSR jumped on a 3-way call with me and AppleCare. I think they did a purchase order but all I remember was it was handled and the Apple repair tech was there the next day.

Just the thought of someone even having that much autonomy nowadays is completely foreign.

What a great story. This is the kind of writing I encourage many of my retired friends to try. Start by a few short anecdotes and stories of things or people you remember. Even though we are not Cicero, our history has changed dramatically in our life times (maybe it was always like this?) Many of them have lived thorough some interesting part of history and witnessed social and cultural, technical, change that will be very interesting in the future. Imagine the characters, the anecdotes, the humor, the disaster that retired: teachers, farmers, mechanics, doctors, and so on, can tell.
This takes me back. Way back in like 2004-2006 or so I was working a computer repair desk at a big retailer and did a ton of side business. The side business honestly paid more than my job did.

I would travel around NYC fixing things for mostly clueless people. People attempting to screw me on payment was common. The frequent move was to offer drugs or sex in lieu of payment after the work was done. The only sane response to this though was to tell them to just pay what they could afford and then get out of there as fast as possible.

I had a few rich and famous clients. It was a fun time, but I got tired of taking long, extended train rides after a full day of work only to do more work and have a long train ride home.

I was once an Apple Certified Technical Consultant, mostly doing managed services-type work for small businesses in NYC but would sometimes get the call to go to someone's house, usually an owner or other senior-level exec at one of these businesses.

These were serious houses. Huge houses out in the Hamptons or four-story brownstones on the Upper East Side.

One call, I was doing work to resolve an issue with a customer's network, which consisted of a number of AirPort Extremes. One of these was in their bedroom, under a bed.

For fifteen minutes or so, I lay on my belly, working away at my laptop trying to reset the godforsaken thing, when I spotted a small chair a few feet away. Pulled it over, and began working in a much more comfortable seated position. As I grew comfortable, I'd lean back on the back two legs of the chair and kind of rock back and forth.

As I'm doing this, the owner pops her head in, saying, "Hey, anything I can get--oh my god please get up."

Turns out the chair was pre-federal (ie from the early 1700s) and was probably worth at least my annual salary. Fortunately no damage, but it scarred me. I was not invited back to do repair work at that house.

My favorite bit, "Threats quickly lost their power when you realized nobody at any point had asked your name or any information about yourself. It's hard to threaten an anonymous person."
He writes well. This is the blog post I'd really like to read:

> Like all of my bosses early on, his primary quality was he was a bad judge of character.

This is a great read! I am fifty years old now, but for many years during my twenties I supported myself as a one-man Mac/PC repair shop...in a college town. I made house calls almost everyday, and every evening was spent in my home shop working on drop-offs.

I got to meet a ton of different people. There were the computer-illiterate business owners with ridiculous expectations; the lonely middle-aged guys with esoteric hobbies who talked my ear off; the single moms on a tight budget raising three kids; the ultra rich people wanting to keep a ten-year-old PC alive; the author who had lost years of data and would pay "whatever it takes"; the religious father with gigs of porn; the helpless college students whose lack of basic computer knowledge actually impressed me....and more

This was like a trip down memory lane. Great read. Thanks for sharing!

I did that for about 10 years from 2000 to 2010. The part about "being part of the furniture" is really on point. It is incredible how little they think of you. This has a side effect, they thrust you. Ebanking logins, emails, personal conversation, photos... You get it all. I was always very discrete and never did anything "bad", but there were moments when I was treated like a nuisance where I really wanted to. There is also a few times when you find out that the husband or wife is cheating, that is always very difficult to handle especially when the other one is here with you saying how great their partner is.
The experiences of people who meet a wide range of customers are always interesting.

I had read a similar story of a man who worked at car showrooms of various brands (such as Honda, Toyota).

> Look it's important that if you see Oprah, you act normally, please don't ask her for an autograph or a photo

I never understood why people drool when they see celebrities.

Movie actors, musicians, sportspersons etc — I like watching them when they're in a movie, or when have sung a song, or when they're on the field playing, but I never really had any inclination to actually meet them. Even if I did meet them, I wouldn't have anything useful to say.

Thought provoking article. I like to think I acknowledge the people I call for services, at least to the extent they want the conversation. I'm sure there are many more in daily life I don't notice but whose work makes my world go around.

The anecdotes about the rich in Chicago match the ones I hear about the rich in California. The divide is nearly complete.

That was the most fun thing I've read all year. I know we're not very far into the year but I do read a lot.

Just an example about a parent requesting tracking be installed on her daughter's phone

"One girl waited until her mom left the room to casually turn to me and say 'I will pay you $500 to lie to my mom and say you set this up'."

I was offended that this 15 year old thought she could buy me, in large part because she was correct."

Part of what made this such a fun read is knowing it's 100% all true.

As someone who has lived here for going on 15 years, he really unintentionally nailed the whole spectrum of experience of living in Chicago.

And “Live in a city for any amount of time and you'll start to develop a subconscious odds calculator.” was very relatable.

From the entire article, this paragraph stood out the most to me

> The golden rule that every single one of these assistants warned me about was not to bother the husband when he gets home. Typically these CEO-types would come in, say a few words to their kids and then retreat to their own area of the house. These were often TV rooms or home theaters, elaborate set pieces with $100,000+ of AV equipment in there that was treated like it was a secret lair of the house. To be clear, none of these men ever cared at all that I was there. They didn't seem to care that anybody was there, often barely acknowledging their wives even though an immense amount of work had gone into preparing for his return.

You often hear anecdotes of the rich family that's got it all yet the kids are all screwed up and the marriage is on the rocks. For me this paragraph offers a glimpse into why that's the case and why people say "money can't buy happiness". I don't know I may be way off base here but that's the impression I got.

Ironically enough, one of the rich people who did not have a large household staff was Steve Jobs himself. One thing that money often seems to buy you is a bunch of strangers in your fucking house and he hated that.
The tales from the 90s of fixing Macs are like pages from a tech thriller novel. Each story is a mix of high-end luxury, unexpected social encounters, and a descent into the murky waters of digital piracy, all wrapped up in the day-to-day life of a computer technician. It’s a fascinating glimpse into a past where the lines between technology, adventure, and moral ambiguity were constantly blurred.
Well written, but man it leaves me kind of depressed. Maybe that speaks to the power of the writing.
Tools specially for Mac repair. Anyone else remember the "case cracker"? It was a very broad hinged wedge you had to use to open up the original all-in-one Macs (with the 9" B&W screens). There were some capacitors in those machines that blew out frequently. Fantastic computer for its time though, if you could afford it.
Hah! I did the same thing for a few years in the early 2000s, but I wasn't affiliated with Apple and just did upgrades, fixes, etc. I rode my bike all over town and charged by the hour. I had all my tools and wallet of CDs for all kinds of stuff with me. Good times!
Finally a comprehensive guide on how to arrange ones home/life once that YC deal goes through.

There's also the tip on bus station prey, should it not.

Great read (seriously).

Interesting read. It reminded me of "Do Things That Don't Scale" https://paulgraham.com/ds.html

I just didn't get the part where he says teens are mean to him, but the only example is where a teen made his job easier...

> I was always uncomfortable with these jobs, in large part because the teens were extremely mean to me. One girl waited until her mom left the room to casually turn to me and say "I will pay you $500 to lie to my mom and say you set this up".

> I was offended that this 15 year old thought she could buy me, in large part because she was correct. I took the $500 and told the mom the tracking software was all set up.

If you liked this, you might like the novella "Laserwriter II" by Tamara Shopsin.

https://www.theverge.com/c/22713440/the-worst-thing-on-earth...

Reminds me that what we really crave is authenticity. It’s the number one rule for writing. Also shows why AI content is so pointless.
It was enlightening to learn about obscure parts of the Mac repair world and to ponder the lives of all the people you met.

Awesome article

mad perspectives. being a tech frontliner you saw so much. in fame, in lives of excess. amazing hearing from your perspective how the wealthy think and live. one of the best articles i've read on the web in a long time, thank you for writing it.
Imagine being a Mac fixer turned pirate king - only in the 90s, right? From smoke-spewing printers to brushing shoulders with the digital underworld, those were the days of real tech adventures. Makes you miss the wild side of tech.
This was eerily similar to my experience about 5 years prior. My experience was in Australia on the software side. Down to the same equipment, same style people, same style interaction with apple.
>I was offended that this 15 year old thought she could buy me, in large part because she was correct. I took the $500 and told the mom the tracking software was all set up. She nodded and told me she would check that it was working and "call me back if it wasn't". I knew she was never going to check, so that part didn't spook me. I just hoped the kid didn't get kidnapped or something

I'm not sure why he didn't take the $500 and set up the software on the little punk's phone.

I love these well written, slyly comical in a dry way, articles.
These anecdotes from the front lines of 90s tech support are nothing short of astonishing. It's a vivid reminder of how the tech industry, often seen as mundane or straightforward, has its share of wild, almost unbelievable stories. From tech mishaps turning into hazardous situations to an inadvertent descent into the world of digital piracy, it's a stark contrast to the current, more sanitized world of tech support and IT.
Great story! This had me confused though:

> Often I'd show up only to tell them their hard drive was dead and everything was gone. This was just how things worked before iCloud Photos, nobody kept backups and everything was constantly lost forever.

Why not suggest sending the drive off to a recovery service? They certainly existed back then, wealthy clients could afford it, and you could add a nice markup.

Excellent title, better article. This described worlds I didn’t know existed.
Surprised to see Wiha mentioned here. The founder lived with his family in my hometown and my mother worked in his household back in the 60s at the age of 14/15. Definitely different times back then!

Edit: Did not follow Wiha and didn’t know that it became this big! When reading it, I only remembered stories of my mother how she took care of the children and was totally blown away to have such a personal connection from a seemingly unrelated story.

Great read and a trip down memory lane for me as I cut my teeth being a field engineer for a small IT support company in London for 2 years was back in 2005.
Nice writing. I like it.

I'm actually thinking about getting a training of electronics technician because I want to learn the soldering/desoldering part of hardware hacking -- which I believe any serious hacking may need such skill. But then the job prospect and salary are not really convincing...

I used to fix computers for doctors when I was a teenager, this brought some memories, fun read.
Talk about tech gone wild! Those 90s Mac repair tales are straight out of a heist movie, complete with inkjet smoke bombs and an accidental dive into the piracy deep end. Makes today's IT work look like a walk in the park!
what an enjoyable read

i felt as if i was teleported to the OPs job