The Internet is a vast place.
The Internet is a vast place. It didn’t always exist. It might go away someday.
I can remember the family gathering around our Windows 95 PC and attempting unsuccessfully to dial up for the first time. That was likely in the mid to late 90’s. I guess we eventually got it working because I have memories of my Dad and brother downloading The Hamster Dance and those banging Phil Collins Tarzan songs on Napster. I didn’t really understand it. My brother was a big video gamer and he would print out walkthroughs and guides off of gamesages.com. What a time to be alive! I also have some vague memories of my brother and Dad going head to head in Command & Conquer while my dad was at work. It might have actually been StarCraft, I’m not totally sure.
I don’t think I really understood the concept of the internet until I was in 6th grade and was forced to take some kind of computer literacy class. It was mostly a lot of Mavis Beacon Teaches Typing, but we also learned basic computer parts like CPU and motherboard, as well as some basic internet skillz. I actually distinctly remember the teacher saying that we were “way behind” on voice recognition software compared to where we should be. I wonder where lines like that come from? I believe the year was 2002.
I remember learning about search engines, and it was at that point I started repping Google as my engine of choice because it was simple and fast. I remember being strictly told never to click the “I’m Feeling Lucky” button and honestly I’m not sure if I ever did. I think there was some assignment where we needed to find something false online and there was this crazy website talking about how Bill Gates had died with a video of him being pied in the face.
I think my first true internet love was email. I had a Juno.com email address and would tie up the family landline 300 times a day so I could check it. I think readers of my blog will understand how much I love email. Back in the day, before big social media networks, it was all email. People would send around what would essentially be considered memes today, little jokes and anecdotes. There were also viral email forward chains like “send this to 10 people or your crush will die tonight” as well as some weird hoax kind of stuff. I think all of that still exists just in different forms. There was also the ever-present threat and fear of viruses such as the Love Bug but I personally never got pwned.
Shortly after, some friends told me about AOL Instant Messenger aka AIM. I’m going to be 100% honest with you, I had a girlfriend in 6th grade and I pretty much exclusively used it to chat with her. We still had just the single landline so I had to be a little sneaky. I’m sure my mom missed so many phone calls because I was on the internet. I’m not sure exactly how to put into words the world that internet messaging and email opened up for me, but man, it felt like a whole new universe.
Surprisingly, I don’t recall ever getting into anything I wasn’t supposed to. Maybe some accidental hentai web banners on sketchy ROM websites. That’s another big aspect I loved about the internet: roms and emulation. Our computer could do both NES and SNES pretty well and I loved getting games. The issue was that only my parent’s computer had internet at that time so we could only get games that were smaller than 1.44MB and could fit on a floppy disk to be transferred to our computer. I guess later I got the internet hooked up to our computer so I could chat with hot chicks all day. If I remember right my website of choice was cherryroms.com. Actually, the first “website” I ever made was called “Dave’s ROM Dungeon” and it was an HTML file on my hard drive with filesystem links to a couple of my favorite ROMs. I didn’t know anything about hosting or how to let other people access my site. I’d just click the link and download the exact same ROM to my computer, from my computer, again and again. It was cool!
Around this time I also had a friend whose dad was a programmer who worked from home so they had a broadband connection. I remember him showing me Runescape and I think I set up an account but just never really got into it. It always just felt kind of weird and sketchy to me, and frankly, it still does. Years later, my little brother’s friend got all his stuff stolen by a scammer which I still think is pretty hilarious. He was devastated.
I was pretty into music during this time and I liked browsing various bands’ websites to see what was out there. I don’t remember finding anything too interesting but it still felt like a cool thing to do. Before that, you could go to the library and see if there might be a book you could check out on a topic but it was almost always outdated and irrelevant. It felt cool to be able to access current information.
That same Runescape friend also showed me eBay and possibly Amazon. I grew up in mostly rural places so stores just didn’t really have that much stuff. For example, to buy a video game we’d drive to the city on a rare occasion but most often we’d have to order it out of a catalog. That kind of makes shopping hard though, just picking something out based on a single box art image and a few-sentence summary. I’ll never forgive myself for ordering some god-awful Rugrats game on the Game Boy Color out of a Sears catalog. What a letdown. The concept of eBay was particularly interesting to me because you could get things used for a pretty good deal. He was into Magic: The Gathering and would order cards. I remember the first thing I bought off Amazon was a used copy of Tell All Your Friends by Taking Back Sunday and my little brother got a used copy of I-Ninja for the Gamecube. When that package finally arrived I was literally shaking with excitement. Still one of my all-time favorite albums too, not ashamed to admit it.
Later, I started selling some of my random junk on eBay. I’m not really sure how but I just figured out how to do it. I 100% lied about my age when I signed up for the account and typed in my mom’s bank account info. I actually still have and use the very eBay account. My eBay account is older than most people alive. That was a real thrill. I also bought some stuff like a Palm Pilot. Again, getting things used for a good deal when you have no money is awesome.
When I was around 13 my parents got divorced. We’d go to my Dad’s every other weekend and it was mostly super boring, we’d just sit around. Because we didn’t live with him full-time, we didn’t have any friends or anything to do. He had a computer with broadband I’d use to browse the web. Around this time, some friends told me about the website AlbinoBlackSheep.com as well as StupidVideos.com. I loved watching those animations. “Someone has set us up the bomb”. What a legend!
That amount of unsupervised time bored on a computer combined with the fact that I was also in the throes of raging puberty meant I ended up dabbling a bit in the “dark arts”. I’d check out IGN.com and they had a whole section called “babes”. It wasn’t pr0n, strictly speaking, mostly hot chicks in bikinis kind of thing. That was the ultimate forbidden fruit but I’m glad I never took it further than that. I was pretty naive about all that stuff, really, which probably means that I was raised in a good way.
This boredom eventually led me to find some cool web forums. There was a group called “AGD Interactive” who was working on a Quest for Glory II VGA remake and I had fun reading their forum. I also was a big fan of The Aquabats and they had a fun forum that I enjoyed hanging out on as well. Kids at school told me they were using MSN Messenger to chat so I picked that up, but I don’t recall using it much. It just wasn’t the same as talking to my 6th grade girlfriend on AIM.
As I got into high school, I started learning more about programming and I found DreamInCode.net which was a programming-focused web forum. I had fun reading it and posting some of my homework questions there. It just felt like a cool place to hang out, but I think my experience there was pretty short-lived.
Towards the end of the 2000’s, my brother learned how to torrent things so we spent a lot of time on The Pirate Bay getting music, movies, and games. This was still pretty much pre-mass digitalization with the exception of maybe iTunes, so it really felt again like it was opening up the world of possibilities. I could watch pretty much any TV show or movie and listen to any music. I never really got into the video game torrenting because it was pretty complicated and also seemed to have a lot of viruses. I remember seeing a Razor 1911 cracktro which really blew my socks off.
One day in 2008, my friend called me on my cell phone and said “Dave, have you heard of Facebook?” and I was like “yeah that stupid thing like myspace?” and he was like “Yeah, but it’s actually really cool. Pretty much the whole school is on there.” I asked if my current crush was on it and he said yeah, so I was in. Maybe it seems like my favorite thing about the internet is the ability to chat with hot chicks all day, I’m just now realizing that. Maybe there’s a lesson there. I liked Facebook a lot. I liked writing on other people’s “Wall” and chatting with my friends from school. I got probably too into it. But man, it was really cool. I’d go hang out with hot chicks, they’d take a bunch of really stupid photos, and then they’d upload them the next day or so and then we got to kind of relive it and make sure everyone else knew how left out they were. It asked about your political affiliation and I remember putting down “social democrat”. How incredibly edgy of me to do so in 2008. I think Facebook was pretty much in a continual downward spiral from that time and around 2018 I deleted my account and haven’t looked back. I sort of wish I could browse Marketplace but it’s just not worth it. Even the stuff my friends who still use it talk about seems really incredibly stupid and toxic. I think I called it a “boomer dementia ward” and it feels pretty accurate.
I’ve always enjoyed YouTube and they seem to have done a pretty good job keeping the platform alive. At first it seemed like a continuation of joke sites like StupidVideos, but then it developed its own culture with big creators gaining large followings. I was never really that into it, but I think the first influencer I really got into was Casey Neistat back in the daily vlog days. It feels like a lifetime ago and I honestly have no clue how he pulled it all off. Looking back, a lot of the content was super vapid but hey, Obama was president, we finally climbed out of a recession, and things were looking pretty good! I still watch more YouTube than I’d like to admit but I’m finding a lot of my favorite channels becoming pretty boring and stale. It feels like there just isn’t that much to make videos about. One honorable mention would be Tor’s Cabinet of Curiosities. It’s kind of like Depths of Wikipedia in YouTube form.
Around 2012 I had a friend who introduced me to Reddit and I got really into it for a while. I remember just looking at the memes and laughing my absolute butt off. It felt politically fresh, socially aware, and smart. Within a year or two I think the veneer started to wear pretty thin. The interactions that seemed smartly sincere started looking more like karma farming. It just felt inauthentic and self-absorbed. One day I just decided I was done and I haven’t really been back since. I’ll still read the occasional thread when I’m trying to figure something obscure out, but the quality is really really low. Sometimes I’ll look at super small/niche subreddits and gawk a bit at how sad it seems. It doesn’t help that they’ve changed the web UI to be so bad it’s nearly unusable and I’m not going to jump through a bunch of hoops to just occasionally look at some super low quality thread about which Gundam OVA I should watch. Today I actually think Reddit is about one of the overall worst places on the internet. I mildly despise it and have a hard time respecting anyone who spends much time there. I think it’s bad for you mentally and emotionally and gives you a really poor outlook on what the real world is like. I’ve actually developed an informal rule about Reddit advice: You should hold the Reddit consensus and the exact opposite view of the Reddit consensus in equal standing. If Reddit strongly agrees that heavy things are the best, you should also consider that light things might also be the best. That rule has helped me out more times than I can count. If your experience there is different, that’s totally fine and you should keep at it. That’s just how I feel about it!
Some time in high school, possibly prompted by that epic Razor 1911 cracktro, I got interested in chip music. Actually, I know exactly how I got into it: I was making an Aquabats point-and-click adventure game. Funny how both of those early web forums I got into combined to lead me to another big interest. There was a big forum called 8bitcollective that was the main place everyone hung out but it just felt a little too “internet-y” to me and I never loved it. Then, another forum called chipmusic.org popped up and it felt more focused, more mature, a bit stricter, but also more fun. People were posting really cool and interesting work back in those fairly early days of Game Boy modding. These days retro gaming is fully commoditized but at that time it was still pretty niche. You could find an original DMG in decent shape for $20 or less. I became a daily visitor of chipmusic.org (dubbed cm.o) for several years. It was through this, that I would start my business Catskull Electronics which probably needs its own lore drop. That experience eventually took me to parts of the world I could have only dreamed about and connected me with good friends spread pretty much anywhere people live. Eventually as everything online conglomerated to Reddit, Facebook, and later Discord, cm.o mostly died out. I’m not sure when it happened but people stopped posting. I still visit every now and then but it’s a ghost town. I assume that most of the people there, like me, moved on to other interests as time went on.
Around the time I swore off Reddit, another friend introduced me to news.ycombinator.com aka “Hacker News”. It felt similar to what I liked about Reddit and earlier forums. Discussions felt more authentic and it felt like a lot of commenters were a bit more plugged into the day-to-day reality of the real world. It felt a bit like being able to take a window seat to the insane hustle going on in Silicon Valley back in the early/mid 2010’s. When I decided to jump ship on a startup in 2020, I found my next job through a Hacker News “Who’s Hiring?” post. Of all the online communities I’ve been a part of, I think HN has had the most direct impact on my real life, since that job provided my income for 5 years and was a huge and amazing learning opportunity for me. Travelling to and working for a “Bay Area startup” felt like something out of a fairy tale.
Today I still read a lot of Hacker News and I feel like it’s a pretty good way to keep your finger on the pulse of the tech industry, but the veneer has started to wear thin. It’s run by a very much for-profit venture capital firm that is very much incentivized to serve their own best interests. A really good post on this topic is The Mysterious Forces Steering Views on Hacker News from マリウス.com.
Back in August of 2025, around the time I burnt out from my position at that acquired startup, I published a pretty emotional and scathing response to the “AI” craze titled “What the hell is going on right now?” To my surprise, someone posted it to Hacker News and it started trending on the front page. I literally woke up one morning and during my morning business noticed it was in my feed. I think it was even in the number 1 spot on the front page for a while. Then, suddenly it was just gone. Not on the front page, not on the second page, not on the third page, just totally gone. It literally went from around the number one spot on the front page to totally buried in about 15 minutes. I’m not completely covering my head in tinfoil here - the post was hasty and lacked a lot of substance. But it seemed to be resonating with people for whatever reason and then it was just gonezo. The mods did leave their trail, though, they edited the title to be simply “What is going on right now?” since I guess “hell” isn’t appropriate language in a Hacker News post? A quick search yields a lot of popular posts over the last decade with the exact same phrasing I used. Like I said, I still read a lot of Hacker News and I enjoy it, but I would suggest you also become familiar with how it works and what interests are being protected. YC is a VC firm first, and a community message board provider second (or maybe even last).
For the past couple of years, I’ve really enjoyed being in The Bullpen Discord server. I never really liked Discord, and I still don’t. Big servers are just way too busy and the chat format doesn’t work super well, in my opinion. However, we’ve got a couple of core folks in The Bullpen who I really enjoy chatting with. If it weren’t for that, I wouldn’t be writing this post since it’s there that we organized this very blog post challenge! I’ve always been super chatty at work, usually being the top chatter on the company Slack instance for better or worse. At some point I figured out you probably shouldn’t wear your heart on your sleeve that much in a professional environment, so it’s been really fun to have an outlet for that kind of “watercooler” talk. Though we’ve all worked together at various times, it’s not a company-sponsored thing so it feels a lot more free and honest. Actually the real lore drop here is that I originally created The Bullpen as a hipchat private room when we all worked in this weird windowless room and I unscrewed the lightbulbs. Then I left that job, and the company banned off-topic chats on the company hipchat, so they made it a Discord server but none of them told me until years later! I also really like Discord’s voice and video, I really think they have the best-in-class offering there.
I think my real favorite place on the internet is personal blogs. I really enjoy finding random blogs and personal sites. There’s no algorithm to be gamed. Most of it is just shouting into a void. But crazy nerds like me spend time and effort on our digital gardens. Motivations are mixed, but there’s just nothing like coming across a cool personal site. I can subscribe with my RSS reader and stay up to date.
As an antithesis to personal blogs, I really don’t care for Substack. Having a “Subscribe?” modal pop up on every post is just annoying! I don’t like the community there either. Maybe I just don’t really care for any online “community” since they inevitably become an echo chamber for whatever “the algorithm” likes the most. I’m not a full “dead internet theory” believer, but there definitely is a lot of fake and inauthentic activity on all online social platforms. It seems people will do anything for fake internet points and state-sponsored actors are pretty good at steering the “consensus” in the direction they want.
I’ve been a Wikipedia reader for as long as I can remember. I love reading Wikipedia. I like knowing a little bit about a lot of things. I understand the limitations of the platform. It’s not free from bias. Individual articles vary wildly in quality. But as a way to get a rough, 1,000-foot view of something, Wikipedia is the best. Did you know if you sign in to an account they’ll actually send you a “Wikipedia wrapped” at the end of the year? I also really like the Wikipedia mobile app. If you want to keep tabs on what I’m Wiki’ing lately, check out my /wiki page, or even subscribe to the RSS feed!.
It’s a bit difficult to even talk about “the internet” as a single concept. Maybe I have an outdated idea, but I don’t really consider “the internet” to be any connected service. I primarily consider it to be the thing you view with a web browser. Maybe “the internet” to me really means the World Wide Web. A smart light switch isn’t “the internet” even if it needs an internet connection to operate. I think that concept is already changing drastically with huge platforms like Roblox. As much as we want to gallivant about making a “new internet”, I think it’s already happened. I don’t think my kids know how to use a web browser or really even have an understanding of the concept. But they play online games. They watch videos. The internet has become the services that operate using a public network connection and the World Wide Web is nearly a relic of the past. But I think I’ll still be here in 50 years, drafting blog posts in nano, sending emails, and subscribing to RSS feeds. I wouldn’t be surprised if I become a modern ham radio operator, but instead of broadcasting airwaves from my basement, I’ll be blogging, connecting with other crazy people who are like-minded enough to figure out how to use the ancient technology.
My friends and I decided to do a weekly blog challenge for the month of April, 2026! Each week, one of us chooses a prompt and we all write posts.
For week 2, Jared chose the prompt:
"What are your favorite places on the internet or favorite things about the internet and why? How do they differ from the parts of the internet that you dislike?"
My friends' posts this week:
My other posts in this series: