Web Masters Episode #40: Stefanie Syman


FEED Magazine

Stefanie Syman:

When I was coming out of college, one, it was a horrible recession. ’91 was bad, and I graduated in ’90, so ’91 was terrible. Two, the options seemed to be four, right? If you were not going to go to med school or law school, you could go become a consultant, you could go work in an investment bank, you could maybe go into journalism, and then I guess there was teaching and things like that. It wasn’t like you saw all these different opportunities. You could go become a starving artist. You could name the things on one hand.

So I was not interested in investment banking, I was not interested in consulting. I flirted with law school and happily avoided it. But in a way, I think a lot of the kids, and we were kids at the time, that got into the internet in the early, mid-’90s were people who had not found their footing professionally. Didn’t fit into that kind of narrow set of roles and industries.

We had relatively low risk. We were not abandoning our investment banking career or our corporate law career. We were just creators, artists, writers who hadn’t really fully landed, and we saw the internet as this opportunity to really shape something.

Aaron Dinin:

You just heard something lots of people forget to consider when talking about web entrepreneurship and the early internet pioneers. These days, being an internet entrepreneur is mainstream. It is, dare I say, cool. That wasn’t the case when the web first launched. And the people building stuff online weren’t following the crowd, they were part of counterculture. They were non-conformists.

Stefanie Syman:

This is going to be hard for a lot of your listeners to understand. The internet in those years was very anti-establishment. Companies were not on there even with brochureware. The New York Times did not have a website when we launched. Google was a distant dream. So it really was this kind of almost backwater, and the people playing there were definitely the rebels and the artists and the tattooed people. Or at least we saw ourselves that way, of course.

Aaron Dinin:

That’s right. The early web wasn’t a place where everyone gathered, it was home to the alt community. It was a place where people gathered who often didn’t feel like they fit in with other parts of society. That community started building its own digital culture. Little did they know they were unwittingly shaping a lot of the culture we recognize today as, well, normal.

That culture was shared and propagated in the same way most culture gets shared and propagated. And by that, of course, I mean through media, specifically online magazines. Writing about digital and tech culture became popular among early web users. The person you just heard from led one of the most popular early online publications. Her name is Stefanie Syman, and she was the founder of FEED Magazine. Are you ready to hear the story? Let’s get dialed in.

[INTRO]

Aaron Dinin:

Welcome to Web Masters. This is the podcast that teaches about entrepreneurship by talking with some of the internet’s most impactful early innovators. My name is Aaron Dinin. When I’m not creating these podcasts, I teach entrepreneurship at Duke University. Before that, I was building venture-backed tech companies. In other words, I was a tech entrepreneur, which was a cool thing to do when I graduated college. However, as we’re going to learn in this episode, that wasn’t always the case. But before we can hear more about the countercultural roots of the early web, I want to take a quick moment to thank this podcast’s sponsor.

Web Masters is being brought to you thanks to the generous support of Latona’s. Latona’s is a boutique mergers and acquisitions broker that helps internet entrepreneurs, no matter how cool or uncool they are, to buy and sell cashflow positive internet businesses and digital assets. That includes things like e-commerce stores, Amazon FBAs, SaaS apps, domain portfolios, content websites, and just about any other type of online work from anywhere internet business you can think of. If you have one of those and are interested in selling it, reach out to the team at Latona’s. They’ve been helping people just like you sell their companies for a long time, and they can help you get a great price. Or if you’re looking to buy a profitable internet business, you can find lots of different options over on the Latona’s website, latonas.com. Check them all out. That’s latonas.com.

These days, the majority of people on the web are mostly passive users of the technology. We browse, we read, we watch, we explore. In its earliest days, the web didn’t have nearly as much content. That made it a lot less exciting for mainstream users. At the same time, the ability to create and publish on what was basically an empty canvas appealed to the kinds of people who liked creating new things. One of those people was Stefanie Syman. She eventually founded FEED Magazine, one of the early internet’s most prominent and popular digital publications. It was a place to explore art, media, and culture, particularly in relation to emerging digital technologies. It was BuzzFEED before BuzzFEED, and Vox before Vox. And in a lot of ways, it was ahead of its time. Which actually isn’t much of a surprise, considering Stefanie was someone who saw and understood how computers were going to impact culture well before most other people.

Stefanie Syman:

I was not a computer nerd as a kid. I think we might’ve had an Apple at the end of high school, but I honestly can’t remember. But in college, we had Apple computers in the basement, I guess. The computer lab was what it was at the time. And everyone was writing their papers and printing them out on computers, but no one had a computer, or I don’t know of anyone that I can remember who had a computer in their room. Certainly, at the beginning of college. By the end, perhaps.

By the time I graduated, we all had computers. In a five-year span, we went from computers being a thing but not something that everyone owned and used all the time, to you just definitely had one. And I became fascinated in how technology was shaping culture.

Aaron Dinin:

Why did that fascinate you? What made you think that was important or unique?

Stefanie Syman:

In some ways, that was a little bit of a continuation from some of my interests in college, because I actually was interested in medicine and culture, and did some crazy thesis which no one really liked. But in any case, I was used to trying to navigate or trying to understand how one domain interacted with another.

So when I started to look at what was going on around me, I went into documentary film, thinking that would combine storytelling and some other of my interests. And I quickly realized that the pace of technological change would change the industry. And then a lot of what you needed to be a successful documentary filmmaker at the time was how to fundraise, because you had to raise a ton of money to just make the actual film. And I realized that the cost of the storytelling would go really far down really quickly, because you could shoot it on digital and you could edit it on Avid. And the reasons you did the things you did would change.

Now, I do think you still have to raise a lot of money for documentary films, but the why and where that money goes is different than it it was. It’s not for just the camera person and the equipment and the film itself. So that was kind of a moment where I got interested in how technology is reshaping or affecting a particular industry.

Aaron Dinin:

Okay, so you wanted to go into documentary filmmaking, but that didn’t happen. I was reading that you became a technology journalist, right?

Stefanie Syman:

I decided to start writing about technology and culture, and pitching stories that were unlike anything other people were writing, because I was pitching technology as a culture story rather than a science or a business story, and was surprisingly successful. Because here I was, I was nobody. I had no clips to my name, and somehow managed to convince people to pay me to write about this stuff. And eventually convinced an editor on the leisure and arts page of the Wall Street Journal to let me have this semi-regular column, and started writing about CD-ROMs and digital games. And then eventually, wrote a piece about the web, which I probably have somewhere. As I was working on these columns, I realized that it was really a matter of time before I started creating in the medium that I was reporting on.

Aaron Dinin:

So even though you were writing for traditional print publications, it kind sounds like you already knew you’d be writing for digital publications in the very near future. Is that kind of what you’re saying?

Stefanie Syman:

It was very obvious to me. Kind of just had it in the back of my mind. Didn’t know how I was going to do it. And then was introduced to Steven Johnson by mutual friends. The reason why we were introduced was because we both had email and we could be email buddies. So that really was the beginning of a really fun friendship, because we had a lot of intellectual common interests and then blossomed into the partnership that became FEED.

Aaron Dinin:

You heard Stefanie mention Steven Johnson. That would be well-known media theorist and award-winning popular science author, Steven Johnson, author of lots of books, involved in lots of tech companies, and even, I believe, a fellow podcast host. Anyways, Steven and Stefanie became sort of like digital pen pals back when you might become friends with someone just because you both had email addresses, which is kind of fun to imagine, I suppose. And through that friendship, they started kicking around the idea for what eventually became FEED Magazine.

Stefanie Syman:

What happened was Steven and I had kind of parallel gigs. He had a column that was much like the one I had at the Wall Street Journal, I believe at the Guardian. The London Guardian.

We would give about our columns and this and that. And I knew I was waiting to jump in, and he actually too, some sort of web media something or some digital media something, and he had an idea for effectively, a zine. He kind of wrote up a little proposal a few pages long that laid out some of the details. He showed it to all his friends and they were like, “It’s a pretty good idea, but you’ll never do it.” I read it. I was like, “Yeah, this is what I’ve been waiting for. Let’s go.” So that’s pretty much what happened.

Because I could see very clearly how we got from a creative brief, essentially, these are the topics we’d cover, this is the kind of voice the magazine would have, to an actual, fully realized media property and the company behind it. So I think it was November ’94, we met up about it in person. I remember taking the train to meet up with him. And we launched in May of ’95. So it was like six months.

Aaron Dinin:

You heard Stefanie describe Steven’s proposal as something like a zine. That’s spelled Z-I-N-E. In case you never heard of the term, zines were like a proto-internet in print form. Basically starting in the mid-20th century, people would create small batch, homemade magazines. We’re talking less than a thousand copies, usually less than a hundred. And they tend to be created by and for super fans of niche topics and/or subcultures. For example, you find zines about things like Star Trek and punk rock music.

Technically, zines and zine culture still exists. But as you can probably imagine, they had their heyday before the worldwide web. And things like blogs and Facebook groups have, for the most part, replaced them.

Stefanie and FEED Magazine were basically the start of that trend of the web replacing zines. FEED Magazine was like a culture and technology zine that published via the web rather than print. Sure, that sounds like an obvious publishing solution today, but remember, in 1994, publishing online wasn’t nearly as easy.

Stefanie Syman:

You needed a server or to rent server spaces. It was not just signing up for Squarespace or WordPress, and you don’t even think about what’s on the other side of it. It was like you laid your eyes on the server.

And I think at the beginning, there was this company downtown that we worked with that gave us some server space in exchange for… I don’t know what. We paid them a little. I mean, it was like a shady deal at the time. It was really shady and shady things went on, and eventually, we severed ties after not too long. But it was kind of like perfect because everything was so new. There was no plug and play situation where you’re just like, “I’m going to buy that much server space.” It was all you kind of knew the few people who had server space, you would physically see the servers your stuff was on. And then getting your code onto the servers was… We were FTP-ing, using FTP technology to upload through a modem that was, you will know better than I, 56? I don’t even think we were at 128 yet.

Aaron Dinin:

Yeah, I think that would have still been 56k timing.

Stefanie Syman:

Yeah, in those years. So we were using modems to upload the files, and we were hand coding these HTML files with these images. And we were having to fake a layout. So this is long before CSS. So there was no easy way to make pages look good. There was no way to create a left margin, so we used an invisible GIF to create a left margin. It was crazy.

So Steve and I were hand coding the pages, all of them. I’m trying to remember if we had any tools. I don’t think so. Any content management system, there was nothing at the beginning. I’m trying to remember what there was towards the end, and I’m not even remembering. So we could fit FEED on like three floppy disks at the beginning. That’s how we thought of it.

Aaron Dinin:

So that was the logistics and the operation side of launching an online magazine in the early ’90s. What about content? What was your vision for the kinds of content FEED would publish?

Stefanie Syman:

I mean, I think our vision was to be skeptically enthusiastic about technology. So I think at the time, Wired had launched in ’93, so a year before, and they were so hypo-tech. There was no critical thinking at all. It was just like, “Tech is always great.” So I think part of what we were doing was trying to kind of marry a real genuine optimism and enthusiasm and passion for technology with some of the appropriate skepticism and investigation of the other possible consequences of what was unfolding at a very rapid pace, which was this digital revolution. So there was that dimension was the technology.

And we really also wanted to be a cultural magazine. And we both had a bunch of writer friends who had a lot to say at our 20-something years old, and kind of non-fiction. We had no reporting budget, so we couldn’t send anyone anywhere. So it all had to be in some ways, almost like meta-commentary on how the story was being crafted. And then occasionally, we would have something a little bit more grounded like Sam Lipsyte, who’s a fantastic novelist now, would do these hilarious pieces. He would go experience something and write it up. I’ve never laughed so hard reading some of his drafts for pieces for FEED.

Aaron Dinin:

Sam Lipsyte would go on to become an award-winning novelist with his first book, Venus Drive, published a few years after the launch of FEED. He’s just one of their many young writers who went on to build successful careers.

Stefanie Syman:

Yeah, so once we had launched, not too long after, I think we were described as a cross between Wired and the New Yorker. And at the time, they were not both Conde Nast properties, and so that seemed like, “Yeah, bringing together these very unlike things.”

Aaron Dinin:

How’d you get readers for it? What was the marketing strategy, if I can call it that?

Stefanie Syman:

That is a very good question. I think there were people out there looking for interesting things on the web and stumbled on us. We did get a lot of press at the beginning, because there just wasn’t much yet going on and we were a kind of lovely story. New York has a little bit of tech going on. It’s Silicon Alley. I don’t know if you remember, Jason Calacanis ran that Silicon Alley Reporter. Someone actually just sent me… They dug up copy of one of the pieces on us. It was a little mention.

And then there were parties. I mean, and this is kind of silly, but there would be launch parties for other things, or we would do parties. We eventually made friends with Wired and became the New York bureau of HotWired. So I think we got some distribution and exposure through posting pieces on their site that linked back to FEED. So it was a combination of just straight up word of mouth, press, deal with Wired, or HotWired, really, and just being part of the scene in New York.

Aaron Dinin:

Can you talk a little bit about the quote, unquote, “New York tech scene” a little bit? Because that was another unique thing about internet culture at the time, right?

Stefanie Syman:

It was so fun. I do feel like I got my youthful moment of being part of a scene and knowing which were the parties to go to. Yeah, it was super fun. We could all fit in a bar for a while. You really did feel like you knew everyone.

I don’t know if that happens anymore. I mean, it must, but we were ultimately somewhat diverse people who ended up in a lot of different directions, but there was a lot of cohesion for like five years, four or five years there. And then September 11th happened. And the internet industry… And it was a single industry, which is a joke, right? There’s no internet industry. But what used to be a very coherent industry just got wiped out. And then when it reformed, it was what it should be, which is it’s a disparate set of industries, because it’s really not an internet industry, it’s a media industry and it’s a financial services industry and it’s just everything now has a layer of digital. And soon, the layer became the dominant thing.

Aaron Dinin:

What you hear Stefanie describing here is something that’s hard to imagine now, but the number of people creating for the web in the early and mid-’90s was so small that at the time, the people involved felt like they knew each other and were part of a community with a shared vision of what the web could be and how it would ultimately impact the world. And for a while, FEED Magazine was one of the most popular voices in that community that was both a strength and weakness of what Stefanie built. On one hand, the small and well connected community is what allowed FEED to build a devoted following. But on the other hand, the limited growth of the web to that point made it difficult to build a profitable and self-sustaining media business.

Stefanie Syman:

I think the thing with FEED is that in some ways, our kind of cultural impact, I think, often outstripped our actual size and reach. And because we never really mastered distribution and built a huge audience, we built a very devoted and healthy sized audience, given how big the web was at the time. So I think part of it was we were aware that we were having an impact, because people were interested in us and people would find us that we had never met and weren’t friends with our friends. It was just this odd thing of someone showing up in the comment section in a completely different state, unconnected to anyone you’ve ever met, and that’s very gratifying. And then there’d be moments where Slashdot, they would link to one of our tech pieces and our site would go down, because they would drive so much traffic.

We started to master a little bit of those dynamics, and then Steven or I would be invited to be talking heads on various situations. So the buzziness was apparent. I think that it was very early days for internet and advertising. Once we started to try to do that, we would sell out our site pretty quickly. But I think we always felt, and I think we were, somewhat undercapitalized, given our ambitions.

And because we really… I think we are in some ways, Steven and I, we’re kind of realists. We were optimistic about where the medium as a web would go and that it was going to be transformative and that… We were really, in some ways, making the case by creating FEED, that the web was going to be the place where culture happened in the future, not just lists or looking for information.

That was a new concept when we launched, but ultimately, the size of the web really did not grow exponentially into something that could really sustain a lot of media companies until the early aughts. So we were kind of always in that awkward position of our ambitions outstripped our budget and having to figure out how to navigate that, because we also didn’t want to… I don’t know, we were not capable of saying, “We’re going to be a $500 million company in four years.” We looked at the numbers. We knew what was likely to happen, and didn’t necessarily tell the story that VCs wanted to hear, which is that we could be a very healthy, organically growing media company that could have been the Vox Media of the early aughts. So there was that tension of our cultural impact and our actual financial reality.

Aaron Dinin:

According to my research, you tried to combat that financial reality by merging with another popular online publisher at the time, which was suck.com. Can you talk a bit about why you made that decision and how it worked out?

Stefanie Syman:

The couple things there, we felt like we could see that there was a lot of duplicative effort to try to turn these sites into a business. We all needed an ad sales team. We all needed some back office stuff. You just need the same things that ends up being duplicative, so why not join forces and realize some economy of scale, and then we could FEED traffic to each other. So that was kind of, from a business perspective, not a crazy idea.

And then we hired someone to be the CEO. Steven and I hired our boss, essentially. He was responsible for really building that infrastructure and fundraising. So that was all very kind of rational and made a lot of sense.

But then the thing that we wanted to do was build a Slashdot for culture, because we felt like that was missing, that community. I mean, now, I mean, come on, again, people don’t remember there was a time before our community online was only in these fragmented comments threads or something like an echo. That community that kind of married bits of content and commentary and this kind of fast hit way was very nascent then.

So we built what we considered the Slashdot for culture, which we called Plastic. It was really the same functionality as Slashdot. If you looked at how Slashdot was structured at the time, Plastic was really modeled on that, but it was really focused on culture and pop culture and being provocative in a cultural way. I would say in some ways, not the extreme parts of Reddit, but there’s some dimensions of Reddit that were very much what Plastic was trying to be. The lighter, friendlier. Not the deeply cruel part of Reddit. So essentially, we were trying to create a site to capture user-generated memes and create community and a lot of network effects around them.

We failed. After we got it off the ground, and then not long after, we folded. It was the dot-com bust and we ran out of money. But I think we all saw it coming, and we just couldn’t figure out how to put the pieces together at the right moment.

Aaron Dinin:

This is what I meant at the beginning of the episode when I described FEED and Stefanie as being ahead of their time. Stefanie could clearly see where the world was headed and how the web was taking us there, and she got there before everyone else. Unfortunately, the scale of the web just hadn’t quite reached a point where it could support an advertising based business model. That’s the risk of being early into an industry as an entrepreneur. You can correctly predict the future, but if you don’t get the timing right, the business will still fail. Though, fail is, of course, a bit of a relative term here. Even though the combined publishing company of suck.com and FEED Magazine failed with their spin-out venture, which was Plastic, that version of Slashdot for culture, FEED Magazine itself was an important and influential part of internet history. And as you can imagine, that’s something Stefanie remembers fondly.

Stefanie Syman:

I mean, just even being there at the time and getting something off the ground and having a voice in that early internet was so gratifying. It was so fun.

We made every mistake in terms of running a company you can make, and yet, it was super fun and no one got hurt, or not hurt badly. We all kind of came out of it having done stuff that affected many people in a positive way. We connected with a lot of people and we had fun and we learned a ton.

Aaron Dinin:

Had fun, learned a ton, and nobody got hurt. And I’ll add one more thing that Stefanie didn’t mention but should be highlighted, especially about FEED Magazine, which is that it provided an enormous amount of positive value for its target community of users.

Yes, I’m sure Stefanie would tell you that a billion dollar exit would have been nice too, but build a company where you have fun, learn a lot, create significant value for a bunch of people, and nobody gets hurt, in a lot of ways, that’s what success looks like when you’re one of the earliest entrepreneurs in an immature industry. And that’s exactly what FEED did at a time when the scale of the internet just couldn’t support the available business models for a publisher.

Eventually, of course, the internet would scale enough to support advertising as a viable business model for a site like FEED. By that point, FEED may have been gone, but what I found most interesting during my conversation with Stefanie was that aside from the number of people on the web, most of the other characteristics of successful web publishing were pretty much in place, and FEED was already leveraging them.

Stefanie Syman:

I think the dynamics you see on the web were present from the beginning, which is to say polemics definitely drew eyeballs in conversation. And some of our best pieces, I think, didn’t go unnoticed, but certainly didn’t have the active engagement that some of our more controversial pieces had. So certainly, the more extreme a view, the more clickbaity it is. And we didn’t really do clickbait, but we saw that the extremes that we represented at FEED were pretty mild compared to what’s out there now. But we did see that the strongly held opinions that were less expected did the best, and the beautifully written piece that had nuanced observations did not do as well.

Tech did well because it would have distribution. It was still pretty tech interested and dominated web at the time, and so Slashdot… Do they even still exist? I haven’t even checked. Slashdot was able to send a lot of traffic our way, and there was no equivalent of Slashdot on the culture side. There was no BuzzFEED. Our culture pieces tended not to do as well as our tech pieces.

Aaron Dinin:

Well, that’s kind of depressing. So you’re saying even on the early, early web, clickbait was already a thing and stirring up controversy was a better way to get traffic than creating quality content? Was there anything different about content production then versus now? Anything you’re surprised to see nowadays?

Stefanie Syman:

Yeah, what I would say is I did not predict the degree to which the algorithms would shape people’s reality. I think I predicted the polarization, because we saw it that early, that the clickbaity stories… That wasn’t a word then, but effectively, those kind of provocative titles and polemic pieces would get much more engagement.

But I don’t at all believe that I imagined a world where the Facebook FEED for someone who could live down the block from me is completely different from mine, and so we have no shared reality. And it’s not just like I read the Times and you read the Journal or similar, that that’s been exponentially magnified and the gulf as wide as it is now. That, to me, is sad, to be honest. The way the algorithms kind of program one’s reality, I find distasteful. I mean, I find myself being very ambivalent about social media and not a huge consumer of it, and I don’t really create it at all.

So that dystopian dimension I did not see coming. Because again, when we started, we were really trying to even make the case that there was a reason to be on the web versus the reasons to withdraw and take care of yourself and engage with the real world. So I’m all for balance.

I actually believe the people in the future, who are really going to be the winners, are the people who actually can focus their attention on things that are not digitally mediated while everyone else is distracted. That might be wishful thinking.

Aaron Dinin:

Well, as someone who creates a podcast and lots of other digital content, this is one case where I hope Stefanie isn’t good at predicting the future of culture and technology. After all, if the quote, unquote, “winners,” as she describes them, are the people in the future who can focus your attention on things that are not digitally mediated, then I’m clearly working on the wrong kinds of things. But oh well, if that’s the case, you did get through this episode, which at least means something good happened, right?

And hey, maybe take a moment to share this episode on social media, and let’s see if we can manipulate those algorithms enough to get Web Masters trending. Worth a shot, right?

I want to thank Stefanie Syman for taking the time to share her story and the story of FEED Magazine. If you want to see what she’s up to, she’s still writing. She’s an author publishing books. Search for her on Amazon and maybe buy a few hundred copies. I’m sure she’ll appreciate it.

Also want to thank our audio engineer, Ryan Higgs, for his help pulling together this episode. And a thanks to our sponsor, Latona’s, for their support. Remember, if you’re interested in buying or selling an internet business, be sure to check out latonas.com.

If you’ve got any questions or comments about this episode, you can find us on Twitter. We are @WebMastersPod. And I’m on Twitter too, @AaronDinin. That’s A-A-R-O-N-D-I-N-I-N. I also write lots of articles about startups and entrepreneurship on medium.com. You can find them all by searching my name over there.

Finally, of course, a thanks to all of you for listening. Be sure you’re subscribed to Web Masters so you get our next episode as soon as it’s released, because well, you’ve reached the end of this episode and it’s time for me to sign off.