Josh Riedel, the first employee of Instagram, says that his debut novel Please Report Your Bug Here was inspired by long nights at a fledgling start-up, and the eventual migration of the company to large, galaxy buildings on campus. The part of the story that’s fictitious, however, is a glitch his narrator encounters that allows him to teleport to a seemingly random place in the world. He discovers it at DateDate, an app that promises a match with your soulmate if you answer hundreds of personal questions, and investigates what technology is exactly at play. He goes to Japan, Las Vegas, enjoying the perks of a well-endowed employer, while sneakily getting friends to help him: Where did he go? And why can’t he replicate the same glitch?
Part love letter to San Francisco, part sci-fi thriller, Riedel provides a deep dive into early 2010s Silicon Valley culture through Ethan, who tells his story 13 years in the future. “Once you sign an NDA it’s good for life. Meaning legally, I shouldn’t tell you this story, “he writes at the beginning of the book.” But I have to.”
Our Culture sat down with Riedel to discuss his tenure at Instagram, identity, and techno-optimism.
Congrats on your debut novel! How does it feel to have this story out in the world?
It’s pretty exciting. I sold the novel in late 2020, so it’s been a while of working on revisions — I finished edits on it about a year ago, so the publishing team’s been doing their thing, but it’s pretty exciting to actually have it coming out.
I have to start by mentioning that you were the first ever employee at Instagram. The book draws influence to Silicon Valley tech startup culture, and it’s easy to connect the plot to your personal life. When you were at Instagram, did you have this story in mind, or was it something that developed later?
It developed later — in college, I wrote fiction and kept doing it through my 20s as I was working in tech, but I was kind of just writing whatever, short stories here and there. It wasn’t until after I left the tech industry and moved to Tucson, Arizona for grad school that I started writing this book.
Our narrator, Ethan, is employed at DateDate, a tech startup with a homely four employees starting out. He’s close with his colleagues, despite mentioning only a new hire, Noma, by name, referring to the founder simply by ‘The Founder.’ Later, when the company gets acquired by the enigmatic Corporation, he’s quickly subsumed by the company’s large campus and glass buildings. Unlike Ethan, I don’t want to break any NDAs, but was this the kind of trajectory that the Instagram office took as it expanded further?
Yes, it was, which was quite a dramatic change. A lot of the setting and these details of place are really drawn from my experience working in tech in 2010s San Francisco. So even the opening pages of commuting to work on your bike, going through these streets lined with Victorian houses, getting into the glassy buildings of SoMa where all the tech start-ups were back then. Instagram started out in this small office in the SoMa neighborhood of San Francisco, and about a year and a half after it started, it was acquired by Facebook, and you know, all these bigger tech companies have these giant campuses down in the south bay. So that part of it, the trajectory, kind of parallels my own working at Instagram.
Yeah, I was going to ask if it was that quick, also. With Ethan, he’s at this small place, and after the acquisition, the next day he’s at this huge campus. I didn’t know if that was just to speed up the novel’s timeline or that actually how it worked in real life.
Yeah, the Instagram timeline was longer. We were independent for a couple of years before we were acquired. In the novel, DateDate is only around for a little bit before it’s acquired. But that actually was not uncommon — I’m not sure about today, but when I was working in tech, it wasn’t uncommon for a small start-up that was getting traction to get acquired by a big company like Google or Facebook. I think in the last few years regulators have tightened up.
So Ethan’s story starts with noticing a bug in the software — a black box that shows up on his content review feed, which seems to be appearing to other users, which eventually presents a big problem. When he’s bored one day, he decides to look up his true match, but a glitch transports him, briefly, to a different world. What made you come up with and decide to go with this mechanism, where technology creates sort of a portal?
I think just writing the story, this happens pretty early. I started writing the novel when I was in Tucson, I just turned 30, I was kind of reflecting on my 20s. I felt my 20s and work in Silicon Valley happened so fast, and I was trying to figure out, ‘What is it about graduating college and getting a new job that compels, at least me, to throw myself into work so much?’ So I started writing the novel in that way, recounting some of my own experience — biking to the office, working in a small office — but then, the portals part is where we take a turn into fiction. I think my fiction had progressively gotten more speculative over the years, and I think a big part of that was working in Silicon Valley, being in San Francisco, where everything is trying out new things before the rest of the country gets to see it. So I think I had this speculative, what-if mindset going on, and that infused itself into my fiction. That’s where the portals came from, then I just decided to keep that in the book because I like the idea of inventing new technology and then not fully understanding how it works. We make these new things, but we might not understand the implications of the new tech totally.
Ethan is really concerned with identity, and after being subsumed by the Corporation, he worries that his individual interests are not being tended to, and that he’s just a cog in the machine. Do you think, with corporate culture and apps like Tinder and such, that it’s a valid concern to have nowadays?
Ethan goes into working at DateDate in this real era of techno-optimism — I think there are some studies that say that after 2015, and definitely after 2016, people got less optimistic about technology. But this is set in 2010, so I think Ethan has a lot of optimism as to what this app can do for the world. He’s bringing a lot into this job that the job isn’t necessarily promising. He’s searching for identity through work, and the app is there, it’s a business, it’s not really promising him everything. But when he gets to the Corporation, it gets really apparent to him, because all of his jobs can be assigned to these different departments. He’s not really special anymore.
DateDate operates on a really interesting premise that says if you answer enough short-response questions about yourself, you are able to find your perfect soulmate. The idea that love can’t be algorithmically solved is called into question a little bit — talk a little bit about this tenent of the job that he works for.
The dating app was another thing, kind of like the portals, that just kind of happened as I was writing the story. But as I worked on the book more I thought to keep it in because I thought it was a good device. I’m really interested in how we connect to each other through technology — I was interested in that when I worked at Instagram, and also in my fiction. I think dating apps are the most straightforward tool to find like-minded people through the internet. It’s a pretty big challenge to create something like that, especially one that promises to help you find your soulmate. Because I can’t code, I thought it’d be fun to invent my own dating app in fiction, and research and explore how I might create one. It ended up being pretty fun to see what I could do to make it feel like a more authentic match with someone, but also thinking about the app as a business. You don’t get to see your top match right away because they don’t want their user turn rate to be too high — they want to keep people on the app and using it. As I wrote the novel, it’s pretty obvious from the start, but there are a lot of things about how we connect with others that aren’t quantifiable or categorizable. I think as a fiction writer, it was pretty fun to explore that gap. If I was a start-up founder, I don’t know what I would do, but I’d say it was a potential way to find people you might get along with. My company would probably tank.
Whereas some novels’ sense of place are liminal, vague projections that could really be anywhere, this story is inextricably linked to San Francisco. It makes sense that the Silicon Valley start-up culture aspect is there, but how did it feel to write about your city so meticulously?
I really loved it. I was missing San Francisco when I wrote this novel, because I was in Tucson. I love Tucson — I was always telling people they should visit or move there. But all of my friends were in San Francisco, I had these good memories of the city, and it was fun to write about the city being away from it. At some point, I came back to the Bay area for a bit, then I moved up to Portland. That was at the start of the pandemic, so I was revising this novel in the lockdown era and I wasn’t coming down to San Francisco. I feel like I had a lot of longing for the city as I wrote the book — it was fun to write an homage to it while I was away from it, because it is where I came of adulthood, I spent most of my 20s there. I used Google Street View a lot, so I did the thing where you compared the views from 2010 to today and it was so wild to see the changes. Even little things like, in early in the novel, Ethan and Noma stop at a Keith Herring sculpture of men dancing — that sculpture has moved a couple of times since 2010 to different points in the city, so it was fun to trace those things.
This book stylistically resembles a memoir, with Ethan writing at the beginning of the book, in 2023, about the things he witnessed in 2010 and 2011. Why did you want it to be a retroactive retelling of the past?
That’s a good question, I mean, I think part of it is that I was reading a lot of nonfiction at the time. Writing it 12, 13 years in the future helped Ethan have more perspective on events. The story takes place within a year — he’s so wrapped up in work and trying to solve this mystery that he doesn’t have a lot of perspective as to what’s going on. Writing it in the past tense, from 2023, allowed him to give him some perspective and I don’t think he’d be able to tell this story as it was happening.
I liked that the science fiction element of the story got more intense as time went on; when you first started, did you want the novel to head in this direction or was it something that came up while writing?
It did escalate while writing — I didn’t have real intentions for that. Just my other work becoming more speculative, and I was reading a lot of speculative fiction, I think all of that just infused into my work. So it just kind of happened. But it’s funny — I read at a reading in San Francisco a few weeks ago, just the first few pages of the novel. Afterwards someone was like, ‘Oh, what else is your book about?’ and I told them, and they were like, ‘Oh, I never would have gotten that.’ Anna Weiner’s blurb, I think, was like, ‘start-up realism with a multiverse twist’ — it really does head in that direction after some realism in the beginning.
Yeah, I liked how it was a little bit of a misdirection from the synopsis — you’re taken on a completely different ride. And I loved Anna Weiner’s book [Uncanny Valley], so her blurb caught my eye.
Yeah, I loved Anna’s memoir. Her work for the New Yorker, too, has this persona of ‘New Yorker dropped in San Francisco.
Finally, what’s next for your writing career? Do you want to do more short stories, or do you have another novel idea in the works?
I’m working on another novel — I actually did just write a short story, but those are just about taking breaks from longer projects for me. But I love writing short stories. I actually just adapted one of mine into a screenplay.
It’s not going anywhere right now. It’s more just for fun and to learn about screenwriting, because I’m interested.
That’s so cool — is that something you want to explore more of?
Yeah, it is — I did this adaptation because I was so deep in novel-world, you know, writing the book, and doing the edits, I just wanted to change my way of thinking. I took one of my short stories and adapted it. One of my friends works in film, so she was helping me. I’m really drawn to how visual screenwriting is — the idea of, if one day, the screenplay were produced, the idea of the world you came up with actually being physically in the world, with set designers and actors saying the words — that’s just really cool. It’s more of just a fun project for me, to start. But now I’ve been doing it a bit more seriously.
Part of the reason I did it is I’ll try to sell film rights to my novel, and I was talking to the film agent about that, like, ‘I want to try to see what this is like.’ It’s totally a different genre — I gained a lot of respect for screenwriting. Just with shows I’ve already watched, like Succession, I was like, ‘I’m gonna just read the pilot.’ You already know what happens and can visualize it, but the dialogue is so punchy. It’s a whole different form, and I still like to do what with shows I watch.
Okay, since you brought it up, you were pitching the book to film agents — who is your dream Ethan?
Oh my god, I’m so bad at this. I’m really bad at remembering actors’ names. There’s this show Sex Education, on Netflix, I think — the main actor [Asa Butterfield] in that is someone I can definitely see playing Ethan. Also, The Sex Lives of College Girls on HBO — there’s a guy who runs the comedy magazine [Mekki Leeper] in that show that I can also see as Ethan. This is another thing where I’d be really open to someone adapting it, and making some changes.
Please Report Your Bug Here is available now.
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