Through the Portal

Josh Riedel ’07 was Instagram’s first employee. His debut novel plunges readers into startup life.

By Rebecca Jacobson | April 14, 2023

In the fall of 2010, Josh Riedel ’07 began a new job at a tech startup. The first hire made by the firm’s two cofounders, Josh was responsible for, as he puts it, “basically everything nontechnical.” That meant tracking bugs, reviewing flagged content, and responding to emails from users who couldn’t remember their passwords—and also, as this was a fledgling company with a shoestring staff, assembling desks from IKEA and making bulk Costco orders for Nature Valley granola bars and sugar-free Red Bull.

In other words, ordinary startup stuff. Except this was no ordinary startup: this was a photo-sharing app called Instagram, and in two months it would go from 80 users to one million. By the end of 2011, the user count would top 15 million.

“I went into it being like, I need a job and this one sounds fun,” says Josh, who knew cofounder Kevin Systrom from a previous startup gig. “We were four people in a little room making an app that people all around the world were starting to use, and that felt really powerful to me.”

At the time he was hired, Josh, who studied English at Reed and wrote a creative thesis under Prof. Nathalia King [English], had been preparing applications for creative writing MFA programs. But when Instagram took off, he tabled that plan. “It picked up momentum so fast,” he says, “and I totally got swept up in it.”

For Josh, Instagram presented electrifying opportunities for both creative expression and social connection. As community manager, he started Instagram’s blog and its social media accounts, documenting in real time how people were using the novel technology—the local news reporters posting live from the scene, say, or the photo walks people were taking through their cities. He organized community meetups for Instagram’s most enthusiastic users. He recruited brands, from the San Francisco Giants to Burberry, to the app. At one point, he found himself on a call with Snoop Dogg’s manager, who wanted a custom “haze” filter that users could apply to their photos. (That request, like all requests for custom filters, was denied.) 

Instagram’s impact has been seismic. From its launch, it helped change the way we relate to our phones, to our photos, to the world around us (just consider, for a moment, what makes one latte more Instagrammable than another). In April 2012, Facebook scooped up Instagram for $1 billion, an unprecedented sum for mobile app acquisitions. Josh, loyal to Instagram and its users, made the move to Facebook’s Menlo Park campus. He expected to last a year. He made it two. “It wasn’t exciting to me anymore,” he says. “That sense of possibility was kind of gone after we got acquired.”

With time suddenly on his hands, Josh started writing short stories again, a habit that had faded during his years at Instagram. He got into the prestigious Bread Loaf Writers’ Conference. Back in workshop for the first time since his classes with Prof. Peter Rock [creative writing] at Reed nearly a decade earlier, he says he felt “a bit like a fish out of water.” But the experience pushed him to return to the MFA applications he’d abandoned, and he was soon studying fiction at the University of Arizona.

Those efforts have paid off: in January, Josh’s debut novel, Please Report Your Bug Here, was published by Henry Holt. The story’s got more than a touch of autobiography. Josh’s protagonist is Ethan Block, a 24-year-old Stanford art history grad in San Francisco in 2010 who’s giving his life over to his job at a rapidly growing startup called DateDate, an app that promises to match users with their soulmates. Ethan spends his days reviewing flagged content, fueled by Red Bull, Nature Valley granola bars, and an adorably optimistic conviction that he is helping to change the way people fall in love.

Then things start to get weird. When Ethan opens DateDate on his phone and views his top match, he suddenly feels like he’s falling. He then finds himself standing in a field, beneath a sky filled with birds, and he can hear the churn of ocean waves nearby. He runs through the field and somehow returns to the office, where he tries to shake off the episode. But later, when DateDate is acquired by the Corporation, a Facebook-esque conglomerate with a sprawling campus and lavish amenities, Ethan learns that what he experienced was a glitch, a bug in a new product called Portals, for which the technology isn’t yet fully understood.

Josh drafted the novel during the summer between his first and second years of grad school as he was reflecting on his 20s. At first he thought he might be writing nonfiction, but then the story swerved. “Once that happened, writing the book was like getting to explore alongside Ethan, figuring out how this happened,” Josh says. “Is there a glitch, or is there something more going on here?”

Josh credits his time living in San Francisco and working in tech with making his fiction more speculative. “When you’re constantly bombarded by new technology, you’re kind of part of the experiment,” says Josh, who now lives in West Marin with his wife, Erin Price ’09. “You’re around all of these startup people trying to come up with new ideas or features for their apps. That question of ‘what if?’ came into my head a lot and really infused itself into my fiction.”

These days, Josh is keen to continue exploring the what-ifs of his own creative future. Since completing the novel, he’s been studying screenwriting, and he recently adapted one of his short stories, published by lit mag One Story in 2020, into a screenplay. It’s a boundless curiosity that Rock remembers from Josh’s Reed days. At the time, Josh was managing the Paradox.

“I remember him saying to me, ‘I’m really interested in beverages,’” Rock says. “And he wasn’t kidding. He was like, root beer—what is it, exactly?”

For Josh, headlong plunges are part of the fun. “It’s exciting to me to be in the unknown, you know?” he says. “And then to try to understand what’s happening.”

Tags: Alumni, Books, Film, Music