Welcome back to Oversharing

It's been too long

John Springer Collection/Corbis via Getty Images

Hello and welcome back to Oversharing, a newsletter about the proverbial sharing economy.

Yes, Oversharing is back! I last published it almost two years ago, in May 2020, a few months into the pandemic. Then I found myself needing a good long break from journalism and did some other stuff—more on that tomorrow—but I missed you all and missed this space. I’m really excited to be back, and hope you are too.

The big news first: After four years of publishing Oversharing for free, I’m taking the plunge and making it a subscriber-supported newsletter. Starting this week, you’ll be able to purchase a subscription to Oversharing for a special launch period rate of $7 a month or $70 a year. Paid subscribers will get three posts a week, the ability to comment and participate (kindly! respectfully!) in community threads, and access to the full Oversharing archive. Everything will be free for the first couple of weeks. After that, there will be one free issue of Oversharing each week, with the rest available to paid members.

I started Oversharing in March 2016. The initial thought was to create a home for reporting scraps and ideas that were too niche for even a wonky place like Quartz, where I was working as a reporter. I also wanted a space for voicier writing, more akin to what I did in my previous job at Slate, free from the feigned objectivity that often comes with working in a newsroom. I signed up a couple dozen friends, coworkers, and sources, and sent them emails I drafted at indecent hours of the morning in TinyLetter. We talked about capitalistic kibbutzim, “profitable profitable,” and those washed up Uber-for-laundry startups. I wanted Oversharing to be smart but accessible, thoughtful but funny, like chatting with a witty friend at a cocktail party.

Slowly, and in spite of a near-total lack of promotion, Oversharing grew. A couple dozen subscribers turned into a couple hundred, and then a few thousand. Cutting room scraps became essays on tech culture, startup business models, the venture ecosystem, and the precarious intersection of gig work and U.S. labor norms. Meanwhile, the gig economy chugged along. Uber launched self-driving cars and ran a red light in San Francisco; Instacart experimented with creative new ways to cut worker pay; gourmet meal-delivery startup Maple’s cookie crumbled. Oversharing readers followed along as I investigated Uber’s shady subprime car dealer partnerships in New York City for Quartz and Hubble’s use of a regulatory loophole to sell lenses direct to consumers, even when they didn’t have a valid prescription.

In February 2018, someone named Hamish McKenzie emailed me. He said he was the co-founder of a new startup called Substack and wanted to talk about moving Oversharing to their platform. I was in San Francisco for the Uber-Waymo trial, enjoying the villainous bromance of Travis Kalanick and Anthony Levandowski (RIP that pound of flesh), and we met up for coffee. Hamish’s pitch was interesting: Substack was a newsletter platform with no subscriber limits that also supported paid subscriptions. That sounded a lot better than TinyLetter, which capped its free newsletter service at 5,000 subscribers, but I was hesitant. I spent my entire job writing about startups that, more often than not, either failed or burned through their venture funding spectacularly, and I was wary of moving Oversharing to a new and unproven platform. I gave Hamish a maybe and asked him to keep me posted, or as I now call it after a few years of living in London, a British no.

A few months later, Hamish reached out again about some big improvements Substack had made to its writer platform. At the same time, several more established writers had moved their newsletters to Substack and the company closed a $2 million seed round. It was looking more like Substack would be around for a while. This time I told Hamish yes. In June 2018, Oversharing moved to its new home on Substack.

Two years was a long time to step away, but it also means we have lots to talk about now. I mean, WeWork went public! The world is a crazy place! Oversharing will, as always, be a newsletter about the sharing economy, but I’m excited to broaden the scope as well. I’m interested specifically in technologies with urban applications. After all, that’s what many gig companies are: tech-enabled services and conveniences that work best in dense urban settings. If you have ideas, research, tips, or general enthusiasm, I want to hear from you! Reply to this email, follow me on Twitter (@alisongriswold), or reach me directly at oversharingstuff@gmail.com. It’s also important to me that Oversharing remains accessible, especially to longtime readers. If you can afford to subscribe and support my work, please do. If that’s not possible for you right now, please email me.

That’s all for today, I’ll be back tomorrow with more on what I was up to the past two years and where we’ll go from here. Until then, happy Tuesday, thanks for reading, and truly, it’s great to be back.