Get thrifty, and your startup might just acquire a generation

Etsy, a marketplace for kitschy and creative DIY goods, acquired Depop, a hippy and thrifty marketplace for resale goods, for $1.625 billion this week. So, today we’ll discuss the tale of two marketplaces, a deal that has given us a peek into the evolving ethos of social shopping.

Depop, for those that don’t know, is a London-based company that targets millennial and Gen Z shoppers. Within the past two years, Depop has grown its user base of stylists, designers, artists, vintage sellers and more, from 13 million to 21 million, And, the company claims, some 90% of its users are under the age of 26.

With the buy, Etsy is growth hacking its way into a younger generation, one that thinks thrifting is trendy and individualism is more interesting than fast fashion. But to me, combining two, two-sided marketplaces is not where the work stops. Etsy, with Depop under its umbrella, has an opportunity to be far more inventive with the way it combines operations.

First, Etsy needs to find other ways — beyond a new volume of fresh goods — to modernize its user experience, from homepage to checkout. Why? Because, and I can say this because I am technically part of the cohort, Gen Z is impatient. Sure, thrifting is trendy — but so is Amazon. The same generation that loves the idea of sporting the individual creative, also loves the idea of low-cost goods and two-day shipping. Sure, there are people that sit at either extreme. But I’d bet an unnecessary milk frother that the majority of Gen Z consumers sit in a more grey space.

Secondly, Etsy and Depop have an opportunity to invest in the growing wave of social shopping experiences. When I saw this news break, I immediately thought of The Landing, a company that is using customizable and collaborative mood boards as a shopping tool. The startup allows users to create mood boards from products that they can then shop from. Right now, it’s starting with interior design, but the vision can easily extend beyond home goods into clothing or CPG products. Similar to Pinterest, The Landing is trying to serve a set of consumers that like shopping in a collaborative, scroll-friendly way. I’m not asking Etsy to go full early-stage startup, but it would certainly be compelling if it found new ways for consumers to experience its broadened marketplace.

I’ll stop there, and end with this: As more and more companies prioritize serving Gen Z, strategy needs to be more than a land grab. As one person put it, Etsy is “ensuring the brand translates through different generational ethos,” with the acquisition. I’m excited to watch this case study in the making play out.

In the rest of this newsletter, we’ll discuss digital health, the beautiful world of S-1 filings and a Medium memo that has caused employees to leave the company. As always, you can find me on Twitter @nmasc_. Scoops keep me happy, so if you have a tip on an early-stage deal or drama that I should know about, DM me or e-mail me at

Digital health is late on this one

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If my inbox is a fair indicator, every other startup right now is trying to get invited to one group chat: the digital health one. We’ve covered the boom in health tech on TC, but one question has haunted me for the past month: Where are all the PCOS startups? The condition, known as polycystic ovary syndrome, impacts one in 10 women and seems to mesh well with the loud drumbeat of personalized medicine. So, I went digging. 

Here’s what to know: I learned that there is a massive opportunity for startups in hormonal health, but the sector is still nascent due to an array of issues, both related to science and stigma.

And speaking of nascent industries:


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The Equity team has probably spent about 3% of our collective recording time manifesting Robinhood’s S-1. Of course, at the time of writing this, our efforts have proven futile. But no worries, we have other public market news to keep you interested as we wait.

Here’s what to know: Confluent’s S-1 revealed slowing growth amid a history of impressive expansion. Sprinklr’s IPO filing showed uneven cash flow, but did have some healthy growth worth noting. And Acorn, everyone’s favorite consumer fintech biz, listed as a SPAC.

Medium’s extreme

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I published a scoop this week about the latest tension at Medium, a startup that has had its fair share of woes and pivots over the years. In April, Medium CEO Ev Williams wrote a memo about the company’s culture. Several employees argue the undertone of the memo has paved the way for an unsafe, “nod-and-smile” work environment, triggering more exits. Of the 241 people who started at Medium, some 50% of that pool are now gone.

Here’s what to know: Similar to Coinbase and Basecamp, Medium’s culture memo has made employees leave due to a change in mission. But, unlike the aforementioned companies, Medium’s memo has a more subtle undertone, exacerbated by tension after a unionization attempt failed the month prior.

And in the early-stage startup world: 

Around TC

Tell me how you really feel, dear Equity listeners! The podcast team put together a survey for Equity listeners. It only takes a few minutes to fill out and will make our entire team very happy. The more information we have about what you want, the better the show will be.

Additionally, TC Sessions: Mobility is happening next week. Here are five reasons for why it’s a must-see event about all things moving. And it’s not too late to grab tickets.

Across the week

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