Get thrifty, and your startup might just acquire a generation

• Etsy is acquiring UK-based social selling site Depop for $1.625B in a mostly cash deal
• Etsy asks ‘How do you do, fellow kids?’ with a $1.6B Depop purchase

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 natasha.mascarenhas@techcrunch.com.

Digital health is late on this one

Image Credits:PM Images (opens in a new window) / Getty Images

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:

• We spoke about why sports tech is bigger than a game
• Once a buzzword, digital transformation is reshaping markets
• The existential cost of decelerated growth

IPO’d

Image Credits: TechCrunch

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

Image Credits: Bryce Durbin

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:

• An early-stage startup decided to raise venture capital to scale its unionizing-as-a-service business across the country. There’s an inherent tension there, but CEO James White explained why he thinks there is still demand for a mass tech solution in a broken process.

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.

• Fill out the Equity podcast listener survey here, and you might even win a surprise prize thrown together by your humble team.

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

Seen on TechCrunch

• SoftBank-backed construction giant Katerra said to be shutting down after raising billions
• Stack Overflow acquired by Prosus for a reported $1.8B
• This one email explains Apple
• Café helps hybrid organizations schedule in-office time
• Europe wants to go its own way on digital identity

Seen on Extra Crunch

• 3 views on the future of meetings
• How to win a consulting board and deal roles with PE and VC funds
• 3 lessons we learned after raising $6.3 miillion from 50 investors
• Opting for a debut round can take you from a Series A startup to a Series B unicorn