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It’s Hip to Be Square

Dorsey’s Gen Z Empire
August 6, 2021

Back in June on the Future Commerce podcast, I predicted that Afterpay would win the physical reopening BNPL wars: 

The biggest cities are coming out of COVID and physical retail is back. Has been since October for Florida. But that's because it's Wild West here. So I feel like Afterpay is the big winner here in the latter half of the year, if I had to bet the way that people would be using this. Everyone, every channel has to deal with the fact that physical retail is coming back. 

My reasoning was simple: on a trip to the mall during the summer, there were kids everywhere toting bags from traditional mall brands: specifically, LUSH, Crocs, and Finish Line. The common thread? Just look at the signage in the mall. While the “DTC thought leader” crowd is talking about luxury, the kids are spending real dollars on fugly shoes. Can’t blame the stimmy for the extra flow; lit-quidity is courtesy of Papa Jack.

Square’s announcement of its $29B acquisition of the Aussie layaway app should come as no surprise. Dorsey is building a Gen Z magnet. Consider a day in the life of a 21-year-old: 

  • Stop at the pour-over coffee spot, pay at a Square register
  • Snap your friend who’s selling her old iPhone, whip out the Cash app
  • On the way to the mall, stream the new Billie on Tidal
  • Self-care tonight. Grab some bath bombs at LUSH, pay with Afterpay
  • BTC is back on the rise. Group buy with some crypto simp friends on Cash app. Split the profits.

We’ve been on this trend since 2019. Right after I penned our seminal piece on Gen Z’s defining persona, C.A.R.L.Y. (Can't Afford Real Life Yet), I bought Crocs stock. Let’s say I’m doing okay.

A modern credit paradigm makes sense for a company that is building a network of touchpoints across entertainment and social behavior. From the things you buy to the way you spend your time, Square is becoming a totem for the next generation. They’re building a physical BTC wallet, and a new DeFi product to boot. Tidal is exploring nouveau digital music ownership with NFTs. 

Square might be the most pivotal digital business focused 100% on Gen Z that there is today.

Jack’s other other project, Twitter, is the digital commons. Square is the entertainment district, the shopping mall, the bank, and the concert venue; purpose-built for a generation that has no need for their analog counterparts.

Excuse me while I rebalance my portfolio from $CROC to $SQ.


Kondo-minium. Move over, Marie. Re-enter our old flame, maximalism. We spent our time living in our own spaces, making them messy, and tie-dying anything white we could find. The furniture pieces we were tired of looking at, we painted bright colors, and we got used to our backgrounds and atmospheres in Zoom calls having a little “character” to them. And we liked it. In her piece, More is More: The End of Minimalism, Mireille Silcoff, dives into this shift and the rise of the “intentional hot mess.” Editor’s note: another trend we’ve been on for years. See our piece on Dadaism, the new Brand Maximalism from June 2020, or our January trends report, Vision 2021, for more. 

Image: Shopify

Let’s get Phygital, Phygital. Shopify has opened a two-story multi-purpose space for entrepreneurs in NYC’s SoHo, complete with a rotating pop-up shop featuring local vendors, rentable photography and recording studios, space for workshops, and more. This isn’t the eCom giant’s first foray into physical space, as Shopify launched a downtown Los Angeles presence in 2019.

Practice your GenZ dance moves mid-flight. American Airlines is now offering free access to TikTok while on flight. And if you’re one of the 3 people who aren’t familiar with what TikTok is, American Airlines has created a “Beginner’s Guide to TikTok” to help get you started.

Right on Target. The competitive hiring landscape is heating up. Target is now offering tuition assistance to more than 340,000 associates, logistics, and warehouse personnel. Undergraduate programs will be reimbursed in-full and master’s programs will receive a maximum of $10,000 of reimbursement. 

7 Degrees of Content Studios. REI Co-Op Studios has teamed up with Kyra Sedwick and Valerie Stadler to create a movie, which proves that retailers are also content producers. The Oracle of Bacon states that this is the second appearance for Sedwick and Bacon in the same film, 2005’s Loverboy, which has a dismal 18% on Rotten Tomatoes.

In Case You’d Rather Stay on Earth, REI has also announced a collaboration with Hipcamp, the largest provider of outdoor stays which will “make it easier for REI members to find and book unique getaways.” And hey, if you’re a Co-op member, you can get 20% off your next camping trip.

High fashion mobile game. To celebrate Louis Vuitton’s 200th birthday, the company is releasing a mobile game starring mascot, Vivienne the wooden doll. Louis: The Game which journeys through LV history will also be embedded with NFTs.

It’s the Honerrhea for Me. Eating frozen honey is the latest trend on Tiktok and dieticians are warning of dangerous side effects, such as bloating, cramping, and diarrhea. Experts are also concerned that this wild and addictive behavior could increase the risk of cavities.

Lady Gaga Cold Brew?. Oreo has opened up a café in New Jersey, complete with drinks, coffees, merch, and limited edition collabs of the famous sandwich cookie. The first physical brick-and-mortar store for the brand signals the growing cultural significance of the cookie, which grew by leaps and bounds in 2020. The Oreo cookie brand, a $3.6 billion global business, registered double-digit growth in 2019 and 2020, “with a clear path to add $1 billion” in the current calendar year.

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