Checkout.com Series D

Tiger Global and Coatue slapping a $40 billion valuation on Checkout.com in January 2022 is like watching someone order bottle service at 1:45am—sure, you're technically still in the club, but the lights are about to come on and reveal what a mess this place actually is. The fintech party had been raging since 2020, valuations floating untethered from reality like balloons filled with VC money and cocaine confidence. Checkout.com, a payments processor that helps businesses accept online payments (groundbreaking, I know), raised a cool billion at a valuation that put it ahead of Macy's, Hasbro, and every punk venue that's ever mattered combined. The timing here is chef's-kiss terrible: three weeks later, the Fed would start its rate-hiking campaign and the entire growth-at-all-costs narrative would faceplant harder than a stage diver at an empty room show. These investors showed up to the wrong party with the wrong drugs, and now everyone's standing around awkwardly waiting for someone to call an Uber.

Let's talk about what forty billion dollars of "value" actually buys you in the payments processing thunderdome. Checkout.com was supposedly processing $500 billion in volume annually across 150 currencies, serving clients like Netflix, Shein, and Grab—legitimately impressive numbers that would make this a solid company at, say, a $10-15 billion valuation. But $40B? That's Stripe's little sibling getting priced like it invented money itself. For context, Adyen—an actual publicly-traded payments processor with transparent financials—was trading at similar multiples despite having better margins and a clearer path to profitability. The competitive moat here is more like a competitive puddle: you're fighting Stripe, PayPal, Square, Adyen, and approximately seven thousand other companies trying to skim basis points off transactions. The "we operate in more countries" differentiator is the equivalent of a band bragging about playing more shitty dive bars than their contemporaries. Volume metrics look sexy until you remember that payments is a race-to-the-bottom business where everyone's competing on price.

The investor syndicate here deserves its own autopsy. Tiger Global was in their full spray-and-pray era, allegedly making investment decisions off Excel models that could've been drawn in crayon. They led or participated in something like 330 deals in 2021 alone—that's almost one per day, which is not "diligent dealmaking" but rather "VC-as-performance-art." Coatue wasn't much better, both firms embodying that particularly toxic strain of growth investing that treated due diligence like an optional side quest. The signaling here isn't "smart money sees something special"; it's "momentum investors chasing each other's taillights off a cliff." Neither firm brought particularly relevant operational expertise to payments infrastructure—they brought capital and FOMO, which in January 2022 was already about as useful as bringing gasoline to a house fire. Where are the strategic corporates? Where are the payments-specific investors who might actually help this company navigate regulation and competition? Nowhere, because this was a valuation round, not a value-creation round.

The exit math on this deal is where my feminist rage really kicks in, because guess who gets fucked when these inflated valuations collapse? Not the Tiger Global partners who've already collected their management fees. Not the founders who got secondary liquidity. It's the employees holding options priced at fantasy-land valuations, and the later-stage employees (disproportionately women and people from non-traditional backgrounds) who joined thinking they were getting a ticket to wealth creation. Checkout.com would need to IPO at like $60-80 billion to make this round look smart, which in the current market is about as likely as major labels deciding to pay artists fairly. The 2022-2024 fintech correction has been brutal: Klarna down 85%, Stripe marked down repeatedly, the entire sector repricing to reality. Maybe Checkout.com executes flawlessly and grows into this valuation by 2027, but that's a lot of maybes stacked on top of a payments processor in a commodifying market. This deal encapsulates everything wrong with late-stage venture: too much money, too little discipline, and a complete disconnect from the fundamentals that actually build sustainable companies.