Brex Series D

Tiger Global moving at their characteristic 2021 sprint speed should have been the first warning sign, but here we are examining a $12.3B valuation for what amounts to a corporate card company with some expense management software bolted on. I've watched enough cycles to know that when the money moves this fast and this loose, someone's holding the bag when the music stops. Brex had real traction with startups—I'll give them that—but this Series D priced them at roughly 50x their rumored revenue multiple, in a sector where even the giants like Amex trade at single-digit revenue multiples. The gap between public market reality and private market fantasy was reaching 2000 levels of delusion, and this deal epitomized everything wrong with late-2021 vintage dealmaking. The October timing is particularly chef's-kiss awful: literally the market peak before tech entered its ice age.

The fundamental problem is that Brex built their empire on the backs of VC-funded startups burning cash with corporate cards, which is roughly as stable as constructing your house on a San Andreas fault line during an earthquake. When I look at their customer base in 2021, it's basically a who's-who of companies that would cut burn rates by 70% over the next eighteen months. Their underwriting model assumed perpetual growth-at-all-costs spending patterns, and their unit economics depended on interchange fees from customers who were about to collectively discover the concept of profitability. The pivot attempts into e-commerce and life sciences feel like someone realizing mid-freefall that maybe diversification matters. Sure, they had some interesting software features and a sleek user experience, but you can't justify a $12B valuation on UI/UX when your revenue base is about to crater.

Let's talk about Tiger and Greenoaks for a moment—two firms that absolutely embodied the spray-and-pray, term-sheet-in-48-hours mentality that defined this era's excess. These weren't patient, diligent capital allocators; they were volume dealers trying to get into every deal at any price, damn the fundamentals. The signaling here isn't "smart money sees something special," it's "hot money chasing momentum in a frothy market." I've got nothing against moving fast when conviction is high, but this vintage of Tiger deals aged like milk in the sun. The investor syndicate reads less like validation and more like a mutual delusion pact among firms who forgot that gravity exists. When your lead investors' strategy is essentially "close deals faster than anyone can think," maybe pump the brakes on celebrating their involvement.

The exit math is where this really falls apart. At $12.3B, you're looking at needing a $25B+ outcome to deliver decent returns to these late-stage investors, which means Brex would need to reach maybe $4-5B in revenue at reasonable SaaS multiples. For context, that's approaching half of what Amex generates from their entire small business segment. In a post-SVB world where fintech darlings are getting repriced by 70-80%, the down-round probability here is near-certain if they need more capital. The competitive dynamics got worse too—every bank launched startup-friendly products, Mercury came in cheaper, and Ramp started eating their lunch with better software. This deal will be studied in business schools as a case study in "what were they thinking," sitting right next to those WeWork term sheets.