The Institutionalization of FinTech 💳🏦
Capital One bought Brex for $5B. Ramp is worth $32B. What happened? 🤔
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In 2020, the valuation gap between Brex and Ramp was 37 to 1 in Brex’s favor. Six years later, Brex sold to Capital One for $5.15 billion - a whopping 58% discount from its 2022 peak - while Ramp raised at $32 billion and remains private and independent.
The two companies launched with nearly identical premises: make corporate cards and expense management work for modern businesses. Both raised enormous sums from elite investors. Both targeted the same CFOs. One is now a division of a bank holding company. The other is the most valuable private FinTech in its category.
The divergence isn’t random. It’s a case study in how business model choices, product strategy, and timing can produce radically different outcomes - even when the starting conditions look the same.
In this deep dive, we’ll unpack:
The deal mechanics and what the $5B price tag really means for Brex’s investors and employees.
We’ll trace the 3 strategic turning points where Ramp pulled ahead - product positioning, customer strategy, and shipping velocity - and explain why Brex’s pivot to enterprise wasn’t enough to close the gap.
We’ll look at Capital One’s rationale for the acquisition, including how Brex’s AI capabilities and non-interest revenue streams hedge against proposed credit card rate caps.
And we’ll draw out the lessons for FinTech founders navigating the new era of institutional consolidation.
You’ll also find the original Brex pitch deck from their $57M Series B in 2019 (a snapshot of how the company positioned itself before the rivalry with Ramp took shape, & a useful artifact for anyone building in the space today) + more strategic dives into how AI is changing the internet and the app economy.
Let’s dive in.
