Darragh Buckley was the first employee at Stripe. He’s since started Increase, the banking infrastructure that moves over $500 billion a year. And he just bought a bank.
We talk about how to buy a bank, why putting an API on a bank is like "strapping a jet engine to a go-kart", operating with high-empowerment, the overnight sprint that turned on Stripe’s first dollar of revenue, why Patrick and John Collison would run across the office, and why you want your banker to be bored.
Thanks to this episode’s sponsors:
Monaco: The revenue engine for startups. https://monaco.com
Flex: Premium banking, 60-day credit at 0% APR. https://home.flex.one/referral/bananacapital
Clerk: Everything you need for authentication. https://clerk.com
Numeral: Sales tax on autopilot. https://numeral.com
Timestamps:
(0:00) Stripe's 1st employee bought a bank
(1:38) Fixing the stone in his shoe building Stripe
(7:59) Banking looks like 2010 payments
(11:11) Merging two layers into one, just like Stripe
(14:52) Why he finally bought the bank
(16:26) How do you actually buy a bank?
(20:20) The first bank that got away
(22:04) Why banks can’t chase new fads
(25:26) Compliance as code, from day one
(29:46) Talking straight to the Federal Reserve
(32:19) The Fed migration that nobody noticed
(33:50) The missing last mile of banking
(35:44) Getting customers to switch
(38:23) The challenger sales model
(40:33) What customers use Increase for
(41:48) How Ramp's bill pay works
(42:37) $500B a year with 33 people
(45:31) Hiring for a high-empowerment culture
(47:08) Growing up with the Collisons
(50:27) 150 test cases in one night
(54:23) What really made early Stripe work
(57:07) Why Patrick and John sprinted everywhere
(1:00:00) “You're not in payments, you're in fraud”
(1:02:31) Where AI hits a wall on fraud
(1:05:08) Giving payment cards to AI agents
(1:09:27) Use boring technology widely
(1:11:37) You want your banker to be bored
Referenced:
Increase: https://increase.com
Careers at Increase: https://increase.com/articles/how-we-work
Stripe: https://stripe.com
Links:
NBA Player Harrison Barnes Buying a Bank: https://sports.yahoo.com/articles/nba-player-harrison-barnes-invests-155500816.html
Acquire or Be Acquired Conference: https://www.bankdirector.com/event/acquire-or-be-acquired-2026/
Choose Boring Technology Essay: https://mcfunley.com/choose-boring-technology
Previous episode with Ron Gabrisko @ Databricks: https://www.youtube.com/watch?v=WYOO0DfeXu4
Previous episode with Will Gaybrick @ Stripe: https://www.youtube.com/watch?v=AM1_NADNSgI
Patrick Collison's "Fast": https://patrickcollison.com/fastAuthorize.net: https://www.authorize.net
Follow Darragh
X: https://x.com/darraghbuckley
LinkedIn: https://www.linkedin.com/in/darragh-increase/
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