Paul Kesserwani
Pitched on the show
Cushion
Post-pitch story
Paul Kesserwani pitched Cushion as a bot that would fight your bank fees for you, using software to negotiate refunds. The idea grew into a bigger personal-finance product. In 2022 Cushion raised a $12 million Series A at an $82 million valuation, part of more than $20 million raised overall. The market got tougher, though. At the end of 2024 Cushion wound down its consumer app because it couldn't reach a sustainable scale, and TechCrunch reported the shutdown in January 2025. The story didn't end there. In 2025 LendingClub acquired Cushion's technology and brought on key members of the team, including Kesserwani, who now leads product work at the bank. It isn't the fairy-tale ending, but the core idea of software that watches your money for you lives on inside a major lender.
Founders
The trail
Outcome · today
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