Intro

If you’re curious about what it’s really like to navigate a multibillion-dollar acquisition deal during a global pandemic, while under intense scrutiny of the Department of Justice, this episode is for you. Jason Pate, Chief Strategy Officer at Plaid, takes us behind the scenes of Visa’s $5 billion bid to acquire Plaid and why it ultimately didn’t happen. Jason also explains the massive evolution of Plaid from a linking infrastructure company to a thriving network business powering some of the biggest names in fintech. The conversation delves into the company’s pivotal moments, including its recent $575 million fundraising round to solve for employee RSU liquidity. Beyond that, Jason shares lessons from his experience, unpacking the importance of understanding a customer's P&L, breaking down how to build durable fintech revenue streams through diversification, and offering candid insights on negotiation, the future of payments, and making big bets to fix something that isn't broken.

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LINKS:

Jason Pate on LinkedIn: https://www.linkedin.com/in/jason-pate-50735310/

Plaid:

https://plaid.com

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

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TIMESTAMPS:

(00:00) Preview and Intro

(01:43) Sponsor – Brex | Aleph | RightRev

(06:08) Duke and “I Hate Christian Laettner”

(07:45) Jason’s Product Development Experience and Career Journey

(10:38) The Importance of Understanding Your Customer’s P&L

(12:41) Plaid’s Transition From Linking Infrastructure to Network Business

(15:23) Sponsor – Navan | Rillet | Pulley

(18:55) Building the Plaid Data Network and Ecosystem

(25:41) Friction in Payments: Feature Versus Bug

(27:46) The Future of Payments: Check-In Versus Checkout

(31:21) Negotiations: Less Like Chess, More Like Marco Polo

(35:21) Identifying Gives That Aren’t Actually Gives

(37:10) Plaid’s Unsuccessful Acquisition by Visa

(40:45) Being Interviewed by the DOJ During the Pandemic

(43:49) Plaid’s Recent Raise and the Unconventional Reason for It

(47:00) Valuations: Fundraises Versus Sales

(48:19) Building an Equity Program When Companies Stay Private Longer

(50:48) Multi-Product Diversification: The Key to Durable FinTech Revenue

(53:07) When & How To Transition From an Infrastructure to a Network Business

(59:03) Jason’s Philosophy on Ramping Team Members

(1:01:04) Lessons From Roger Federer

(1:02:52) Long-Ass Lightning Round: A Career Mistake

(1:04:03) Advice to Younger Self

(1:04:48) A Helpful Tactic for Negotiations

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SPONSORS:

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RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit

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and schedule a demo.

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#Plaid #Fintech #acquisition #fundraise #employeeRSU #BusinessTransition

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