You’re Never Wrong, You’re Just Late with Mitch Caplan, Yieldstreet
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What does it really take to lead through uncertain times while growing with focus and vision?
On this episode of Electrifying Growth, Chris Sugden is joined by Mitch Caplan, a fintech pioneer whose career includes CEO roles at E-Trade and Jefferson National, as well as leadership at Telebank and Yieldstreet. With three decades of financial services experience, Mitch brings a rare perspective on building durable businesses across multiple market cycles.
He reflects on founding the first branchless bank, scaling through crises, selling to E-Trade, and stepping in to stabilize Yieldstreet as interim CEO. Mitch explains what founders often miss about timing, distribution, and customer trust, and how private markets are being reshaped in real time.
In this episode, you’ll learn:
How Mitch turned Telebank into the first internet bank
Why valuation isn’t the end goal for building lasting companies
What fintech founders should know about navigating downturns and rebounds
Jump into the conversation:
(00:00) Introduction
(04:32) Buying a bank during the RTC collapse
(07:15) Building the first internet-only financial institution
(09:10) Selling to E-Trade over sushi
(13:06) Cutting a billion dollars in costs
(17:47) Creating the original E-Trade baby spokesperson campaign
(22:40) Lessons from four major financial crises
(30:13) Why private markets are the next wave
(34:54) Distribution vs. manufacturing in fintech today
(42:10) Boardroom best practices for startup CEOs
(47:47) The advice that changed Mitch’s career
57 episodes