Mitch Caplan was the CEO of E*TRADE, where he helped pioneer the first fully integrated online brokerage platform and led through the highest of highs (building a $3 billion business) and the lowest of lows (the 2008 financial crisis). Mitch is currently the CEO of Willow Wealth. Mitch joins Adam to share his journey and his best lessons and advice. Mitch and Adam discuss a wide range of topics: leadership, humility, collaboration, growth and scale, innovation, navigating crisis and chaos, and much more.
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Read the full transcript of Adam’s conversation with Mitch Caplan.
Episode Summary
Mitch Caplan joins Adam on Thirty Minute Mentors to trace a career that spans building the first branchless bank in the United States, scaling it into E*TRADE, leading the company through the 2008 financial crisis, and building two more companies since. Caplan was the CEO of E*TRADE from 2003 to 2009, after building and selling Telebank, the bank that became E*TRADE’s online banking arm. He later built and sold Jefferson National to Nationwide, and today serves as CEO of Willow Wealth after leading his family office’s investment in what became Yieldstreet.
Caplan traces his comfort with leadership back to college, where he says surrounding himself with a supportive network let him get comfortable in his own skin, a precondition he sees for effective communication and leadership. He points to a specific phrase he considers essential for any leader: being willing to say “I don’t know.” In his view, admitting the limits of your own knowledge is what allows you to build a team of people who are better than you in specific areas, rather than trying to project false certainty.
Much of the conversation centers on how Caplan built businesses from scratch. He and a partner bought a failed savings and loan in 1990 with the idea of building America’s first branchless bank, modeled on a UK company called First Direct, despite a regulator telling him directly that he expected the idea to fail. Caplan grew that bank, Telebank, from $50 million in assets to roughly $8 billion before it was acquired by E*TRADE, an experience he says taught him to always bet on being a platform rather than a product, since only a platform can scale to meet customers where they are.
Caplan is direct about what leading through the 2008 financial crisis actually required. He estimates he was only right about half the time when predicting in advance which members of his leadership team would rise to a crisis versus freeze under it, a finding that reshaped how he evaluates people today as an investor. He describes the crisis as forcing him to question a lending philosophy that had worked for nearly two decades, and to separate his own identity from the company, since E*TRADE had grown out of the bank he considered “my fourth child.”
Caplan closes with his philosophy on resilience: when one door closes, another opens, and the same skills that built one successful business can build the next. After stepping down from E*TRADE, he rejoined former colleagues to build and sell Jefferson National, proof to himself that his ability to innovate wasn’t tied to any single company. He sums up his approach to leadership in a single phrase: relentless optimism in the face of endless hardship.
What You’ll Learn
- Why “I don’t know” is a leadership strength, not a weakness. Caplan explains how admitting the limits of his own knowledge let him build teams of people who were better than him in specific areas.
- How he pitched regulators on America’s first branchless bank. Caplan walks through convincing skeptical regulators to back a business model that didn’t yet exist in the United States.
- Why he’d always bet on a platform over a product. Caplan breaks down the distinction that shaped his approach to scaling Telebank into E*TRADE.
- What he got wrong about who could lead through crisis. Caplan was only right about half the time predicting which leaders would rise to the 2008 financial crisis versus freeze under it.
- How the 2008 crisis forced him to question a decades-old lending philosophy. Caplan describes separating his own identity from a company he calls his “fourth child.”
- Why collaborative leadership beats an autocratic style. Caplan explains how building consensus, and knowing when to make the final call yourself, shaped every business he’s run.
- How he rebuilt after leaving E*TRADE. Caplan describes reuniting with former colleagues to build and sell Jefferson National as proof his skills weren’t tied to one company.
About Mitch Caplan
Mitch Caplan is the CEO of Willow Wealth. He previously served as CEO of E*TRADE Financial from 2003 to 2009, after building Telebank, one of the first branchless banks in the United States, which E*TRADE acquired in 2000. He later built and led Jefferson National Financial Corp, which was acquired by Nationwide, and served as interim CEO and chairman of the board at Yieldstreet. Caplan is also President of the Tarsadia family of companies, overseeing investment verticals across financial services, healthcare, technology, and real estate. He holds a BA in history from Brandeis University and a JD and MBA from Emory University. Learn more via his Tarsadia bio and his Greenwich Economic Forum bio.
Related Episodes
- Episode 79: Citizens Bank CEO Bruce Van Saun
Like Caplan, Van Saun led a major bank through good times and bad, and speaks directly to the leadership and organizational culture themes running through Caplan’s own crisis story. - Episode 325: Northwestern Mutual CEO Tim Gerend
Gerend’s conversation on decision making, hiring, and trust at a large financial services company echoes Caplan’s own framework for building teams equipped to handle crisis. - Episode 332: LPL Financial CEO Rich Steinmeier
Steinmeier’s episode on trust, resilience, and adaptability closely mirrors Caplan’s own account of rebuilding after leaving E*TRADE. - Episode 328: Stonepeak Co-Founder and CEO Michael Dorrell
Dorrell’s episode on investing and decision-making pairs naturally with Caplan’s own current work as an investor evaluating leaders for how they handle crisis. - Episode 330: Priceline Co-Founder Paul Breitenbach
Breitenbach’s episode on leadership and innovation offers another founder’s perspective on the platform-building instincts at the heart of Caplan’s own career.
