Dee Choubey, Founder and CEO of MoneyLion, has spent the last 12 years building one of fintech’s most recognizable platforms. But his path wasn’t linear. It was shaped by market shifts, strategic pivots, and a deep commitment to using technology to empower everyday consumers.

What started as a fintech lender became a multi-product platform, offering everything from banking and investing to education and credit. Along the way, Dee led MoneyLion through the highs of going public, the lows of market skepticism, and ultimately, a billion-dollar acquisition by Gen Digital. Now, he shares how the deal came to life, why it made sense, and what it takes to lead through uncertainty without losing your edge.

In this episode, you’ll learn:

• How a casual commercial convo led to acquisition talks

• What made the CVR deal structure so unconventional

• Why financial wellness and cybersecurity are more connected than ever

• The hardest leadership lessons from a decade of pivots

• How AI is changing fintech strategy and talent decisions

Jump into the conversation:

(00:00) Introduction

(01:55) How the Gen Digital acquisition came together

(04:16) Why the CVR structure stood out strategically

(07:04) When early partnership talks became something more

(10:09) Gen’s retention strength and synergy with MoneyLion

(12:12) Navigating twelve years of fintech market cycles

(14:12) Pivots, pressure, and keeping the team aligned

(20:04) Leadership growth and building the right culture

(28:18) AI’s impact on products and cost structure

(34:10) Market shifts, optimism, and Dee’s economic outlook