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What does it take to keep building when your company loses 98% of its value publicly? Jason Wilk knows firsthand what it feels like to live on the financial edge. Before building one of the biggest names in fintech, Jason was overdrafting his checking account while trying to survive as a young entrepreneur.

Today, Jason is the founder and CEO of Dave, the fintech company helping millions of Americans avoid overdraft fees and access short-term credit in a smarter, more personalized way. But the road to success wasn’t smooth.

In this episode, we chat with Jason to understand what it actually takes to survive as a founder when the market turns against you, why mission-driven companies endure, and how AI is completely changing the future of banking and credit.

Tune in for tactical lessons on:

✅ Why the best businesses start with a personal pain point

✅ What it’s like to watch your company’s stock collapse 98%... and then recover

✅ The mindset founders need to stay calm during public failure and market chaos

✅ Why “growth at all costs” stopped working in tech and fintech

✅ How AI is transforming lending, underwriting, and access to credit

✅ Why traditional credit scores may become less important over time

✅ Why Jason believes discipline, patience, and self-belief matter more than credentials

This episode is a masterclass in resilience, founder psychology, financial innovation, and what it really takes to build through uncertainty. We hope you enjoy!

Timestamps:

00:31: Episode intro

00:46: Intro to Dave

01:20: What shaped Jason the most as an entrepreneur

02:15: What’s behind the best companies?

03:50: Jason’s origins in fintech and early Dave days

06:10: How Jason built self-belief (and maintained it)

07:50: How he dealt with Dave’s stock collapse

10:07: Going public via SPAC (Special Purpose Acquisition Company)

14:38: How to lead during a crisis

17:59: Where Jason sees the biggest opportunities in AI and fintech

22:42: What should founders in fintech learn from Jason’s challenges with Dave?

25:50: For someone who feels stuck financially, what should they do RIGHT now?

26:11: Mark Cuban’s all-time financial advice

27:10: “Mild and Wild” Questions

31:11: Closing thoughts

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