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35 - Choosing Legacy Over Lifestyle After a Billion-Dollar Exit
Episode 3517th February 2026 • The Breakout CEO • Jeff Holman
00:00:00 00:33:35

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Small business credit isn’t broken because of a lack of data; it’s broken because the system was never designed for how businesses actually operate.

In this episode, host Jeff Holman speaks with Sal Rehmetullah, CEO and Founder of Worth AI. He has scaled, exited, and re-entered fintech at the highest levels. After building Stax Payments into a market leader and navigating a billion-dollar recapitalization, he turned his attention to one of the most persistent problems in small business finance: underwriting. Sal explains why incremental fixes fail in regulated, legacy systems and why rebuilding from scratch was the only viable path.

Sal also walks through why small businesses can’t be evaluated like individuals, how legacy financial systems accumulated regulatory debt, and what finally made it possible to rethink underwriting end-to-end. The episode explores the real CEO tradeoff between patching broken systems and having the conviction to rebuild them especially when credibility, timing, and execution all matter.

After exiting a billion-dollar fintech, he faced a familiar CEO question: optimize what exists or start over entirely. His answer reveals how timing, infrastructure, and judgment are not just ideas, determining whether systemic change is possible.

Check out Sal's work at https://worthai.com/.

Say hello to Sal!

LinkedIn: https://www.linkedin.com/in/sal-rehmetullah-59704741/

LinkedIn: https://www.linkedin.com/company/worth-ai/

Facebook: https://www.facebook.com/worthai.risk

Instagram: https://www.instagram.com/salrehmetullah/

Instagram: https://www.instagram.com/joinworth

Twitter: https://x.com/worth_AI

Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/

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