AI can organize information faster than any team you’ve ever built. It can surface patterns, speed up workflows, and remove friction from execution. But it still can’t make judgment calls when the data is incomplete, the market is shifting, and real money is on the line.

In this episode of The Breakout CEO, Jeff Holman talks with entrepreneur and financial advisor Luigi “Lou” Rosabianca about where AI actually fits in a scaling business and where CEOs still have to step in and decide.

Lou has built and advised small and mid-sized businesses through multiple disruptions, from 9/11 to financial crises to the pandemic. His perspective is shaped by operating when capital tightens, banks pull back, and clean answers don’t exist. That experience informs how he thinks about AI, cash flow, and resilience today.

The conversation centers on a simple reality that many CEOs are living right now. Tools are more powerful than ever, but businesses still fail when leaders confuse automation with judgment. AI can help organize the ingredients, but CEOs still decide what gets cooked, what gets scrapped, and when it’s time to pivot.

This episode is for CEOs and founders who are navigating uncertainty, experimenting with AI, and trying to scale without losing control of the fundamentals. It’s a grounded conversation about decision-making, resilience, and why leadership judgment still compounds when everything else levels out.

Listen to the full episode of The Breakout CEO for a candid, operator-level discussion on scaling through chaos without outsourcing your judgment.

Check out Lou's work at https://www.shieldadvisorygroup.com/ and https://creditbanc.io/.

Say hello to Luigi!

LinkedIn: https://www.linkedin.com/in/luigi-rosabianca/

Enclosed is also a copy of his book (free audio version), Buying The American Dream - A Strategic Playbook for Acquiring Small Businesses. https://drive.google.com/file/d/1iCSh0yb8PrwKFo0AZnpjV4Z84YZj2Elx/view

If you want a paper copy, it’s also available on Amazon. http://bit.ly/3ZwSHnz.