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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: / 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/1iCSh... If you want a paper copy, it’s also available on Amazon. http://bit.ly/3ZwSHnz Think you'd be a great guest on the show? Apply https://go.intellectualstrategies.com/ Get in Touch with Jeff Holman ⤵️ Website: https://www.intellectualstrategies.com/ Instagram: / holmantech Facebook: / jeff.holman.9678 LinkedIn: / holman Timestamps: 00:00 - Introduction to Lou Rosabianca 02:12 - The Drive Behind Entrepreneurship 04:52 - Growing Up with Immigrant Values 08:01 - Educational Path and Career Beginnings 12:10 - Navigating the Financial Landscape 19:20 - Key Financial Metrics for Small Businesses 22:43 - Resilience Through Challenges 29:42 - Lessons from Business Failures 33:17 - The Role of AI in Business Scaling 36:47 - Future Goals and Aspirations 39:20 - Teaching Work Ethic to the Next Generation ➖➖➖➖➖➖➖➖ The Breakout CEO is a podcast for growth-stage business leaders: founders, CEOs, and executive advisors who are scaling companies, navigating inflection points, and leading through rapid growth. Hosted by Jeff Holman, CEO advisor, legal strategist, and founder of Intellectual Strategies, the podcast features 30-45 minutes of insight-packed episodes with innovative entrepreneurs, scaling CEOs, expert operators, and CEO coaches behind high-growth ventures.