In this episode, I sit down with Brian Root, former Amazon and Walmart Labs product executive, US patent holder in e-commerce product classification, and now the founder of two simultaneous ventures: Norris Advisory, where he helps SMB buyers navigate due diligence and acquisitions, and Rooted in Product, his fractional CPO practice helping companies scale through smart technology decisions.

Brian's story is one of the most grounded and practical we have had on the show. After a layoff from big tech, he spent six to nine of the hardest months of his life before finding his footing, building two businesses from a $25 website, and developing a framework for evaluating technology in small businesses that most buyers and operators have never heard of.

We discuss:
– Brian's path from programming games in QuickBasic at age 10 to supply chain, business school, Amazon, Walmart Labs, and eventually being laid off and building two businesses from scratch.
– Why being laid off from what felt like a stable tech career was the shock that forced him to discover what he actually wanted, and how entrepreneurship through acquisition became the answer.
– What "tech enabled" actually means when evaluating a business for acquisition, and why a chatbot on a website is not the same as real technology differentiation.
– How to evaluate whether a business is using AI in a meaningful way or just slapping a label on it, and the signals that tell you the difference during due diligence.
– Why the biggest red flag in a tech-enabled acquisition is not bad software, it is undocumented thought process, and what good structured thinking actually looks like in a business.
– How to identify the two categories where technology genuinely adds value: growth levers that scale reach without proportional cost, and internal process automation that lowers the cost basis of the business.
– Why owner dependence is not just a relationship problem but a systems problem, and how one founder Brian worked with literally coded his own thought process into proprietary software before selling.
– Why AI content and outreach often fails, what Amazon figured out about automation that most companies still get wrong, and why the hidden use of AI almost always outperforms the obvious use.
– How Brian structures his week running two service businesses simultaneously, and why he is building systems now so the business scales disproportionately to his effort later.

Want to connect with Brian? Visit rootedinproduct.com and norisadvisory.com.

Ready to grow and plan your exit? Visit www.BizExitGrow.com, where thoughtful systems and strategies help build lasting value and legacy.