Do you own a transportation or 3PL business doing $3M or more in revenue? Visit www.bizexitgrow.com to find out how we can help you grow, scale, and exit at maximum value.
2026 is the year to stop running AI pilots and start deploying into production.
In this episode, we break down how to implement AI that drives immediate ROI, how to prepare your company for a clean exit, and why owning your AI stack matters, with Andrew Brooks, the Princeton-educated founder behind exits to Sun Microsystems, ReachLocal, and Samsung, now CEO of Contextual.io. Andrew co-founded Smart Things (acquired by Samsung) and has built multiple companies with the same core team over 20 years.
We cover:
– How Andrew built and exited companies to Sun, ReachLocal, and Samsung.
– Why building with the same trusted team for 20 years creates a startup advantage.
– What changes after the deal: integration, standalone units, and earnout risk.
– The paperwork and contracts to button up from day one to avoid diligence scrambles.
– Why lower mid-market companies can now leapfrog into purpose-built AI systems.
– The biggest AI mistakes: waiting, going too big, and fearing messy data.
– What “Own Your AI” means and how to avoid hyperscaler lock-in.
– Andrew’s tip: set up long-running AI assistants by function and start today.
Check out Andrew’s work at contextual.io.Â
Ready to grow and plan your exit? Visit www.BizExitGrow.com.
Related episodes:
– Ep. 75: Why Most Paid Ad Spend Fails (And How to Fix It) with Ari Pirutinsky
– Ep. 74: How AI Turns One Story Into Content for Every Channel with Siva Chellamuthu
00:00 Intro: Meet Andrew Brooks of Contextual.io
00:55 From Princeton chemistry to startups and exits
03:36 The power of building with the same team for 20 years
05:22 Three exits: Sun, ReachLocal, and Samsung
07:25 What to understand about life after the transaction
11:10 How to prepare your business and paperwork for a sale
13:38 What an AI business system actually is
16:19 The biggest mistakes companies make implementing AI
19:58 “Own Your AI” and avoiding vendor lock-in
21:36 How AI compares to past Technology shifts
25:08 Managing energy, focus, and AI task switching
28:16 Andrew’s tip: set up long-running AI assistants now
#AIforBusiness #BusinessExit #ExitStrategy #AIImplementation #AIROI #SellYourBusiness #PrivateEquity #MidMarket #AIStrategy #VendorLockIn #ScaleSmarter #SellStronger #ExitAlgorithms #BusinessGrowth #Entrepreneurship
