Jeff Rothbart

Jeffrey Rothbart speaks on real estate, entrepreneurship, artificial intelligence, and law, drawing on 22+ years as an attorney, licensed broker, career investor, law professor, and serial founder who has lived at the intersection of all four. On real estate, he's been on every side of the table — participating in more than $3 billion in transactions nationwide, valuing over $4 billion in assets, and disposing of more than $1.75 billion in commercial and residential property. Since 2006, he's worked as a real estate expert witness and litigation consultant, retained over 200 times, drafting 150+ expert reports and testifying in 30+ trials, giving him a rare, battle-tested view into what actually goes wrong in real estate deals, valuations, and disputes. On law, he's an Illinois-licensed attorney and Managing Broker with an LL.M. in Taxation from Northwestern, has taught as an Adjunct Professor of Law at both the University of Illinois Chicago and IIT Chicago-Kent, and has published 40+ articles cited in over 100 industry publications, including Forbes.

On entrepreneurship and AI, Jeff is a serial founder who has built and operated a wide portfolio of companies simultaneously — from Stack Real Estate and its affiliated brokerage, expert-witness, and legal-directory ventures, to a growing suite of AI-driven service businesses he's launched from the ground up and used to automate his own sales, marketing, and operations. He speaks candidly about what it actually takes to start, market, and scale multiple ventures at once, and about what AI can and can't yet do for a business — insight drawn from tools he's personally built and run, not just researched. Whether the audience is real estate professionals looking to diversify, entrepreneurs building their first company, lawyers navigating an AI-disrupted industry, or business owners exploring AI's real operational impact,