Can AI Solve the Silver Tsunami with Jonathan Cheung

Welcome to the Artificial Intelligence Podcast with Jonathan Green! In this episode, we tackle a massive generational challenge: can AI help solve the “silver tsunami” of baby boomer business owners looking to exit their companies—and do it in a way that protects jobs, preserves legacy, and maximizes value? Our special guest is Jonathan Cheung, a business broker with Transworld Business Advisors, the world’s largest business brokerage firm. Jonathan specializes in helping small and medium sized business owners successfully exit, and he brings a rare combination of big firm valuation expertise (KPMG, Facebook, tech valuations) and hands-on experience with traditional, Main Street businesses. Notable Quotes: “I think it's a historical moment where trillions of dollars are expected to transfer over the next two decades. It's really the largest wealth transfer in history.” – [Jonathan Cheung] “AI as a source of labor… works for you 24/7 and is able to have more predictable outcomes.” – [Jonathan Cheung] “Every business someone started themselves, there’s no instruction manual. That’s why their first hires struggle—nothing is documented.” – [Jonathan Green] “People either massively overvalue or massively undervalue their business. They’ll shut down a thriving business and say, ‘Nobody wants it,’ or think it’s worth 10, 50, 100 times what it is.” – [Jonathan Green] Connect with Jonathan Cheung: Email: jcheung@tworld.com Phone/WhatsApp: +1 (626) 8643369 LinkedIn: If you’re interested in how AI can protect your legacy, increase your exit valuation, and help your business survive into the next generation, this episode is a must listen. Connect with Jonathan Green The Bestseller: ChatGPT Profits Free Gift: The Master Prompt for ChatGPT Free Book on Amazon: Fire Your Boss Podcast Website:

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Can AI Solve the Silver Tsunami with Jonathan Cheung is an episode from Serve No Master : Escape the 9-5, Fire Your Boss, Achieve Financial Freedom by Jonathan Green : Artificial Intelligence Expert and Author of ChatGPT Profits.

This episode is 29:03 long.

This episode was published on Dec 29, 2025.

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