Navigating the Shift: From CEO to Tech Enthusiast

After selling the business he built over 12 years, what’s next for Bill D’Alessandro? In this episode, Andrew reconnects with Bill, longtime friend, returning guest, and co-host of Acquisitions Anonymous, to talk about life post-exit, the unexpected challenges of newfound freedom, and how he’s thinking about AI, identity, and investing in today’s wild market.

They also chat about the blurred lines between personal and entrepreneurial success, dealing with changing relationships after wealth, and whether using AI versions of yourself is a smart move or just plain creepy.

You can find show notes and more information by clicking here: https://bit.ly/3TTVAfB

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