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May 19, 2025 56 mins

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“Take the first step.” - AJ Wasserstein

“It’s all going to be OK.” -Jeffrey Swearingen

Exclusive Insights from This Week's Episodes

Post-exit entrepreneurs AJ Wasserstein and Jeff Swearingen pull back the curtain on the unspoken struggles of life after the deal. In this explosive episode, they reveal 6 critical decisions every entrepreneur MUST make to avoid regret and reclaim purpose. Backed by hard data, they expose why 80% fail to plan for post-exit life and only 22% find it matches their dreams. 

00:07:00 AJ Wasserstein defines a post-exit entrepreneur and why most overlook planning for life after the sale.

00:09:00 Jeff Swearingen shares common mistakes, like underestimating the loss of structure and purpose post-exit.

00:19:00 Swearingen and Wasserstein discuss why complex investments like private equity often disappoint, favoring simple index funds.

00:49:00 Wasserstein urges entrepreneurs to plan post-exit life before the sale, not after, to avoid being blindsided.

Click here for full show notes, transcript, and resources:

https://podcast.deepwealth.com/439

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