The Deep Wealth Podcast - Unlock Your Deep Wealth—In Business and Life Post-Exit Entrepreneurs AJ Wasserstein & Jeff Swearingen Reveal 6 Critical Decisions You MUST Make After Selling Your Business (Or Else You’ll Regret It) (#439)
May 19, 2025
AJ Wasserstein, a senior lecturer at Yale and former entrepreneur, teams up with Jeff Swearingen, who achieved a significant exit after selling his own businesses. They delve into the critical decisions every entrepreneur faces post-exit and highlight that 80% fail to plan for life after selling. The duo warns against common pitfalls like the loss of structure and purpose, and they advocate for simple investment strategies over complex ones. Ultimately, they urge listeners to proactively define their new identity and goals to avoid regret.
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Missing Purpose After Exit
- Many post-exit entrepreneurs underestimate how much they miss the structure and purpose of their business life.
- The loss of routine and leadership roles creates a surprising void despite financial freedom.
Poor Post-Exit Preparation
- Only 20% of entrepreneurs prepare for life after exit, focusing mostly on the deal itself.
- Merely 22% find their post-exit life matches their expectations.
Simplify Investments Post-Exit
- Simplify your investments by favoring low-cost index funds over complex private equity or hedge funds.
- Avoid complications like multi-property management and excessive investment details to reduce headaches.
