1. Tax Planning
Minimize capital gains: Use QSBS, installment sales, or charitable trusts where applicable.
Estimated tax payments: Plan for IRS deadlines post-liquidity.
State residency planning: Consider relocating before an exit to reduce state tax burden.
2. Asset Protection
Shield wealth from lawsuits or creditors: Use LLCs, irrevocable trusts, and umbrella insurance.
Prenuptial/Postnuptial agreements: Especially important if exiting while married or planning to remarry.
3. Investment Diversification
Rebalance out of concentrated stock positions: Many founders exit with large exposure to one company.
Core allocations: Anchor portfolio in low-cost index funds (like the S&P 500), complemented by private credit, real estate, or venture.
4. Liquidity Management
Plan cash flow needs: Budget for lifestyle changes, taxes, and large one-time purchases.
Establish cash reserves: Even after a big exit, founders can experience income gaps during their next venture or transition.
5. Estate Planning
Update or create a will and trust: Ensure your wealth passes according to your wishes.
Use lifetime gifting strategies: Leverage annual exclusion gifts or set up GRATs and SLATs.
Philanthropic goals: Donor-advised funds, private foundations, or impact investing.
6. Identity & Purpose
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What’s next? Many founders face identity loss after an exit. Helping them find meaning through advising, investing, or starting again is key.
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Avoid lifestyle inflation: Provide behavioral guidance and mindset coaching if needed.