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What to do with the money after selling your business. This comprehensive guide covers the critical financial steps and considerations for business owners post-sale, including retirement planning, investment strategies, tax implications, and emotional transition management. If you've recently sold your business or are in the process, what you do in the next 6 to 12 months can determine your long-term financial security. Actionable advice on planning for retirement, managing windfalls, and protecting your wealth after a sale. Key Topics: • How to assess if your sale proceeds cover your retirement needs • Navigating expenses and major purchases post-sale • Importance of comprehensive financial planning and stress testing with Monte Carlo simulations • Strategies for investing a large windfall, including dollar cost averaging and risk management • How to reduce capital gains tax after the sale and how to optimize tax efficiency through techniques like direct indexing • Diversification strategies to reduce concentration risk • Emotional transition from business owner to retiree and managing financial stress 00:00 - Introduction: Key considerations after selling a business 00:21 - How to determine if proceeds sustain your retirement goals 01:27 - Accounting for holdbacks, escrow, and earnouts in cash flow 02:34 - The importance of waiting until the deal closes for financial planning 02:52 - Using Monte Carlo simulations to assess retirement feasibility 03:30 - Managing emotional challenges in transitioning from CEO to retiree 04:11 - Developing an investment strategy to safeguard and grow wealth 05:07 - Benefits of dollar cost averaging to manage market volatility 05:50 - Planning for income needs and liabilities using treasury ladders 06:14 - Revisiting risk appetite versus capacity in your investment plan 07:09 - Tax-efficient strategies like direct indexing and loss harvesting 08:13 - Understanding the complexities of after-tax proceeds calculations 09:00 - Importance of professional support for liquidity management 09:37 - Personal insights from Kristin McKenna on navigating the exit process Resources & Links: https://darrowwealthmanagement.com/cl... https://darrowwealthmanagement.com/bl... https://darrowwealthmanagement.com/co... Content should not be misinterpreted as personalized advice of any kind or a recommendation for any specific investment product, financial or tax strategy. This is a general communication should not be used as the basis for making any type of tax, financial, legal, or investment decision.