Selling your business is more than a liquidity event—it also marks a fundamental shift in how your wealth supports your life. After years of relying on business income, many owners face a new challenge: creating a sustainable income stream from the assets they’ve built.
In the second installment of Navigating the Sale of Your Business: Before, During, and Post, William Blair’s Chris Brathwaite explores strategies for replacing a paycheck, anticipating expenses, and building a long-term financial plan designed to support your lifestyle.
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If you’re a business owner, your company is likely your primary source of income. But what happens when you sell that business? How do you replace that paycheck when the regular salary stops? How do you maintain the lifestyle that you desire?
Consider that transitioning from running a business often means moving from a less liquid, accumulation phase—building value—to a more liquid decumulation phase. In other words, it’s a phase in which people must rely on their financial assets, a shift that is both psychological and financial.
With the right strategy and thoughtful planning, you can recreate the stability of a paycheck, ensuring your newfound liquidity supports your lifestyle, your legacy, and your peace of mind.
It starts with structuring a portfolio designed for income, not just growth. We look beyond basic equities and use dividend-paying stocks, bonds, and alternative investments to generate cash flow that isn't dependent solely on market highs. Ultimately, we design a cash flow waterfall that incorporates return of principal, tax-free bond income, qualified dividends, realized long-term capital gains, and, finally, fully taxable income…in that order.
It’s important to do some financial modeling to solve for a sustainable or “safe” level of spending. Flexible withdrawal strategies—adjusting your spending slightly based on market performance—can often significantly improve long-term financial outcomes. It’s about being dynamic, rather than rigid.
The ability to recreate a paycheck or otherwise support your lifestyle also hinges on tax strategy and long-term planning. Tax efficiency is critical. By using strategies like tax-loss harvesting and careful asset location, we aim to minimize the tax drag on your withdrawals.
Long-term planning is just as crucial. With lifespans increasing, your plan needs to account for 30, maybe 40 years of inflation and healthcare costs.
You’ve spent a lifetime building your wealth. We can help you design the plan that sustains it. At William Blair, we provide intersectional expertise and proprietary research needed to navigate this transition with confidence.
Connect with a William Blair wealth advisor today, and let’s define your vision of success.