SKIP TO CONTENT
You sold your business. That doesn’t mean you need to make decisions tomorrow.
The day the sale of your business closes marks the beginning of something new. The ink dries on documents, wire transfers complete, and suddenly you’ve gone from business owner to… what exactly? After years or even decades of building something valuable, you face a blank canvas.
It’s a time of possibility. It’s also when many newly-liquid entrepreneurs make decisions they later wish they hadn’t.
The most successful business sellers take their time. They don’t rush to deploy capital, upend their lives, or jump into new ventures. Instead, they move step by step through several phases after the sale.
Here’s how successful business sellers typically handle what to do after selling a business.
Your First 90 Days: The Breathing Room
The most important thing to do after selling your business is nothing urgent. The capital markets will be there in three months. What you need now is clarity.
Start by parking your proceeds in safe, liquid accounts. Treasury bills, money market funds, and FDIC-insured accounts spread across multiple banks work well for this initial period. You’ll give up some yield, but the safety and options you gain are worth it. This temporary parking is an essential first step in any liquidity event strategy.
Next, get acquainted with your new circumstances. Your identity, daily schedule, and financial picture have all changed dramatically. Many former business owners describe feeling adrift during this period. Harvard Business Review captured this experience well in an article by entrepreneur Jeff Giesea, who noted, “When you spend years architecting your life around a business and suddenly it’s gone, you’re probably going to have an identity crisis.”
This adjustment matters. Business owners benefit from creating a simple plan for their first six months—not centered on investment choices, but on personal readjustment. This might include:
- Taking a break after years of constant pressure
- Reconnecting with family and friends
- Thinking about the parts of building your business you actually enjoyed
- Exploring interests you put on hold during growth years
During this time, you also need to handle immediate financial tasks. How your sale was structured—asset sale, stock sale, earnout, or other deal—creates specific tax issues. A good CPA will help verify proper classification of proceeds, explore offsetting strategies, and walk you through any installment sale treatments.
For sales with earnouts or consulting arrangements, set up tracking for future payments and obligations. These ongoing elements often slip through the cracks in the post-sale shuffle but need proper attention.
The first 90 days is also when you should build or redirect your advisory team. The accountant who handled your business taxes might not specialize in personal wealth matters. The same goes for your attorney, wealth advisor, and risk management professionals. Find experts who’ve specifically helped other business sellers through this process.
Your Next Three Years: Building the Framework
Once the initial transition passes, it’s time to create a practical approach for your wealth. This isn’t about picking stocks or funds yet. It’s about forming a philosophy that will guide decades of decisions about investing after business sale.
Start by dividing your capital according to purpose rather than asset classes. Good wealth management separates money into different buckets:
Lifestyle Capital supports your standard of living, providing steady income with reasonable safety. This covers your home, cash reserves, and stable investments that deliver predictable cash flow.
Growth Capital aims for long-term appreciation, typically with more market risk and less immediate access. For many former entrepreneurs, this includes both stocks and private market opportunities.
Legacy Capital serves goals beyond your lifetime, whether family, philanthropy, or other impact objectives. Tax planningmatters deeply here, with strategies often spanning generations.
Opportunity Capital stays ready for future ventures or investments. Many entrepreneurs still want to build and invest in businesses, and keeping money available for these opportunities makes practical and personal sense.
By organizing your wealth according to purpose rather than just “stocks vs. bonds,” you set natural guardrails that help during market volatility. Each bucket follows specific guidelines based on what that money needs to do.
Your broader investment approach should reflect your personal values. Write down your ideas on risk comfort, involvement level, public versus private market mix, tax concerns, and social impact goals. This isn’t about picking specific investments yet—it’s about setting ground rules for what comes next.
Former business owners bring practical insights about risk and opportunity from their company-building experience. Many discover that private equity, venture capital, real estate, or direct investments make sense in their portfolio. Whether you’re figuring out how to invest $5 million or $50 million, your expertise, portfolio size, and actual cash needs all matter in these decisions.
This period is also when many business sellers begin thinking about giving. “The sale of a business is often an opportunity to take steps toward your philanthropic goals,” notes Morgan Stanley’s wealth management team. “It can have the added benefit of providing an opportunity to engage your children or grandchildren in conversations about the family’s shared values.”
Charitable vehicles like donor-advised funds, foundations, or charitable trusts can serve your goals while providing tax benefits and ways to involve family. As Jason Cross of Corient Wealth points out, “using a strategy called ‘charitable bunching,’ the owner makes a significant donation in the year their business is sold.” This donation can offset ordinary income taxes from the sale while establishing a longer-term giving strategy.
Comprehensive legacy planning also develops during this phase. Beyond tax-efficient wealth transfer, this means expressing your wealth values, teaching financial concepts to younger generations, and balancing help for heirs with encouraging self-reliance.
The Long View: Implementation and Evolution
With your framework established, focus turns to steady implementation and periodic review.
Investment implementation typically means entering markets gradually, building positions over time, following consistent rebalancing rules, and developing tax-efficient withdrawal methods.
For many business sellers, this steady approach differs from their entrepreneurial experience of quick decisions and concentrated risk. Getting comfortable with this different rhythm eventually delivers benefits over decades.
Scheduled check-ins on your financial picture provide proper oversight without encouraging needless changes. As Bruce Werner notes in Forbes, “Entrepreneurs and business owners typically spend decades building their businesses. They are focused on the future, without a set timeline.” After a sale, your horizon and goals shift.
As your life changes and priorities evolve, your financial approach should too. Major life events—starting new ventures, moving, family changes, or new interests—bring fresh considerations for how you manage your wealth.
Healthcare Considerations
An often overlooked aspect of post-sale wealth planning involves healthcare coverage, especially if you’re selling your business before age 65 when Medicare eligibility begins. As one wealth advisor notes, “Many owners exit their business well before being eligible for Medicare at age 65.” Without company-sponsored coverage, your insurance costs may jump considerably.
Working with healthcare insurance specialists can help find good coverage that keeps your preferred doctors at reasonable rates. These healthcare costs should be part of your liquidity event strategy and cash flow planning.
The Post-Sale Psychology
The months and years following a business sale often bring mixed emotions. Many owners go through a grieving process as they separate from their former identity. As one business seller put it: “I worry more about money now than I did before I had it. When the money first hits your account it’s a surreal moment. But it quickly becomes a responsibility.”
Growing money takes different skills than making money. This change explains why having a good plan matters – it gives you structure during an unsettled time.
A second challenge many sellers face is finding purpose. Without the daily demands of running a business, you suddenly have freedom to choose what you do. This freedom creates opportunity mixed with some uncertainty. Many former entrepreneurs find meaning through board roles, mentoring other business owners, giving back, or pursuing interests they had postponed.
As Bruce Werner advises in Forbes, when planning what to do after selling a business, you should “set goals for your next chapter that fit what makes you happy and avoids what makes you fearful.” This often means trying new things to see what really interests you beyond the company.
Finding Balance After the Sale
The post-sale period requires juggling several competing priorities: growing wealth versus enjoying it, preserving capital versus taking new risks, privacy versus legacy, and family support versus encouraging independence.
There’s no one-size-fits-all answer to these questions. Each person’s situation and priorities are different. What worked for another business seller may not be right for you.
This is why thoughtful planning helps. Working with advisors who ask good questions rather than push products helps you sort out what matters most and builds a plan that fits your personal situation.
Common Challenges to Expect
Business sellers typically face several predictable challenges after the sale.
Identity shifts. Many entrepreneurs get much of their meaning from their businesses. The Small Business Administrationnotes that selling your business “can mean big changes for your life, both personally and financially.” Finding new direction often involves mentoring others, board service, philanthropy, or pursuing interests you set aside while building the company.
Family dynamics. New wealth can change family relationships in unexpected ways. Honest talks about expectations help create understanding. Think about how open you want to be about money matters, what support you might provide for family members, how you’ll handle funding requests, and what financial education might help your family.
Investment uncertainty. Business owners often find investment choices challenging after selling. Your business gave you clear performance measures and direct control; markets offer neither. Working with advisors who understand this transition helps build your confidence. Start with defined principles and a practical approach rather than sorting through endless investment options.
You Don’t Need a Pitch. You Need Clarity.
The journey after selling your business isn’t about rushing decisions or chasing trends. It’s about carefully handling a significant change and developing an appropriate liquidity event strategy.
At Croak Capital, we’ve guided numerous business owners through this exact process. We understand you’ve spent years making complex business decisions. You don’t need someone pushing products—you need a clear approach to turning business success into lasting financial stability and personal satisfaction.
We start by learning where you stand today and where you want to go. Then we apply thoughtful allocation strategies matching your goals, risk comfort, and time frame whether you’re determining how to invest $5 million or significantly more.
If you’re ready for a different kind of conversation about your post-sale journey and investing after business sale, we’re here to help you move forward with confidence.Let’s collaborate. Our wealth management process puts you in the driver’s seat of your investing and financial management. Contact us to start a conversation.