I Sold My Business … Now What?
The rich cash infusion that comes from selling a business can create a liquidity conundrum that's a challenge to manage.


America is full of innovators, disrupters and entrepreneurs. The opportunity to start a business has never been greater, and according to the Small Business Administration (SBA), 44% of economic activity is from small business. In fact, much of the wealth we see in the wealth management industry is created from the eventual exit (via sale or IPO) of these businesses. For the average person the sale or IPO of a business may seem like a dream come true, but it does not come without its share of changes and considerations.
Fortunately, there have been many others who have traversed the landscape of business sales. In fact, there are wealth management firms that work specifically with this type of client. Finding a specialist that employs Certified Exit Planning Advisors (CEPA), Certified Private Wealth Advisors (CPWA) and Wealth Strategists is a good start. These financial professionals can help guide you through your post-sale decision-making process.
In my experience, the newly created liquidity from a business sale or IPO comes with the following three questions:

Sign up for Kiplinger’s Free E-Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Question #1: How do I maintain my standard of living?
I have traded my income from my business for large infusion of cash. How do I maintain my standard of living while ensuring there are sufficient funds for the rest of my life and possibly future generations? The relief that comes with mapping out your financial future in the form of a financial plan is never more acute than in this situation. Replacing fear and speculation with data is paramount in reducing the anxiety associated with an unknown financial future. From this planning exercise, your practitioner will guide you through identifying, “what it takes for you to keep being you,” from a cash-flow perspective. This will inform the appropriate investment strategy to make sure your goals are attainable and sustainable.
Question #2: What about taxes?
How do I mitigate the potentially enormous tax bill that comes along with realizing a business transaction? This is where the CEPA® and CPWA® practitioners and of course a CPA will come in handy. Every transaction is different as are the tax implications. Is it an asset sale or a stock sale? Is there QSBS (section 1202) stock involved? Is there an earn-out? What happens if I roll my stock into acquiring company stock?
As you can see, this question is multi-faceted and the structure of the deal will play the biggest part in determining the tax implications. For those charitably inclined, there may be some additional options to reduce taxes such as a donor-advised fund or charitable lead trusts, but a thorough plan is required to consider whether these are viable options.
Question #3: What do I need to talk about with my family?
What kind of conversations should I be having with my significant others and our children who now understand the level of wealth created by this sale? On its surface, this may seem like an odd question. However, when you consider that 70% of family wealth does not make it to second generation, and 90% does not make it to the third generation according to Nasdaq, the importance becomes apparent. This is more than an estate planning conversation (here is a good checklist for getting started with that). Think, “the softer side of estate planning.” These family governance conversations include family values discussions and revolve around the vision you have for the legacy you are creating. Having a skilled family governance professional to navigate these conversations is key in engaging the next generations in what could otherwise be an awkward and uncomfortable discussion.
Congratulations on the realization of your hard work into a potentially life-changing business transaction. You have reached an enviable position, and now have the means to shape your destiny. While by no means simple, the reality is that there are professionals who can guide you through this new phase of your life. Engaging these professionals early in the process is always a smart move.
Get Kiplinger Today newsletter — free
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Chris Creed is a Senior Lead Adviser for Venturi Wealth Management. Chris partners with new clients to organize, plan and manage all aspects of their family's financial life. As a Certified Financial Planner® professional and a Certified Private Wealth Advisor®, Chris creates customized wealth planning strategies unique to highly affluent clients.
-
The AI Doctor Coming to Read Your Test Results
The Kiplinger Letter There’s big opportunity for AI tools that analyze CAT scans, MRIs and other medical images. But there are also big challenges that human clinicians and tech companies will have to overcome.
By John Miley Published
-
The Best Places for LGBTQ People to Retire Abroad
LGBTQ people can safely retire abroad, but they must know a country’s laws and level of support — going beyond the usual retirement considerations.
By Drew Limsky Published
-
Financial Planning's Paradox: Balancing Riches and True Wealth
While enough money is important for financial security, it does not guarantee fulfillment. How can retirees and financial advisers keep their eye on the ball?
By Richard P. Himmer, PhD Published
-
A Confident Retirement Starts With These Four Strategies
Work your way around income gaps, tax gaffes and Social Security insecurity with some thoughtful planning and analysis.
By Nick Bare, CFP® Published
-
Should You Still Wait Until 70 to Claim Social Security?
Delaying Social Security until age 70 will increase your benefits. But with shortages ahead, and talk of cuts, is there a case for claiming sooner?
By Evan T. Beach, CFP®, AWMA® Published
-
Retirement Planning for Couples: How to Plan to Be So Happy Together
Planning for retirement as a couple is a team sport that takes open communication, thoughtful planning and a solid financial strategy.
By Andrew Rosen, CFP®, CEP Published
-
Market Turmoil: What History Tells Us About Current Volatility
This up-and-down uncertainty is nerve-racking, but a look back at previous downturns shows that the markets are resilient. Here's how to ride out the turmoil.
By Michael Aloi, CFP® Published
-
Home Insurance: How to Cut Costs Without Losing Coverage
Natural disasters are causing home insurance premiums to soar, but don't risk dropping your coverage completely when there are ways to keep costs down.
By Jared Elson, Investment Adviser Published
-
Markets Roller Coaster: Resist the Urge to Make Big Changes
You could do more harm than good if you react emotionally to volatility. Instead, consider tax-loss harvesting, Roth conversions and how to plan for next time.
By Frank J. Legan Published
-
Why Homeowners Insurance Has Gotten So Very Expensive
The home insurance industry is seeing more frequent and bigger claims because of weather, wildfires and other natural disasters.
By Karl Susman, CPCU, LUTCF, CIC, CSFP, CFS, CPIA, AAI-M, PLCS Published