Help! I Can’t Afford to Sell My Business
Even if the deal sounds good on the surface, the effect on your personal finances may shock you. If so, you have options.

The process of selling a business involves fine-tuning every piece of its financials before marketing it and seeking a buyer. But even if everything seems in order, it may not be the right time to sell. Perhaps something — or rather, someone — isn’t ready
An important question to ask before you sell your business: Can you actually afford to do it? With a multimillion-dollar payday in the offing, the answer seems simple. But in all of the fine-tuning of the business, could you have neglected your personal finances to the point that a sale won’t offer enough financial freedom?
Too frequently business owners sacrifice their own financial health or unknowingly tie it too close to their company, only realizing the situation upon the sale, creating anxiety as the regular income and safety of the business disappears. This begs two questions: Why can’t some owners afford the sale of their business, and what are their options?

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 No. 1: Why can’t some folks afford to sell?
Let’s say a 55-year-old owner is ready to sell their business for $5 million cash with additional rolled equity. They don’t have an extravagant lifestyle, spending $200,000 per year. The $5 million sales price seems like a reasonable amount to continue living their lifestyle, right?
But what if they’re neglecting the fact that their car is owned by the business; their travel is taken care of by a company card; their health and life insurance were covered by the business; and countless other expenses are about to be the responsibility of their personal checking account, not their soon-to-be former business? Suddenly, that sale price might not be enough to live comfortably on for the next couple of decades.
Sellers must understand their true spending before thinking about any potential sale. The adjusted figure will drive all related decisions. In addition, having a handle on personal liquidity and spending assists with estate planning decisions prior to the transaction.
Question No. 2: What are my options?
It looks like $5 million just isn’t going to work to meet the lifestyle our example owner requires. There are plenty of options to get back on track, including:
- Make a push to ramp up the business’s value. This can be easier said than done, but it’s time to get aggressive, grind it out and find creative solutions. Perhaps new partners with differing skillsets can inject some life into the venture and increase the value of the company.
- Evaluate your capital structure. Some people make the error of leaving liquidity in the business for their own vanity, rather than any true opportunity. Ask yourself if you can start taking money out of your business earlier so you can stay on target for your growth objectives while building personal liquidity. Can your business support debt and servicing the debt? Debt brings its own inherent challenges and risks. Additionally, it may be time to bring in a minority partner that can infuse some capital and allow you to relinquish some of your financial stake in the business.
- Reassess the original deal. Is it possible to get more cash upfront and decrease the rolled equity amount or overall value of the business? There are risks to shrinking any offered rolled equity or declining it altogether (not the least of which, insulting the buyer), but it can buff the seller’s personal finances to get more cash up front.
The best option, of course, is avoiding this situation entirely. No matter where they are in their business’s lifecycle, owners must understand the true value of their personal spending and overall financial health. This process needs to start early, or else by the long-awaited time they’re ready to sell, they might not be.
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.
Matt Helfrich is President of Waldron Private Wealth, a boutique wealth management firm located just outside Pittsburgh, Pa. He leads Waldron's strategic vision, brand and value proposition and overall culture of the firm. Since 2002, Helfrich has served in a number of roles including: Chief Investment Strategist and Chief Investment Officer, where he was instrumental in creating and refining Waldron's investment discipline.
-
7 of Warren Buffett's Biggest Misses
Warren Buffett's investing wins are highly regarded across Wall Street, but no one can bat a thousand. Here are some of Buffett's biggest misses.
By Kyle Woodley Published
-
Why Toll Brothers Stock Is Falling After Earnings
Toll Brothers stock is lower Wednesday after the homebuilder missed expectations for its first quarter. Here's what you need to know.
By Joey Solitro Published
-
Rethinking Income When You Retire: No Paycheck, No Problem
When you retire, you'll need to adjust to the reality of depending on assets instead of a regular paycheck. For that, you'll need a new financial strategy.
By Joel V. Russo, LUTCF Published
-
How to Support Your Parents Without Derailing Your Finances
Putting your aging parents' financial house in order can give you a clearer picture of where they need support and how to balance that with your own plans.
By Vincent Birardi, CFP®, AIF®, MBA Published
-
Why 'Standard' Digital Background Checks Can Be So Unreliable
Missing online data, as well as stringent federal and state privacy rules, make it difficult to discover a prospective employee's or tenant's criminal past.
By H. Dennis Beaver, Esq. Published
-
Are You a High-Income Earner? Three Unexpected Reasons to Save More Than You Think You Should
High-income earners sometimes put off saving because they think they have plenty of time and money to do it later. That's not always the case, though.
By Eric Roberge, Certified Financial Planner (CFP) and Investment Adviser Published
-
How Financial Professionals Can Empower Their Female Clients
These three strategies can help advisers better serve women as they navigate unique financial challenges and build confidence.
By Jake Klima Published
-
Student Visas: Older Americans' Ticket to Living in Europe
Do you envision strolling about Europe, a book in one hand, a glass of wine in the other? You could make that happen by studying there, even if you're older.
By Kim Englehart Published
-
Three Reasons It May Be Time for an Annuity 'Refresh'
Because of higher interest rates, inflation and newer annuity products, you could get a better deal today. Don't wait, though: Interest rates could start falling.
By David S. Corman Published
-
Three Common Cash Flow Mistakes and How to Fix Them
Better cash flow management could have a bigger impact on your retirement savings than simply making more money. Here's how to manage that.
By Mike Decker, NSSA® Published