Small-Business Owners’ Biggest Retirement Mistake
After spending a lifetime concentrating on their companies, many small-business owners find themselves in a tough spot near the end of their careers. They’ve neglected planning for succession or a sale.


Investors often enjoy the excitement that comes with a strong bull market as we watch our investment portfolios grow. During these times, we aim to maximize the value and performance of our investments. And when bear markets hit, we seek to protect these assets.
Whether we’re dealing with expansion cycles or recessionary risk cycles, we’re constantly seeking to build, protect and optimize our portfolios. Whether it’s stocks, bonds, real estate or other private investments, experienced professionals such as CPAs, wealth managers, investment bankers and attorneys are utilized to help investors navigate through these cycles. But when it comes to how business owners manage their largest investment — the closely-held business that they’ve built — they often do not seek the same necessary professional help and guidance needed to accomplish their goals.
As a wealth manager and investment adviser over the past 25 years, I’ve developed and counseled a diversified clientele. I’ve had the opportunity to help a substantial demographic: the small-business owner. One critical area I’ve discovered they need help with is business strategy and enhancement.

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.
The small-business owner often overlooks their most valuable investment for their retirement and their legacy: their business. Most business owners work tirelessly year-after-year to operate, sustain and grow their companies, but they may not be spending nearly as much time examining planning and strategy. Implementing proper business strategy, in alignment with their goals, will help them capitalize and increase the value of their largest investment.
One man’s stumbling blocks to selling his business
A prospective client recently came to our firm looking for guidance with a business succession strategy for his food and beverage distribution company, which he has been operating for over 25 years as the sole owner. The company is very profitable, with high margins, the owner is in his late 60s and enjoys a comfortable lifestyle. However, he’s currently working about 45 hours a week, and he’s concerned about the future of his business if he dies or becomes disabled. Since he’s feeling the fatigue of his age and yet still working hard, he wants to sell his business and retire.
I discovered that this business owner is facing three common challenges that will diminish the value of his company when he sells:
- The company is heavily owner-dependent; the owner is spread too thin among many areas of business operations and client relationships.
- The business is dependent on the owner’s ability to run the company and lacks a talented management team that could resume operations in the event of a long-term absence, sale or a succession plan.
- The company currently has a highly concentrated client base, where two clients represent over 55% of the revenue, lacking diversity.
Some disturbing small-business stats
Take a look at these statistics from the Exit Planning Institute, a provider of education and tools for exit-planning professionals, keeping in mind that one’s business is typically the largest asset in a small-business owner’s investment portfolio:
- 70% to 80% of businesses put on the market don’t sell.
- 95% of mergers and acquisitions professionals believe a business owner’s unrealistic expectation of their company’s value is the biggest obstacle to a sale or transfer.
- Only 30% of all family-owned business survive into the second generation, and just 12% into the third.
- 78% have no formal professional transition team; 83% have no written transition plan; and 49% have done no planning at all.
- Half feel ownership-transition plans require the company to remain profitable for plans to be properly executed, yet 86% have not taken on a strategic assessment or a business value enhancement project.
3 vital plans to put into place, for your own sake
Considering that in many cases a privately owned business is a self-employed person’s largest asset, many of these owners are failing in three of the most important areas of planning and running the business. Smart planning in these three areas can help with their retirement goals and the transfer of wealth to future generations or family members:
- Execute a business value enhancement plan involving trackable key performance indicators.
- Build a business succession plan with buy-in from other stakeholders, enabling the business owner to have a smooth transition into retirement.
- Prepare for the possibility that the owner might wish to sell the business. Explore the five most common methods for maximum value: a strategic third-party acquisition, financial buyer such as a private equity firm, purchase by company management, family purchase (or a combination of both) or finally an ESOP (employee stock ownership plan) sale.
With mindful planning, small-business owners can greatly reduce or eliminate the challenges that are faced during the inevitable times of transition. It can also help enable the business owner to maximize their investment to its fullest potential. With focus, diligence and a proper strategy we have the ability to achieve a comfortable, rewarding retirement. One that will fulfill not only our hopes, goals and dreams, but also enable us to leave a legacy, if planned properly, for our families, heirs or our favorite charities into future generations.
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.
Nick Giacoumakis is the founder and president of New England Investment & Retirement Group Inc. (NEIRG) and a nationally recognized wealth management adviser with a passion for helping business owners achieve success throughout all stages of ownership.
-
The US Postal Service Does More Than Deliver Mail: Six Ways It Helps Older Adults
With talk of cuts to the USPS swirling, here are the ways it provides vital services to the nation’s older adults.
By Donna Fuscaldo Published
-
Stock Market Today: Stocks Seesaw After Big Market Rally
The latest consumer confidence data showed sentiment remains low.
By Karee Venema Published
-
Would You Benefit From Investing in Cryptocurrency?
Understanding the complexity of adding digital currency to your investments is critical, especially since drastic price changes can happen very quickly.
By Robert Cannon, MBA, CFF®, AIFA® Published
-
Why Company Stock May Be Riskier Than Employees Realize
Stock compensation has its perks, but employees must be realistic (and unemotional) about their investments' prospects. Sometimes strategic sales are smart.
By Michael Aloi, CFP® Published
-
Can You Be Fired for Going to Work When You're Contagious?
What's an employer to do when an employee shows up at the office with a cold or the flu and spreads germs to co-workers?
By H. Dennis Beaver, Esq. Published
-
Social Security Fairness Act: Five Financial Planning Issues to Revisit
More money as a public-sector retiree is great, but there could be unintended consequences with taxes, Medicare and more if you're not careful.
By Daniel Goodman, CFP®, CLU® Published
-
Social Security Warning: Five Missteps Too Many Women Make
Claiming Social Security is complicated, and for women the stakes are high. What you don't know can cost you, so make sure you do know these five things.
By Daniela Dubach Published
-
To Buck the Third-Generation Curse, Focus on the Family Story
The key is to motivate the next generations to contribute to the family business in a productive way. You can look to Lawrence Welk's family as a prime example.
By John M. Goralka Published
-
How Roth Accounts Can Ease Your Tax Burden in Retirement
Strategic Roth IRA conversions can set you up for tax-free income in retirement and a tax-free inheritance for the people you love.
By Jim Hanna Published
-
Are You a High Earner But Still Broke? Five Fixes for That
If you're a HENRY (a higher earner, not rich yet) but feel like you still live paycheck to paycheck, there are steps you can take to get control of your financial future.
By Mallon FitzPatrick, CFP®, AEP®, CLU® Published