Boomers Want to Sell Their Businesses And Retire, But No One’s Qualified. 20 Reasons Why

Home » Boomers Want to Sell Their Businesses And Retire, But No One’s Qualified. 20 Reasons Why

Boomers Want to Sell Their Businesses And Retire, But No One’s Qualified. 20 Reasons Why

Share: TwitterFacebookPinterestRedditVKDiggLinkedinMix

Older man with glasses and gray hair, wearing a green sweater, sits at a table with a laptop, resting his chin on his hand while looking thoughtfully at the camera.Image Credit: DepositPhotos

Baby Boomers dominate the U.S. business landscape, but as many approach retirement, they face challenges in passing their companies to the next generation or finding suitable buyers. This situation creates both obstacles for Boomers and opportunities for younger entrepreneurs.

According to estimates, Boomers control over 50% of privately held U.S. businesses, comprising roughly 3 million companies valued at approximately $10 trillion as of early 2024. The sheer scale of this potential ownership transition makes it a significant economic event.

Despite the importance of these businesses, younger people are less inclined to take them over, particularly in industries like skilled trades. Boomer owners now face the difficult task of preparing their businesses for sale or transition as interest from successors wanes. 

The following discussion will provide an in-depth look at the current state of Boomer-owned businesses, the reasons behind the growing difficulties in transferring ownership, and how this trend will likely reshape the business landscape in the near future. 

Boomer Dominance in Business Ownership

An older man with a gray beard sits at a wooden desk in an office, wearing a dark suit and blue tie, with documents and stationery in front of him.An older man with a gray beard sits at a wooden desk in an office, wearing a dark suit and blue tie, with documents and stationery in front of him.

Older entrepreneurs dominate the U.S. business landscape. The U.S. Census Bureau’s 2022 Annual Business Survey reveals that 52.3% of business owners are 55 or older. Breaking this down further, 29.5% fall into the 55-64 age range, while 22.8% are 65 and above. 

This concentration of ownership among older generations highlights the pressing need for successful transitions as these owners approach retirement age.

Wealth in Transition 

Two women are shaking hands in a modern office setting with a neon sign that reads Two women are shaking hands in a modern office setting with a neon sign that reads

Boomer-owned businesses represent a massive potential transfer of wealth. These companies collectively hold about $10 trillion in value. According to a 2024 report, an estimated 12 million privately owned businesses will change hands in the coming years. 

Over 70% of these companies are expected to be sold or passed down to new owners. This shift presents a unique opportunity for younger entrepreneurs and investors looking to enter established markets or expand their business portfolios.

Stop Feeling Entitled: Why More Boomers Are Choosing Not to Pass Down Their Wealth

Service Industry Highlight

A worker wearing a yellow hard hat and gloves uses tools to work on an electrical panel mounted on an exterior wall.A worker wearing a yellow hard hat and gloves uses tools to work on an electrical panel mounted on an exterior wall.

Many Boomer-owned businesses operate in essential service sectors. These include plumbing, electrical services, and HVAC repair. Despite their importance to daily life, these fields often struggle to attract younger workers or potential owners. 

Earn Free Gift Cards

Swagbucks: Coupons, Paid Online Surveys & Free Gift Cards

Do you want to make money online simply by searching, shopping, surveys, or playing games? 

Pros:

  • Account creation is free
  • Big bonus on sign up
  • Many ways to earn free money
  • Mobile-friendly rewards site and apps
  • Simple to complete tasks
  • $10 to sign up

Cons:

  • Not exactly passive income
  • Redeeming SB points sometimes takes awhile
  • It isn’t easy to qualify for all surveys
  • Customer service isn’t the greatest (or fastest)

Swagbucks: Coupons, Paid Online Surveys & Free Gift CardsSwagbucks: Coupons, Paid Online Surveys & Free Gift Cards

This mismatch between the critical nature of these services and the lack of interest from the next generation creates a growing challenge for succession planning and industry sustainability. 

Why Companies Won’t Hire Gen Z: 20 Surprising Reasons They’re Struggling to Land Jobs

Reasons Boomers Are Having Difficulty Passing Their Businesses

An older woman with short gray hair, wearing glasses and a beige shirt, sits at a wooden desk in an office with shelves of books behind her, accompanied by documents, a typewriter, and a notebook.An older woman with short gray hair, wearing glasses and a beige shirt, sits at a wooden desk in an office with shelves of books behind her, accompanied by documents, a typewriter, and a notebook.

Boomer business owners face numerous challenges when trying to pass on or sell their companies. These obstacles range from family dynamics to broader economic factors. 

Let’s examine the key issues preventing smooth transitions of Boomer-owned businesses to the next generation of entrepreneurs. 

Want to Retire Early? Dave Ramsey’s Top Tips for Making It a Reality

Lack of Family Interest

A woman in a business suit sits at a desk, looking stressed with her head resting on her hand, in front of an open laptop. Office supplies and file folders are visible in the background.A woman in a business suit sits at a desk, looking stressed with her head resting on her hand, in front of an open laptop. Office supplies and file folders are visible in the background.

Children of Boomer business owners often show little interest in taking over the family enterprise. They witness firsthand the long hours, stress, and personal sacrifices required to run these businesses. 

This direct exposure can deter them from following in their parents’ footsteps. Instead, many opt for careers they perceive as less demanding or more aligned with their personal goals. 

This lack of family interest leaves many Boomer owners without a clear succession plan within their immediate circle.

22 Life Lessons Boomers Wish They Could Tell Their Younger Selves (With Video)

Different Career Aspirations

Person using a laptop on a wooden desk with books, a notebook, an iPhone, and a framed photo nearby.Person using a laptop on a wooden desk with books, a notebook, an iPhone, and a framed photo nearby.

Younger generations frequently gravitate towards careers in technology, finance, or creative fields. These industries often promise higher salaries, more flexible work arrangements, and greater perceived prestige. 

Traditional businesses in manufacturing, retail, or repairs may seem less appealing in comparison. This shift in career preferences creates a gap between the types of businesses Boomers own and the industries that attract younger workers and entrepreneurs.

Boomers Built These 28 Work Traditions, Now Millennials and Gen Z Are Rejecting Them

Lack of Relevant Skills in Family

A woman in a white shirt reviews a large folder while sitting at a desk in an office environment, surrounded by filing cabinets and office supplies.A woman in a white shirt reviews a large folder while sitting at a desk in an office environment, surrounded by filing cabinets and office supplies.

Many Boomer-owned businesses, especially those in skilled trades, require specific technical expertise. Fields like construction, plumbing, or electrical work demand years of hands-on experience and specialized knowledge. 

Younger family members may lack these skills or show little interest in acquiring them. This skills gap makes it challenging for Boomers to pass their businesses directly to their children or other relatives. 

It also limits the pool of potential buyers who possess the necessary qualifications to take over these specialized operations.

More Grandparents Now Raising Grandchildren: 15 Legal and Social Battles You Need to Know

Perception of Low Profitability

A woman with long blonde hair in a light blue blazer is holding and looking at a fan of U.S. dollar bills.A woman with long blonde hair in a light blue blazer is holding and looking at a fan of U.S. dollar bills.

Some younger people view traditional small businesses as financially unstable or operating with narrow profit margins. This perception can stem from observing the day-to-day struggles of their parents’ businesses or comparing them to high-growth tech startups. 

The idea of investing significant time and capital into a business with potentially modest returns may not appeal to risk-averse younger buyers. 

This hesitation makes it harder for Boomers to find enthusiastic successors willing to take on the financial challenges of running these enterprises.

23 Certifications That Are Actually Easy To Get If You Want A High Paying Job

Lifestyle Incompatibility

A person with long hair, wearing a white shirt, sitting at a desk with a laptop, holds up one finger in a gesture indicating A person with long hair, wearing a white shirt, sitting at a desk with a laptop, holds up one finger in a gesture indicating

Running a small business often demands a significant time commitment, including long hours and weekend work. Younger generations increasingly prioritize work-life balance and personal time. 

The all-consuming nature of managing a small business conflicts with these values. Potential buyers may view taking over a Boomer-owned business as sacrificing their quality of life. 

This lifestyle mismatch reduces the number of interested parties willing to step into the shoes of retiring Boomer owners.

OK Boomer! 30 Habits That Younger People Find Annoying

Outdated Business Models

A woman with blonde hair wearing a blue shirt sits at a desk with her hands on her temples, looking concerned or stressed. A pencil cup with various items and part of a laptop are visible in the foreground, as she ponders why companies do not hire over 50.A woman with blonde hair wearing a blue shirt sits at a desk with her hands on her temples, looking concerned or stressed. A pencil cup with various items and part of a laptop are visible in the foreground, as she ponders why companies do not hire over 50.

Many Boomer-owned businesses have not kept pace with modern business practices. They may lack a strong online presence, digital marketing strategies, or e-commerce capabilities. 

This technological gap can make these businesses appear outdated or less competitive to younger buyers. Modernizing these operations often requires significant investment and expertise. 

Potential successors may feel overwhelmed by the prospect of bringing an older business up to speed in today’s digital marketplace.

12 Reasons Companies Secretly Refuse To Hire Workers Over 60 

Lack of Succession Planning

A man in a light blue shirt and striped tie sits at a desk, resting his head in his hand while looking down at paperwork, seemingly pondering why companies do not hire over 50.A man in a light blue shirt and striped tie sits at a desk, resting his head in his hand while looking down at paperwork, seemingly pondering why companies do not hire over 50.

Some Boomer owners neglect to develop comprehensive succession plans early in their business lifecycle. They may avoid thinking about retirement or assume they’ll always find a buyer when needed. 

This lack of foresight can lead to rushed, poorly executed transitions as owners approach retirement age. Without a clear plan, Boomers may struggle to identify suitable successors or prepare their businesses for a smooth handover. 

This oversight can reduce the pool of interested buyers and lower the overall value of the business.

If You Love Your Loved Ones, Don’t Leave These 25 Things Behind When You Die

Geographical Constraints

A man in a plaid shirt and cap sits at a desk, looking at a large computer monitor, with windows showing trees in the background.A man in a plaid shirt and cap sits at a desk, looking at a large computer monitor, with windows showing trees in the background.Image Credit: iStock

Many Boomer-owned businesses operate in smaller towns or rural areas. These locations often hold less appeal for younger generations who prefer urban centers with diverse job markets and lifestyle options. 

The geographical mismatch between where these businesses exist and where potential buyers want to live creates a significant barrier to successful transitions. 

Relocating established businesses can prove costly and risky, further limiting the options for Boomer owners seeking to sell.

🙋‍♀️If you like what you are reading, then click like and subscribe to my newsletter. We share tips to waste less time and money.

Emotional Attachment

An elderly woman with gray hair and a blue sweater looks pensively at the camera, resting her hands against her chin in a brightly lit room.An elderly woman with gray hair and a blue sweater looks pensively at the camera, resting her hands against her chin in a brightly lit room.

Boomer owners often have deep emotional ties to the businesses they’ve built over decades. This attachment can make it difficult for them to let go or accept changes proposed by potential buyers. 

Owners may set unrealistic conditions for the sale, insisting on preserving certain aspects of the business that no longer make economic sense. 

This emotional factor can complicate negotiations and deter pragmatic buyers looking to acquire and potentially transform these enterprises.

Boomers Were Right! 20 Times They Showed Us They Knew Best

Complexity of the Sale Process

An elderly man sitting on a sofa holds his head with both hands, appearing concerned or distressed, perhaps reflecting on the advice to stop doing these if over 60.An elderly man sitting on a sofa holds his head with both hands, appearing concerned or distressed, perhaps reflecting on the advice to stop doing these if over 60.

Selling a business involves navigating complex legal, financial, and operational challenges. Many Boomer owners find this process daunting and struggle to manage all aspects of a sale effectively. 

They may lack experience in areas like valuation, due diligence, or contract negotiation. This complexity can lead to delays, misunderstandings, or even failed deals. 

Without proper guidance, Boomer owners may make costly mistakes or miss opportunities to maximize the value of their businesses during the sale process. 

12 Flexible Jobs That Pay $20 an Hour (With Video)

Valuation Gaps

An elderly woman and a middle-aged man in a suit discuss documents at a table in an office setting.An elderly woman and a middle-aged man in a suit discuss documents at a table in an office setting.

Boomer owners often place a higher value on their businesses than the market supports. This inflated valuation stems from years of emotional investment and personal sacrifice. Potential buyers, in contrast, focus on current financial performance and future growth potential. 

This disconnect in perceived value creates obstacles in negotiations. Boomer owners may resist offers they see as too low, while buyers hesitate to pay what they consider inflated prices. This valuation gap frequently stalls or derails potential deals, leaving businesses unsold.

22 Careers Expected To Be Gone In A Few Years

Fear of Change

Elderly woman with short gray hair stands by a sheer curtain, resting her cheek in her hand and looking thoughtfully ahead. She wears a light blue sweater.Elderly woman with short gray hair stands by a sheer curtain, resting her cheek in her hand and looking thoughtfully ahead. She wears a light blue sweater.

Many Boomer-owned businesses rely on outdated systems and practices. Potential buyers recognize the need for significant updates to remain competitive. This modernization often requires substantial investment in technology, training, and infrastructure. 

The prospect of these additional costs and the effort required to implement changes can deter buyers. They may worry about the risks associated with overhauling established but outdated business models. 

This fear of change limits the pool of willing buyers for Boomer-owned enterprises.

The 31 Hardest Parts of Aging, That No One Really Wants To Talk About (With Video)

Economic Uncertainty

An older woman signs a document with a red pen while a man in a suit observes, seated at a table in an office setting.An older woman signs a document with a red pen while a man in a suit observes, seated at a table in an office setting.

Fluctuating economic conditions create hesitation among potential business buyers. Factors like inflation, interest rate changes, and market instability inject uncertainty into business valuations. 

Buyers may worry about taking on a business that requires significant investment during unpredictable times. They might prefer to wait for more stable economic conditions before committing to a purchase. 

This cautiousness in the face of economic uncertainty prolongs the selling process for Boomer owners looking to exit their businesses.

20 Reasons Why Many Americans No Longer Believe They Can Retire at 65 

Private Equity Competition

Two people in business attire sit on a sofa, engaged in a conversation. One holds a tablet.Two people in business attire sit on a sofa, engaged in a conversation. One holds a tablet.Image Credit: Pexels

Private equity firms actively pursue small business acquisitions, often outcompeting individual buyers. These firms can offer more attractive terms and higher purchase prices due to their financial resources. 

They also bring professional management expertise to the table. Individual buyers, especially younger entrepreneurs, struggle to match these offers. 

This competition from well-funded private equity groups narrows the field of potential individual buyers for Boomer-owned businesses.

🙋‍♀️If you like what you are reading, then click like and subscribe to my newsletter. We share tips to waste less time and money.

Family Businesses and Legacy Issues

Image Credit: Pexels

Family-owned businesses face unique challenges in succession. Owners often desire to keep the business within the family, even when younger generations show little interest. This preference can lead to delayed transitions or forced handovers to reluctant family members. 

Tensions may arise if multiple family members compete for control or disagree on the business’s future direction. These complex family dynamics can complicate or derail smooth business transitions, leaving Boomer owners in a difficult position.

30 Things Likely To Vanish With Baby Boomers: A Farewell to What Was Normal

Market Saturation

Image Credit: Pexels

Some industries, like retail or hospitality, face intense competition and market saturation. In these crowded markets, standing out becomes increasingly challenging. Potential buyers may view acquiring a business in a saturated market as risky. 

They worry about the difficulty of attracting customers and maintaining profitability in highly competitive environments. This perception of market saturation makes some Boomer-owned businesses less attractive to buyers, especially those in industries with low barriers to entry.

Always Tired at Work? These Industries Are Most Likely to Burn You Out

Unwillingness to Change Ownership

A bearded man sits at a desk in an office, with two colleagues working at computers in the background.A bearded man sits at a desk in an office, with two colleagues working at computers in the background.Image Credit: Pexels

Some Boomer business owners struggle with the idea of relinquishing control. They may doubt others’ ability to run the business successfully or fear changes to their legacy. 

This reluctance can manifest as micromanagement tendencies or unreasonable conditions during sale negotiations. Potential buyers often shy away from deals where the previous owner seems unwilling to fully hand over the reins. 

This attachment to control can significantly hinder the sale process and deter qualified buyers.

Retired but Want More Money? 27 High-Paying Jobs Retirees Can Start Immediately

Lack of Financial Literacy Among Buyers

Image Credit: Pexels

Many potential buyers, especially younger ones, may lack comprehensive understanding of business finances. They might struggle with concepts like cash flow management, debt structuring, or tax implications of ownership. 

This financial knowledge gap can make them hesitant to take on the complexities of running a business. Boomer owners may find it challenging to explain their business’s financial intricacies to less experienced buyers. 

This mismatch in financial literacy can lead to misunderstandings and failed negotiations.

13 Pieces of Horrible Financial Advice (That Most People Still Believe)

Increased Regulation

A woman sits at a table with her hands on her temples, surrounded by papers and graphs, while two people standing next to her hold documents.A woman sits at a table with her hands on her temples, surrounded by papers and graphs, while two people standing next to her hold documents.Image Credit: Pexels

Many industries face growing regulatory requirements. Fields like healthcare, finance, and construction must navigate complex compliance landscapes. 

Potential buyers may feel intimidated by the legal responsibilities and potential liabilities associated with these regulated industries. The cost and effort of maintaining compliance can deter buyers who lack experience in heavily regulated sectors. 

Boomer owners in these industries may struggle to find buyers willing to take on these regulatory burdens.

High-Paying Jobs, No Takers: Industries in Dire Need of Applicants

Cultural Misalignment 

An elderly woman stands by a table with three younger adults seated, engaged in a discussion. A whiteboard with notes, a refrigerator, and office supplies are visible in the background.An elderly woman stands by a table with three younger adults seated, engaged in a discussion. A whiteboard with notes, a refrigerator, and office supplies are visible in the background.

Boomer-owned businesses often maintain traditional workplace cultures. These may clash with the expectations of younger workers and entrepreneurs. Potential buyers might view these established cultures as resistant to change or incompatible with modern management styles. 

They worry about the difficulty of reshaping company culture while maintaining business continuity. This cultural mismatch can deter buyers seeking workplaces aligned with contemporary values and practices. 

No Thanks! 19 Reasons Young People Are Choosing Not to Work 

The Bottom Line

A man with a gray beard and mustache, wearing a dark suit and tie, sits in an office with shelves and plants in the background, pondering why companies do not hire over 50.A man with a gray beard and mustache, wearing a dark suit and tie, sits in an office with shelves and plants in the background, pondering why companies do not hire over 50.

The challenges facing Boomer business owners in passing on their enterprises are complex and multifaceted. Economic, technological, and generational factors all play roles in complicating these transitions. Understanding these obstacles is crucial for both sellers and potential buyers.

Boomer owners can take proactive steps to address these challenges. Modernizing operations, developing clear succession plans, and realistically valuing their businesses can increase their appeal to potential buyers. 

Younger entrepreneurs and investors should recognize the opportunities hidden within these challenges. With the right approach, they can acquire established businesses and transform them for future success.

As millions of Boomer-owned businesses change hands in the coming years, overcoming these obstacles will be key to ensuring smooth transitions between generations of business owners and entrepreneurs. 

🙋‍♀️If you like what you just read, then subscribe to my newsletter and follow us on YouTube.👈

AI was used for light editing, formatting, and readability. But a human (me!) wrote and edited this.

Originally Appeared Here