November 1, 2025

20 Reasons Many Boomers Can’t Find the Right Buyers for Their Businesses

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.

Baby Boomers lead the U.S. business world, but as many near retirement, they find it hard to hand over their companies to the next generation or find the right buyers. This causes problems for Boomers but also opens chances for young business owners.

It is estimated that Boomers own more than half of the private U.S. businesses, about 3 million companies worth around $10 trillion as of early 2024. The size of this possible ownership change makes it a major event for the economy.

Even with these important businesses, younger people are less willing to take them over, especially in skilled trades. Boomer owners now must face the tough job of getting their businesses ready to sell or move on, while fewer successors show interest.

The next part will look closely at the current state of Boomer-owned businesses, why it is getting harder to pass them on, and how this will change the business world soon.

Reasons Boomers Are Having Difficulty Passing Their Businesses

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Boomer business owners deal with many problems when they want to hand over or sell their companies. These problems include family matters and bigger economic issues.

Let’s look at the main reasons why passing Boomer-owned businesses to the next group of business owners is not always easy.

Lack of Family Interest

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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.

Different Career Aspirations

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Younger people often choose jobs in technology, finance, or creative areas. These fields usually offer better pay, more flexible work hours, and are seen as more respected.

Old-style businesses like manufacturing, retail, or repair work can seem less interesting by comparison. This change in job choices causes a difference between the businesses Boomers run and the ones that young workers and new business owners like.

Boomer Dominance in Business Ownership

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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 

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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.

Service Industry Highlight

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Many businesses owned by Boomers work in important service areas like plumbing, electrical work, and HVAC repair. Even though these jobs are needed every day, they usually have a hard time bringing in younger workers or new owners.

This gap between how important these services are and the low interest from younger people causes a bigger problem in planning for the future and keeping these industries strong.

Lack of Relevant Skills in Family

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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.

Perception of Low Profitability

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Some younger people think traditional small businesses are not stable money-wise or make only small profits. They get this idea by seeing the daily problems their parents face or by comparing these businesses to fast-growing tech startups.

Putting a lot of time and money into a business that might give small returns may not attract younger buyers who do not like taking risks.

This makes it tougher for Boomers to find eager new owners ready to handle the money challenges of running these businesses.

Lifestyle Incompatibility

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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.

Emotional Attachment

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Boomer owners usually feel strong emotions about the businesses they have worked hard to build over many years. This connection can make it hard for them to let go or agree to changes suggested by buyers.

They might ask for terms that are hard to meet, wanting to keep parts of the business that no longer work well financially.

These feelings can make deals more difficult and scare away practical buyers who want to buy and possibly change the business.

Complexity of the Sale Process

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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. 

Valuation Gaps

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Boomer owners often think their businesses are worth more than the market says. This higher value comes from many years of hard work and personal effort. Buyers, on the other hand, look at how the business is doing right now and how much it can grow later.

This difference in value causes problems during talks. Boomer owners might reject offers they believe are too low, while buyers may not want to pay what they see as too high. This difference in value often stops or breaks deals, leaving businesses not sold.

Outdated Business Models

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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.

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.

Some Boomer owners do not create full succession plans early in their business life. They might not want to think about retiring or believe they will simply find a buyer when the time comes.

This short-sightedness can cause sudden, badly handled changes when owners near retirement. Without a clear plan, Boomers may have trouble finding the right people to take over or getting their businesses ready for a smooth change.

This mistake can cut down the number of interested buyers and make the business worth less.

Geographical Constraints

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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.

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Fear of Change

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Many Boomer-owned businesses use old systems and ways of working. Buyers see that big changes are needed to keep up with others. Updating usually needs a lot of money for new technology, training, and fixing the setup.

These extra costs and the work to make changes can scare buyers. They might be concerned about the risks of changing well-known but old business methods.

This fear of change makes fewer buyers interested in Boomer-owned businesses.

Economic Uncertainty

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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.

Private Equity Competition

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Private equity firms often buy small businesses and usually beat individual buyers. These firms can pay more and give better deals because they have more money. They also provide skilled management. Individual buyers, especially younger business owners, find it hard to compete with these offers.

This tough competition from rich private equity firms reduces the number of individual buyers for businesses owned by Boomers.

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Lack of Financial Literacy Among Buyers

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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.

Increased Regulation

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Many industries have more rules they must follow. Areas like healthcare, finance, and construction deal with many laws and regulations.

People thinking about buying in these fields might feel worried about the legal duties and risks involved. The time and money needed to keep up with the rules can stop buyers who do not have experience in strict industries.

Owners from the Boomer generation in these areas may find it hard to get buyers ready to handle these rules.

Cultural Misalignment 

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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. 

Family Businesses and Legacy Issues

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Family-owned businesses have special problems when passing the business down. Owners usually want to keep the business in the family, even if younger members are not interested. This can cause delays or force handovers to family members who do not want the job.

Disagreements can happen if several family members want to take control or do not agree on the business’s future. These family issues can make it hard to pass the business smoothly, putting older owners in a tough spot.

Market Saturation

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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.

Unwillingness to Change Ownership

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Some Boomer business owners find it hard to give up control. They might not trust others to run the business well or worry about changes to what they built.

This can show up as wanting to closely control every detail or making tough demands during sale talks. Buyers often avoid deals when the owner does not want to let go completely.

Holding on too tightly to control can slow down the sale and keep good buyers away.

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.

The problems Boomer business owners face when handing over their companies are many and complicated. Money issues, new technology, and differences between generations all make these handovers harder. Knowing these problems well is important for both sellers and buyers.

Boomer owners can take steps to fix these problems. Updating their business, making clear plans for who will take over, and setting fair prices can make their companies more attractive to buyers.

Younger business people and investors should see the chances hidden in these problems. With the right plan, they can buy these businesses and make them successful in the future.

As many Boomer businesses change hands soon, solving these problems will be important for smooth changes between business owners and new entrepreneurs. 

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

Author

  • Michael Gregory

    Will Think is the founder and owner of WilThink.com. After a long career in finance, he retired early and decided to put his knowledge to work in a different way—by helping others. He is also a dad and an avid runner.

    Will is a Chartered Financial Analyst (CFA) with over 20 years of experience in real estate investing. He’s also a published journalist whose writing has appeared on MSN, the Associated Press, and other major outlets.

    His content combines real expertise with a clear, no-nonsense style that’s both smart and accessible.

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