Mistakes to Avoid When Buying a Second Business

Katie Fleming

Katie Fleming

Co-founder and COO of Owner Actions

A person thinks about the mistakes to avoid when buying a second business.

From overlooking key issues to making missteps in negotiations, there are mistakes to avoid when buying a second business. In this article, you’ll learn about some of the most common mistakes buyers make. You’ll also find some actionable advice you can use to navigate around the pitfalls.



Entering the process without a clear objective

Often, prospective buyers begin their search because they’ve heard of others’ successes in buying a second business that’s compatible with their first.

While the advantages to this approach can be great, it’s important that you

take the time to assess whether acquisition is a choice that aligns with your business’s needs—or your personal investment goals—and your ability to invest the time and resources that are required to succeed.

This guide can help you firm your objectives:




Underestimating the work that goes into buying a business

Many business owners find that it takes up to 12 months to source the right second business. Some search for two years or more. If you’re determined to buy a business, you should recognize that the process can be long and complicated. Plan to spend months reviewing business listings, signing non-disclosure agreements, and reviewing the financials and practices of multiple businesses before settling on a target and completing your acquisition.

These two articles can help you set yourself up for success:



Forgetting to think like a seller

Buyers can fair far better in negotiations by considering a seller’s needs and goals alongside their own. Put this concept to work in your negotiations by considering a seller’s attachment to his or her business and avoiding harsh criticisms and shows of disrespect when discussing the business’s drawbacks.

You should also try to connect with the seller and build a positive working relationship that’ll serve you both well as you discuss confidential matters and negotiate terms. By establishing a good working dialogue, you may access better information, and you’ll be able to discuss the business’s blind spots and attempts to work around them.

This guide can help you learn more about this part of the acquisition process:



Accepting the success of a business at face value

It’s a broker’s job to present a seller’s business in the best possible light. Here are two tactics many take to do this:

  1. In some cases, they may make adjustments to the earnings and include add-backs to improve the financial picture of the business.
  2. They may coach the seller through some pre-sale moves, such as selling off excess inventory or temporarily slashing prices, to boost the attractiveness of their business.


By working with an accountant, you’ll be able to spot these moves and discover irregular financial behaviors that may signal trouble in a seemingly good business.

Learn how to find a great accountant with this guide:



Failing to assess the seller’s base of customers

As you may know, many small business owners cultivate sales among their personal base of contacts. While these sales are completely appropriate, you should be concerned if a business’s sales depend on the relationships that existed between the seller and the business’s customers—and further, that the customer base may disappear when the owner exits the business.

Avoid this mistake by asking sellers to disclose the percentage of customers who have personal connections with them. Then, you should assess whether the customers who remain represent a large enough percentage of the business’s sales history to proceed with the transaction.

Our article on due diligence can help you spot other red flags.



Trusting the accuracy of the seller’s data

In every transaction, a seller will present balance sheets, income statements, and other financial documents that demonstrate a business’s strength and hint at its future viability. These documents should never be accepted at face value. It’s imperative that you study and verify the business’ financials. Hire an accountant to assist in the assessment and ensure that there are no red flags, questionable line items, or evident problems in the business’s cash flow or performance.



Relying on numbers alone

Sometimes, buyers complete their evaluations of a business without considering external factors, such as customer reviews, employee satisfaction, competitive positioning, environmental concerns, legal claims, and regulatory issues that can impact a business’s long-term success and sustainability.

Be sure to conduct outside research, perhaps with the help of an attorney, to build a clear picture of the business before proceeding with your acquisition.

Learn about why you should have an attorney on your team in our article:



Missing the mark in valuations

Buyers tend to overestimate the value of businesses because they miscalculate the magnitude and frequency of future capital expenses. To avoid this mistake, you should account for both working capital needs and the costs that’ll be required to boost infrastructure, upgrade technologies, and maintain equipment. An accountant can help you with these projections.

Learn more about valuations with this guide:



Forgetting to set aside money for working capital

Some owners raise funds for acquisition without setting aside money to cover operational concerns and emerging needs. When this occurs, buyers create a scenario that may require them to take on more debt or put off improvements that are necessary for the success of their business.

You can avoid this mistake in two ways. First, set up a contingency fund that equals approximately 10 percent of your business’s purchase price. And second, create a working capital account that can cover at least three months of expenses.

Interested in ideas for raising capital? This guide will help you explore your options:



Many of these mistakes can be avoided by connecting with legal and accounting experts who are familiar with the small business acquisition process. If you’re ready to build your team, we can help you get started.

First, find an attorney who can help you through every step of the acquisition process. You can get started here:


You can also check out some of our favorite accounting firms here:

Play Video


Your Business Deserves the Very Best

Reconciled is an award-winning organization and one of the fastest-growing accounting firms in the country. Their team of entrepreneurship gurus, e-commerce pros, and tech-loving cloud accounting specialists look at your business holistically and help you analyze your spending, measure costs, and find opportunities to enhance margin and profitability, along with taking on your day-to-day bookkeeping. Want to learn more? Click the connect button below for an introduction.

Play Video


Be Tax Ready All Year Long

With Xendoo, you can access a dedicated team of expert CPAs and accountants who provide monthly bookkeeping, tax preparation and filing, and tax consulting, three services that will help you stay on top of all your financial needs. Their team can also help you with your personal tax returns, too. You can explore their plans with totally transparent pricing by following the link below, and for a limited time, you can try their online bookkeeping service free for one month. Restrictions may apply. See Xendoo’s site for details.

Play Video


Say Hello to Better Online Accounting

Business owners love 1-800Accountant. Here’s why. First, the service pairs you with a CPA who is an expert in your state and industry and can answer the tough questions you have about your business. Second, while many others charge by the hour, or worse, by minute, 1-800Accountant sets you up with an affordable, flat-rate pricing plan so you always know what you’ll be paying. Follow this link to try 1-800Accountant for 30 days with a money-back guarantee.


.Ready to start your search?

Log into your owner’s portal for free articles and advice that’ll help you source, evaluate, negotiate, and close on your small business acquisition.


Want to take on other tasks?

Owners like you love our free step-by-step guides. Build one that's customized to your goals.



Leave a Reply

Related Posts