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from IAG M&A Advisors

How to Define and Measure Risk when Buying a Business


Guest post provided by Acquira, a business acquisition in-a-box service that helps entrepreneurs find, buy, and grow cash-flowing businesses.


Business acquisitions can be an exciting thing. 


There are often large sums of money at play; negotiations can get heated; and generally, there is a lot at stake.


But if you’re not careful you can get swept up in the excitement and end up with a bad deal.


The best protection against this is a well-defined investment thesis. An investment thesis allows you to lay out your risk tolerance in order to quickly and efficiently disqualify bad deals or identify good deals. 


An investment thesis can be built around a number of criteria, including geographic scope, industry, brand moat, company culture, and more. Whatever criteria you use, the thesis will help to remove subjective opinions and emotions from the analysis of a deal, as well as quickly screen opportunities and separate the signal from the noise. 


Despite the fact that it is so important, many Acquisition Entrepreneurs will skip this step due to their eagerness to get started – or ignore it entirely.


This eagerness can lead people to make bad decisions and buy bad companies. In this article, we’ll go into how you can define your risk tolerance and what factors you can use to analyze deals, plus we’ll share a cautionary tale from our own acquisition experiences.


Determining Your Risk Tolerance


Without risk, there is no reward. But you need to be aware of exactly how much risk you’re willing to take because it won’t be the same for everyone.


As the US Securities & Exchange Commission states on its own website:


“When it comes to investing, risk and reward go hand in hand. The phrase “no pain, no gain” – comes close to summing up the relationship between risk and reward. Don’t let anyone tell you otherwise: all investments involve some degree of risk.”


While the SEC is speaking specifically about securities, they correctly point out that there is a degree of risk involved in all investments.


Before you begin looking into potential acquisition targets, you need to define your risk tolerance. 


Generally speaking, those with a high risk tolerance are willing to risk losing money for potentially greater results. Investors with a low risk tolerance favor investments that will maintain their original investment.


Here are some questions you can ask yourself to help determine your own risk tolerance level:


1. What are your investment goals?


People invest in securities for a number of reasons. People who invest in small businesses are often looking for something more specific.


At Acquira, we believe that small businesses will become the next trillion-dollar asset class, driven in large part by acquisition entrepreneurs (AEs) who are looking for financial freedom, independence, and the opportunity to create generational wealth.


Other AEs are merely looking for something to help them earn money to put toward their retirement or their children’s education.


Deciding what your goals are is the first step to determining your personal risk threshold.


2. What is your time horizon?


Once you know your investment goals, it becomes easier to establish the time horizon for your investment. Your time horizon is the point when you plan to use the money you’ve invested. In the world of small business acquisitions, this can be thought of as your exit. 


Exiting from the company amounts to cashing in on all of the hard work you’ve put into the business during your time as the owner. Acquira offers AEs an exit path by issuing a warrant on the companies they acquire, ensuring the opportunity for the AE to sell the business for more than what they paid. 


The timeline for this is multiple years, though the time horizon can shrink significantly if you’re able to systematize the business and change it from owner-operated to management-run by installing a leadership team. (Which members of our Accelerator Program are trained to do as part of our ACE Framework.)


We talked about how different time horizons might look for different career paths in our Third Path video:



3. How comfortable are you with short-term loss?


Nearly every investment will experience short-term losses at some point. There will be a market correction or recession and investments will take a dip. [Incidentally, this is why Acquira recommends recession-resilient businesses like home services companies.]


In the world of business acquisition, there are additional reasons you may experience short-term loss. As we mentioned above, systematization and creating a leadership team are the best ways to speed up your exit from the business, but implementing those takes time and money which can result in a temporary dip in gross profits for the company.


Given the goals and time horizon you set, are you able to stomach a loss in the short term? This can be unnerving for some Acquisition Entrepreneurs.


4. Do you have any non-invested savings?


If you’re dumping every penny you have into buying a business, you may want to rethink your strategy. At the very least, you should consider buying a smaller company. Even the best laid plans can meet with ruin, so ensuring you have a financial safety net is always recommended. 


The size of that safety net will help you determine your risk tolerance. Those with more to fall back on, generally speaking, can take greater risks than those without much in the bank.


Flagging Risk


Once you’ve determined your risk tolerance, you need a system to quickly identify any deal-killers in a potential acquisition. In Acquira’s training, we teach AEs to use our Deal Flagging System. You’ll come across items when analyzing a business that will cause varying degrees of concern. You need to weigh those concerns against your risk tolerance and that’s where the flag system comes in:


A Green Flag: There are no issues with a particular item. 


A Yellow Flag: There is a small issue that needs to be monitored, but isn’t anything to be alarmed over.


A Red Flag: There is an alarming issue, but it could be mitigated with a certain amount of negotiation or planning.


A Black Flag: The deal killer. This is an issue that indicates the business doesn’t fit your investment thesis and it can’t be fixed no matter what you do.


Three yellow flags constitute a red flag and three red flags make a black flag.


By determining your individual risk tolerance and understanding how to flag specific items, you can quickly determine whether a deal is outside of your comfort zone. Of course, the scoring system outlined above is based on personal opinions and we like to look at the data here at Acquira. In the next section, we’ll explore what exact points we weigh to determine whether a deal is too risky or whether it offers some hidden value.


Creating Your Investment Thesis


Your investment thesis acts as a checklist of required criteria to do a deal, based on the terms of that deal. For example, Acquira’s investment thesis for any deal that we might invest in would require the following criteria to be met:


  • The business has existed for at least 5 years
  • The business is doing at least 500k in annual SDE (Seller Discretionary Earnings) – smaller businesses just don’t have as much room to invest in growth and still provide a yield
  • There is a diverse customer base (no large customer concentration)
  • Has a large enough serviceable market so that if you really hit a homerun on carving out market share through digital marketing, you can at least 5x the business
  • The team has a strong culture of having each other’s backs

As long as the business fits the above, we will consider it.  We analyze the deal based on the following factors (we’ll go further into detail on these factors in the next section of this article):


  • Company Culture
  • Industry and Company Moat
  • Demographics and Industry Dynamics
  • Pricing and Margin Health
  • SDE Trend
  • Seasonality
  • Customer/Sales Concentration
  • Key-Man / License Holder Risk
  • Recession Resilience
  • Management Depth
  • Operations Sophistication
  • Acquisition Entrepreneur Fit

To define your own investment thesis, you can ask yourself the following questions:

  • How flexible are you as to the location of the business? Which cities or states?
  • How much time can you spend physically at the business in the first 6 months?
  • What additional items would you add to the screening criteria?
  • What industries are you most interested in buying a business in?
  • How much cash do you need to be distributed to yourself, per year, for the first three years?
  • If you had to remove only one of the ten screening criteria, which would it be?
  • If you had to keep only three of the screening criteria, which would they be?


How To Weigh The Risks


Acquira’s training is an entrance-to-exit program designed to find and close a business for you within seven months, integrate our ACE Framework within the following nine months, and exit the business to earn more than what you paid for the business. 


It includes in-depth analysis, case studies of real business acquisitions, and various proprietary tools to help you in the business search process – including an Investment Thesis Calculator.


The calculator is designed to help you appraise businesses relatively quickly. We do this by weighing ten different risk factors that we have identified as being important enough to impact the value of a business.


With the calculator, we teach you how to measure each item, then give you a suggested formula to adjust the multiple based on your measurement. This spits out a final internal value price. If that price is above the asking price, you’ve found a good deal.


As Warren Buffet said, “Better to buy a wonderful company for a fair price, than a fair company for a wonderful price.”


The factors are weighted so that, depending on their score, they will raise or lower the value of a business. First, there are two important terms to lay out:


1. The asking price: This is, quite simply, how much the seller is asking for the business. It is usually based on a multiple of the company’s SDE (Seller’s Discretionary Earnings) or EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization). So if a seller is asking for $1 million, and the business is valued at 2.5x, then its SDE is $400,000.


2. The internal price: This is what the buyer values the company at based on their own due diligence findings. The internal price should not impact the asking price. If, after conducting due diligence research on a business, you find that its internal price is higher than its asking price, then you have found a good deal.


The Investment Thesis calculator takes a business’ SDE and begins with a starting multiple. This multiple is different for each industry, and we have a matrix of multiples based on 6 EBITDA ranges and 15 industries that we actively buy in:


So, for example, if the company’s SDE is $600,000, the starting multiple for a business of that size is 3.5, which means the purchase price would be $2.1 million total. If you were to finance the payment for that business through an SBA loan, you might pay $210,000 of your own money. The calculator provides a range of valuations based on company size.


The AE then runs through the weighting factors that will raise or lower that multiple. We’ve laid this out in past articles, but it bears repeating. The factors we look at include:


1. Company Culture


We’re looking for whether employees are engaged and enjoy working there. The best way to test for this is to test for the opposite – disengaged, disgruntled employees tend to quit or be laid off.


In order to discern the health of a company’s culture, we look at the average tenure of employees by department. If the average is under three years, that can lower a company’s multiple. If it’s higher than six years that can raise the multiple.


We also look at health benefits offered compared to the local average. Specifically, if the benefits package is well below the industry average, that can lower a company’s multiple.


There may be instances where you would limit this appraisal to the amount of turnover by segment. For example, you may want to confine your analysis to the leadership team or technicians while excluding CSRs or warehouse workers. We’ve seen companies with good culture in the field, but bad culture in the office.


2. Brand Moat


This looks at how long it would take to replace the business’ review-base / referral base (including word of mouth).


Put another way, if you were doing a startup competitor from scratch, how long would it take and how much would it cost just to recreate the brand/marketing strength of this business?


A company scores lower if it would take less than two years to build up its brand moat.


We are mainly looking at replacement costs. For context, building out a great web presence and at least 200 5-star reviews would cost about $100,000 and can be done in about a year for most businesses, where the average ticket is in the hundreds of dollars (longer for larger ticket items like roofs). 


Note that you should also take into account your own skills, network, and assets as an acquisition entrepreneur.


3. Demographics


This is a combination of demographic growth (new people moving in over the next decade), as well as overall existing marketshare. To calculate the overall existing market share, we divide the total serviced households by the estimated total number of serviceable households.


We look at two things here:
1) What is the natural growth of this business if you don’t take away marketshare from competitors?
2) What is the growth if you hit a home run, and end up getting 20% of your addressable market?


An investment in integration and digital marketing optimization will cause a small business to grow simply by sifting business away from its competitors. That means that over five percent of a business’ growth rate can NOT come from natural/organic/demographic growth.


4. Gross Profit Trend


Is the business’ gross profit growing or stable? The gross profit trend should measure both margin and total dollars.


We measure this instead of revenue because different service or product offerings can often have drastically different contribution margins, and we measure it instead of EBITDA because post-close we can control operating expenses.


5. Seasonality


Is the business highly seasonal, meaning that revenue or profitability vary depending on the month? This is important to understand the working capital needs of the business. Seasonality is often managed by furloughing the workforce or introducing new, non-seasonal products or services.


6. Customer/Sales/Vendor Concentration


If a single customer takes their business elsewhere, how much will that impact the business’ bottom line?


This is important to measure from the perspective of both the economic user and the referring user. That’s because, financially, it may seem like no single customer has more than 10 percent of your sales, but you may find that a single General Contractor is referring 25 percent of those customers to you. 


Additionally, this is important to measure from a gross profit standpoint, as different work gets different margins.


7. Key Man / License Holder Risk


Are there any employees who are absolutely crucial to the business’ operations? If they left, could it stop the business from operating? For how long? 


This could be based on an employee holding a key license, holding a key customer relationship, or being the only person in the company outside of the owner that is capable of doing a key job that is very difficult to replace.


8. Recession Resilience


How exposed to the overall economy is the business? This primarily impacts your down-side pro-forma financial model. We want to make sure that in the event of a recession, the owner is still able to make their debt payments and pay themselves a living wage. The living wage part is important, as you don’t want to be forced to return to the workplace and thereby neglect your business.


We include asset value in this part of the calculation as well because if it is high enough, it can override recession risk. If a business’s furniture, fixtures, and equipment are a high percentage of its purchase price, your risk is lower as you can flip those assets in case of insolvency. 


Banks are also aware of this, and are more likely to approve you for a loan, and require less collateral (though this would be through a non-SBA loan).


You want to look at the likelihood of a recession impacting the business, as well as the impact a recession would have.


9. Management Depth


Introducing layers of management takes both time (opportunity cost) and has risk (potential profit decline).


a) Mid-level Managers


Getting a manager to a point where they are trusted, capable, and confident, is generally a six-month process. So finding a business that already has this in place will allow you to accelerate your growth by six months. If the cultural health of the company is poor, however, this could take up to a year (and the risk of alienating other employees is higher). You also run the risk of promoting/hiring the wrong person and thus affecting the retention of the people they manage, as well as their output.


b) Leadership


Building a leadership team within the company to the point where they are trusted, capable, and confident is typically a year-long process. So finding a business that already has this in place will allow you to accelerate your growth by 12 months. If the cultural health of the company is poor, however, this could take up to 18 months (and the risk of alienating other employees is higher). You also run the risk of promoting/hiring the wrong person and thus affecting the retention of the people they manage, as well as their output.


10. Operations Sophistication


Here we measure how well the company uses technology, and how well they make goals and decisions based on data. This is important as the owner will want to implement this in their business, and the implementation process takes time and carries some risk. 


Typically you shouldn’t introduce large technology changes in the first six to 12 months post-close, as that can create friction. The business owner should strive to instill trust before making any sweeping changes. 


If these technological tools are in place, growth could be accelerated. Note that you could implement them sooner, but the risk of alienating your team grows the faster you do it post-close.



Weighing all of these factors becomes easier with a tool like Acquira’s Investment Thesis Calculator, but of course, you can always come up with your own weighting system. Just make sure that you test it at regular intervals and use it consistently to measure deals.


Better to buy a wonderful company for a fair price, than a fair company for a wonderful price.

– Warren Buffet


The goal of our calculator is to take make life easier for deal searchers. Once you know how to measure each item, put it through the suggested formula you can adjust the multiple based on your own criteria. This will give you a final internal value price and if that price is above the asking price, you’re golden.


How To Identify A Good Deal


Once you’ve defined your personal risk tolerance threshold and you know how to weigh the risk factors of a business, you need to identify the good deals when you find them.


This happens during the due diligence process. After signing an NDA (non-disclosure agreement), you will receive a prospectus to go over. The prospectus will lay out the history of the business, its assets, its financials, and other facts.


Certain factors like company culture may be more difficult to discern from the prospectus. This is why you need to do two diligence passes of any business: one pre-LOI (letter of intent) and one post-LOI. The calculator will help you weigh the business based on the above criteria on the first pass and second pass. As you gain more clarity on the business, how well the business matches your investment thesis will become more well-defined.


When you go over a business’ prospectus, flagging any items that don’t match your investment thesis or risk tolerance, this is pre-LOI diligence. 


The goal of the Investment Thesis Calculator is to find a business with a higher Internal Price than the asking price – these are the good deals. 


If the business looks like a good deal after the first pass, matches your investment thesis, and doesn’t surpass your risk tolerance, you can issue a Letter Of Intent (LOI) for the business. The LOI is a non-legally binding document that is an integral tool in the process of buying a small business. Once the LOI is issued, the seller will provide more information on the business and the post-LOI diligence phase begins. This is a much more in-depth diligence process that involves in-person site visits to the company, one-on-ones with key employees, and a deeper financial analysis of the business. We lay out these steps in our Last Mile training.


Once you have the additional information on the business, you can run it through the Investment Thesis Calculator for the second pass to see if the internal price rises more. 


When there’s a big variation to the upside between the internal price and the asking price, you’ve found a good deal.


Risks VS Low-Hanging Fruit: A Cautionary Tale


The strictest investment theses are only helpful if you stick to them though, and it’s not uncommon for Acquisition Entrepreneurs to get caught up in the excitement of the process and overlook red flags in order to acquire a company. Almost every time this happens, they end up making a bad deal. It happens time and again, and Acquira’s leadership is no exception.


As the company’s CEO Hayden Miyamoto explains, this exact situation happened with a previous business of his. It was 2016 when he was still relatively new to acquiring businesses, and his company specialized in acquiring online businesses. They already owned an existing business with a high referral program that netted them $220 per sign-up. They found a new site that was a much smaller competitor that was making just $120 per sign-up with the same referral partner. It was for sale at 2x its valuation.


“So we figured we could nearly double the income by just combining the accounts,” explained Hayden. “But the new site was new. Like a year old. And our investment thesis at the time was to only buy companies over three years old. But the thought of doubling it overnight, meaning we could make our money back in a year, was too appealing.”


According to Hayden, the site went under about two weeks after the purchase. 


“It dropped to zero.”


Hayden and his partners were so attracted by the potentially easy revenue boost that they overlooked a key component of their investment thesis: don’t buy anything younger than three years old. They forgot the wisdom of Mr. Buffet, that it’s “better to buy a wonderful company for a fair price, than a fair company for a wonderful price.”


When analyzing a potential business acquisition, you’ll often come across aspects of a business operation that could easily be made better, improving efficiencies and boosting profits. These easy-to-scale growth items are what we think of as low-hanging fruit. 


Depending on the business, some examples might include:

  • Local optimization (Google Local, HomeAdvisors, Yelp, Angieslist, etc.)
  • Revamping the website and improving conversions and tracking
  • Digital Advertising (SEO, Adwords, Facebook)
  • Testing pricing and value proposition remodels
  • Referral marketing programs
  • Marketing to existing customers
  • Onboarding an external call and e-mail center for emergency calls, lead responses, etc (for better response time)
  • Tracking lead-response times and bringing this down to under 1 hour
  • Optimizing copy and scripts for calls and emails


Don’t let the potential for profit that could come from this low-hanging fruit override any aspect of your investment thesis.


However, once you have acquired a company and identified those deceptively easy wins, taking advantage of those opportunities should be the first step you take to grow the company. This will create the fastest results and help instill trust from your new employees as they see that you are making positive changes.




Business acquisitions can be very exciting. It’s easy to let low-hanging fruit opportunities make you forget about carefully considered aspects of your investment thesis – but don’t do it! 


Risk is inherent in any investment, but the best tool you have to mitigate that risk is a well-thought out investment thesis. The thesis allows you to scrutinize potential deals quickly, disqualifying bad deals or identifying good ones. 


This process is the best way to find any diamonds in the rough – but in order to accomplish that you must first know your risk tolerance and how to weigh the risk factors before you can identify a good deal.


Acquira’s training was designed specifically to teach people this process. Our Accelerator Program is a stem-to-stern, entrance-to-exit business acquisition program that will train you how to source and vet a business, walk you through the negotiation and closing processes, provide post-acquisition growth, and offer you a potential exit for more than what you initially paid. 


The first step is to schedule a call with one of our representatives. Someone will be in touch within 24 hours.


Do you have any instances where the potential for a quick payoff overrode a carefully considered strategy? Let us know in the comments below.


Key Takeaways


  • Risk is an intrinsic part of any investment.
  • The best tool to mitigate risk is a strong and well-thought-out investment thesis.
  • In order to create your investment thesis, you must first understand your risk tolerance.
  • Define what your investment goals are and your time horizon.
  • Don’t let low-hanging fruit opportunities override aspects of your investment thesis.

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