WHEN SELLING A BUSINESS, RELATIONSHIPS MATTER

When Selling a Business, Relationships Matter

You can buy or sell a home and never meet the other party in the transaction. This is almost never the case in the sale of a business. In fact, the relationship between a buyer and seller in a business sale may be the single most important element of the transaction. However, the significance of this relationship is too often overlooked.


The majority of small business transactions (sub $10m) are between a first time seller and first time buyer. Buyers and sellers often describe the process as far more complicated and frustrating than they had anticipated. This is because business transactions are quite complex. In the sale of a home, there is a significant amount of predictability to the process. If a buyer finds a home that fits their needs, qualifies for the loan and there are no major inspection issues, the transaction is likely to be completed, with very few obstacles.


Business sales have far more levels of complexity. The price and terms are often dictated by many of a company's individual characteristics as opposed to industry comparisons. Beyond getting a buyer and seller to see eye to eye on valuation, there are ongoing potential changes that a business may experience throughout the length of a transaction, whereas real estate is seldom affected by outside influences in the length of time it takes to complete a transaction. i.e A business may gain or lose value during the duration of the sales process due to changes in market conditions, lost or gained clients and key employees, litigation, inventory fluctuations, bad debt...the list goes on and on. Beyond being susceptible to obstacles from a changing environment, there are a vast number of deal points that need to be negotiated beyond the price and payment structure. i.e. non-compete agreement, training and transition, included vs excluded assets, transfer of accounts, licenses, IP, etc.


These complexities are often what leads to the compromise of a solid relationship between a buyer and seller. If there is a single issue, there is generally a reasonable amount of give and take by both sides and the relationship remains intact. When there are a multitude of issues with outstanding resolutions, often a buyer and seller will perceive the gap to be much larger than what is reality. Given the nature of buying or selling one's first ever company, emotions may run high. When this occurs, it is paramount for buyers and sellers to take diligence in how they communicate with the other party. Small problems can result in big blowups that lead to terminating a deal that actually made sense for both parties.


Upon completing the sale of a business, the transition period is going to likely involve a significant amount of interaction between the buyer and seller. With this in mind, it should be an absolute priority to maintain a cordial relationship throughout the duration of the negotiations, due diligence and contingency periods. At times, giving in to the other party's wants could cost very little while the upside of an improved relationship could result in much greater overall value.

Here are some best practices for establishing and maintaining a solid relationship with the other side:


  • Avoid In-Person Negotiations: Not only will you avoid committing to something in jest, misunderstandings are very prevalent during in-person negotiations. All proposals should be in clear writing to avoid any ambiguity.


  • Don't Overreact: Overreaction is the leading cause of a failed negotiation process. Take your time in responding, even if you are certain of your position. Allowing both parties to "sleep on it" will generally result in a more rational response and better reception.


  • Put Yourself In Their Shoes: This advice applies to all relationships but is easier said than done. Keep in mind, the process is just as challenging and frustrating to the other side. If they have never bought or sold a business, it can be increasingly fragile. If you're a buyer, don't forget that in addition to selling to you, the seller has a business to continue operating in the interim so some of their frustrations may have to do with day to day challenges that don't involve you. If you're a seller, don't forget that the buyer is investing their hard-earned money. They don't need to buy your business or any business, for that matter.


  • Separate Each Issue: When there are a million little things, they collectively feel very big. This is tip for problem solving in general. Don't let one problem give more weight to the next problem. If you isolate each issue and focus on a singular solution, the perceived enormity of the situation won't feel so vast.


  • Prioritize: Some buyers and sellers become very entangled in principal. i.e "5% interest on the seller financing is unreasonable! It should be 7%." If you take a step back and calculate the difference in total interest, you may find this to be a $10,000 gap. $10,000 is certainly a lot of money but it is all relative. If you are negotiating a $2,000,000 deal, $10,000 may not be such a priority. It may be helpful to actually write down each outstanding issue and order them from most important to least, again tackling one at a time.


  • Choose The Right Intermediary: If you are attempting to buy or sell a business and are working directly with the other party, you are far more likely to experience a failed transaction. A skilled intermediary will help coach you on what to expect and will be the glue that keeps the deal together. Keeping your distance from the other party in the negotiations can help you focus all of your time with one another on relationship building.



For more information on this and other important business selling advice, please contact the author, Dustin Sigall. dustin@sdbiz.com (858) 382-4974.


By Dustin Sigall April 18, 2026
Overview Industry: Digital Marketing (Financial Sector / PR & Content) Founded: 2016 Employees: 30 (full-time, part-time, and contractors) Transaction Year: 2022 Adjusted Earnings: $382,000 Asking Price: $1.2M (3.14x multiple) The Situation The seller founded the agency in 2016 and successfully scaled it from the ground up to a team of 30. By 2020, the business was performing well and positioned for further growth. After conducting a detailed growth analysis with her business coach, the seller mapped out a clear path to the next stage—complete with the required time, capital, and staffing. While the opportunity was attractive, she ultimately decided she did not want to take on the demands of scaling the business further. Like many entrepreneurs, she recognized her strength was in building and growing businesses—but not necessarily operating them at the next level. Preparation & Strategy The seller engaged us in 2021 to begin the sale process. The initial phase focused on positioning the business for a successful exit: Cleaned and normalized financials to ensure clarity and credibility Clearly defined owner responsibilities and team structure Identified the ideal buyer profile and strategic fit Developed a targeted go-to-market strategy Through market analysis and comparable transactions, we established a valuation of $1.2M, representing a 3.14x multiple of adjusted earnings. Market Response Once brought to market, the business generated strong interest: 233 buyer inquiries 152 signed NDAs 5 qualified offers This level of activity validated both the quality of the business and the effectiveness of the positioning strategy. Buyer Selection The seller ultimately chose an existing agency owner as the buyer. While several offers presented stronger financial terms, this buyer stood out due to: Relevant industry experience Complementary service offerings A clear vision for scaling the business The acquiring agency provided broader digital marketing services, while the seller’s firm specialized in financial-sector content and PR. This created a strong strategic fit and clear synergy. Deal Structure & Negotiation The accepted offer met the full asking price of $1.2M, but included a notable structure: 60% seller financing This is significantly higher than typical transactions, where seller financing more commonly ranges between 10%–20%, if included at all. The buyer’s rationale was to preserve capital for immediate growth initiatives post-acquisition. While other offers included more favorable upfront cash terms, they lacked the strategic alignment and operational expertise the seller prioritized. After extensive discussions, the seller chose to move forward based on: Confidence in the buyer’s ability and integrity Desire to see the business continue to grow Commitment to employees and clients Outcome The decision proved successful: The business has continued to grow post-sale Employees and clients experienced a smooth transition The buyer has consistently made payments on the seller note, which is now nearly paid off Key Takeaways Strategic fit can outweigh stronger financial terms Seller financing can unlock the right buyer when structured thoughtfully Preparation and positioning drive competitive buyer interest Alignment of values (team, clients, legacy) is often critical in final decision-making Testimonial From Seller "I met Matt through a successful entrepreneur at my business coaching group. She had recently sold her business and found freedom. I knew I wanted to do the same. She told me about her experience with Matt, so I reached out to him about selling my firm. To be honest, my firm was pretty unsellable at that point, but Matt spent a year with me cleaning up the books, improving the value, marketing the business and finding the perfect buyer. There were a few times I almost gave up or lowered the price, but Matt kept us on track and we found the perfect buyer and got our asking price. Matt is trustworthy, reliable, experienced and has a tireless work ethic. The most important characteristic is his calming force throughout a stressful process. I knew I could count on him and trust him to get me to the finish line. Now I have my life back and money in the bank. So thankful to have met Matt!"
By Dustin Sigall April 3, 2026
Closed at 4.3x EBITDA in Less Than 6 Months A retiring owner of a highly profitable niche design and manufacturing company engaged SD Business Advisors to find the right buyer — not just any buyer. Seller’s Goals Cash out 85% of equity Retain 15% ownership Stay on post-sale as a design employee Key Challenge This was a highly specialized opportunity requiring a buyer with both: Strong business operations experience Relevant design sensibility and industry fit Additional complexity included: All fabrication was subcontracted, creating perceived continuity risk under new ownership The seller wanted a partial equity rollover , requiring a buyer aligned with a more sophisticated deal structure Our Process 150 buyer inquiries generated 80 signed NDAs 3 qualified offers received The Result We successfully identified and closed with a buyer who had the right mix of operational capability, design alignment, and comfort with the seller’s continued involvement. Outcome: ✔ Sold at 4.3x EBITDA ✔ Closed in under 6 months ✔ Seller achieved liquidity, retained upside, and stayed involved in the business Client Feedback “Todd communicated quickly and efficiently and found the buyer that was not only qualified, but who also had an affinity for what we do… I have never experienced the quality of buyers that I did working with Todd.”
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By Dustin Sigall February 20, 2026
Understanding the true value of your business is one of the most important and often misunderstood parts of ownership. At its core, business valuation answers one fundamental question: What would a knowledgeable, willing buyer pay for this busi ness today? The answer is rarely as simple as a multiple you saw online or what a competitor sold for last year. Real valuation blends financial performance, risk, growth potential, and market demand. Two businesses with identical revenue can have dramatically different valuations. Why? Buyers evaluate business fundamentals as much as any financial metrics. Key value drivers include: Consistent and growing cash flow Diversified customer base Recurring or contracted revenue Strong management team Clean financials and documented processes Low owner dependency Favorable industry trends Stable margins Conversely, risks such as customer concentration, inconsistent earnings, or owner-centric operations reduce value. Business valuation is not just a formula. It is a blend of data, judgement, and real-world transaction experience. Business owners tend to focus on the overall potential selling price while the deal structure is of equal importance. An all cash transaction will likely carry a different value than a structure that includes seller financing, an earn-out, working capital adjustments, or seller equity roll. The best time to understand your company's value is before you plan to sell. Early valuation allows time to fix weaknesses, increase profitability, and position your business for a stronger exit. Business valuation is not a one-time event. It is an ongoing measurement of how attractive your company is to buyers at any given time. Owners who treat valuation as a strategic tool, rather than a last-minute requirement, consistently achieve better outcomes. If you're asking yourself, "How much is my business worth?", it's never too early to find out. Whether your business is located in San Diego or anywhere else, our team of experienced advisors is happy to provide a free and confidential business valuation. We sell businesses nationwide. Please fill out the form below to get the process started.
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By Dustin Sigall February 4, 2022
Top Qualities Of A Valuable Business What are the top drivers of value in a privately held company? Is it revenue, longevity, industry type? These certainly come into play but they don’t make our top 10. We have sold over 170 businesses over the past 12 years and have conducted well over 1,000 valuations of small and medium size businesses. We have encountered very few business owners over the years who were well versed in the most important elements of what creates value in a company. How many of the features listed below can you identify as attributes of your business? 10. REPUTATION: Perhaps not the most important item on this list, reputation remains a significant quality as it often affects the first impression of prospective buyers. It is reasonable to expect a buyer to Google your company within the first five minutes of their initial assessment. If the results are full of negative reviews, you may immediately lose interest. 9. BARRIER TO ENTRY: If your company is easy to replicate and there is a significant cost-benefit to a buyer simply starting from scratch, your company’s value could be negatively impacted. On the contrary, if you have something unique about your company such as a patent or proprietary software, your company likely has a significant barrier to entry, thus resulting in a higher value. 8. QUALITY OF BOOKS AND RECORDS: Having clean, well organized financials greatly improves your ability to sell your business for a top of market valuation. If you have a lot of “creative” write-offs, you will need to be able to provide supporting evidence of the adjustments. These adjustments (aka add-backs) should be limited to a degree as a more tedious due diligence process will likely limit your buyer pool and reduce the likelihood of a buyer being able to leverage with bank financing. 7. QUALITY OF EMPLOYEES: There is a fine balance between having all-star employees and creating a situation where one or more employees become so key to the operation that there is risk if they don’t transition with the company. Cross training your staff can help alleviate concerns of an employee becoming irreplaceable. Never create a situation where an employee is in such a leverage position that they can hold you hostage from selling your company. 6. CLIENT CONCENTRATION: What’s better…3 clients who generate $300,000 profit per year for your business or 15 clients generating the same amount? The answer depends on who you ask. Certainly 3 clients sounds easier to manage than 15 but if one of your 3 clients disappears, your business will tank. Most buyers will view a business as having a client concentration issue if one or more of your clients equates to greater than 10 – 15% of your overall revenue. Client concentration doesn’t necessarily impact the overall value of your business but will most certainly affect the terms of the purchase. i.e. A buyer will want to mitigate against risk by adding an earn-out component to the deal. An earn-out is simply a portion of the purchase price that is tied to future events post sale, such as client retention or maintaining certain performance metrics. 5. PROFITABILITY: Profit is king, right? There’s a reason it’s not number one on my list. Although most businesses are valued based on a multiple of net profit, the appropriate multiple is based largely on the qualities of the business as indicated in this list. The more of these traits your company possesses, the higher your company is likely to sell for. 4. VOLATILITY: Most businesses experience ebbs and flows but consistency is a valuable trait. If your company is highly affected by outside influences such as the overall strength of the economy, consumer spending trends, seasonality, etc., the unpredictability of future performance will have a negative impact on valuation. Even if you are coming off your best year in business, if the year over year performance is overwhelmingly better in the current year, buyers will remain cautious about the viability of maintaining such a level of success. The optimal scenario is three consecutive years of incremental growth. 3. BUYER POOL: Your company can check a lot of boxes on this list but if the buyer pool for your business is relatively small, these other factors may not save your valuation. i.e. If your company requires certain credentials that the general population of buyers do not possess, you will lack leverage for a substantial offer with a low level of demand. 2. SCALABILITY: One of the most important features of a company is its ability to scale. Retailers have the least appealing model when it comes to scalability. Yes, you can always open more stores but the success of location dependent businesses is certainly not bankable. Rather, a service based company may be well equipped to expand operations into other regions with less risk and more upside potential. 1. RELIANCE ON OWNER: Once again, if your business checks all of the other boxes, you may not even be able to sell your company if it is highly reliant on you as the owner. Here are some tips on making your business more turn-key: Avoid significant personal interactions with your clients to the point where they only want to work with you. Create written policies and procedures so that you and your employees can easily be replaced. Whenever possible, focus your energy on the big picture agenda for your company and less on putting out fires. If you are constantly putting out fires, learn to delegate better and reward those who demonstrate a capability of taking on more responsibilities such as scheduling, training, etc. If you found this information to be helpful, we have a lot more tips to share with you on how you can create the ideal exit strategy for your company. The advice is free and we are always happy to provide free and confidential valuations. DRE#01790469 DRE#01790467
By Dustin Sigall February 4, 2022
Selling a business - Do's and Don'ts A Seller’s interaction with a buyer can have a huge impact on their ability to achieve top dollar for their business. In fact, this may be one of the most under-appreciated elements of a sale. You may have a thriving business but how you communicate with a buyer can make a world of difference in valuation and the likelihood that your business will even sell at all. I have been a part of countless “Wanna Get Away?” moments in meetings with Buyers and Sellers so I thought I would share some insights with you on how to put your best foot forward when you are meeting a potential buyer for the first time. Do: Refer to your business as We and Us, not I. This is one of the most common mistakes that I see sellers make. It may not seem that important but the more you separate yourself from the company, the easier it is for a buyer to envision the company operating without you. Don’t: Use the opportunity to vent about your frustrations. As common sense as this may seem, I have been in all too many meetings where the seller forgot they weren’t on their therapist’s couch. There is a way to discuss inefficiencies and conflicts in a manner that suggests opportunity. For example, if you know the Buyer is technologically savvy and it is an area you lack in, you can feed them a subtle ego boost while conveying opportunity for bettering processes or cutting overhead. Do: Be completely honest with the Buyer. If you want to avoid a disaster down the road, be upfront with your skeletons in the closet. If they aren’t discovered now, they will during due diligence. Sweeping potential deal killers under the rug is more damaging than being upfront from the beginning. Don’t: Oversell your company. Some sellers are so afraid of saying something negative about their business that they come off as a used car salesman. Yes, it is okay to highlight your company’s accomplishments. Don’t brag, overstate, or over promise unless you are prepared to put your money where your mouth is. My most common example: Seller states he anticipates 50% growth next year. Buyer’s solution: Make the purchase price contingent on future performance. Do: Discuss your plan for how you envision a seamless transition. This is one of the best ways you can wrap up your initial meeting if there seems to be common ground. One of the buyer’s greatest fears is how the business will be transitioned. Come up with a plan before meeting with the buyer so that you can communicate it effectively. You can eliminate a lot of the buyers concerns by making them feel that you are going to be very hands on and supportive during the transition. Don’t: Negotiate in person. I have seen sellers commit to something they wish they hadn’t in the spur of a moment. Buyers may put you in an uncomfortable spot at times. An easy way to avoid making a knee jerk decision is by asking the buyer to submit their proposal in writing. If they don’t respect this method, they are not a real buyer. They should appreciate the fact that you carefully consider your decisions. It demonstrates that you truly care about the best direction for the company.
By Dustin Sigall February 4, 2022
How much is my business worth?