Avoiding the 75%: Why So Many Owners Regret Selling Their Business
If you’re planning to sell your business someday, here’s a statistic worth sitting with: research from the Exit Planning Institute and PwC found that 75% of business owners feel “unhappy” or “profoundly unhappy” one year after exiting their company. Three out of four owners who worked hard to build something, then sold it or handed it off end up regretting how it turned out. That’s not a small problem. And it’s been true for over a decade, which tells you something: most exit planning still focuses almost entirely on the transaction, not on what happens to you after the deal closes. The real issue isn’t the money; it’s the identity loss If you’ve run a business for any length of time, your company isn’t just an asset. It’s woven into who you are. Your family may see you as the success story. Your friends, many of whom are probably your employees, envy that you don’t answer to a boss. Your community expects you (and your company) to show up and give more, because you’re “the owner.” Your business shapes your daily interactions, your standing among peers, and your sense of purpose. So when you sell or step away, it’s not simply a financial transition; it’s a personal one. Being introduced as a “former owner” or lumped in as “retired” can feel like erasure, not freedom. That disorientation is a huge part of why so many owners end up unhappy, even when the deal itself went well financially. Most owners don’t plan for what comes next Business owners are goal-driven. You’ve spent years chasing targets and clearing the next hurdle. Yet when it comes to planning life after your business, most owners are flying blind: only 17% have a written plan, and nearly half have no plan at all. Think about what that transition actually demands. You’re not just changing your income source, you’re losing: The steady stream of small wins that come from daily decision-making 40, 50, or 60 hours a week that used to be filled with purpose The satisfaction of building strategy, developing people, and steering a team If nothing replaces that, boredom, restlessness, and regret tend to fill the gap — regardless of how large the check was. What a good exit actually requires A successful exit isn’t just about maximizing sale price. It’s about walking into something you’re genuinely excited about — not just walking away from something familiar. That means thinking through, well before you sign anything: What does a fulfilling week look like without the business? What replaces the sense of purpose and decision-making you’re used to? Are your expectations about timing, value, and readiness realistic? Selling your business will likely be the largest financial event of your life. But it’s also one of the most significant identity shifts you’ll ever go through. The owners who avoid the 75% are the ones who plan for both. John F. Dini, CExP, CEPA is an exit planning coach and the President of MPN Incorporated in San Antonio, Texas. He is the publisher of the Awake at 2 o’clock blog and has authored three books on business ownership. The single largest transaction and transition of your life deserves special attention. Are you planning to exit and sell your business? Exit planning is quickly becoming a buzzword in the legal and financial communities. Your professional advisors position themselves to provide tax, risk management, wealth management, and contract preparation services. The BEST-PivotPoint Exit Plan Advisor is trained to manage your team of tax, legal, business, and financial planners as you navigate your exit strategy. Click here to learn more about how to get started. If you want to see how prepared you are for transition, take the 15-minute Assessment at no charge: One indisputable fact: 100% of owners will eventually exit their business. The Assessment is a multiple-choice questionnaire that does not ask for confidential or financial information. Nevertheless, it is a critical first step in starting the discussion and planning process. Click here for more information concerning our free, no-obligation exit planning assessment.
The Hidden Metric That Can Transform the Value of Your Business
Revenue matters. It gets you in the room with acquirers, it signals that customers want what you sell, and it is the foundation everything else is built on. But revenue alone does not make a business valuable. What often transforms a revenue story into a valuable business is gross margin: the difference between what you sell and what it costs you to make. Jeff Church learned this the hard way. He built Suja, a cold-pressed juice company, from zero to $120 million in revenue in about five years. He landed Whole Foods as his anchor retailer, won their supplier of the year award out of fifty thousand vendors, and attracted investment from Coca-Cola at a $300 million valuation. Then Coke walked away from their option to buy the rest of the business. Jeff found out on the eve of July 4th. He walked downstairs to where his kids and wife were waiting and broke down in tears. He had a $120 million company, $40 million in debt maturing in six months, and a business losing $9 million a year. The revenue had been there all along. The gross margin had not. What Jeff Did Next With the board pushing to sell at whatever price they could get, Jeff made a different bet. He did not cut his way to a slightly smaller loss. He rebuilt the business around a completely different product. Suja had a line of wellness shots that had been sitting largely ignored for years. The shots had 65% gross margins. The cold-pressed juice they were famous for had 30%. The kombucha they had launched had 15%. Jeff got rid of the kombucha. He pulled back on the juice. He went all in on the shots. Within two years, Suja went from losing $9 million a year to generating $20 million in EBITDA. Not because revenue exploded. Because the margin on what they were selling changed everything underneath it. The company sold for $325 million. Why This Matters for Your Business A financial buyer looking at your business is not buying your revenue. They are buying your future cash flow. And gross margin is the clearest signal of whether that cash flow is durable. Jeff’s wellness shots did not just improve his profit. They changed the fundamental quality of the business. A company doing $120 million at 15% gross margins and a company doing $120 million at 65% gross margins are not the same business. Jeff had the shots sitting in his product line for years. The answer was there. He just had not reorganized around it yet. The Question Worth Asking Look at your own business and ask where your margin comes from. Not which product line has the most revenue, but which one has the highest margin. Are you spending most of your time and energy on the high margin work, or are you running hard on the low margin work because that is where the volume is? Your highest margin product or service is not just your most profitable offering. It is the version of your business a buyer would most want to own. The single largest transaction and transition of your life deserves special attention. Are you planning to exit and sell your business? Exit planning is quickly becoming a buzzword in the legal and financial communities. Your professional advisors position themselves to provide tax, risk management, wealth management, and contract preparation services. The BEST-PivotPoint Exit Plan Advisor has been trained to manage your team of tax, legal, business, and financial planners to navigate your exit strategy. Click here for more details on how to get started. If you want to see how prepared you are for transition, take the 15-minute Assessment at no charge: There is one indisputable fact – 100% of owners will eventually exit their business. The Assessment is a multiple-choice questionnaire that does not ask for confidential or financial information. Nevertheless, it is a critical first step in starting the discussion and planning process. Click here for more information concerning our free, no-obligation exit planning assessment.
What to Watch Out for When Getting Outside Advice
When you bring in an outside advisor — whether it’s an accountant, attorney, consultant, or broker — you’re doing the right thing. You’re acknowledging there’s something you don’t know and going to find someone who does. That’s smart ownership. But there’s a trap hidden in that process that most business owners never see coming. Every Expert Has a Favorite Tool There’s an old saying: to a hammer, everything is a nail. Think about it this way. You go to your doctor and say, “My shoulder has been killing me — I need help.” The doctor genuinely wants to help you. But whether you walk out with a prescription, a surgery date, a chiropractic adjustment, or a set of acupuncture needles depends less on what’s actually best for your shoulder — and more on which type of doctor you happened to walk in to see. The internist reaches for anti-inflammatories. The orthopedic surgeon schedules an operation. Each one treats your pain. Each one probably helps. But you’ll likely never realize that your treatment was shaped by who you chose to see, not by some universal best practice for shoulder injuries. The same thing happens when business owners seek outside help. The Advisor You Hire Shapes the Advice You Get When it comes to something as significant as planning your exit from a business, the type of advisor you engage will heavily influence the direction you’re pointed — often without you realizing it. Bring in an accountant and the plan will likely center on minimizing your tax burden. Hire an attorney and you’ll probably end up focused on asset protection or employment contracts. Work with a business consultant and the conversation will revolve around improving operations and boosting profitability. None of that advice is wrong. But it may not be complete — and it may not actually align with what you’re trying to accomplish in your life. A few years ago, a business broker added “Exit Planner” to his business card. When asked how he approached exit planning, his answer was straightforward: if an owner would agree to accept 100% seller financing, he’d help them sell. That was his tool, and he applied it to every situation. To a hammer, everything is a nail. What This Means for You Before you take any advisor’s recommendation and run with it, it’s worth asking yourself: Is this the best solution for my situation — or is it the best solution this particular advisor knows how to deliver? That’s not cynicism. Most advisors genuinely want to help. But their training, their experience, and frankly their business model all point them toward certain kinds of answers. The best advisors — the ones worth your time and money — will ask a lot of questions before they start offering solutions. They’ll slow down, make sure they understand your real objectives, and resist the urge to jump straight to their preferred tool. If an advisor walks into your first meeting already knowing what you need, that’s worth paying attention to. The clarity that comes from being genuinely heard saves time, prevents costly missteps, and leads to a plan you’ll actually follow through on. The right advice starts with the right questions — not the other way around. John F. Dini, CExP, CEPA is an exit planning coach and the President of MPN Incorporated in San Antonio, Texas. He is the publisher of the Awake at 2 o’clock blog and has authored three books on business ownership. The single largest transaction and transition of your life deserves special attention. Are you planning to exit and sell your business? Exit planning is quickly becoming a buzzword in the legal and financial communities. Your professional advisors position themselves to provide tax, risk management, wealth management, and contract preparation services. The BEST-PivotPoint Exit Plan Advisor has been trained to manage your team of tax, legal, business, and financial planners to navigate your exit strategy. Click here for more details on how to get started. If you want to see how prepared you are for transition, take the 15-minute Assessment at no charge: There is one indisputable fact – 100% of owners will eventually exit their business. The Assessment is a multiple-choice questionnaire that does not ask for confidential or financial information. Nevertheless, it is a critical first step in starting the discussion and planning process. Click here for more information concerning our free, no-obligation exit planning assessment.
How to Identify Top Candidates through Behavior-Based Questions
Recently, I came across an article in my newsfeed that claimed to share the best job interview questions from executives. When articles like this show up in my news feed, it feels like “clickbait.” I can’t help but read it and see what “experts” are saying. I often think to myself, “What are they doing differently, and what might I learn from them?” or “Is there anything of value that might help me do better in my role as Practice Leader for Strategic Human Resource Solutions at BEST Human Capital & Advisory Group?” However, reading these questions, I was appalled. Why? Most questions cited were future-looking, asking candidates to craft an imaginary response about what they “would” do. A response to such questions would lack behavioral evidence of future success. Any response to a future-phrased question is dependent on the real/actual situation with the employer where a candidate is seeking employment, which is unknown to the candidate at the time of an interview. A comprehensive understanding of the situation and environment cannot be adequately communicated to a candidate during the interview process to provide the proper context for them to frame an appropriate response. The questions asked by executives in the article, which we review below, lacked job relevance. Relevance to the job is critical when asking any question in a job interview. Asking questions lacking job relevance increases employer risk. Candidates have a right, and I would say a responsibility, to push back on these questions to seek understanding around their relevance. What’s Better? While past performance is not a perfect predictor of future occurrences, it is all one has to go on. Knowing what they have done, and the circumstances around the actions taken – behavior-based questions – helps an interviewer understand the potential performance a candidate brings to any role. Let’s examine how the questions from the article can be reframed as behavior-based questions: Don’t ask: “Imagine the scope of work has increased, but resources have not; what would you do?” Reframe and do ask: “Tell me about a time when the scope of work on a project you led or on which you were a key participant increased (encountered scope creep), yet the resources available to complete the project remained the same. What adjustments did you make to ensure the project was completed on time and on budget? How did you adapt existing resources, team member participation, or your own performance to ensure the project was completed at the quality level expected?” The ”Tell me…” statement sets up the scenario you want the candidate to discuss. The questions that follow provide the appropriate context. They dig for more details from the candidate to encourage a response that can demonstrate relevance to the job. It is general enough to encompass a wide variety of projects that a candidate can draw on as a response, yet specific enough to help the interviewer understand the candidate’s thought processes, knowledge, skills, abilities, and decision-making style. All projects are challenged by scope creep, time, resource, and budget constraints. An adequate response would address these concerns and shed far more light on what is important for the role – because it draws on what the candidate has done. Don’t ask: “What impact will you have on your team?” Reframe and do ask: “Describe a situation when you stepped into a leadership role for an existing team. Why were you tapped to lead the team? What were the top 2 – 3 challenges the team was facing at the time you stepped into this leadership role? Share the key actions you took to address each of these top challenges and the impact your actions had on the team’s success.” The “Describe a situation…” statement sets up the scenario for the candidate to respond. The supporting questions provide critical context that a candidate needs in order to formulate a proper response. This behavior-based question is rooted in what the candidate has done. Any interviewer can hear the response, evaluate it in the context of what this person would be doing in the role for which they are being interviewed. It gets to the heart of the job – stepping into an existing team, confronting challenges they may not fully understand or even be aware of until they take on the role, and having to develop a plan of action to address these challenges. The interviewer will be able to see how the candidate has accomplished this in the past, which informs them on how they will do it in the future without providing a fictitious answer. Don’t ask: “What brings you here today?” Eliminate this question entirely: The reason for a person to be in the interview today should have been uncovered well in advance of any “executive” interview. During an introductory conversation, usually with an internal or external recruiter, candidates should be asked about the reasons for their career transitions. For example, “I see you worked for Acme from 1/2020 through 5/2024. What prompted you to leave Acme and join Beta Corp?” What you are listening for is if there is a legitimate, positive reason for the transition – were they recruited? Was it for a career growth opportunity? Were there family concerns necessitating the change? – or reasons that are just beyond their control – Acme suffered financial distress, and their role was eliminated as part of a downsizing. This should be uncovered well before any “Executive” interview. Don’t ask: “How do you receive negative feedback?” Reframe and ask: “Share a time when you were unsuccessful. What feedback did you receive, and how did you personally and professionally deal with this situation?” This reframing gets to the heart of dealing with failure, receiving feedback, and whether or not the individual handles feedback about a failure positively. It is never the mistake or failure that is important, it is how we deal with it and recover that truly tells you something about the perseverance, ethical persuasion, temperament, and mental flexibility of a
Planning for Life After Business: Achieving Your Freedom Point
Spring marks the peak selling season— and a time to dream about the future. For many horticulture business owners, 80–90% of their net worth is tied up in their business. Yet, according to the 2024 State of Succession and Exit Planning in the Horticulture Industry survey, 54% of owners lack a formal business valuation. To turn your retirement dreams into reality, you need to determine your Freedom Point— the moment when selling your business provides enough resources to sustain your ideal lifestyle. Understanding Your Freedom Point Your Freedom Point is unique to you. It represents the financial threshold at which selling your business generates enough cash to maintain your desired lifestyle. To determine your Freedom Point, consider these three key factors: Current Business Value – What is your business worth today? Financial Needs – How much do you need for a comfortable retirement? Value Gap – The difference between your business’s worth and what’s needed to fund your future. Start by adding up your savings, including investments and retirement funds, and estimate your expected proceeds from selling your business. The net proceeds from the sale will depend on EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization). The EBITDA multiple determines the price a prospective buyer may offer. Next, calculate your anticipated post-retirement expenses, including everyday costs and bucket-list goals, up to age 95 (gulp). Unlike your grandparents, if you live to 75, there’s a good chance you’ll reach 95. Lastly, you will need to pay 5–15% in transaction costs and advisor fees, and expect to pay Uncle Sam his share using your current tax rate. What remains after subtracting your expenses, retiring any remaining debt, transaction costs, and taxes is your Freedom Point! Sounds simple? It’s not. To quickly estimate your Freedom Point, use the complimentary online Freedom Point Calculator: CLICK HERE! It takes less than 10 minutes and provides a full, confidential report. The Importance of Early Planning Many business owners delay exit planning, but starting early provides flexibility and control. Preparing years in advance allows you to increase profitability, strengthen management, and improve operational efficiency. A rushed sale often leads to lower valuations, fewer buyer options, and missed financial opportunities. Think of your exit strategy as an evolving process rather than a last-minute decision. Strategies to Maximize Business Value The pool of potential buyers in the horticulture industry is limited. How can you make your business stand out? Achieving your Freedom Point requires preparing your business for a profitable sale. Focus on these 10 essential steps: Get a Business Valuation – Obtain an independent valuation to understand your business’s current worth. Be prepared to share at least three years of financials and tax returns. Increase Profitability – Optimize sales and cost efficiencies to enhance earnings. A clear sales growth strategy sets your business apart from others on the market. Organize Financial Records – Ensure key financial statements and tax returns are accurate, up to date, and easy to explain. Separate non-recurring expenses, such as bonuses or personal costs, to present true profitability. Improve Cash Flow – Minimize large expenses unless they are mission-critical. Buyers don’t want to make significant investments on day one of ownership. Strengthen Your Management Team – Reduce owner centricity by developing strong internal leadership. A management team capable of running the business without you makes for a smoother transition. Diversify Revenue Streams – Mitigate risk by expanding your customer base and product offerings to reduce dependency on a few large customers or products. Document Standard Operating Procedures – Well-documented processes decrease owner dependency, increase business value, and simplify the transition to a new owner. Enhance Customer Loyalty – Loyal customers are valuable assets to potential buyers. Know your Net Promoter Score (NPS)—if it’s below 9.0, fix it. Strong customer relationships add significant value. Develop a Clear Exit Strategy – Exit planning is a team effort. Involve professional advisors, your management, employees, and family to plan your transition well in advance. Address Legal and Compliance Issues – Anticipate issues surfacing during due diligence. Resolve outstanding contracts, licenses, and legal matters to avoid roadblocks during a sale. When done properly and in a timely manner, these steps help bridge the gap between your business’s current value and the amount needed to fund your future lifestyle, ensuring you achieve your Freedom Point. Your business is your legacy. Plan ahead, maximize its value, and secure the future you’ve worked so hard to build. Are You Ready? Take Our Complimentary Assessments Let’s find out— They take about 15 minutes or less, but are incredibly insightful as you begin your succession and exit planning journey. Take the assessments today, and let’s have a confidential discussion about the future. Personal Readiness PREScore™ is an 8-minute, online questionnaire that evaluates a business owner’s readiness to exit their company on a personal level. Using an exclusive algorithm, it calculates an owner’s readiness by identifying their status on four drivers of a satisfying exit. TAKE THE PRESCORE™ ASSESSMENT Business Readiness Value Builder™ is used by over 80,000 businesses that evaluates a business on the eight core values acquirers consider when buying companies. The Value Builder™ Score provides a comprehensive assessment of the “Sellability” of your business. TAKE THE VALUE BUILDER™ ASSESSMENT Financial Readiness The Freedom Score is a 10-minute online questionnaire that evaluates your financial readiness to fund the next phase of your life after your business, when the sale of your company will generate enough to fund your desired lifestyle for the rest of your life. TAKE THE FREEDOM SCORE ASSESSMENT Let’s Talk We are happy to provide you with a complimentary and confidential consultation. This is an opportunity to ask any questions about your succession and exit planning. Please let us know some days and times that work for you to have a phone call or a video meeting, and we can talk about the future. Contact Chris BOOK A MEETING WITH ME