Exit Strategies Archives - Your ExitMap

Exit Planning: If Not Now, When?

John F. Dini — Thu, 14 May 2026 14:36:37 +0000

You’ve probably said it yourself: “Talk to me in five years.” It’s the most common response advisors hear — and it makes sense. You’re heads-down building, not winding down. Exit planning feels like a conversation for later. The business is performing. You have time. And honestly, it’s a lot to think about. But here’s the uncomfortable truth: later is exactly when most exits go wrong. You’re already doing exit planning — just not deliberately Think about the early-stage tech founder. Obsessed with product, grinding 80-hour weeks, convinced the exit is the last thing they should be thinking about. Yet their investors demand an exit strategy ... Read more

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What to Watch Out for When Getting Outside Advice

John F. Dini — Tue, 28 Apr 2026 16:05:40 +0000

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 ... Read more

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Manufacturer Stuck in the “Neutral Zone”

John F. Dini — Fri, 06 Mar 2026 16:07:44 +0000

Here is how exit planning helped a business owner out of the Neutral Zone. This manufacturer reached out to an exit planning consultant after receiving a book on planning as a gift from a local professional. He was in no particular hurry to leave his business. In the preceding twenty years of ownership, he had grown it from a local vendor to home builders into a nationally known specialty house. The company provided him with a good living, generating roughly $700,000 a year in free cash flow for each of the previous five years. He wanted to continue for at least a few more years ... Read more

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How Much does the Big Picture Count?

John F. Dini — Tue, 17 Feb 2026 17:41:35 +0000

It is currently difficult to have a business conversation without discussing the Big Picture. The voracious 24-hour news cycle needs plenty of fodder to attract eyeballs. It almost seems like the media must pick and choose what will create the most concern. “Seventeen dead in drone attacks? Let’s put that sixth on the schedule.” Big Picture Issues Wars in Ukraine, Israel, and Sudan. Attacks on shipping. Russian hacker ransomware. The battle between the U.S. executive and judicial branches. Tariffs, sanctions, inflation, interest rates, boycotts. Will the price of raw materials go up? How much will transportation cost next week? Should I load up on inventory—or ... Read more

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Creating the Perfect Business Exit Timeline!

David Lupberger — Thu, 08 Jan 2026 16:05:51 +0000

When is a good time to start planning the eventual exit from your business? Simply, you will be leaving your business and hopefully, this will happen in a planned and deliberate fashion. This is something every business owner will address. Unfortunately, things do not always happen in a planned fashion. Those of you in the remodeling industry deal with project-driven plan and schedule changes on a weekly basis. This is nothing new to you! If we follow the advice from the book The 7 Habits of Highly Effective People by Stephen Covey, we want to implement Habit 2: Begin with the End in Mind! We ... Read more

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What Business Owners Should Know from the 5th Annual Exit Planners Survey

John F. Dini — Tue, 07 Oct 2025 16:55:45 +0000

Between February 1 and March 2, 2025, ExitMap conducted its 5th annual survey of professionals who help business owners plan successful exits. This is the only survey that gathers insight across multiple advisory specialties—offering a wide-angle view of the professionals supporting entrepreneurs like you during one of the most critical transitions of your life. The survey included 30 questions and was distributed to over 7,000 experienced advisors worldwide. These are professionals with recognized credentials in exit planning, active roles in professional organizations, or who publicly position themselves as specialists in business transition. We received 434 responses from advisors in eight disciplines, representing six countries and ... Read more

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20 Red Flags to Look Out for When Buying a Business

Joe Gitto — Tue, 07 May 2024 14:08:44 +0000

Buying a business is an opportunity to skip the growing pains of launching a startup. It’s a chance to start with a proven model with customers and cashflow. How can you tell if the prospective business is a genuine investment opportunity or a disguised escape route for a burnt-out owner? The following is a list of the top five things to consider when prospecting a business purchase – and some red flags for each category so you can recognize trouble a long way away. This list is no way exhaustive and there are many other issues to consider when buying a business. However, nailing these ... Read more

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Personal Vision – Life After the Sale Part I

John F. Dini — Tue, 30 Jan 2024 16:09:13 +0000

Life after the sale is often both the most important and most neglected factor in exit planning. Although (according to two different surveys in 2013 and 2022,) 75% of owners report regrets or unhappiness a year after the transition, exit plans continue to be constructed primarily around financial targets. In the event you haven’t heard this since you were five years old, “Money doesn’t fix everything.” Superficial Planning To be fair, most advisors include some conversation about “life after” in their planning conversations. Unfortunately, they are often satisfied with the features associated with an abundance of free time. Visiting the family, RV’ing through the country, ... Read more

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What are the Critical Elements in Training My Business Successor?

Pat Ennis — Fri, 13 Oct 2023 15:38:14 +0000

Training your Business Successor is crucial in ensuring a smooth transition of ownership and leadership. The following are critical elements to consider when preparing your Business Successor: Knowledge Transfer: Identify the knowledge and skills necessary to run the business effectively. Document and share critical information, processes, and best practices with your successor. This includes financial management, sales and marketing strategies, operational procedures, customer relationships, vendor management, and industry-specific knowledge. Mentoring and Shadowing: Provide your successor with hands-on experience by allowing them to shadow you and observe your day-to-day activities. Encourage them to ask questions, participate in decision-making, and gradually take on more responsibilities. Act as ... Read more

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Exit Strategies – The Road Less Traveled

John F. Dini — Thu, 28 Sep 2023 16:20:46 +0000

The road less traveled is often a misimpression when considering a transition from business ownership. Surveys show that roughly 85% of owners expect their exit to happen via a sale of the business to a third party. A third-party sale is certainly attractive. The idea of monetizing decades of work in one lump-sum payoff seems equitable. Years of sacrificing to “invest in the business” is supposed to generate a return. “He (or she) sold the company” when applied to someone who is clearly enjoying a comfortable lifestyle in retirement acts as an advertisement for the benefits of cashing out. Unfortunately, that isn’t only less frequent ... Read more

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“Work From Anywhere” Comes Full Circle

John F. Dini — Wed, 15 Mar 2023 15:00:41 +0000

Work from anywhere has been a necessity, an epithet, an obstacle, and an opportunity over the last 3 years. To paraphrase Aristotle’s axiom about Nature (“Horror Vacui”), business abhors a vacuum. Where one occurs, it is quickly filled. Work from anywhere started as a COVID-induced necessity. During the lockdowns of 2020-2021 (and longer in some places) we all had a crash course in video calling, VPNs, and virtual meetings. Employees quickly expanded the definition of anywhere. They tired of shunting the children off to a bedroom during conference calls, or using office-like backdrops to hide their kitchen cabinets. Soon they began changing their backgrounds to ... Read more

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Family Succession Planning: Who Gets the Office?

John F. Dini — Thu, 09 Feb 2023 15:47:33 +0000

Sometimes the most sensitive question in family succession planning is “Who gets the office?” Dad’s (or Mom’s) office is usually perceived as the center of authority by the employees and other family members. That is where you got called on the carpet, where you were informed of promotions, or where you took an insolvable problem. When a parent/CEO is handing off operating responsibility, there is often a lag, sometimes measured in years, between stepping back from the daily decisions and completely separating from the premises. There is great value in having that experience available for coaching, mentoring, or just to lend perspective on new ... Read more

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