Updated 8/2025
Most entrepreneurs invest years - often decades - building, growing, and managing their companies. But many overlook a crucial step: planning their exit. It’s easy to get caught up in day-to-day operations and defer the long-term strategy of selling a middle market company. However, when the time comes, being unprepared can cost you.
Owners often want to sell when the market is hot and they feel personally ready to retire. But is that truly the best time to sell a business? Not always. Timing your exit isn’t just about the market. It’s about aligning your personal goals, company performance, industry trends, and valuation metrics.
This guide outlines the key personal and business considerations you should evaluate—plus insights into how to value your business, prepare it for sale, and work with M&A advisors to maximize your return.
An important consideration in determining the right time to sell is whether you have achieved financial security and if the sale of your business will support your current life style. It is essential to factor in your existing debt and cash flow needs, including other sources of income and potential long-term expenses.
Maybe you simply want a fresh start based upon new business interests. Have you achieved your personal goals for the business? Maybe your original strategy was to build a business and sell it, or you seek the opportunity to cash out to enter a new venture.
A health issue may necessitate placing the sale of your business on a shorter time horizon than originally planned.
Lifestyle changes such as a divorce or the illness of a loved one may unexpectedly necessitate the liquidation of assets, including your company. An owner will want to avoid unfavorable circumstances causing a sale under duress, such as when the illness of a business partner compels a sale. Conflict with a business partner or family member is another common personal reason owners put their business up for sale.
Your stage of life is another personal factor. Perhaps over time the hours you currently invest begin to yield the desire for more personal time to pursue hobbies or personal interests. The challenge of owning and running a business may no longer be a priority, and you desire a less intensive, lower-stress life.
Life changes can be positive as you look forward to new horizons.
Various matters facing your company factor into the decision to sell, including the current stage of the business’ cycle, how the economy is faring, and who is at the company’s helm.
Often the best time to sell is when a company has a solid record of growth, and its market is expanding. Buyers purchase the future, and demonstrating a solid, consistent record of sales growth will make your company attractive to potential purchasers. Don’t try to time the market, or assume that a buyer will be naively unaware of the state of your niche or industry in the future when the outlook is not as strong.
A favorable economic environment, including low interest rates, is a strong factor pointing toward an advantageous sale. Has the business’s value increased significantly? An important preparatory measure to consider is having a business valuation prepared, so that you know your company’s worth if you receive an unsolicited offer to purchase your company. Knowing your company valuation will help you assess unsolicited offers to buy your business and make informed decisions. Can you take advantage of a low capital gains tax rate? A frothy mergers and acquisitions market, or strong activity in your space, portends to good timing for a sale. The key is awareness, preparation and knowledge of your company’s value.
Does your company need new leadership to bring it to the next level, or require significant additional investment to continue growing? A business owner must be honest about these dynamics and determine if finding a solution is preferable to a sale of the business. Consider whether you wish to invest the time and effort needed. Perhaps your skill set, or available capital, creates limitations that you are no longer willing to develop.
For a seller, action is key. Planning and taking advance steps work in favor of your business, as well as your employees. Review these pre-sale due diligence tips to streamline the process. Staying ahead keeps you in advantageous sales territory, where your company’s financial results and cost structure are positive selling points.
Maximize the opportunity for a rewarding sale, and avoid selling because of an ill-timed event or under extreme circumstances when your company’s value may be suboptimal. When timing conflicts between personal and business needs, an owner needs to review their strategic plan and synthesize the best compromise between dueling priorities.
A professional business valuation is essential to evaluate whether now is the right time to sell. Your company’s value will often be assessed using EBITDA multiples—a common metric in the middle market. Here's how it works.
Your advisor will start by analyzing your financials:
This helps normalize earnings to reflect true performance.
Experienced M&A advisors will access databases like Capital IQ to compare your EBITDA to recent transactions in your sector. They may also use revenue multiples when appropriate. The result: a realistic valuation range and list of potential buyers.
Valuation is only half the equation. The other half is your personal financial picture.
A qualified wealth advisor can model your income, assets, and long-term goals to determine what you need to secure your lifestyle after the sale. Expect questions like:
If your expected sale proceeds exceed what you need — you're in a strong position. If not, you’ll need to decide whether to grow the business further or adjust expectations.
You don’t have to make this decision alone. Working with M&A advisors ensures you understand your business value, market conditions, and the buyer landscape.
Experienced investment bankers:
A good advisor will also tell you when not to sell — and help you prepare if now isn’t the right time.
Whether you’re ready to sell now or in a few years, taking action early puts you in control. Here’s how to start:
Know what your company is worth today to make informed decisions, especially if you receive an unsolicited offer.
Outline your goals, timing, and ideal buyer profile. Document personal and business readiness milestones.
Working with experienced professionals helps you navigate buyer negotiations, due diligence, and valuation complexities.
Ensure the sale supports your long-term financial goals.
Only you can answer that, but don’t make the decision without facts. Two economic downturns in the past 15 years have shown that waiting for “the perfect time” can backfire. If your business is performing well and the market is strong, now may be your best opportunity.
Delaying too long can lead to erosion in value due to market changes, competitive shifts, or burnout. Conversely, if you're not ready emotionally or financially, it may be wise to wait, but only if you have a plan to improve value in the meantime.
PCE has helped many middle market owners evaluate whether the time is right, and often we advise holding off. If you’re thinking about selling your business, we can provide a complimentary valuation range and connect you with trusted wealth advisors.
Ali Masoud
Ali Masoud is a Director in PCE’s M&A practice, specializing in buy-side and sell-side transactions, recapitalizations, and corporate advisory services. With deep expertise in software and technology deals, Ali brings extensive experience from top global investment banks and a background as a Turnaround CEO. He holds a Master’s in International Finance and Economics and is known for his strategic insight, team leadership, and commitment to client success.