Westport Wealth Partners serves business owners throughout Fairfield County, Connecticut and Westchester County, New York.
Between 70 and 80 percent of businesses put up for sale every year don't sell. Of the ones that do sell, research from the Exit Planning Institute shows that 76 percent of owners report regret within 12 months of closing. They got the money. They didn't get the life they expected on the other side.
Those two numbers explain why exit planning is not primarily a transaction problem. It is a financial planning problem that happens to end in a transaction.
Matthew T. Streif, CEPA® and Nicholas DiFalco, APMA® CEPA® hold the Certified Exit Planning Advisor designation from the Exit Planning Institute, established in 2007. The CEPA® credential requires five years of direct experience working with business owners, completion of a rigorous multi-day program, and a proctored closed-book exam. Fewer than 2,500 professionals hold it nationwide. Both partners at Westport Wealth Partners hold it, which is uncommon, because both believe the exit is the most consequential financial event in a business owner's life and it deserves the full weight of specialized expertise.
What Is Your Business Actually Worth to a Buyer?(Not What You Hope: What They'll Pay)
Westport Wealth Partners uses the same framework buyers use: normalized EBITDA multiplied by a market multiple. Your business is worth what someone will pay for it on the day they're writing the check, not the number in your head, not what your neighbor got for a different business in a different industry in a different year.
Three factors suppress multiples that business owners can change if they start early enough:
Starting the work of addressing these factors five years before an exit produces materially different outcomes than starting the year before. The CEPA® process exists precisely because these improvements compound over time.
The Three Gaps Every Connecticut Business Owner Needs to Understand
The Exit Planning Institute's Value Acceleration Methodology defines three gaps that determine whether a business exit actually produces the life the owner planned for. Matthew Streif works through all three at the beginning of a planning relationship.
the difference between what you need to fund the rest of your financial life and what your current net worth actually is. Many business owners are wealthy on paper but cash-poor. The business is the net worth. If the business sells for less than expected, or if the deal falls through, or if the market turns at the wrong time, the gap becomes the problem. A complete financial plan built before the exit process begins answers the question: does this business need to sell at X for you to be okay, or is the number actually Y?
the difference between what your business is worth today and what it could be worth if you addressed the suppressors. A business generating $1.5M in normalized EBITDA at a 4x multiple is worth $6M. The same business at a 6x multiple is worth $9M. The multiple change is driven by reducing customer concentration, deepening management, documenting processes, and building recurring revenue. Three years of intentional work on these variables has produced meaningful valuation improvements for business owners we have worked with. Raymond James does not guarantee any specific transaction outcome.
what stops the day the deal closes. The business has been generating income, providing health insurance, funding the retirement plan, and providing deductions. After the sale, all of those stop simultaneously. The personal financial plan must account for what replaces each of them, at what cost, and from what source. This is the planning that most business owners do last. It should be done first.
What Are the Realistic Exit Paths for a Connecticut Business Owner?
Most lower-middle-market Connecticut businesses, those with EBITDA under $20M, have four realistic exit options. Each has different financial implications, different timelines, and different post-close roles for the owner.
Matthew Streif's role in this evaluation is to build a financial model around each path (after-tax proceeds, income replacement, estate implications, and risk) so the decision is made with visibility into the personal financial outcome of each option, not just the transaction headline.
What Does the Raymond James Investment Banking Relationship Mean for Connecticut Business Owners?
Most wealth advisors can help clients manage the personal financial proceeds after a business sale. Very few can also coordinate the transaction itself. Westport Wealth Partners' affiliation with Raymond James Financial Services provides access to Raymond James investment banking, a full-service middle-market M&A platform with dedicated industry coverage teams.
Raymond James investment banking has completed transactions across a range of industries, deal sizes, and transaction structures. For Westport Wealth Partners clients who are beginning to evaluate a transaction, this access is included in the relationship, not a separately contracted service from a different firm.
How to StartThe Discovery Conversation
Frequently Asked QuestionsBusiness Exit Planning in Connecticut
What does a CEPA® do that a standard financial advisor doesn't?
A Certified Exit Planning Advisor holds a credential from the Exit Planning Institute that specifically addresses the financial mechanics of business transitions: business valuation methodology, exit structure analysis, the three gaps framework, and the Value Acceleration Methodology. A standard financial advisor is trained in investment management and personal financial planning. A CEPA® integrates those disciplines with specific knowledge of how businesses are valued, what buyers look for, and how the personal financial plan needs to be structured around a transaction that may be three to five years away. Both Matthew Streif and Nicholas DiFalco hold the CEPA® designation, which is uncommon for a two-partner practice and reflects a deliberate choice to build the practice specifically around business owner planning. Investment advisory services offered through Raymond James Financial Services Advisors, Inc.
How early should I start working with a CEPA®?
Three to five years before your intended exit is the most commonly cited window, and the honest answer is that earlier is always better. The improvements that produce the highest valuation impact (management depth, customer diversification, recurring revenue) take time to implement and even more time to show up in audited financials that buyers will rely on. Owners who begin the CEPA® planning process three years out consistently report that the business improved in ways that made it more enjoyable to run before the sale ever happened. The Exit Planning Institute's research shows that 70 to 80 percent of businesses put up for sale do not sell, and early preparation is the primary variable separating the businesses that sell at full value from those that don't.
How is my business value determined?
Most lower-middle-market businesses are valued using a multiple of normalized EBITDA. Normalized EBITDA strips out owner-specific expenses, one-time items, and non-arm's-length transactions to arrive at the recurring cash flow a buyer would expect to receive after the purchase. That number is then multiplied by a market multiple that reflects the buyer's assessment of quality, risk, and growth potential for your specific business type. At a 5x multiple, every $100,000 of defensible normalized EBITDA represents $500,000 of enterprise value. The multiple itself is determined by factors including customer concentration, management depth, industry dynamics, and revenue quality, all of which can be improved before a sale process begins. Raymond James does not guarantee any specific valuation outcome.
What is the wealth gap and why does it matter?
The wealth gap is the difference between what you need from the sale of your business to fund the rest of your financial life and what your current net worth actually is, excluding the business. Many business owners discover, when this gap is calculated explicitly for the first time, that their retirement plan depends almost entirely on a single illiquid asset producing a specific price in a specific market at a specific time. Understanding the wealth gap early in the planning process allows time to build personal wealth alongside the business, to address the variables that affect the multiple, and to build a personal financial plan that is not dependent on a single transaction going exactly as hoped.
What happens to my income, my health insurance, and my retirement plan when I sell?
All three stop the day the deal closes. Business income is replaced by investment income from the sale proceeds, which requires a complete personal financial plan built around the post-sale balance sheet. Health insurance requires an individual or marketplace plan, or COBRA if available, until Medicare eligibility. The business retirement plan must be wound down and assets transferred. These planning items are almost universally addressed last, when they should be addressed first. Westport Wealth Partners builds the post-sale income plan before the transaction begins, so the owner knows exactly what the financial life looks like on the other side before they sign anything.
Can I sell my business to my employees through an ESOP?
Yes. An Employee Stock Ownership Plan is one of four realistic exit paths for most lower-middle-market Connecticut businesses. For C-corporation owners, Section 1042 of the Internal Revenue Code may allow deferral of federal capital gains tax on sale proceeds, making an ESOP transaction potentially the most tax-efficient exit available. (Raymond James does not provide tax advice, coordinate with a CPA and ERISA counsel.) ESOPs require the business to have sufficient cash flow to service the transaction debt, and the valuation methodology is specific to ESOP law. Westport Wealth Partners evaluates the ESOP path alongside strategic and financial buyer options as part of the complete exit planning analysis.
What is the difference between a succession plan and an exit plan?
A succession plan addresses leadership continuity, who runs the business after the current owner. An exit plan addresses ownership transition, how the equity changes hands and on what terms. Most family-business plans require both. Third-party sales typically require only the exit plan, although buyers will evaluate management depth as a key factor in due diligence. The CEPA® process addresses both dimensions: the business value, the exit structure, and the owner's personal financial readiness for life after the business.
