Succession Planning
What Are the Best Succession Planning Strategies for Business Owners?
The best succession planning strategies for business owners combine a clearly defined exit path with integrated tax, estate, and ownership transfer planning executed years before the transition occurs. Waiting until you are ready to exit is one of the most common and costly mistakes an owner can make.
Why Timing Matters
Most Business Owners Start Too Late
Succession planning is not an exit event. It is a multi-year process that touches ownership structure, tax positioning, estate design, leadership development, and personal financial planning simultaneously. According to a 2024 survey by the Exit Planning Institute, approximately 83% of business owners have no formal written succession plan in place, despite the fact that most of their net worth is concentrated in the business itself.
For business owners navigating a business transition in Pittsburgh, the complexity is compounded by Pennsylvania-specific tax considerations, including the state's 3.07% flat income tax on business sale proceeds and a distinct inheritance tax structure that differs significantly from federal estate tax rules. A succession plan that works in another state may carry unexpected costs here.
At Defiant Capital Group, Jonathan Dane, CFA, CFP, and Stuart Strasner, CFA, work with business owners across Allegheny County and the greater Pittsburgh region to build succession strategies that reflect both the financial and personal dimensions of exiting a business you have spent years building.
Key Planning Realities
- 1 Effective succession planning typically requires 3 to 7 years of lead time to execute properly, depending on deal complexity and ownership structure.
- 2 Pennsylvania's inheritance tax applies to certain business transfers, with rates varying by relationship to the recipient. Transfers to children are taxed at 4.5%, while transfers to siblings are taxed at 12%, as of 2026.
- 3 The structure of your exit — asset sale vs. equity sale — can significantly affect your net after-tax proceeds, sometimes by millions of dollars.
- 4 Many owners underestimate how much of their post-exit wealth depends on financial planning that begins before the transaction closes, not after.
The Five Primary Exit Paths
Succession Planning Strategies: Which Path Fits Your Goals?
The right succession strategy depends on your timeline, financial objectives, the business's transferability, and whether you prioritize legacy, liquidity, or continuity. Here is a structured overview of the five primary paths available to most business owners.
Sale to a Third Party
A sale to a strategic or financial buyer — such as a private equity group or a competitor — is often the path that maximizes enterprise value. It typically requires 1 to 3 years of preparation, including financial statement cleanup, customer concentration analysis, and management team depth. Tax structure negotiations can meaningfully affect net proceeds; buyers often prefer asset sales for tax step-up advantages, while sellers generally prefer equity sales for capital gains treatment. Outcomes vary significantly based on deal structure, market conditions, and tax planning executed prior to the transaction.
Transfer to Family Members
Intra-family transfers are among the most complex succession strategies because they blend financial, estate, and relational considerations. Techniques that may be relevant — depending on individual circumstances — include grantor retained annuity trusts (GRATs), family limited partnerships (FLPs), intentionally defective grantor trusts (IDGTs), and installment sales. Pennsylvania's inheritance tax applies to family business transfers at rates tied to the recipient's relationship to the owner. Planning well in advance of a transfer may create opportunities to reduce transfer tax exposure, though outcomes depend on a range of legal, financial, and actuarial factors. Coordination among a financial advisor, estate attorney, and CPA is essential.
Management Buyout (MBO)
Selling to your existing management team preserves culture and operational continuity, but it introduces financing complexity. Because most management teams lack the capital for a full buyout, these transactions often rely on seller financing, earnouts, or SBA lending. The owner typically receives payments over time rather than a lump sum at closing, which introduces credit risk and changes post-exit income planning needs. MBOs require thoughtful structuring to align the interests of the seller, the management team, and any lenders involved.
Employee Stock Ownership Plan (ESOP)
An ESOP transfers ownership to employees through a qualified retirement plan. For C-corporation owners, Section 1042 of the Internal Revenue Code may allow deferral of capital gains taxes on the sale proceeds when those proceeds are reinvested in qualified replacement property, subject to eligibility and holding-period requirements. ESOPs are not appropriate for all businesses and involve substantial administrative and regulatory complexity. They are most commonly considered by owners who have a strong commitment to employee ownership as a legacy objective. A qualified ESOP attorney and financial advisor should be engaged early in the evaluation process.
Planned Wind-Down or Liquidation
For businesses where enterprise value is largely tied to the owner's personal relationships or expertise, a sale may not be viable at a meaningful multiple. In these cases, a structured wind-down — retiring client relationships, converting assets to cash, and distributing equity over time — may be the most prudent path. While often overlooked in succession discussions, a well-planned wind-down requires the same rigor as a sale: tax planning, estate coordination, and a personal financial plan that accounts for the loss of ongoing business income.
Not Sure Which Path Fits?
Many business owners begin with a general preference — "I want to sell to a strategic buyer" or "I want to keep it in the family" — that changes once they model the financial outcomes of each path. A fiduciary advisor can help you stress-test each option against your personal retirement income needs, estate goals, and tax exposure before you commit to a direction.
Schedule a ConsultationBuilding the Plan
Seven Steps to a Sound Succession Plan
A succession plan is more than a legal document. It is a coordinated financial, tax, and estate strategy. The following steps reflect the planning process we use with business owners in Pittsburgh and throughout western Pennsylvania. Each step involves trade-offs that depend on your specific situation. For an overview of the key risk events that can force an unplanned transition, see our guide to the 5 D's of succession planning.
Define Your Personal Financial Finish Line
Before evaluating exit structures, quantify what you need from a transition. How much capital do you require to sustain your lifestyle in retirement, fund philanthropic goals, or transfer wealth to heirs? This number anchors every downstream decision — including whether a particular exit path is financially viable at all. Many owners discover their required number is different from what they assumed, which is why this step must precede valuation conversations.
Obtain a Business Valuation
A professional valuation — conducted by a certified business appraiser — establishes an informed baseline for planning. It also identifies value drivers and gaps: customer concentration, management depth, recurring revenue quality, and other factors that buyers and transferees evaluate. Valuations should be updated periodically as the business evolves, not treated as a one-time event. Note that business valuations are estimates and may differ from what a buyer ultimately offers in a transaction.
Model After-Tax Proceeds for Each Exit Path
Different exit structures carry meaningfully different tax outcomes. A third-party asset sale, an equity sale, an installment sale, an ESOP transaction, and an intra-family transfer each trigger different combinations of ordinary income, capital gains, Pennsylvania state tax, and potential estate tax exposure. Working with a fiduciary advisor and a qualified CPA — before you enter a transaction — may create opportunities to structure the deal in a more tax-efficient manner. Results depend on individual tax situations and applicable law at the time of the transaction.
Strengthen Business Transferability
A business that depends entirely on its founder commands a lower multiple and faces a narrower buyer pool. Building transferability means reducing owner dependency — documenting key processes, deepening management, diversifying the customer base, and creating recurring revenue streams. These improvements take time, which is another reason early planning tends to produce better outcomes than late-stage planning. We work with business owners to identify specific transferability gaps and prioritize which improvements are most likely to influence valuation.
Coordinate Estate Planning with the Exit Strategy
A business exit is one of the most significant estate planning events in an owner's lifetime. The sequence and structure of transfers — what moves before a sale, what transfers at death, and what is gifted during life — can affect both estate tax exposure and Pennsylvania inheritance tax liability. Strategies such as irrevocable trusts, family limited partnerships, or charitable vehicles may be relevant depending on the owner's goals, but each involves complexity and trade-offs that require careful legal and financial analysis. See our guide to tax implications of selling a business in Pennsylvania for a deeper look at the state-specific considerations involved.
Build Your Advisory Team
Succession planning at this level requires a coordinated team: a financial advisor (fiduciary), a transaction attorney, an estate attorney, a CPA with business transaction experience, and often a business broker or investment banker depending on deal size and complexity. Each professional brings a distinct perspective, and misalignment among advisors is a common source of planning failures. At Defiant Capital Group, we coordinate across your advisory team to ensure financial, tax, and legal decisions are aligned rather than made in isolation.
Plan for Life After the Exit
Many business owners focus entirely on the transaction and underinvest in the financial plan that follows. Post-exit, the central challenge shifts from building wealth to managing it — deploying sale proceeds across a diversified investment strategy, navigating a significantly different income tax situation, and constructing a retirement income plan that may need to fund decades of lifestyle expenses. This transition requires a fundamentally different financial approach, and having a plan in place before the close makes the shift substantially smoother. See our detailed guide on financial planning before selling a business for a closer look at what this preparation involves. Learn more about our approach on our financial advisory services for business owners page.
Pennsylvania Considerations
Succession Planning in Pittsburgh: What Makes It Different Here
Western Pennsylvania's business landscape includes a significant number of privately held, multi-generational companies in manufacturing, healthcare, professional services, and construction — many of them approaching ownership transitions as founders and second-generation owners consider retirement.
Succession planning in Pennsylvania involves considerations that are often overlooked by advisors without local tax expertise. Pennsylvania does not conform to the federal exclusion for inherited property basis step-up in all contexts, and the state's inheritance tax applies to transfers of business interests at rates that vary by family relationship. For business owners in Allegheny County and the surrounding region, integrating state tax planning with the federal framework is a critical element of a sound exit strategy.
Defiant Capital Group works with business owners across Pittsburgh, Wexford, Sewickley, Oakmont, Gibsonia, and the broader Allegheny County area. Our team holds CFA and CFP designations and serves as a fiduciary in all client relationships — meaning our recommendations are driven by your interests, not by product relationships or institutional incentives.
Schedule a ConsultationPennsylvania-Specific Planning Factors
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State Income Tax on Sale Proceeds
Pennsylvania levies a flat 3.07% income tax on gain from a business sale, in addition to federal capital gains and net investment income taxes. The combined rate can be meaningful on a large transaction.
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Pennsylvania Inheritance Tax on Business Transfers
Transfers of business interests to family members at death — or in some cases during life — may be subject to Pennsylvania's inheritance tax. Rates vary: 0% for surviving spouses, 4.5% for lineal heirs, 12% for siblings, and 15% for all others, as of 2026.
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Family Business Exemption Considerations
Pennsylvania provides a partial inheritance tax exemption for qualified family-owned business interests under specific ownership and employment conditions. Whether your business qualifies requires a careful review of the statutory requirements; not all family-owned businesses meet the criteria.
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Federal Estate Tax Interaction
The federal estate tax exemption, approximately $13.99 million per individual in 2026, is scheduled to revert to a lower level after 2025 tax legislation sunsets. Business owners with significant estate values should evaluate whether current exemption amounts create a planning window that may not remain available.
Our Perspective
Why We Approach Succession Planning Differently
Most financial advisors treat a business exit as a wealth management opportunity — they focus on what to do with the proceeds after the deal closes. At Defiant Capital Group, we engage earlier in the process because we believe the most consequential financial decisions are made before the transaction, not after.
Defiant Capital Group was founded by entrepreneurs. Jonathan Dane, CFA, CFP, and Stuart Strasner, CFA, have navigated the complexity of building and managing wealth at the intersection of private business ownership and sophisticated investment strategy. That perspective shapes how we advise business owners on succession — not as an abstract process, but as one of the most consequential financial events of your life.
As an independent, fiduciary RIA registered with the SEC, we are legally obligated to act in your interest in every recommendation we make. We do not earn commissions on products, and we do not have institutional relationships that influence our advice. This matters in succession planning, where the coordination of tax, legal, and investment decisions requires objectivity above all else.
Read: What Business Owners Get Wrong About Succession-
+Fiduciary, fee-based advisory — recommendations driven by your interests
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+CFA and CFP credentialed advisors with business ownership experience
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+Integrated planning across tax, estate, investment, and exit strategy
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+Pennsylvania-specific expertise across Allegheny County and western PA
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+Independent RIA — no product sales, no institutional conflicts
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+Access to private market investments alongside traditional wealth planning
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+Nationally recognized — featured in Barron's, Kiplinger, MarketWatch, and more