Smarter Business Exit Strategies

Too many business succession plans don’t work out as planned, but smart owners can get back on track and stay that way for the long-term.

Key Takeaways:

  • Most business owners create unnecessary risks for their families, employees and clients by failing to fund business succession plans.

  • Every business owner should establish a clear vision for his or her transition and look for ways to improve after-tax returns.

  • Business owners can reduce the costs of succession plans by 50 percent by using pre-tax dollars to pay for insurance.


Many successful entrepreneurs, especially Boomers, may be thinking that now is the right time to exit their businesses. Unfortunately, business transitions don’t usually go as smoothly as expected. The failure rate of succession plans is now at eyebrow-raising levels. But it doesn’t have to be this way.

What motivates most business owners to think about a business succession plan?

Scary stories about failed companies motivate business owners to consider implementing a business succession plan. Despite the obvious need, few plans are actually designed, drafted and funded properly. High professional fees and insurance costs often take the blame when business owners are asked why they did not implement a succession plan.

Why do so many succession plans miss the mark?

Most business succession plans fail. According to Harvard Business Review, only 30 percent of the businesses make it to Generation Two and a mere 3 percent survive to generate profits in Generation Three. Estate planning experts such as Perry Cochell, Rodney Zeeb and George Hester came up with similarly disappointing numbers. Given this dismal success record for family business transitions, it is no wonder that 65 percent of family wealth is lost by the second generation and 90 percent by the third generation. By the third generation, more than 90 percent of estate value is lost despite the efforts of well-meaning advisors. It does NOT have to be this way.

What is the biggest problem business owners face when they try to implement succession plans?

Unless a business succession plan addresses tax issues, company owners can lose much of their wealth to taxes on income, capital gains, IRD, gifts, estates and other taxes. In most successful businesses, the company will generate taxable cash flow that exceeds what is needed to fund the owner’s lifestyle. This extra cash flow is usually taxed at the highest top marginal state and federal income tax rates. When the after-tax proceeds are invested, the growth is subject to the highest capital gains rates. Ultimately, when the remaining assets are passed to family members or successor managers, there could be a 40 percent gift or estate tax applied.

How can owners and their advisors solve this tax problem?

Every business owner should establish a clear vision for his or her transition and look for ways to improve after-tax returns. Tax-efficient planning strategies are needed to guide decisions about daily operations and business exit strategies. An astute advisor can help you find ways to fund business succession agreements in ways that generate current income tax deductions while allowing the business to generate tax-free income for the business owner and/or successors.

What are some other ways to reduce taxes?

There are many tax-advantaged business succession techniques that give business owners a competitive edge. Qualified plans provide tax deductions in the current years, but they are not typically as tax-efficient for funding a buy-sell. More advanced planning strategies involving Section 79 and Section 162 plans can provide tax-free payments for the retiring executive or death benefits for family members, but limit the tax deductions when the plans are funded. There are very few options when owners seek up-front tax deductions, tax-free growth and tax-free payments to themselves and/or their heirs.

Bottom line

Advanced planning strategies allow business owners to fund business continuity plans more cost-effectively. Business owners should work with advisors who can design a plan that can convert extra taxable income into tax-free cash flow for retirement and/or the tax-free purchase of equity from the business owner’s estate.

Once the plan has been designed, experienced attorneys will draft legal documents to facilitate the tax-efficient plan funding. This integration of design, drafting and funding helps ensure effective implementation of the strategy as well as proper realization of benefits under a variety of scenarios. An experienced advisor should be able to help you quantify how planning costs are just a small fraction of the expected benefits. More important, these financial benefits bring peace of mind to the business owner, the owner’s family and to key executives. Great clarity and confidence results from having a business continuity plan that has been designed properly, drafted effectively and funded tax-efficiently.

Robert J. Pyle, CFP®, CFA is president of Diversified Asset Management, Inc. (DAMI). DAMI is licensed as an investment adviser with the State of Colorado Division of Securities, and its investment advisory representatives are licensed by the State of Colorado. DAMI will only transact business in other states to the extent DAMI has made the requisite notice filings or obtained the necessary licensing in such state. No follow up or individualized responses to persons in other jurisdictions that involve either rendering or attempting to render personalized investment advice for compensation will be made absent compliance with applicable legal requirements, or an applicable exemption or exclusion. It does not constitute investment or tax advice. To contact Robert, call 303-440-2906 or e-mail


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