Most of the business owners who walk into my office for succession planning fall into one of two camps. The first kind has been thinking about it for years and finally wants to put something on paper. The second kind is reacting to bad news – a co-owner just got a serious diagnosis, a spouse passed unexpectedly, or a CPA flagged that the partnership agreement they signed in 1998 doesn’t reflect anyone’s current intent. Both groups can be helped, but the first group has many more options than the second.
I’m Lawrence Israeloff. I’m an attorney and a CPA, and for over two decades I’ve been helping owners of closely held businesses on Long Island and in New York City work through what happens when they exit, retire, become disabled, or die. The legal piece and the tax piece of that planning are deeply tangled, which is why having both credentials in one professional usually saves clients time, money, and the awkwardness of two outside advisors disagreeing about strategy.
Why succession planning isn’t optional
The hard truth: a business without a succession plan is a business whose future is being decided by default rules – your operating agreement’s silent gaps, New York’s intestacy statutes, the IRS’s valuation methods, and whoever happens to be in the room when something goes wrong. Default rules rarely match what the owner would have actually wanted.
I’ve seen what happens when there isn’t a plan. A 50/50 partnership where one partner dies and the surviving partner now owns the business jointly with the deceased partner’s spouse – who has no operational role but full voting rights and a different idea about distributions. A family business where one child runs the day-to-day and three siblings inherit equal shares, and within eighteen months the operating child has bought out the others at a discount they later regret. A C-corporation owner who never updated the buy-sell after the entity converted, leaving the funding mechanism mismatched to the structure.
Good succession planning heads off these scenarios. It clarifies who gets ownership, who gets control, how the price is set, where the money comes from, and what the tax consequences look like before any of that becomes urgent.
How I work with succession clients
Every plan I draft starts with the same question: what do you actually want to happen? The answer is rarely “sell to the highest bidder.” It’s usually some version of “I want my kids to have the option but not the obligation,” or “I want my partner protected but not at the expense of my spouse,” or “I want to be done in five years with the business intact.”
From there, the work falls into a few interrelated areas.
Choosing the right transition path
There’s no single correct succession structure. The right one depends on who’s available to take over, what the business is worth, what the owner needs to retire on, and how much tax exposure can reasonably be absorbed. The realistic options usually include selling or gifting to family members, a buyout among existing partners, a sale to a key employee or management team, a sale to an outside buyer, or a phased exit that combines a transition role with a gradual transfer of ownership. Each path has different tax treatment, different funding requirements, and different risks if it falls apart partway through.
Restructuring the entity, where it helps
Sometimes the entity that was the right choice when the business was founded is the wrong one for an exit. An S-corp election, a holding-company structure, or a recapitalization into voting and non-voting shares can substantially change the tax outcome of a transfer. For family transfers in particular, valuation discounts on non-voting interests (though scrutinized by the IRS) remain a legitimate tool when the structure is set up properly and well in advance. I’ll tell you when restructuring is worth the cost and when it isn’t.
Drafting buy-sell agreements that actually work
A buy-sell is the single most important document in a multi-owner business, and most of the ones I review have at least one serious flaw. Common ones: a fixed valuation that hasn’t been updated since the agreement was signed; life insurance funding that doesn’t match the structure (cross-purchase versus entity-redemption gets this wrong constantly); triggers that cover death but not disability or divorce; and price terms that bear no relation to what a third-party buyer would actually pay. A good buy-sell specifies the trigger events, the valuation method, the funding source, the payment terms, and the consequences of non-performance. It gets reviewed every few years.
Coordinating with the personal estate plan
A succession plan that ignores the owner’s estate plan can produce avoidable estate tax. New York has its own estate tax with a 2026 exemption of $7.35 million and a notorious “cliff” that can fully tax estates that exceed the exemption by more than 5 percent. The federal estate exemption was permanently increased to $15 million per person under the One Big Beautiful Bill Act of 2025, but the gap between federal and New York exposure now matters more than ever for closely held business owners on Long Island. For business owners with valuable closely held interests, tools like IRC §6166 estate tax deferral, §2032A special-use valuation (for qualifying real-property-heavy businesses), grantor retained annuity trusts, and intentionally defective grantor trusts can be relevant, but they have to be set up while the owner is healthy and the entity is structured to support them.
Who I work with
My succession clients tend to be owners of professional practices (medical, dental, legal, accounting), family-owned operating businesses in the second or third generation, real estate holding companies, partnerships in the trades and construction, and solo entrepreneurs whose business is essentially their retirement plan. Some are years from any transition. Others are in active negotiations and need a deal closed cleanly. Most are somewhere in between.
If your situation is urgent (a partner has died, a sale is on the table, or a diagnosis has shortened the timeline) say so when you call. Some of the most valuable planning options collapse the closer you get to the triggering event.
Long Island, NYC, and the surrounding metro
I work out of Melville, NY and represent clients across Long Island, the five boroughs, and the rest of the New York City metro area. Where the work touches federal tax law, IRS guidance applies; where it touches state-level estate tax, fiduciary duties, or business law, New York’s rules govern. Useful starting points if you want to read on your own: the IRS small business resources, the New York State Bar Association, and the Small Business Administration. None of those replace a conversation with someone who knows your specific facts.
Let’s talk
If you’re ready to put a plan together, or to pressure-test the one you already have, contact my office to schedule a consultation. The first conversation is mainly listening on my end: I want to understand the business, the people, and the goals before I recommend anything. From there we can build something that fits.
