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Exit planning for $10M–$150M business owners. What will your family actually keep? Deane School of Law at Hofstra University and a BBA in Finance from Hofstra.

Robert DePalo Jr., JD, CExP®, AEP®, is the Founder and Chief Planning Strategist of The Strategic Business Planner, a Garden City, NY practice serving business owners approaching an exit or succession event. His work centers on advanced exit planning, tax strategy, and estate architecture for owners of privately held businesses valued between $10 million and $150 million. Robert created the Legacy Alpha™ framework, which shifts the owner’s question from “what is my business worth” to “what will my family actually keep.” The framework identifies the tax friction, structural inefficiencies, and overlooked snares that erode wealth in a transition, then engineers them out before the exit happens. A Forbes Best-In-State honoree and member of Guardian’s President’s Council, Robert holds a JD from the Maurice A. He is a Certified Exit Planner (CExP®) and Accredited Estate Planner (AEP®). His book, Maximizing Legacy Alpha: Avoiding the Often-Overlooked Snares, publishes in fall 2026. Registered Representative and Financial Advisor of Park Avenue Securities LLC (PAS). OSJ: 900 STEWART AVENUE, SUITE 500, GARDEN CITY NY, 11530, 516-7455600. Securities products and advisory services offered through PAS, member FINRA, SIPC. Financial Representative of The Guardian Life Insurance Company of America® (Guardian), New York, NY. PAS is a wholly owned subsidiary of Guardian. The Strategic Business Planner is not an affiliate or subsidiary of PAS or Guardian. Not practicing JD for Guardian or its subsidiaries or affiliates. This material is intended for general use. By providing this content The Guardian Life Insurance Company of America, Park Avenue Securities LLC, affiliates and/or subsidiaries, and your financial representative are not undertaking to provide advice or make a recommendation for a specific individual or situation, or to otherwise act in a fiduciary capacity. Guardian, its subsidiaries, agents and employees do not provide tax, legal, or accounting advice. Consult your tax, legal, or accounting professional regarding your individual situation. Links to external sites are provided for your convenience in locating related information and services. Guardian, its subsidiaries, agents and employees expressly disclaim any responsibility for and do not maintain, control, recommend, or endorse third-party sites, organizations, products, or services and make no representation as to the completeness, suitability, or quality thereof.

11/04/2026

A tax return shows what happened. Tax strategy helps you consider your options before the year is over.

Many people wait until tax season to ask their accountant what can be done. By then, some opportunities may already be off the table.

Preparing throughout the year gives you and your accountant time to review decisions, classifications, and other details that can affect how your taxes are reported.

Small adjustments can make a meaningful difference. The key is to look at them before the year closes.

I share more about this in my monthly newsletter, the Legacy Alpha Brief. Comment “BRIEF” and I’ll send it your way.

11/03/2026

December 31 is more than a year-end date. It is the first deadline that can close important tax strategy opportunities for business owners.

Your W-2 compensation, personal 401(k) contributions, and certain asset moves may need attention before the calendar turns. Other decisions may have later deadlines, but waiting can narrow your options.

The key is knowing which decisions have which deadlines, and preparing before the window closes.

I share a full year-end strategy checklist in my Legacy Alpha brief. Comment "BRIEF" and I’ll send it to you.

11/02/2026

Traditional bonuses can hand a large share to the IRS.

A cash bonus is taxed as income, and for high earners that can mean losing up to 40% of it. Rewarding the people who drive your company is worth doing well, and how you do it matters.

Split-dollar structures are one alternative to explore. Depending on whether the arrangement is set up as a loan or an economic benefit, it may offer death benefit protection and access to cash value. The right structure depends on your company, your executive, and your goal.

Rewarding key executives with a lasting benefit can be more meaningful than a one-time payout.

DM me to review how your executive compensation is structured.

10/30/2026

The strongest business sale outcomes often start years before the sale.

It is not just about your industry, company size, or the state of the economy. Starting early gives you time to address value gaps, rethink ownership, reduce key-person risk, and prepare your business to go to market on your terms.

That kind of preparation is learnable. But it takes time.

If a sale may be part of your future, do not wait until the decisions become urgent and your options narrow.

DM me to start preparing for the outcome you want.

10/29/2026

How you take income from your business can matter just as much as how much you make.

A distribution, a loan, a return of capital, and W-2 income are not treated the same. For S corp owners, reasonable compensation requirements matter. And taking more income as W-2 wages than necessary may mean missing other options, depending on your situation.

The right approach depends on your business structure and your broader tax strategy. But it is worth knowing which decisions are within your control before you make them.

Comment "BRIEF" if you’d like to receive more tips in the Legacy Alpha Brief.

10/28/2026

The biggest mistake business owners make when preparing for an exit is assuming there is nothing to do until a buyer makes an offer.

By then, many of the most important decisions may already be harder to change.

A thoughtful exit strategy can start years in advance. That gives you time to consider how the proceeds may flow, identify potential roadblocks, and make informed decisions before the process becomes urgent.

If an exit is on your horizon, the work should start well before the offer.

DM me to discuss the strategy behind your exit.

10/27/2026

Paperwork can be perfect and the outcome can still miss.

A well-drafted estate document defines what you are allowed to do. It does not make sure the money, the liquidity, and the timing behind it actually work. That gap is where families get hurt.

Tax, legal structure, and financial strategy have to work together. When one operates in isolation, even strong legal work can leave something critical unaddressed.

The strategy has to cover the money behind the documents, not just the documents themselves. Review your estate strategy with your tax, legal, and financial professionals before the outcome is set.

DM me to review how the pieces fit together.

10/26/2026

Two owners. Nearly the same business. The same offer.

One kept nearly twice as much.

The difference was preparation. Victor understood where his business was in its lifecycle, adjusted its structure to support his exit, prepared his estate, and made the business more appealing to the market.

The way you prepare can shape what you keep when it is time to sell.

I break down the story of Victor and Arthur in Maximizing Legacy Alpha. Comment “Alpha” and I’ll add you to the book’s pre-release list.

10/23/2026

Your business is worth what survives the transfer.

Not what your accountant says the book value is. Not what a broker says it will sell for. Taxes, fees, and clawbacks come out first. What actually hits your bank account is the number that changes your family’s world.

Comment BRIEF and I’ll send you a few that break it down.

10/20/2026

You saved it... now keep the tax code from taking it back.

Most business owners and high net worth professionals are great at saving. They fund the qualified accounts. They build the assets.

That’s accumulation.

Very few have worked on decumulation.

That’s where taxes quietly eat into what you built. Roth conversions before retirement. Converting in a down market year while you’re still working. How you draw assets down once you stop.

Each one changes how much you actually keep.

I built the Retirement Roadmap to sit alongside the Legacy Alpha™ framework for exactly this.

Comment ROADMAP and I’ll send it over.

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http://www.thestrategicbusinessplaanner.com/, http://www.thestrategicbusinessplanner.com/

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