Tax-Smart Selling

Proactive, not reactive.

When it comes to tax, timing is everything. Handled early, tax planning can be one of the most valuable moves of your entire transaction. Handled late, it can quietly cost you a fortune. We prepare you for the questions a sophisticated buyer will ask, work to structure the deal with the lowest defensible tax outcome in mind, and keep finding efficiencies long after the sale closes.

Timing Is Everything

By the time most people plan, it’s already too late.

Most owners think about tax once a deal is already on the table. By then, the most powerful strategies have expired. How you hold the business, how the sale is structured, and when you recognize income all shape your final bill, and most of those levers have to be set in motion years ahead. Planning early gives you options. Planning late leaves you reacting to a number someone else decided.

The Full Arc

Before, during, and after the sale.

Good tax planning isn’t a single event. It runs the length of your transaction and well beyond it, with different priorities at each stage. Here’s where we focus across the three phases that matter most:

Before the sale

We help position the business and your ownership well ahead of a transaction, so the structure is set early.

During the sale

We plan for the income tax on your gains and time recognition wisely to keep the deal as efficient as possible.

After the sale

We pursue ongoing efficiency through direct indexing and harvesting, plus legacy and charitable giving plans.

Working Together

Coordinated with your CPA and attorney.

We don’t replace your CPA or your attorney. We make sure the whole team is asking the right questions, early. As the hub of your financial life, we bring the transaction and the long view into the same room, flag the tax issues a sale will surface, and keep your professionals coordinated so nothing falls through the cracks. The tax and legal advice stays with them. The orchestration is ours.

Any opinions are those of Bespoke Capital and not necessarily those of Raymond James. This material is being provided for information purposes only and is not a complete description, nor is it a recommendation. Tax laws, deal structures, legal agreements, and market conditions are complex and subject to change. You should consult your own qualified tax advisor, attorney, and financial professional before making any investment decision. Raymond James and its financial advisors do not provide tax, legal or business valuation advice.

Direct Indexing strategies are subject to certain risks, including, portfolio tracking error, which is a portfolio’s deviation from the performance of the target market index. This can be caused by the strategy’s representative sampling methodology and client portfolio customization.

Tax-loss harvesting can have unintended tax consequences and there may be higher fees or costs associated with a replacement security or stock position. There is no guarantee that a favorable tax outcome will be achieved.

The best plans start with a conversation.

Your business built more than a career, it built a future for the people you love. Let’s start with a conversation, no pressure and no obligation, and help you prepare for the future with confidence. Give us a call or fill out the form, and we’ll connect you with a financial professional to discuss your goals and the best path forward.

Call (770) 325-6957

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