Here's a pattern that repeats itself. A Connecticut business owner or high-net-worth family works with a financial advisor for portfolio management. They work with a CPA for tax compliance. The two never talk to each other. And the decisions made on the investment side can frequently create tax consequences that the CPA has to manage after the fact, not strategies they were able to plan for in advance.
Westport Wealth Partners works differently. Tax strategy is a coordinated part of the financial plan, not an afterthought. Matthew T. Streif, CEPA® and Nicholas DiFalco, APMA® CEPA® build tax strategy coordination into client engagements, working alongside your CPA to identify approaches designed to reduce your tax exposure before decisions are made, not after.
Raymond James does not provide tax or legal services. Every strategy discussed here requires implementation with a qualified tax professional. Our role is to ensure your investment decisions, income timing, business exit structure, and estate plan are all being made with the tax implications visible, and that your CPA has the information they need to act on them.
Schedule a Conversation About Your Tax Exposure
No obligation. One meeting to map where the opportunities are.
Why Tax Matters More for Business Owners and HNW Families
Not every client faces the same tax planning challenges. For high-earners in Connecticut, for business owners planning an exit, and for executives with equity compensation, the tax decisions are often the most consequential financial decisions they make.
A business sale generates significant taxable income. The structure of the deal (asset sale versus stock sale, installment arrangements, deal timing) can have a substantial effect on after-tax proceeds. Certain structures that reduce the tax burden at the time of a sale require planning years in advance. By the time a letter of intent is signed, many options are no longer available.
Connecticut's maximum individual income tax rate of 6.99% and its estate tax threshold (lower than the federal exemption) create planning considerations specific to state residents. Investment income, deferred compensation distributions, and retirement account withdrawals all interact with Connecticut's tax structure.
RSU vesting, stock option exercises, and concentrated stock positions create irregular, large income events. Managing those events tax-efficiently (including timing, sequencing, and offsetting strategies) is a distinct planning challenge from managing a standard portfolio.
Tax Strategy Areas We Address
The following are areas where Westport Wealth Partners coordinates tax strategy in collaboration with clients' CPAs. These are not tax services, they are financial planning disciplines that require tax coordination to implement properly.
investment portfolio construction designed to minimize unnecessary taxable realizations; tax-loss harvesting to offset gains; consideration of holding periods for long-term capital gains treatment.
working with your CPA well in advance of any transaction to evaluate deal structures that may reduce total tax burden; installment sale analysis; Qualified Opportunity Zone investments as a capital gains deferral strategy; coordination of charitable vehicles with a business sale.
Roth conversion analysis in lower-income years; required minimum distribution planning; sequencing of account types in retirement income distribution.
donor-advised funds as a vehicle for both tax efficiency and philanthropic goals; charitable remainder trusts for appreciated assets; qualified charitable distributions from IRAs for eligible donors.
Connecticut's estate tax threshold requires planning for HNW families. Strategies coordinated with estate planning attorneys include annual gifting, irrevocable trust structures, and life insurance for estate tax liquidity. Raymond James does not provide legal services.
ISO/NSO exercise timing; Section 83(b) election analysis for early exercise; tax modeling for concentrated stock positions. Implemented in coordination with a CPA with equity comp experience.
The Coordination ModelHow This Works Alongside Your CPA
In practice, this looks like:
Frequently Asked Questions About Tax Strategies
Does Westport Wealth Partners provide tax advice?
No. Raymond James does not provide tax or legal services. Tax strategy coordination means identifying planning opportunities and ensuring your financial decisions are aligned with your tax situation, in close coordination with your CPA, who implements the actual tax strategies.
I already have a CPA. Do I need a separate financial advisor for tax planning?
CPAs are focused on tax compliance and optimization. Most don't build the investment strategy, the estate plan, and the business exit plan alongside the tax work. Coordinating across all of these disciplines together, in a way that ensures decisions in one area don't create unintended consequences in another, is the role of a comprehensive financial advisor.
How do capital gains from a business sale get planned for?
Ideally, planning begins years before the sale. Deal structure (asset vs. stock sale), installment arrangements, deal timing, and charitable strategies can all affect the tax treatment of sale proceeds. By the time a buyer is at the table, many planning windows have closed. We work with business owners on this well in advance.
What is a donor-advised fund and when does it make sense?
A donor-advised fund (DAF) is a charitable giving vehicle that allows a donor to make a tax-deductible contribution in one year and distribute grants to charities over time. For clients with a large taxable event (a business sale, RSU vesting, or a high-income year) contributing appreciated assets or cash to a DAF in that year can be a meaningful tax strategy. Implementation requires coordination with your CPA.
Can you help me reduce my Connecticut state tax burden specifically?
Connecticut has a maximum individual income tax rate of 6.99% and estate tax rules that differ from the federal exemption. We coordinate financial planning strategies specific to Connecticut residents, particularly for those who have recently relocated from New York. Raymond James does not provide tax or legal services, coordinate with a CPA familiar with Connecticut tax law.
What is tax-loss harvesting and should I be doing it?
Tax-loss harvesting involves selling investments that have declined in value to realize a capital loss, which can offset capital gains or ordinary income subject to applicable rules and limits. It's a standard portfolio management technique that requires attention to wash-sale rules and overall portfolio construction. We incorporate it into portfolio management where appropriate.
I'm retiring in three years. What tax planning should I be doing now?
Pre-retirement is one of the highest-value windows for tax planning. Decisions about Roth conversions, pension lump-sum elections, Social Security timing, and the sequence of account drawdowns all have material tax implications, and are best made with a financial plan and CPA coordination in place before the event, not after.
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Any opinions are those of the author, are subject to change without notice and are not necessarily those of Raymond James. This material is being provided for information purposes only, it does not purport to be a complete description of the securities, markets, or developments referred to in this material and does not constitute a recommendation. The information has been obtained from sources considered to be reliable, but we do not guarantee that the foregoing material is accurate or complete. Every investor's situation is unique and you should consider your investment goals, risk tolerance and time horizon before making any investment. Prior to making an investment decision, please consult with your financial advisor about your individual situation. Be sure to contact a qualified professional regarding your situation before making any investment or withdrawal decision. Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional.
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.
Donors are urged to consult their attorneys, accountants or tax advisors with respect to questions relating to the deductibility of various types of contributions to a Donor-Advised Fund for federal and state tax purposes. To learn more about the potential risks and benefits of Donor Advised Funds, please contact us.
Unless certain criteria are met, Roth IRA owners must be 59½ or older and have held the IRA for five years before tax-free withdrawals are permitted. Additionally, each converted amount may be subject to its own five-year holding period. Converting a traditional IRA into a Roth IRA has tax implications. Investors should consult a tax advisor before deciding to do a conversion.
Please be aware that there may be substantial fees, charges and costs associated with establishing a charitable remainder trust.