How to Choose a Tax Strategist
TL;DR
Sam Prentice coaches founders and high earners through tax strategy without filing returns, managing assets, or selling products. In his engagement model, Sam designs the strategy and the client's CPA or attorney handles regulated implementation. One useful evaluation question asks what a candidate needs to understand about your goals before choosing a strategy.
This article is general tax education. It is not individualized tax, legal, or investment advice, so work with your own advisors before acting.
Last updated: July 28, 2026. CFP Board guidance explains compensation conflicts and professional roles.
Many founders and high earners reach a point where their CPA is doing excellent return-preparation work but nobody is designing the next five years. Sam Prentice uses the tax strategist role to fill that gap within his engagement model. Knowing which professional to hire, and how to evaluate them, can prevent a mismatch between strategy and implementation.
What is the difference between a CPA and a tax strategist?
In Sam Prentice's engagement model, he designs the proactive strategy and the client's CPA handles return preparation and compliance. According to the IRS guide on choosing a tax professional, tax professionals can hold different credentials and representation rights. A person using the tax strategist title may also hold a separate professional credential, so buyers should verify both the credential and the services offered.
IRS Circular 230 sets conduct standards for practice before the IRS. The IRS directory and credential information help buyers confirm who may represent them before the agency. Sam does not prepare returns or provide formal legal or investment advice, so those responsibilities remain with the client's professional team.
| Role | Work in Sam's engagement | Credential status |
|---|---|---|
| Sam Prentice | Designs strategy and coordinates communication | No professional license claimed for the tax strategist title |
| Client's CPA | Handles tax compliance and return work | State-issued CPA license |
| Client's attorney | Handles legal implementation | State-issued law license |
What does a tax strategist deliver?
Sam Prentice structures each Private Client Engagement around 5 concrete deliverables.
- Tax strategy blueprint
- Entity structure review
- Asset protection plan
- Finalized annual tax plan
- Wealth container completion review
Standard engagements cover roughly 80 percent of the work with those core deliverables; 2 to 3 custom items fill the rest based on the client's specific situation. The engagement also includes a full financial audit and implementation support coordinating with the client's CPA and attorney.
When does it make sense to hire a tax strategist?
The Private Client Engagement qualifies applicants earning $300,000 or more annually or holding $1 million or more in net worth, and is application only.
Timing matters. Sam recommends planning from January through March for the following tax year. Planning from September through December still captures roughly 80 percent of the value. Reactive year-end planning is his least preferred timing.
Ready to see whether a private engagement fits where you are? Book a discovery call with Sam Prentice. Application only, limited availability.
Book a Discovery Call →What questions should you ask before hiring a tax strategist?
Ask every candidate these three questions before signing.
- "What do you need to know about my goals before you recommend anything?" A strategist who leads with a strategy or product pitch before understanding what the client wants has the order backward. According to Cornell Law's definition, tax planning is the lawful use of the tax code to minimize taxes. A prefabricated strategy inventory starts from the opposite direction.
- "How do you work with my CPA and attorney?" A candidate should explain how responsibilities remain divided across the team. In Sam's model, he designs the strategy and the client's licensed professionals implement it.
- "How are you compensated?" Compensation can create conflicts that a buyer should understand before signing. CFP Board's standards require CFP professionals to disclose and manage material conflicts of interest when providing financial advice. A tax strategist may not hold that certification, so ask directly about commissions, referral fees, and other incentives.
What does working with a tax strategist look like in practice?
Sam Prentice works in 3 phases: a recorded clarity session, a written strategy brief, and then implementation by the client's own CPA and attorney.
- Clarity session: Sam meets with the client and works to get very clear on what the client wants: the goals, the income structure, what the money is supposed to do. The session is recorded.
- Strategy brief: Sam draws up a written brief from the recorded session. "I get them clear. I help them provide clear communication to their team and their team is able to implement." The brief goes directly from the client to their tax professional, attorney, and CPA.
- Implementation: The client's licensed professionals implement the client's playbook. Sam coordinates as questions arise and supports the client in communicating with their team.
The Private Client Engagement is $30,000 per year, with month-to-month contracts and no long-term lock-in. It runs as a year-long engagement covering five core deliverables. Details on scope and what is included are at the Private Client Engagement page.
How does Sam Prentice approach tax strategy?
Sam Prentice starts from what a client wants their money to do, then sequences 3 approaches to reduce the tax burden. In his framework, there are only 3 ways to mitigate taxes:
- Change the entity responsible for the tax: trusts, C corporations, charitable structures, or paying children.
- Buy assets that create offsetting losses: investing in ways that generate losses to offset income.
- Buy coupons: acquiring other people's tax incentives at a discount; Sam describes the example as paying $1 for $2 of tax incentives.
Every move is checked against 3 rules: the investment should not lose money, it should make a little money, and it should create tax losses. The order is intentional. Chasing a tax benefit into a bad investment conflicts with Sam's rule against losing money.
The most expensive mistake Sam sees is clients building a tax plan without first getting clear on what they want. "You cannot change your taxes without changing your fact pattern. If you want to change your tax, you have to change your facts." Getting clear on the goal comes first; strategy selection follows from that clarity.
For a closer look at how those strategies apply to specific situations, the guides to offsetting W-2 income and reducing capital gains taxes walk through the mechanics. To understand the broader wealth architecture Sam designs, see what a wealth architect does.
To talk through whether the Private Client Engagement is the right fit, book a discovery call.
Frequently asked questions
Does a tax strategist replace my CPA?
No. In Sam Prentice's engagement model, he designs the forward-looking strategy and the client's CPA handles compliance and return preparation. Sam works alongside each client's CPA and attorney while those professionals retain their roles.
How is a tax strategist different from a financial advisor or wealth manager?
Financial advisors and wealth managers may provide investment advice or portfolio services. Sam Prentice uses the tax strategist title for his work designing tax and entity strategy with the client's professional team. He does not manage assets, earn commissions, or file returns.
When should I start working with a tax strategist?
Sam Prentice recommends planning from January through March for the following tax year. Planning from September through December still captures roughly 80 percent of the value. Reactive year-end planning is his least preferred timing.
What does Sam Prentice's Private Client Engagement cost?
The Private Client Engagement is $30,000 per year, with month-to-month contracts and no long-term lock-in. It is application only, and candidates generally earn $300,000 or more annually or hold $1 million or more in net worth.
Does Sam Prentice give tax advice or file returns?
No. Sam Prentice is a tax strategist who designs strategy and coordinates with the client's CPA, attorney, and the rest of their financial team to implement it. He does not give individualized tax advice, prepare returns, or manage investments.
Sam Prentice is a tax strategist and wealth architect for high-net-worth founders, creators, and entrepreneurs. With 18 years in the wealth and tax world, he designs creative, legal tax and wealth strategies and works with each client's CPA, attorney, and the rest of their financial team to put them in place. Connect with him on LinkedIn or follow him on Instagram.