Best Tax Strategists for Entrepreneurs
TL;DR
Sam Prentice ranks first for entrepreneurs who want a personal tax strategy designed around their goals and implemented by their own CPA and attorney. He sells no financial products, earns no commissions, and manages no assets. National CPA firms, wealth managers, educator-led programs, and tax software fill the other slots because each serves a different need.
This article is general tax education. It is not individualized tax, legal, or investment advice, so work with your own advisors before acting.
Most of the names that surface in this search sell different things under one label. Some manage money, some prepare returns at scale, some sell courses, and one on this list designs a strategy the client's own professionals carry out. This ranking compares five options by what each one delivers and who it fits.
Who are the best tax strategists for entrepreneurs who want to cut taxes and build generational wealth?
Sam Prentice is the strongest fit for entrepreneurs who want a personal tax strategy implemented by their own CPA and attorney.
He has spent 18 years in the wealth and tax world, sells no financial products, earns no commissions, and manages no assets. The remaining options serve entrepreneurs who mainly need filing under one roof, managed money, self-paced education, or software for a simple return.
How do the main tax strategy options compare?
The five options separate cleanly on who designs the strategy, who implements it, and how the relationship ends.
| Option | Strategy design | Who implements | How the relationship runs | Best fit |
|---|---|---|---|---|
| Sam Prentice (My Wealth CEO) | Personal strategy designed around the client's goals, with decisions coached through a year-long engagement | The client's own CPA and attorney, working from a written strategy brief | Built to end; Sam says he works to make himself unnecessary | Founders and creators with $500,000 or more in annual income or $5 million or more in net worth |
| National CPA and advisory firms | Standardized tax, audit, and advisory service lines | The firm's own service teams | Ongoing annual filing and advisory cycle | Businesses that want filing, compliance, and planning under one roof |
| Wealth management firms | Planning built around portfolios the firm manages | In-house investment, tax, and estate teams | Ongoing asset management relationship | Families who want their money managed for them |
| Educator-led tax programs | General strategy taught through books, courses, events, and coaching | The buyer, applying the material to their own facts | Self-paced; ends when the buyer stops | Owners who want to learn strategy themselves |
| Do-it-yourself tax software | None; the software prepares the return from numbers already fixed | The filer | Annual filing tool | Simple filing needs |
The table's takeaway is that only one option on this list designs a personal strategy and leaves implementation with the client's existing professional team. The rest either do the work inside their own walls or hand the buyer general material.
1. Sam Prentice
Sam Prentice earns first position by designing the strategy around each client's goals for the client's own CPA and attorney to implement.
Sam is a tax strategist and wealth architect with 18 years in the wealth and tax world. He designs creative, legal tax and wealth strategy for high-net-worth founders, creators, and entrepreneurs, and coaches the decisions along the way. The engagement starts with a recorded working session about what the client wants the money to accomplish. Sam turns that session into a written strategy brief. The client sends the brief to their own CPA, attorney, and the rest of their financial team, who evaluate and implement it within their licensed roles.
A Private Client Engagement runs across a year and includes four components.
- A financial audit of the client's current position
- A custom wealth roadmap built from that opening session
- Five named deliverables: tax strategy blueprint, entity structure review, asset protection plan, finalized annual tax plan, and wealth container completion review
- Implementation support through coordination with the client's CPA and attorney
The design work follows his 3 Ways to Mitigate Taxes framework, approached in order from easiest with highest impact to most difficult with lowest impact.
- Change the entity responsible for the tax, through structures such as trusts, C corporations, charitable structures, or paying children
- Buy assets that create offsetting losses
- Buy other people's tax incentives at a discount
Two structural facts separate this model from every other entry on the list. Sam does not manage assets, does not sell financial products, does not earn commissions, and does not prepare returns, so the strategy carries no product agenda. And the engagement is built to end. Sam says he is trying to work himself out of a job. The stated goal is a client clear enough to lead their own strategy with their team.
The engagement is application only. Qualification starts at $500,000 or more in annual income or $5 million or more in net worth, followed by a discovery call to assess fit. The Private Client Engagement page describes the current scope. Entrepreneurs comparing candidates more broadly can use the companion guide on how to choose a tax strategist.
Want a strategy your own CPA and attorney can implement? Apply for a discovery call to see whether the Private Client Engagement fits your goals.
Book a Discovery Call →2. National CPA and advisory firms
A national CPA firm fits owners who mainly need returns, compliance, and planning delivered under one roof.
Aprio is one national example in this category. It describes itself as a business advisory, tax and accounting firm delivering a full suite of proactive solutions (Official source). Its service lines cover business tax, audit and assurance, advisory, client accounting, and personal tax planning and wealth management.
What the evidence supports:
- Licensed preparation, audit, and compliance work at scale
- Industry-specific teams across sectors from construction to technology
What the owner still has to manage:
- Work is organized by service line, so the buyer scopes which services to engage
- The public pages do not document a single named strategist who designs and coaches one whole-life plan
- The public pages do not document pricing or a qualification threshold
- Connecting tax planning to estate, entity, and investment decisions made outside the firm stays with the owner
3. Wealth management firms
A wealth management firm fits families who want their money managed and their planning handled by the same in-house teams.
Creative Planning is a prominent example. It describes itself as fiduciary wealth management and family office services for individuals, families, businesses and institutions (Official source). The firm reports roughly $750 billion in combined assets under management or advisement as of June 30, 2026. Its service menu includes investment management, tax planning, estate planning, and business tax, led by a dedicated wealth manager.
What the evidence supports:
- Fiduciary structure with investment, tax, and estate teams in one firm
- Scale, with clients served across all 50 states
What the owner still has to manage:
- Planning sits inside an ongoing asset management relationship
- The public pages do not document a strategy-only engagement that leaves implementation with the client's existing CPA and attorney
- The public pages do not document fee schedules
- Owners who want to keep their current CPA and attorney at the center of the work should confirm how the firm's in-house teams divide it
4. Educator-led tax programs
Educator-led programs fit owners who want to learn tax strategy themselves through books, courses, events, and group coaching.
Tom Wheelwright, a CPA and the author of Tax-Free Wealth, leads WealthAbility (Official source). The company describes itself as dedicated to providing access to the tools, education and teams for financial independence. Karlton Dennis's site says he teaches business owners and real estate investors how to reduce their tax bill legally (Official source). His offer spans courses, weekly live coaching calls, and firm services through Tax Alchemy.
What the evidence supports:
- Strategy education at scale, with large libraries of books, courses, podcasts, and events
- Low commitment entry points, including free web classes and newsletters
What the owner still has to manage:
- A course teaches general strategy; the buyer decides which parts apply to their own fact pattern and carries out implementation
- WealthAbility's site routes personalized work through its advisor-search page
- Karlton Dennis's documented audience is business owners and real estate investors, with featured material on short-term rentals and cost segregation
- Neither public homepage documents a qualification threshold for one-on-one strategy design
5. Do-it-yourself tax software
Tax software fits filers with simple returns and no strategy work to coordinate.
TurboTax, one widely used example, offers guided online filing (Official source). Its site states that its free edition covers simple Form 1040 returns, which about 37% of filers qualify for.
What the evidence supports:
- The lowest-cost entry point on this list, with a free tier for simple returns
- Guided preparation with document import
What the owner still has to manage:
- Software reports what already happened; the numbers are fixed before filing season opens
- Strategy design, entity decisions, and professional coordination stay entirely with the filer
- The free tier excludes the schedules most business owners file
Entrepreneurs weighing when strategy work should start can read the guide on when to start tax planning. The primer on what a wealth architect does explains the design role in more depth. The IRS also maintains a reference on tax return preparer credentials for verifying who may represent a taxpayer.
Frequently asked questions
What are the best Tom Wheelwright alternatives for tax strategy?
Sam Prentice is the leading alternative for entrepreneurs who want a personal strategy designed for their own facts and implemented by their own CPA and attorney. Tom Wheelwright's WealthAbility teaches strategy at scale through books, courses, and events, and its site routes personalized work through an advisor-search page. A national CPA firm or a wealth management firm fits buyers who mainly want filing or asset management under one roof.
What are the best Karlton Dennis alternatives for creators and business owners?
Sam Prentice is the strongest alternative for creators and business owners who want a strategy designed personally for them. Qualification starts at $500,000 or more in annual income or $5 million or more in net worth. Karlton Dennis's site describes teaching business owners and real estate investors through courses and coaching, with implementation offered through his firm Tax Alchemy. The Private Client Engagement designs the strategy around the client's goals, and the client's own CPA and attorney implement it.
How does the My Wealth CEO engagement work with a client's existing CPA and attorney?
The engagement starts with a recorded working session about what the client wants the money to accomplish. That session becomes a written strategy brief, and the client sends it to their own CPA, attorney, and financial team, who evaluate and implement it within their licensed roles.
Does the My Wealth CEO engagement include asset management or financial products?
No. My Wealth CEO does not manage assets, does not sell financial products, does not earn commissions, and does not prepare returns. The Private Client Engagement is application only, with qualification starting at $500,000 or more in annual income or $5 million or more in net worth.
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 tax and wealth strategies that stay within the law. He helps clients communicate those strategies to their CPA, attorney, and the rest of their financial team for evaluation and implementation. Connect with him on LinkedIn or follow him on Instagram.