Join John Skabelund as he discovers how to increase and safeguard your wealth and legacy by combining tax strategy and asset protection planning with his guest, CPA, entrepreneur, and keynote speaker, Tom Wheelwright.
Tom Wheelwright is a CPA, CEO of WealthAbility (Tempe, Arizona) and Best-Selling Author of Tax-Free Wealth. Wheelwright is a leading wealth and tax expert, global speaker, and Entrepreneur Magazine Contributor. Tom is best known for making taxes fun, easy and understandable, and specializes in helping entrepreneurs and investors build wealth through practical and strategic ways that permanently reduce taxes.
As a Rich Dad Advisor to Robert Kiyosaki (Rich Dad Poor Dad), Tom frequently speaks at conferences worldwide to entrepreneurs on these topics. His work has been featured in The Wall Street Journal, Washington Post, Forbes, Accounting Today, Investor’s Business Daily, FOX & Friends, ABC News Radio, NPR, Marketplace and many more media outlets.
In this episode, explore how the combination of tax and asset protection planning is necessary in reducing taxes and generating wealth, tips on how to build your A-Team of advisors, and the partnership that must take place with your team to truly succeed.
Podcast Overview:
Attorney John Skabelund sits down with Tom Wheelwright, CPA, author, and founder of the Tax-Free Wealth Advisors franchise, to explain how strategic tax planning and asset protection work best when they are designed together.
The conversation focuses on a simple idea with huge consequences: taxes can quietly erode wealth over time, especially for entrepreneurs. When you pair proactive tax strategy with smart legal structures, you can keep more of what you earn and protect what you keep.
What You’ll Learn in This Episode:
Meet Tom Wheelwright
Tom Wheelwright brings decades of tax experience to the discussion. He began his career at Ernst & Young, including time in its national tax office during the Reagan era, where he trained CPAs across the country. He later worked at a Fortune 1000 company in Phoenix and spent 14 years as an adjunct professor at Arizona State University in the Master’s of Tax program, where he created a course on multi-jurisdictional tax.
Over the years, Tom also built, bought, and sold CPA firms, and he has worked alongside Robert Kiyosaki for decades on financial education. Today, he leads multiple businesses, including tax advisory firms and a software development company.
Why Entrepreneurs Need a Tax Strategist, Not Just a Tax Preparer
A major theme of the episode is the difference between tax preparation and tax strategy.
Tom explains that most CPA firms operate like production shops. Their model is to process as many returns as possible, which can leave entrepreneurs without proactive planning. In contrast, Tom’s firm focuses on tax advisory, where the goal is to reduce taxes through decisions made throughout the year.
Tax preparation still matters, but Tom frames it as a checkpoint:
- it documents last year’s strategy
- it sets the foundation for next year’s strategy
In other words, entrepreneurs do not just need a return filed. They need guidance that shapes the decisions that create the return.
The Three Questions That Drive Holistic Tax Planning
Tom shares a framework he believes every entrepreneur should use. Real tax planning, he explains, starts with three questions:
- How do you make your money?
- What are you going to do with your money?
- What are you going to do with your money when you die?
That third question surprises many people. Tom notes that most people will not face federal estate tax, but nearly everyone still faces income tax issues tied to legacy and estate planning decisions.
This is why he emphasizes a holistic approach. Tax planning, wealth planning, and legacy planning are not separate silos.
Why Lower Taxes Can Create a Massive Compounding Advantage
Tom explains that the impact of taxes is not just what you pay today. It is what you lose over decades in compounding growth.
He gives a simple example: investing $10,000 for 30 years at 10% returns. If an entrepreneur is paying roughly 40% tax on that investment growth, the ending result is dramatically smaller than if the money can compound without that yearly tax drag.
His bigger point is that taxes do not just reduce your income. Over time, they can reduce the size of your legacy.
That matters for entrepreneurs who worry about longevity risk, inflation, and outliving their money.
“If You Want to Change Your Tax, You’ve Got to Change Your Facts.”
Tom’s most well-known line is one he repeats in this episode:
“If you want to change your tax, you’ve got to change your facts.” — Tom Wheelwright
He explains that tax outcomes are fact-based. A tax return does not create strategy. It reports what already happened.
If someone asks, “Is this deductible?” the answer depends on the facts. But if the question becomes, “How do I make this deductible?” now you are thinking like a strategist. The difference is proactive planning and changing the underlying fact pattern.
Tom also adds a crucial point: advisors can guide you, but they cannot change your facts for you. The client must implement the actions that make the strategy real.
Why Your Tax and Legal Team Must Work Together
Both John and Tom emphasize that strong planning requires coordination.
Tom points out that entrepreneurs often need a full team: CPAs, attorneys, insurance professionals, and, depending on the situation, financial planners and other specialists. The goal is collaboration, not finger-pointing.
John reinforces this with a reality he sees often. Even strong plans can fail when they fight each other.
Build Your A‑Team
John summarizes it this way: asset protection and tax planning are not separate projects. They are connected systems. A plan is strongest when each professional understands the broader strategy and the team communicates.
Asset Protection and Tax Planning Should Not Compete
Tom notes that he frequently sees problems when one advisor designs a plan without considering the other discipline.
- some asset protection structures can create unnecessary tax complexity
- some tax-driven structures can create unnecessary legal exposure
In most cases, Tom says, the client does not have to choose one priority over the other. With thoughtful design, both goals can be achieved together.
He also highlights an important issue in the advisory world: some professionals act primarily to protect themselves.
Is Your Team Protecting You, or Protecting Themselves?
Tom argues that great advisors advocate for the client’s best outcome, even when it creates extra work. That means the team should pursue the best strategy, not just the easiest strategy.
When It Is Time to Upgrade Your Tax Advisor
John shares something he sees in his own practice: many high-achieving clients are still working with someone who functions as a return preparer, not a strategist.
Tom says one major sign it is time to upgrade is growth.
- you are earning more than you used to
- you are investing in new areas, such as real estate
- your financial life is more complex than it used to be
He also addresses the cost objection directly. Upgrading is not free, but he encourages clients to view advisory fees as an investment, not an expense.
He believes proactive tax strategy can produce returns that outperform nearly anything else a client spends money on.
What to Look for in a Great Strategic Tax Advisor
Tom suggests starting with a simple question:
“What are we going to do to reduce my taxes?”
He is clear that a professional should not give away a full plan for free, but a strong advisor should be able to review a return and quickly identify issues, missed opportunities, and priority areas.
Even more important, Tom believes you can judge an advisor by the quality of their questions. Great advisors uncover strategy by asking better questions, not by waiting for the client to guess what to ask.
Best Advice: You Are in a Partnership With Your Advisors
Tom closes with a message that ties the entire conversation together:
“You are in a partnership with your advisors.” — Tom Wheelwright
Tax strategy requires education and follow-through. Clients need enough understanding to implement the fact changes that support the plan.
And just as important, Tom encourages entrepreneurs to think beyond how they earn and protect money. The question of what you will do with your wealth is part of the strategy too.
Bringing Tax Strategy and Asset Protection Together
This episode makes one point clear: tax planning and asset protection are strongest when they are built together. When your CPA and legal team communicate, you can reduce unnecessary complexity, preserve more wealth through compounding, and create a plan that protects both your assets and your legacy.
To learn more about Tom Wheelwright and the Tax-Free Wealth Advisors network, visit tfwadvisors.us. For more information on asset protection strategies and how they integrate with tax planning, visit UltimateAssetProtection.com.