Explore Legal & Tax Restructuring Opportunities By Asking Your Clients These
"FOLLOW THE MONEY™" QUESTIONS
The Logic Behind "Following The Money"
In 2005, the bank's lawyers pierced my corporate and personal entities and liquidated all my assets to offset business liabilities, despite having "robust asset protection structures" (what the lawyers called it) in place - it was like taking candy from a baby to be very frank.
That's also the manner in which the IRS recaptures unpaid "Death taxes" from thousands of estates, whether it's unpaid income, capital gains, inheritance, gift, or estate taxes, among others. If you "follow the money" - and where the money goes, who controls it, how it's put back into circulation, etc. - you'll gain more clarity on where gaps start to emerge - gaps that can cause entities to be pierced during a liquidation or lawsuit, or liquidated after the death of a person (estate cases).
So, if you want to add "value" and "insights" that no other "competitors" are talking about or exposing to your clients, this line of thinking will help you truly stand out as a trusted advisor that your clients and their advisors will want to have on their side.
Ask Your Clients (Old, Current, or New) These Questions:
Questions Intellectual Property Lawyers Can Ask
How do you plan to monetize this IP—licensing, selling, or keeping it exclusive?
(Different paths trigger different tax and legal strategies.)
Would you like a professional evaluation of this IP’s value?
(This helps with licensing, investor negotiations, and protection.)
Are you earning or expecting royalties or passive income from this IP?
(Passive IP income can be restructured for major tax benefits.)
Would you like to transfer this IP to an LLC, trust, or foundation for long-term control?
(This adds legal protection, tax deferral, and estate planning advantages.)
Could this IP be used to secure investment or non-dilutive funding?
(Grants, licensing deals, and corporate partnerships may be untapped sources.)
Have you decided what happens to this IP after you pass—heirs, sale, or donation?
(This is often overlooked in estate plans, but IP lives far beyond you.)
Would you like to place a UCC lien on your IP to ward off copycats or creditors?
(This creates a public claim and strengthens your legal defenses.)
Questions Personal Injury (PI) or Employment Lawyers Can Ask
7 Strategic Questions PI & Employment Lawyers Can Ask Clients
Have you been advised on how your settlement will be taxed—income, capital gains, or estate?
(Many assume it’s all tax-free. It’s not.)
Would you like to explore ways to protect your settlement using trusts, entities, or foundations?
(This can reduce taxes, shield assets, and preserve wealth.)
Do you plan to use your settlement for personal spending, investment, gifting, or legacy purposes?
(Each use has different tax and legal consequences.)
Is your spouse or family prepared to manage this money and the responsibilities that come with it?
(Many families need legal guardrails to avoid future chaos.)
Would you like a second opinion to ensure you're not missing out on major tax-saving strategies?
(Most CPAs and advisors miss legal structuring opportunities.)
Have you considered donating a portion to a cause you care about—while keeping control and gaining tax advantages?
(This opens the door to strategic philanthropy and private foundations.)
Would you like a custom report showing how much of your settlement you could legally protect or reinvest tax-efficiently?
(We use legal and tax tools designed specifically for high-value settlements.)
Questions Corporate Lawyers Can Ask
What will you do with the proceeds—reinvest, distribute, or take them personally?
(Each choice triggers different tax outcomes and planning needs.)
Are you planning to reduce capital gains tax or defer it using trusts or charitable structures?
(Strategic entities can delay or even eliminate the tax.)
Would you like to protect your equity by transferring shares to a family trust or foundation?
(This shields your stake from creditors, lawsuits, and probate.)
Have you planned for succession—who takes over if you step away or pass on?
(Buy-sell agreements and trust structures can prevent chaos.)
Can your spouse or heirs run the business? Can they handle your partners or investors?
(If not, legacy plans must include legal and operational training.)
Do they know the trade secrets and financial controls that you manage daily?
(What you know isn’t always documented or transferable.)
Would you like to preserve your business goodwill and value using pre-sale restructuring tools?
(This can add millions to your valuation and cut post-sale tax in half.)
Questions Estate Planning Lawyers Can Ask
How do you plan to distribute your wealth—through gifting, trusts, or philanthropy?
(Each option has drastically different tax and control implications.)
Have you considered legacy models that extend beyond basic wills and revocable trusts?
(True legacy planning often involves entities, not just documents.)
What’s your strategy for minimizing estate, gift, and generation-skipping transfer taxes?
(Failure to plan can cost your family millions.)
Do you own any businesses, real estate, or intellectual property that require advanced planning?
(These often get misclassified or mishandled in traditional plans.)
Would you like to integrate a foundation or donor-advised fund to reduce taxes and build purpose?
(Strategic giving can preserve wealth and create generational impact.)
Can your heirs handle your business, assets, and tax matters the way you do?
(If not, trusts alone won't protect them—legal strategy must match capability.)
Have your advisors filed proper gift tax forms for ILITs or GRATs?
(If not, you may face audits, penalties, or unintended tax consequences.)
Questions Real Estate Lawyers Can Ask
How do you plan to hold title—personally, in a trust, or through an LLC?
(The entity you choose impacts taxes, liability, and inheritance.)
Are you planning to use a 1031 exchange or opportunity zone fund to defer taxes?
(Most investors leave huge savings on the table by not exploring this.)
Would you like to shield equity or rental income from lawsuits and creditors?
(Smart structuring can lock in protection for years.)
What’s your estate plan for this property—sell, gift, or pass it down?
(Each option changes how much tax is owed and who keeps control.)
Have you considered gifting this property to a foundation for major tax offsets?
(You can give with purpose and still retain influence.)
Are you aware of the strategies to avoid depreciation recapture when selling?
(A good plan reduces not just capital gains, but phantom income too.)
Would you like to explore whether paying capital gains is cheaper than irrevocable trust mistakes?
(Sometimes simple is smarter—especially with basis and step-up issues.)
Questions Family Lawyers Can Ask
How will marital assets be divided—cash, businesses, real estate, or investments?
(Each asset class needs different legal and tax tools.)
Would you like to create or update trusts for your children or dependents?
(This ensures continuity, especially in blended families.)
Are there high-value assets like IP, collectibles, or crypto that require special treatment?
(These often fall outside standard division agreements.)
Have you factored in the tax impact of child or spousal support payments?
(Structuring payments right can reduce tax burdens for both sides.)
What happens if one party passes away—do you want to protect children and shared assets?
(Estate planning should be woven into every separation.)
Would you like to explore philanthropy as a form of prenup—donating assets to avoid future claims?
(Foundations can reduce risk, taxes, and future fights.)
Would you like to protect inherited or premarital assets through trusts or separate entities?
(Failing to structure properly can turn protected assets into marital property.)
Questions Immigration Lawyers Can Ask
How do you plan to fund your relocation or business activities in a new country?
(A legal entity or trust may offer better control and compliance.)
Do you have assets in multiple countries that may be subject to double taxation or reporting rules?
(Cross-border tax and legal issues need strategic alignment.)
Would you like to protect wealth using international trusts or holding companies?
(These tools reduce risk and simplify future estate transfers.)
Are you interested in building a business or nonprofit to support your visa or citizenship application?
(Entities can strengthen your case and build long-term roots.)
Do you know how to manage U.S. tax obligations as a non-citizen or dual resident?
(Mistakes here lead to audits, penalties, or even visa issues.)
Would you like to set up a foundation to direct charitable work while supporting immigration goals?
(This aligns legal, philanthropic, and personal objectives.)
Will your family or heirs inherit property or business interests across borders?
(Without a plan, these assets could be frozen or heavily taxed.)
Questions M&A Lawyers Can Ask
What will you do with the sale proceeds—invest, donate, distribute, or defer?
(How you answer changes the structure we recommend.)
Would you like to explore ways to reduce or eliminate capital gains taxes?
(Trusts, foundations, and installment sales are powerful tools.)
Are you planning to reinvest into a new business, real estate, or other assets?
(That can unlock new tax deferral strategies.)
Would you like to allocate some proceeds to a foundation or donor-advised fund pre-sale?
(This can boost your charitable impact and slash your tax bill.)
Have you thought about adding a nonprofit entity to increase business valuation pre-exit?
(Social impact and goodwill can raise enterprise value.)
Do you have a succession, legacy, or estate plan in place before the sale?
(The timing of entity structuring is everything.)
Would you like a second opinion before closing to make sure no value is left on the table?
(Post-sale regrets are often preventable with a pre-sale legal tune-up.)
Bolt-On Nonprofit & Foundation Strategy Calculator
Choose your practice area to see how a public nonprofit and/or private foundation can be integrated to reduce tax exposure, increase impact, and create long-term value.
