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Selling a business, exercising stock options, or receiving a large inheritance changes how you approach estate planning overnight.
What used to be a simple will and a few account beneficiaries becomes a balance sheet with real tax exposure, multi-state assets, and heirs who may not be ready for the decisions that come with wealth.
For families with $2M+ in investable assets, the question is no longer, “Do I have a will?”, but instead “Is my estate plan fully integrated with how my capital is invested, taxed, and ultimately transferred?”Croak Capital is a fiduciary, fee-only wealth advisor based in Toledo that works alongside your estate attorney and CPA. Our role is to sit in the middle of the picture and keep your investment strategy, trust design, tax plan, and family goals moving in the same direction.
Why does estate planning change after a business sale or liquidity event?
A business sale or major liquidity event usually does three things at once:
- Converts a private asset into a large, visible balance in cash and securities
- Shifts risk from “business survival” to “capital stewardship over decades”
- Pulls estate tax, income tax, and family dynamics into the same conversation
The documents that worked when most of your wealth was tied up in an operating company rarely fit well once you are holding liquid assets, concentrated positions, and multiple entities.
For many of the families we work with, the real risk is not a single bad investment. It is:
- An estate plan that no longer matches how assets are titled
- Beneficiary designations that contradict the trust
- No clear plan for who will lead when you are not in the room
Estate planning after a liquidity event is not just about documents. It is about coordination.
What does “high-net-worth estate planning” actually cover?
For families in the $5M to $25M range, estate planning usually needs to handle:
- Trust design — Revocable living trusts for privacy and probate avoidance. Targeted irrevocable trusts for moving future growth out of the taxable estate and adding asset protection.
- Powers of attorney and healthcare directives — Designating who can act if you are incapacitated, so investment and tax decisions do not freeze at the worst possible time.
- Business and entity succession — Operating agreements, buy-sell terms, and transfer restrictions for closely held entities that may continue after a sale or recapitalization.
- Beneficiary and titling alignment — Making sure retirement accounts, life insurance, brokerage accounts, and real estate are titled and designated to work with, not against, your trust plan.
The technical pieces are handled by your attorney. The difference at your level is that your estate plan has to be synchronized with your investment and tax strategy, rather than built in a vacuum.
The current estate tax landscape, explained
As of 2025, the federal estate and gift tax exemption is $13.99 million per person (about $27.98 million for a married couple with proper planning), with a 40% federal tax rate on amounts above that threshold.
Beginning in 2026, the One Big Beautiful Bill Act increases that exemption to $15 million per person, indexed for inflation going forward.
- That means a married couple can pass at least $30 million under current law before federal estate tax applies.
- The exemption is high, but not unlimited. Families in the $10M–$40M band still need to be intentional, especially if portfolios continue to grow.
In Ohio, there is no state estate tax or inheritance tax for deaths after 2012, which simplifies planning for many of our clients based in Toledo and Northwest Ohio.The takeaway: the window for tax-efficient transfers is still open, but your strategy has to work under current law and remain adaptable in case Congress moves the goalposts again.
The foundation: Documents, titling, and beneficiary coordination
For post-exit families, the most common failure is not the absence of advanced structures. It is misalignment.
Core documents most families need
Your estate attorney will typically build a foundation that includes:
- Your will
- A revocable living trust
- Financial power of attorney
- Healthcare power of attorney and directive
- For owners, updated operating agreements and buy-sell provisions
Where things usually break
Two areas cause the most problems after an exit:
- Titling
- Taxable investment accounts that haven’t been moved into the trust
- Real estate that is still in individual names or defunct entities
- Business interests not being reflected correctly in the trust schedule
- Beneficiary designations
- Retirement accounts or life insurance bypassing the trust entirely
- Old designations that still point to a former spouse or an outdated trust
- Complex payouts that do not match what the estate plan assumes
For high-net-worth clients, a large portion of the work is simply mapping the actual balance sheet to the estate plan and cleaning up inconsistencies.
That is where a fiduciary wealth advisor adds real value. We sit with the current statements, entity charts, and trust documents to ensure the plan and the assets are speaking the same language.
Tax-aware wealth transfer tools (At a high level)
Your estate attorney may use a number of tools. Our job is to help you understand how they affect cash flow, investment risk, and long-term flexibility.
Examples include:
- Lifetime gifting and use of the exemption — Strategic transfers to irrevocable trusts or directly to heirs, using today’s high federal exemption while it is available.
- Grantor trusts and GRATs — Structures that move future growth out of your taxable estate while allowing cash flow back to you. Often useful when a business has just been valued and future appreciation is expected.
- Spousal planning — Tools like spousal lifetime access trusts (SLATs) that can remove assets from the estate but keep some access within the marriage, subject to legal and tax guidance.
- Charitable structures
- Donor-advised funds for flexible, low-friction giving.
- Charitable remainder trusts that can pair diversification of a concentrated position with income and a charitable legacy.
These tools are not products to “check off.” They are design choices that need to be modeled against your spending needs, risk tolerance, and family goals before documents are drafted.
Are there special considerations for entrepreneurs and business owners?
For business owners and practice founders, a sale or recapitalization creates its own set of estate issues, such as:
- Concentrated stock or rollover equity — A large portion of net worth may remain tied to one company or sponsor. Estate planning must be coordinated with the diversification plan, so you aren’t solving one problem while creating another.
- Deferred compensation, stock options, RSUs — Many of these benefits have specific rules at death. Unexercised options may expire. Deferred compensation can accelerate into income. Planning needs to account for those triggers.
- Entity complexity — Families often hold real estate, operating companies, and passive interests across multiple LLCs and S-Corps. A clear “who owns what” diagram becomes essential for both estate planning and future liquidity.
- Liquidity for estate taxes and buyouts — Even with higher exemptions, estates can still owe tax or need cash to buy out partners or children who are not involved in a business. Thoughtful use of insurance, cash reserves, and staged liquidity can prevent forced sales at bad prices.
Our role is to put the entire picture on one page, model “what if” scenarios, and work with your attorney and CPA; this way, the estate design fits the economics of your actual holdings.
Alternative assets and digital wealth
Modern balance sheets rarely stop at public stocks and bonds. Today, assets can come in many forms, including:
- Private equity, private credit, and real estate partnerships — These often have transfer restrictions, capital calls, and valuation questions at death. The estate plan needs clear guidance on who can step into your role and how those assets are valued and managed.
- Operating LLCs and joint ventures — Succession language, rights of first refusal, and buy-sell triggers should tie into your estate plan so heirs are not negotiating from a weak position under time pressure.
- Digital assets and online accounts — From cryptocurrency to domain names and content businesses, access is everything. Without written instructions and a clear inventory, heirs can know value exists and still be unable to reach it.
Croak Capital helps inventory these positions, quantify their role in your overall plan, and flag the legal items that require attention with counsel.
Preparing heirs, not just transferring assets
Most failures in multi-generational wealth are not tax failures. They are people failures.
Effective plans at your level usually include:
- Education and transparency at the right pace — Introducing heirs to the family balance sheet over time, not in one overwhelming conversation.
- Family governance — Regular family meetings, clear decision-making roles, and written guidelines around what the capital is “for” so heirs are not guessing.
- Thoughtful distribution design
- Staged distributions rather than a single age-based lump sum
- Incentive structures for education, work, or entrepreneurship, where appropriate
- Safety valves for addiction, divorce, or creditor issues
A good estate plan documents the rules. A good advisory team helps the family live with them.
How does Croak Capital fit into estate planning?
Croak Capital is not a law firm, and we do not draft legal documents.
What we do is own the coordination so your estate plan, tax plan, and investment strategy operate as one system.
In practice, that looks like:
- Building a clear, current view of your balance sheet and entity structure
- Helping you and your attorney define what you want capital to do for your family
- Modeling scenarios so you can see the trade-offs of gifting, trusts, insurance, and charitable strategies before you sign documents
- Aligning account titling and beneficiary designations with the final plan
- Managing portfolios with estate objectives in mind, including asset location, tax-loss harvesting, and Roth conversion timing
- Keeping the plan current as laws, markets, and family dynamics evolve
Because we are a fee-only fiduciary, our compensation does not change based on which estate strategy you choose. That keeps the conversation focused where it belongs: on outcomes for your family.
Frequently asked questions:
As of 2025, the federal exemption is $13.99M per person and about $27.98M per married couple with proper planning.
Under current law, this increases to $15M per person in 2026, indexed for inflation, with a 40% tax rate on amounts above the exemption.
No. Ohio repealed its estate tax for deaths after January 1, 2013, and does not impose an inheritance tax. Federal rules still apply, and other states may have their own taxes if you own property there.
A will goes through probate, which is public and often slow. A trust avoids probate entirely, keeps your affairs private, provides incapacity planning, and offers stronger tax and asset-protection benefits. For families with multi-state real estate, a trust prevents separate probate cases in each state.
Usually, within 30 to 90 days of closing. Once the deal value is known and proceeds are in transit, it is important to confirm titling, beneficiaries, and initial trust design before you fully deploy the capital.
Yes. The exemption protects many families from federal estate tax, but it does not address probate, incapacity, family conflict, or poorly prepared heirs. Planning is still critical, even if you never pay federal estate tax.
You can modify a revocable trust at any time during your lifetime. Irrevocable trusts are more restrictive but still offer flexibility through trust protectors, decanting provisions, and state-approved modification processes.
A large position in one company increases both market risk and estate risk. Diversification, charitable strategies, and trust design should be coordinated so you are not creating unnecessary tax while trying to reduce exposure.
Life insurance can provide liquidity to pay taxes, equalize inheritances, or replace assets given to charity. Often, policies for estate purposes are held in an irrevocable life insurance trust (ILIT) so the death benefit is outside the taxable estate.
At least every 3 to 5 years, or immediately after major events such as a business sale, significant liquidity event, marriage, divorce, birth, death, or a major tax law change.
A fiduciary advisor builds and manages the financial model that sits underneath your plan. That includes organizing the balance sheet, projecting cash flow, coordinating with your attorney and CPA, aligning titling and beneficiaries, and managing investments in a way that respects the estate structure you put in place.
Coordinate Your Estate Plan With Integrated Wealth Management
If you’ve recently sold a business, hold $2M+ in investable assets, or expect a significant wealth event, this is the right time to ensure your estate plan, tax strategy, and investment approach are aligned.
Croak Capital works directly with your estate attorney and tax team to:
- Clarify what you want your capital to do for your family
- Model the impact of various planning strategies before you implement them
- Keep your portfolio and estate plan on the same page over time
To discuss your situation in confidence, call (419) 464-7000 or request a conversation at croakcapital.com/contact. A senior advisor will follow up to understand your current structure and outline next steps.
Also Read:
How to invest $5M+ after selling my company: Do I need a family office
Why Ann Arbor Professionals Should Work with a Fiduciary Financial Advisor
Risks of keeping $5M+ in one bank: how do UHNW families manage wealth safely
What a Fiduciary Approach Means for Post-Exit Entrepreneurs and High-Net-Worth Families