In this week’s livestream with Kevin Brunner he and I broke down how a real-world, nine-figure business sale reveals what happens when depreciation recapture, a ticking 1031 exchange deadline, installment-sale planning, and professional loyalty collide.
Read and listen to the entire thing to find out why the most important decision an entrepreneur makes after decades of building a company may be choosing who gets to advise them through the next chapter.
The conversation also goes much further: into AI-driven tax intelligence, the changing value of professional advice, generational stewardship, and why ownership—not simply wealth accumulation—may become the defining skill of the next economy.
Why You Should Listen
Imagine spending 25 years building a business, negotiating a $100 million exit for your efforts, and finally approaching the moment when all those late nights, payroll headaches, personal guarantees, and sacrificed weekends are about to turn into financial independence. Then your CPA delivers the estimated tax bill, and suddenly the celebration gets complicated.
That’s the real-world situation Kevin Brunner brought to this week’s episode of The Exit Advisors, our Friday ATOMIQ LEVEL office-hours series. The transaction involves a medical equipment company, associated real estate, years of depreciation, a buyer-backed installment note, and a 1031 exchange approaching its critical identification deadline.
For background, the seller has a long-time established CPA and financial advisor. The seller also has an opportunity to consider alternative tax planning. But the two advisory perspectives are colliding at precisely the moment when time, transaction structure, and decision-making matter most.
What makes this conversation so important isn’t simply whether a particular installment sale strategy works. That requires careful legal and tax analysis specific to each transaction. It’s the bigger question every owner must eventually confront:
Are the advisors who helped you build your fortune necessarily the right advisors to help you protect, convert, and transfer it?
Kevin and I explore the actual transaction, the tax mechanics he proposes, the conflict with the existing CPA, and the uncomfortable reality that familiarity and competence are not always the same thing.
We also discuss the rapidly emerging role of AI in professional services and what happens when the value of routine analysis approaches zero while the value of judgment, trust, coordination, and ownership rises.
If you’ve built a business worth $2 million, $20 million, or $100 million, this is an episode worth hearing before you sign your next letter of intent.
TL;DR — Key Takeaways
A $100 million exit can become a collection of separate tax problems. Business assets, real estate, depreciation, seller financing, and earnouts require distinct analysis.
Your 1031 exchange clock does not care about your emotional readiness. The 45-day identification and 180-day completion requirements create real transaction pressure.
Installment sales deserve consideration before closing. IRC Section 453 may offer timing flexibility for qualifying gains, but not every asset or payment qualifies.
Professional discomfort is not a substitute for professional analysis. The right response to a proposed strategy is to identify its legal basis, execution risks, alternatives, and consequences.
AI is changing the economics of tax preparation and financial advice. Human judgment, fiduciary responsibility, and the ability to coordinate complex decisions are becoming more important.
The best advisor for your accumulation years may not be the best architect for your liquidity event. Loyalty should never prevent an objective evaluation of expertise.
Post-exit wealth demands a different operating system. You must transition from building and managing productive assets to governing capital, income, risk, and family legacy.
Your ultimate return is not only financial. The purpose of a successful exit is to regain control over your time, relationships, health, and next chapter.
The $100 Million Deal That Started With an Uncomfortable Phone Call
We opened the episode with a transaction Kevin is actively helping navigate.
The seller owns a medical equipment business with related real estate. The buyer is strategically integrating the operating business into an existing company, using capital connected to private equity.
It is not a simple all-cash sale.
Approximately half of the overall business transaction involves immediate cash consideration, while the other half is structured around a five-year seller-financed obligation with interest-only payments and a balloon payment.
There are also continuing obligations and potential earnout considerations.
And then there is the real estate.
The real estate portion has already closed separately. Proceeds are sitting with a qualified intermediary as part of a Section 1031 exchange. The seller has enjoyed years of depreciation deductions, including accelerated depreciation on equipment, and now must confront what those previous tax benefits mean when the underlying assets are sold.
This is where an ordinary-looking liquidity event can become extraordinarily complex.
A seller can agree on the enterprise valuation and still have unresolved questions about how the consideration is allocated, when gain is recognized, how much depreciation must be recaptured, and which obligations survive the closing.
Those are not minor technicalities.
They are decisions that can materially affect how much capital remains available to support the seller and their family.
Kevin entered the transaction after documents had already been signed. The seller’s existing advisors had previously suggested involving him, but the ownership group believed its established CPA and legal counsel already had everything covered.
That changed when the estimated tax liability arrived. Suddenly, the owner wanted another perspective, and that’s the first lesson I want every business owner to recognize.
You do not want the tax bill to be the first moment you begin designing your exit.
By then, transaction commitments may already constrain your options. Some planning strategies depend on taking action before a binding sale obligation or closing. Others require particular ownership, trust, financing, or reporting arrangements.
The closer you get to the finish line, the fewer moves may remain available.
The 45-Day Clock and the Problem With Staying on the 1031 Treadmill
Part of this transaction centers on a familiar strategy for real estate investors: the Section 1031 like-kind exchange.
Properly executed, a qualifying 1031 exchange permits an investor to defer recognition of certain real estate gains by exchanging investment or business-use real property for qualifying replacement real property.
But the rules impose strict deadlines.
The investor generally must identify replacement property within 45 days of transferring the relinquished property and complete the exchange within 180 days, or an earlier applicable tax-return deadline unless extended.
In Kevin’s case, the seller was approaching the identification deadline without finding replacement property they actually wanted to own.
This is more than a tax problem. It’s a capital allocation problem.
Think about it. You spent decades operating a business, owning facilities, supervising people, managing property, and absorbing operational risk.
Now you’ve finally sold the company.
Do you really want your next major financial decision to be purchasing another property simply because the tax calendar is telling you to?
For some investors, absolutely. They love owning real estate. They understand the economics, appreciate the cash flow, and want to remain exposed to the asset class.
For others, especially owners approaching retirement or designing a transfer to children who have no desire to manage buildings, buying replacement property may extend the very responsibilities they were trying to leave behind.
During our discussion, Kevin described a proposed transition from the existing exchange arrangement into an installment-sale structure involving a trust, a promissory note, and what he called a defeasance letter.
His stated objective was to create an alternative to acquiring another replacement property while pursuing eligible gain deferral under Section 453.
It’s an intriguing concept, and one that requires careful examination.
An already-initiated 1031 exchange cannot simply be assumed convertible into a qualifying installment sale. The timing, rights to proceeds, identity of the seller and buyer, trust arrangements, constructive-receipt rules, and applicable tax authorities all matter. Private letter rulings also generally cannot be relied upon as precedent by taxpayers other than the requesting taxpayer.
Nevertheless, the broader planning question is a valuable one.
Are you choosing an investment because it is the right asset to own, or because it is the only tax strategy anyone has shown you?
Those are very different motivations.
When “I’m Not Comfortable” Becomes the Entire Argument
The most entertaining—and instructive—part of Kevin’s story involved his interaction with the seller’s existing CPA.
Kevin described presenting a lengthy due diligence package supporting the proposed structure, including tax-code references, court rulings, and private letter rulings.
The CPA remained unconvinced.
According to Kevin, the objections increasingly centered on the advisor’s personal discomfort rather than specific unresolved technical issues.
Now, I want to be careful here.
An experienced CPA absolutely should be uncomfortable with a complicated transaction when important facts, legal interpretations, or implementation safeguards remain unresolved. Professional skepticism is not a character flaw. In fact, it can be one of the most valuable things a business owner pays for.
There are legitimate reasons to challenge installment-sale arrangements, trust structures, basis calculations, related-party provisions, depreciation treatment, and aggressive deferral claims.
But here’s the distinction.
There is a massive difference between saying, I have identified a specific legal concern that needs to be resolved, and saying, I simply don’t feel comfortable.
The first gives the client something actionable.
The second may leave the client unable to distinguish between a substantive legal risk, a lack of familiarity, and an advisor’s personal risk tolerance.
Kevin eventually became frustrated enough to ask the CPA why the client should bear an unnecessary tax expense if the advisor could not articulate the technical objection.
It made for a lively exchange, but beneath the personality conflict is a lesson about governance.
When you’re the owner, you are responsible for making sure competing advisors explain their reasoning in a way that can be independently evaluated.
You don’t have to become a tax attorney.
You do have to insist that the people you hire distinguish between rules, assumptions, risks, and preferences.
A well-documented recommendation should survive informed questioning.
And when two qualified professionals disagree, that is often the moment for independent specialist counsel—not a contest over which personality is more persuasive.
The Tax Code Is a Rulebook, Not a Personality Test
Kevin shared an analogy he says came from a conversation with an IRS representative.
Imagine entering a grocery store with legitimate manufacturer coupons. You have the qualifying products in your cart, the coupons are valid, and the checkout system recognizes them.
Would you refuse to use them because you were worried the store manager might dislike you?
That’s how Kevin encourages owners to think about legitimate deductions, exclusions, and deferral provisions. The tax code contains rules that taxpayers may use when their facts qualify.
You should not intentionally overpay simply because claiming an available benefit feels uncomfortable.
I agree with the underlying principle, with one important qualification: tax-law eligibility is often far more complicated than redeeming a coupon. A provision might be available in principle yet inapplicable to a particular transaction because of its timing, structure, related parties, documentation, or anti-abuse rules.
The correct answer is neither aggressive improvisation nor reflexive conservatism. It is documented, supportable, transaction-specific planning.
Kevin also discussed tax-return preparer penalties and suggested that concern about personal liability can influence an advisor’s recommendation.
That is worth understanding, although preparer penalties are not automatic whenever a taxpayer loses an audit. They depend on the applicable statutory standards and conduct.
The questions I would encourage every owner to ask are simple:
What is the actual risk to me?
What is the potential benefit?
What evidence supports the recommendation?
Your advisors should be able to answer all three. If they can’t find the ones who can.
Why Form 6252, Basis, and Documentation Matter
As the discussion continued, we moved into the mechanics of installment-sale reporting.
Kevin explained the role of IRS Form 6252, which is used to report qualifying installment-sale income.
He said that one of the recurring challenges his team encounters is incorrect tax-basis information submitted on returns.
This detail matters enormously.
Your adjusted basis is an important component of determining taxable gain. The original purchase price is only the starting point. Capital improvements, depreciation, asset acquisitions, allocations, and other adjustments can affect the calculation.
And in a multi-asset business sale, various components of the consideration may receive different tax treatment.
One of the most dangerous oversimplifications is the idea that installment treatment automatically defers every dollar of gain merely because part of the purchase price will be paid later.
It does not.
Depreciation recapture, inventory, certain other assets, interest, and installment obligations can have distinct reporting requirements.
That is why the actual purchase agreement, asset allocation, valuation, tax-basis schedule, financing terms, and reporting positions must be examined together.
Kevin described using specialized processes to prepare transaction-related reporting information and resolve discrepancies. Whether you use his team or another qualified advisory group, that process discipline is the real lesson.
A sophisticated exit strategy is only as strong as its execution and documentation.
A beautifully designed arrangement with incorrect reporting can create a problem years after the celebration.
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CASH OUT CLEAN — Tax Strategy for Your Big Exit
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Whether you’re preparing to sell in the next 12 months or planning a succession several years away, this is an opportunity to begin modeling the decisions before they become irreversible. You can talk with the book agent or type in answers to its questions and even add in optional questions around your numbers and receive a completely customized and confidential 537IST revenue and tax estimator report in Chapter 9.
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Explore your options before you commit to a structure. Your personalized playbook is a planning starting point, not a substitute for independent legal, tax, or investment advice. It is 100% free and arrives in both PDF and as a paperback copy delivered to your door.
AI Is Coming for the Errors. What Happens to the Advisors?
Around the middle of our conversation, the discussion took a turn that I believe is just as important as the original $100 million transaction.
Kevin described an AI-based tax-return review system developed by his organization’s technology team.
According to Kevin, the system has identified multiple errors in returns it has examined, with many of the mistakes resulting in excessive taxes being paid. Those are observations from his practice, not independently validated industry-wide error rates.
But the implication deserves attention.
Historically, professionals have been compensated partly because they possess specialized information that clients cannot efficiently access, understand, or apply. That information advantage is changing rapidly.
Tax codes, case law, financial statements, transaction documents, and thousands of pages of supporting material are becoming increasingly accessible to AI-assisted systems.
These systems can help identify inconsistencies, surface potentially relevant provisions, compare documents, and flag issues for professional review.
They are not infallible. AI can misinterpret legal authority, invent citations, or miss critical facts, particularly in consequential tax work.
But when used with appropriate controls and expert verification, the technology may materially improve the speed and scope of professional analysis.
So what does that mean for the advisors?
Kevin and I discussed how routine analysis and portfolio monitoring are already becoming more automated. He described a portfolio process that uses AI to evaluate a basket of ETFs, flag changes, and recommend adjustments for human review.
That is a very different operating model from the old image of analysts manually producing repetitive reports, and it raises a question that applies far beyond accounting or wealth management.
When a machine can perform much of the analytical work, what exactly is the human professional being paid to do?
My answer rests on five increasingly valuable capabilities: context, judgment, taste, coordination, and trust.
Context is knowing what matters to the specific family and what does not.
Judgment is understanding the consequences of competing options.
Taste is knowing which opportunities to pursue and which to reject.
Coordination is assembling the right people, capital, tools, and legal structures around a common outcome.
Trust is the cumulative result of applying those capabilities in ways that consistently serve the client.
An AI system might surface 20 technically interesting strategies. A valuable human advisor helps the owner understand why perhaps only two deserve serious consideration.
That is not a small distinction.
It may define the economics of professional advice over the next decade.
Your Longtime Advisor May Be Your Friend. That Doesn’t Automatically Make Them Your Exit Architect.
I made a point during the episode that I hope every business owner takes seriously.
The people who got you here are not necessarily the people best equipped to take you where you’re going next. This is not an indictment of longtime accountants, attorneys, brokers, or financial advisors.
Quite the opposite.
Many of these relationships were built through difficult years when the business was barely profitable, cash flow was inconsistent, or personal guarantees kept the owner awake at night.
Those people earned their place at the table, but consider what happens when a company that once generated $2 million in annual revenue becomes a $100 million enterprise.
The owner’s financial life has changed dramatically.
Their balance sheet has changed. Their exposure to litigation, taxes, liquidity risk, estate planning, family governance, and investment complexity has changed.
Yet the advisory roster may look exactly the same. That creates a potentially dangerous mismatch. You might trust your CPA completely, enjoy spending time with them, and appreciate decades of good service. None of those facts alone establish that they have the specialized experience to structure your largest lifetime liquidity event.
Kevin shared an example of an owner who, in his telling, accepted approximately $2.5 million of additional transaction tax cost because of reluctance to go against a longtime CPA’s advice.
That is a cautionary anecdote, not evidence that all longstanding relationships create such costs, but it captures the emotional difficulty of changing roles.
Friendship and professional responsibility can coexist without requiring you to keep everyone in the same position forever.
In sports, a beloved veteran can remain an important part of the organization without being the starting quarterback.
In business, an established advisor can remain trusted without serving as the lead specialist on every transaction.
You can preserve the relationship and still bring in additional expertise.
Loyalty is a virtue. Abdicating your responsibility as an owner is not.
The mature conversation is not about telling someone they have become worthless. It is about recognizing that your family has entered a new financial chapter and the advisory structure must evolve accordingly.
The $100 Million Question: What Are You Actually Trying to Preserve?
This is where our discussion moved beyond the tax code and into a much larger question.
Why do entrepreneurs work so hard to build significant wealth?
Most of them did not begin with a desire to manage an intricate network of trusts, asset allocations, financial institutions, and tax advisors.
They wanted freedom. They wanted to build something meaningful. They wanted to create opportunities for their families, employees, and communities. Some wanted to prove that an idea could become a real enterprise. Others simply enjoyed solving problems and building something from nothing.
Over time, however, the company becomes a remarkably effective engine of wealth creation.
The owner grows accustomed to being the operator. They know how to sell, hire, negotiate, manage cash flow, read customers, and navigate uncertainty.
Then comes the exit, and in an instant, the central challenge changes.
Instead of managing the enterprise that produced the wealth, the owner must manage the capital and responsibilities created by the sale.
It’s a completely different skill set.
You have to graduate from builder to guardian or steward.
Building requires an appetite for risk, reinvestment, concentration, and execution.
Stewardship requires a deliberate approach to liquidity, resilience, income, governance, preservation, and long-term optionality.
The two disciplines overlap, but they are not interchangeable.
An owner who is brilliant at growing a business may have little experience managing a diversified post-exit balance sheet.
And there is nothing unusual about that. Most people only experience one major exit in their lives. They don’t get five practice rounds before the real event. That is why the design of your post-exit life must begin before the transaction occurs.
In the AI Economy, Ownership Becomes the Skill That Matters Most
As the conversation turned toward artificial intelligence and the future of work, I returned to a theme I’ve been exploring across Wealth Matters 3.0.
We are entering an economy where more forms of productive work can be performed by intelligent software and increasingly capable automated systems.
The speed and ultimate extent of this transition remain uncertain, but the direction of technological progress is already changing the way many organizations create value.
For decades, a great deal of wealth was built by controlling scarce labor, specialized knowledge, distribution, and capital. Now some, almost all forms of knowledge work are becoming cheaper, faster, and more abundant.
That shifts our attention toward a question:
Who owns the productive assets, the business systems, the capital, the intellectual property, and the economic rights associated with this new capacity?
The person who merely performs a repeatable task will face increasing competition from automation.
The person who owns a productive system has a different set of opportunities and risks.
This is not an argument that ownership guarantees prosperity. Assets can depreciate, companies fail, and technology can disrupt incumbents just as readily as employees, but it is an argument that understanding ownership becomes increasingly important.
When an entrepreneur exits a company, they are effectively converting concentrated ownership of an operating enterprise into another form of economic ownership.
That capital needs a new purpose.
It may be invested in diversified financial assets, income-producing businesses, private markets, real estate, or other structures appropriate to the family’s circumstances.
The point is to be deliberate about what the family owns, why it owns it, how the risks are governed, and what the assets are expected to accomplish.
This is especially important when the next generation will inherit wealth created in a very different economy.
Your children may never run the company you built. They may not even understand the industry that made your fortune possible, but they can learn how to govern capital, evaluate opportunities, understand risk, preserve relationships, and make consequential decisions.
That is the human capability I want families to pass forward.
The Real Exit Is Getting Your Time Back
Toward the end of the episode, Kevin and I discussed something that rarely gets enough attention in conversations about eight- and nine-figure transactions.
Time.
Kevin talked about becoming more disciplined with his calendar and protecting time with his son.
He described spending time together working on projects, riding electric bikes, and enjoying the freedom of being present without constantly reacting to the phone.
And then he made an observation that captures much of what Wealth Matters is about. He said the more intentional he became about saying no to unnecessary demands on his time, the wealthier he became. That does not mean working less automatically makes a person financially richer.
It means that clarity about what matters can change how a person allocates attention, makes decisions, and measures success.
I shared some of my own experiences with the physical costs of pursuing things I loved, including years of playing football and eventually needing a hip replacement.
Would I erase those experiences?
No.
But I can recognize that the benefits came with costs. Entrepreneurship works the same way.
Nobody builds a business worth tens of millions of dollars without giving something to it. Time, energy, relationships, health, and opportunity costs all become part of the hidden purchase price of success.
When the exit finally arrives, it’s worth asking what the proceeds are actually meant to buy.
Another demanding project?
A more expensive version of the same lifestyle?
Or the freedom to spend time differently?
Maybe it’s being able to sit with your grandchildren without checking your phone.
Maybe it’s having the energy to travel with your spouse.
Maybe it’s starting another business because you genuinely love building things, not because the bank account demands it.
And maybe it’s finally having enough space to teach your children the lessons that helped you build the fortune in the first place.
Because money can be lost and earned again. Time cannot.
Five Questions to Ask Before You Sign Your Exit Documents
If you’re considering a business sale in the next one to five years, I would encourage you to begin with five questions.
1. Have we modeled the transaction after taxes, not simply at the headline valuation?
Understand how the purchase price, asset allocation, financing, depreciation recapture, and transaction costs may affect your actual proceeds.
2. Have independent specialists reviewed the proposed structure early enough to preserve legitimate options?
Some planning opportunities disappear after particular agreements, transfers, or closing events. Timing is part of the strategy.
3. Can every advisor explain their recommendations in terms of identifiable risks and applicable rules?
Ask for the assumptions, legal support, reporting requirements, potential challenges, and alternative approaches.
4. Have we defined what happens to the proceeds after the sale?
Liquidity is not a retirement plan. Your income requirements, investment objectives, estate arrangements, family responsibilities, and risk tolerance need to be considered as a complete system.
5. Are we designing for the life we want after the transaction?
The family should understand what success means beyond the sale price. Otherwise, you can achieve the financial exit without ever experiencing the personal freedom you expected it to produce.
These are not questions to answer the week before closing.
They are questions to start answering while you still have options.
Final Thought: You Built the Fortune in One Economy. Your Family Will Inherit It in Another.
One of the great mistakes business owners make is assuming the skills required to create wealth are sufficient to preserve it.
They aren’t always.
The world that rewarded your hustle, your relationships, your knowledge, and your willingness to take concentrated risk is changing.
AI will reshape professional advice. Tax and estate rules will continue evolving. Capital markets will cycle. Business models will be disrupted.
And your family will eventually confront decisions in an environment that looks very different from the one in which you built your company.
That is why the conversation with Kevin matters.
The story started with a $100 million medical equipment transaction, a complicated tax estimate, and a CPA who was uncomfortable with an alternative strategy, but the larger lesson is about accepting responsibility for the next stage of ownership.
You cannot outsource all your judgment.
You cannot assume yesterday’s advisory structure will remain adequate tomorrow.
And you cannot measure the success of an exit solely by the number on the closing statement.
The objective is to preserve the capital you need, design the income and freedom you want, and prepare your family to govern what comes next.
You built the family fortune in one economy. Your children and grandchildren will inherit it in another run primarily by machines, with humans as the beneficiaries.
Make sure you are preparing them, your portfolio, and your estate plan for that reality.
The real risk is doing nothing!
— Chris J. Snook
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The Exit Advisors — Weekly Friday Office Hours AMA
Hosted by Chris J. Snook with Kevin Brunner.
We explore the critical decisions business owners face before, during, and after a liquidity event—from tax strategy and installment-sale planning to income security, asset protection, succession, and generational wealth stewardship.
Bring your questions, challenge our assumptions, and use these conversations to become a more informed owner.
Editorial note: This article reflects the discussion and opinions expressed during the November 13, 2026 episode. Transaction details are presented as described by the speakers. Certain audit statistics, professional-industry forecasts, and claims about specific tax strategies were not independently verified. This material is educational and does not constitute individualized tax, legal, or investment advice. Proposed installment-sale trust structures, Section 1031 alternatives, and other tax-planning approaches require review by qualified independent professionals before implementation.
Thank you to everyone who tuned into my livestream video! Join me for my next live video in the app.
