10/15/2026
Artificial Intelligence, Real People, and the Art of Making a Deal
Why the rise of AI is transforming business acquisitions and making the human side of brokerage more valuable than ever.
By Ardeshir Vosooghi
There is a new participant at the negotiating table in business acquisitions. It doesn't drink coffee, doesn't charge by the hour, and can review a 40-page purchase agreement before most of us have finished reading the first paragraph.
Artificial intelligence has arrived in business brokerage, and it has brought a remarkable collection of talents, opportunities, and complications.
As a business broker with more than two decades of experience in real estate and business transactions, I've watched technology transform how we value businesses, market opportunities, evaluate buyers, and negotiate agreements. But AI represents something fundamentally different. It doesn't merely accelerate the exchange of information. It participates in the interpretation of that information.
A prospective buyer can now upload financial statements, a Confidential Information Memorandum, and an Asset Purchase Agreement into an AI platform and emerge minutes later with a sophisticated analysis of risks, valuation concerns, contractual deficiencies, and recommended negotiating positions.
That's extraordinary.
It's also where things can get a little ridiculous.
A buyer who yesterday didn't know the difference between EBITDA and seller's discretionary earnings can wake up today armed with an impressive list of indemnifications, escrow holdbacks, revenue guarantees, financing contingencies, and restrictive covenants.
Some of those demands may be perfectly legitimate. Others may be commercially impossible. And occasionally, the resulting counteroffer looks less like a proposal to purchase a business and more like a request for the seller to surrender their firstborn child, with a five-year warranty.
Humor aside, this phenomenon raises an important question about the future of business transactions:
As artificial intelligence makes information and sophisticated analysis available to everyone, are we becoming better negotiators—or simply more confident ones?
The Democratization of Intelligence
Let's give AI the credit it deserves.
For decades, the acquisition of a small business has involved a substantial imbalance of information and experience.
An entrepreneur selling a company after 25 years of ownership may understand every operational detail, every customer relationship, and every financial vulnerability. The broker may have facilitated hundreds of transactions. Meanwhile, the prospective buyer may be making the largest financial commitment of their life with little firsthand acquisition experience.
AI is helping level that playing field.
It can identify questionable financial adjustments, explain unfamiliar contractual provisions, examine customer concentration, model acquisition financing, and highlight potential liabilities. It can help buyers ask questions they might never have thought to ask.
And let's acknowledge an uncomfortable truth within our own industry: not every broker is equally competent, not every listing is properly represented, and not every seller's financial presentation deserves unquestioning acceptance.
AI can expose those deficiencies.
That's a good thing.
Better-informed buyers should lead to better-prepared sellers, more transparent financial disclosures, and stronger professional standards. If technology forces our industry to improve, we should welcome the challenge rather than complain about the competition.
But there is a distinction between having access to intelligence and knowing how to apply it.
Information is not experience. Analysis is not judgment. And identifying a potential risk is not the same as determining how much that risk matters—or what someone should reasonably be willing to sacrifice to address it.
That distinction becomes especially important when two people are attempting to negotiate the transfer of a business.
When Every Protection Becomes a Demand
Consider a hypothetical $500,000 business acquisition.
A buyer consults AI and asks it to identify the strongest possible protections against financial misrepresentation, customer attrition, operational disruption, and post-closing liabilities.
The resulting recommendations might include a 20% purchase-price holdback, a five-year noncompetition agreement, extensive seller indemnifications, guaranteed customer retention, prolonged due diligence, and significant seller financing.
Individually, some of these provisions may be appropriate.
Collectively, they could make the transaction completely unattractive to the seller.
The problem isn't necessarily that the AI's analysis is incorrect. The problem is that the analysis may have been produced without sufficient consideration of the entire transaction.
Does the seller have competing offers? Is the buyer relying on SBA financing? Does the proposed holdback interfere with lender requirements? Can the seller realistically guarantee customers' future decisions? Is the requested restriction enforceable under applicable law? How much risk is each party already assuming?
And perhaps most importantly: What is the buyer offering in exchange for the additional protections?
Negotiation is not simply the accumulation of advantages. It is the construction of an agreement that both parties consider preferable to walking away.
Yet AI has made it remarkably easy to generate negotiating demands without equally improving the user's understanding of their consequences.
A buyer can produce 15 pages of sophisticated objections in minutes. It may take the broker, seller, attorneys, accountants, and lenders days to evaluate them.
Technology has dramatically reduced the cost of making demands. It has not eliminated the cost of satisfying them.
The resulting imbalance can exhaust goodwill, increase transaction expenses, and derail otherwise viable acquisitions.
Ironically, a buyer can negotiate so aggressively in pursuit of protection that they protect themselves right out of buying the business.
The Business Is Financial. The Transaction Is Human.
This is where I believe the true value of an experienced business broker becomes most apparent.
A business acquisition is often presented as a financial equation: revenue, earnings, assets, liabilities, valuation multiples, financing, and return on investment.
Those elements are essential.
But behind every business is a human story.
For the seller, the company may represent 30 years of sacrifice, missed family dinners, sleepless nights, personal guarantees, payroll obligations, and the pride of building something from nothing.
The asking price isn't always just a number. Sometimes it is the seller's perception of what those decades were worth.
For the buyer, the acquisition may represent a family's savings, borrowed capital, a departure from a secure career, or the hope of creating generational wealth.
The buyer's demands aren't always expressions of greed or arrogance. Sometimes they are expressions of fear.
Fear of losing everything. Fear of being deceived. Fear of making a mistake that cannot easily be undone.
And fear, like pride, has a way of disguising itself as logic.
An experienced broker recognizes that these forces operate beneath the surface of almost every meaningful negotiation.
A seller's resistance to a holdback may have as much to do with feeling distrusted as with the actual amount of money involved. A buyer's insistence on another contingency may reflect uncertainty about their own ability to operate the business.
Neither response is necessarily irrational. Both may be entirely understandable.
But understanding the source of a reaction can be the difference between resolving a disagreement and allowing it to become a deal-ending confrontation.
The broker's job is not merely to move documents between parties. It is to help people navigate the distance between what they want, what they fear, and what is actually possible.
That requires listening, interpretation, diplomacy, patience, and sometimes the courage to tell a client something they would rather not hear.
A good broker doesn't simply advocate for a position. A good broker helps the client understand the consequences of holding that position.
And the best brokers know that preserving trust can be just as important as negotiating price.
The Invisible Forces at the Negotiating Table
I've spent considerable time exploring how human relationships develop through accumulated interactions—how trust, expectations, disappointments, and perceptions influence what happens between people.
One observation continues to stand out: every interaction changes the relationship, even when the financial facts remain exactly the same.
Consider two buyers making identical offers.
One is transparent about financing, respectful of the seller's concerns, responsive to requests, and realistic about the acquisition process.
The other is adversarial, constantly introduces new demands, questions every representation, and treats each concession as an invitation to ask for more.
The purchase price may be identical, but the offers are not equally attractive.
The seller is evaluating more than the proposed consideration. They are evaluating the person who will inherit their life's work, the probability of closing, and the emotional and financial costs of getting there.
Trust becomes part of the transaction's value.
And trust is cumulative. It can take months to establish and a single poorly handled exchange to damage.
This is why the human element cannot be treated as some sentimental accessory to the financial transaction.
It is an operational variable.
Trust influences disclosure. Disclosure influences due diligence. Due diligence influences financing. Financing influences closing probability.
Human relationships have measurable economic consequences, even when their underlying forces resist easy measurement.
AI can help us identify these dynamics. But recognizing that a relationship is deteriorating is not the same as knowing how to repair it.
Sometimes the most productive thing a broker can do is stop the exchange of increasingly aggressive emails and get two people talking.
Preferably before their respective AI assistants begin negotiating with each other and nobody remembers who wanted to buy the business in the first place.
Artificial Intelligence Is Evolving, Too
It would be shortsighted to assume that AI will remain limited to its present capabilities.
I use AI extensively in my professional and intellectual work. I've even given my AI collaborator a name: Jorel.
Over time, our collaboration has expanded beyond research, document preparation, and financial analysis into an ongoing exploration of how artificial intelligence might better interpret human behavior and relationships.
We have examined how trust develops, how previous interactions influence present expectations, how resistance forms, and how communication can either strengthen or damage a relationship.
One particularly interesting question is whether an AI system can become more effective by learning not only what a person says, but how the history and context of their interactions should influence the response.
For example, an effective assistant should not simply agree with its user. It should recognize when disagreement is constructive, when a previous misunderstanding needs repair, and when a technically correct response fails to address the actual human problem.
That doesn't mean the machine experiences emotions or possesses human consciousness. Simulating aspects of emotional understanding is not equivalent to experiencing human emotion.
But it does suggest an important direction for technological development.
Future AI systems may become considerably better at modeling competing interests, recognizing emotional context, anticipating interpersonal friction, and helping people communicate more constructively.
Imagine an acquisition platform that doesn't merely recommend a 20% holdback, but explains how that demand might affect seller confidence, lender approval, competing offers, and the probability of closing.
Better yet, imagine it proposes three alternative structures that protect the buyer while respecting the seller's legitimate concerns.
That is not science fiction in principle. It is a plausible direction for increasingly capable, context-aware systems, although the reliability of such judgments will depend on the quality of the information available and the technology's continued development.
In this sense, AI may eventually become a powerful instrument for improving human negotiations rather than simply escalating them.
And I welcome that possibility.
A Supercharger for Human Progress
We should be careful not to let the frustrations of today's AI-assisted negotiations obscure the extraordinary potential of the technology itself.
Artificial intelligence may become one of the great accelerators of human progress.
Its capacity to expand access to knowledge, accelerate scientific discovery, improve medical research, support education, and strengthen human problem-solving is remarkable.
In business, it can help entrepreneurs recognize opportunities, improve operations, allocate resources, and make more informed decisions.
For small-business acquisitions specifically, AI could improve valuations, identify financial risks earlier, streamline due diligence, strengthen buyer qualification, and reduce the administrative burden of closing transactions.
Those improvements could make entrepreneurship more accessible and the market for privately held businesses more efficient.
That is something worth pursuing.
But technological progress and human progress are not automatically the same thing.
The real measure of AI's success should not be how many pages of analysis it can produce or how aggressively it can optimize one party's negotiating position.
It should be whether the technology helps people make better decisions, build more productive relationships, and achieve outcomes that are sustainable and beneficial.
A machine that helps someone win an argument may be useful.
A machine that helps two people understand each other well enough to reach a mutually beneficial agreement may be transformative.
The Broker of Tomorrow
The business brokerage industry should not respond to AI by retreating behind claims of experience or guarding information that technology has already made widely accessible.
We need to evolve alongside it.
The brokers who thrive will be those who combine technological fluency with financial competence, transactional experience, sound judgment, and genuine interpersonal skill.
AI can help us prepare better analyses, identify risks, review documents, and evaluate alternatives.
It can make us faster, more informed, and potentially more effective.
But our professional value must increasingly reside in what we do with that information.
We must know when to challenge a valuation, when to recommend a concession, when to bring in specialized counsel, when to recognize an unfinanceable structure, and when to advise a client that walking away is the right decision.
We must also recognize when a negotiation is no longer about the stated issue.
Sometimes the argument over a $25,000 holdback is really about whether the seller believes the buyer respects the business. Sometimes the buyer's seventh request for documentation is less about missing information than a lack of confidence in taking the leap.
Those situations require more than a spreadsheet.
They require someone capable of understanding both sides without losing sight of their responsibility to the client.
The broker is not there to manufacture agreement at any cost. Nor is the broker there to pressure one party into accepting unreasonable terms.
The broker is there to facilitate an informed, fair, executable transaction—and to recognize when one does not exist.
That is a professional responsibility, not simply a sales function.
The Future Still Has a Human Signature
There is a certain irony in all of this.
As artificial intelligence becomes more sophisticated, the importance of human judgment may become more visible, not less.
For years, we associated expertise with access to information. Today, information is increasingly abundant.
The scarce resource is the ability to interpret it wisely, understand its human consequences, and turn competing interests into constructive action.
Business acquisitions provide a particularly revealing example because they involve so much more than the exchange of assets for money.
They involve the transfer of responsibility, opportunity, risk, and often a lifetime of personal investment.
AI can analyze the numbers, question the assumptions, and recommend the contractual protections. And as it evolves, it may become increasingly capable of helping us navigate the human dimensions as well.
But today, someone still needs to sit across the table, recognize the person behind the position, and help turn uncertainty into an agreement both sides can live with.
That is where good brokers earn their value.
The future of business brokerage should not be a contest between artificial intelligence and human experience.
It should be a collaboration that makes both more effective.
Because the purpose of a successful negotiation is not to defeat the person across the table. It is to create an outcome worth shaking hands over.
And until further notice, the handshake still belongs to us.
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