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Punching Out: Can I Sell My Business Using AI?

Let’s ask AI (Microsoft Copilot) if you can use it to sell your business: “Absolutely. You can sell your business using AI, and it’s becoming a powerful strategy for entrepreneurs and owners looking to streamline the process.”

Well, there you go. Easy-peasy. I guess I’ll join my former clients and retire now that AI can do the job for me. Or maybe it’s not as simple as AI claims.

While AI has streamlined many of the processes, it does not solve many of the key issues in an M&A transaction. My query to AI also produced a list of risks and considerations when using AI to sell your business: 

• AI is not a substitute for legal or financial advisors. It enhances efficiency but still requires expert oversight.
• Data privacy is critical. Ensure sensitive business information is protected when using AI platforms.
• Over-automation can feel impersonal. Buyers may prefer human interaction during key stages of negotiation.

Aha, AI is smart enough to realize that it has its own limitations. I very much agree with the AI’s assessment: While AI keeps getting better, it can still be very frustrating to follow. In many situations, AI can be 95% or even 98% correct. Depending on the occasion, that rate can be either excellent or terrible. If you are ordering a combo meal at Wendy’s, 95% correct on the first try is much better than average (so I hear). If we are talking about an Asset Purchase Agreement, a few seemingly small mistakes could be critical.

Here are some common areas in which AI can be very helpful:

• Valuation and financial analysis
• Buyer prospecting
• Marketing and presentation
• Due diligence automation
• Initial Negotiation and deal structuring

AI is also useful for owners who need to understand the market prior to engaging their trusted advisors about moving through the process.

For example, owners often have expectations of value that are much too high. It is good to shoot for the stars, but unreasonable expectations make it very hard to complete a deal. Before talking to the experts, owners can prepare for a sale by familiarizing themselves with valuations in the PCB and/or EMS industries.

Even as experts in M&A in our areas of focus, we do not know everything. We use AI to look for new buyers who are interested in the industry and welcome any tool that can help us perform better for our clients.

Word of caution: AI is not helpful in concerns about confidentiality, accuracy, and judgment. For example, AI can create great-looking presentations, but confidential information should not be put into public AI systems. The reports also tend to be heavy on fluff and low on originality. An experienced M&A professional knows what to include and how to position sellers to help attract buyers.

AI can be helpful in scanning a massive amount of data and flagging items for further scrutiny. For example, it can quickly scan for change of control clauses in contracts, which can be flagged for further attention. An experienced person judges whether to raise a red, yellow, or green flag, depending on the situation.  

In some cases, technology can simplify due diligence. In my experience, however, due diligence is getting longer and more onerous, probably because technology generates questions more easily, but the ability to answer questions has not kept pace.

While you might be able to find legal templates online, I would caution against using these plain solutions other than to educate yourself about what is commonly found in a typical agreement. Only an experienced attorney can draft an agreement that is appropriate for your situation. Saving a few bucks can definitely bite you in the buttocks later on.

How well does AI do when it comes to negotiating? “While AI doesn’t replace human judgment, it can simulate deal scenarios, model financing options, and suggest optimal terms based on historical data” (Microsoft Copilot). For now, this seems to be the biggest gap between AI and reality. Humans are humans, and we have been negotiating with each other for millions of years. We have developed negotiating into an artform.

My only experience negotiating with AI has been trying to get a human representative on the phone when I have a tricky insurance question! I am usually not successful, so I often revert to the “nuclear option” of hanging up.

In M&A negotiations, only an experienced human can judge what to push for, what hills to die on, what is market, and when to compromise—at least, so far. Check back in with me in six months.

Tom Kastner is the president of GP Ventures, an investment banking firm focused on sell-side and buy-side transactions in the tech and electronics industries. GP Ventures has offices in Chicago and Tokyo, with five people in total. Tom Kastner is a registered representative of, and securities transactions are conducted through, StillPoint Capital, LLC—a Tampa, Florida, member of FINRA and SIPC. StillPoint Capital is not affiliated with GP Ventures.