Can AI Sell Your Business? We Put ChatGPT to the Test

March 27, 2025

With all the buzz around artificial intelligence, especially ChatGPT. No wonder people in industries like copywriting, law, and education are starting to wonder if AI might eventually replace their jobs. Naturally, we at Bluebox Corporate Finance were curious too. Could ChatGPT handle the complex world of mergers and acquisitions?

So, we decided to find out. We asked it the kind of questions we deal with every day about valuing businesses, finding buyers, and offering strategic advice. The results? Let’s just say we won’t be handing over our advisory roles anytime soon.

Take business valuation, for example. When we asked ChatGPT basic financials, including revenue and EBITDA. It did what many of us do in the early stages: applied a broad range of multiples (between 5x and 15x) to give a rough estimate. Helpful? Sure, to an extent. But when it came to the finer details like assessing growth potential, market position, or the specific value drivers unique to a business, ChatGPT fell short. Its go-to response? “You should consult an appropriate advisor.” We couldn’t agree more.

And what about identifying potential buyers? Well, ChatGPT confidently suggested big names like WPP, Deloitte Digital, and Bain. Global firms you could probably name yourself. While these suggestions aren’t wrong, they’re also far from the nuanced and tailored buyer lists that M&A advisors curate. If your business operates in a niche market say SEO or martech finding the right acquirer requires a lot more than just pulling a list of well-known firms.

When we asked for recent deal data or precedent transaction metrics, ChatGPT admitted defeat. M&A deal information is often confidential, so it understandably doesn’t have access to proprietary databases. Its suggestion? Hire a market research firm or, well…Google it.

Even on broader strategic questions like post-merger integration or private equity trends the AI played it safe. It dished out high-level frameworks and generic advice but couldn’t offer anything resembling the customised, deal-specific insights that come from years of hands-on experience.

In fairness, we were impressed by its ability to articulate the basics. If you’re new to the world of M&A, ChatGPT does offer clear, logical explanations without the hassle of sifting through multiple websites. But when it comes to the real work of selling a business building relationships, negotiating terms, and navigating the unpredictable human elements of a deal there’s no substitute for an experienced advisor.

So, will AI be replacing M&A advisors anytime soon? Not likely. While ChatGPT is an interesting tool for quick answers and general knowledge, it can’t replicate the judgment, experience, or personalised guidance that comes from working with a specialist.

For now, we’ll leave the machines to handle the basics and stick to what we do best: helping business owners achieve the best possible outcome when they decide to sell.

If you’re considering selling your business or need expert M&A advice, don’t leave it to algorithms. At Bluebox Corporate Finance, we bring the experience, insight, and tailored strategies that no AI can match. Get in touch today to discuss how we can help you achieve the best possible outcome.

quote marks icon

Testimonials