Phone calls and handshakes: why human connection still matters in founder-led deals

When’s the last time you received an email and asked yourself, “did a human write this?”

If you’re like me, it happens almost every day. AI-generated emails, messages and even phone calls have become a routine part of doing business.

Most of these interactions are relatively low stakes, but the same technology is being used to make much bigger asks, including one of the most consequential questions a business owner can receive: Would you consider selling your company? That’s where I believe human connections have become much more important.

I’m not anti-AI. Charles Aris Transaction Services uses it regularly, particularly during the early stages of research. Generative AI can help us map markets, surface potential acquisition targets and organize information much faster than we could manually. That information still needs to be verified, but AI can significantly accelerate the research required before we start connecting with founders.

The line we draw comes at the point of contact.

It’s tempting to keep automating from there. Technology can write emails and even place a call designed to sound like a person. That may create more activity, but human-written messages generate more replies and get flagged as spam less often than fully AI-generated messages.

Plus, most founder-owners we contact have not yet decided to sell their business. They may be thinking about growth, succession, liquidity, their employees, their family or what they want the next chapter of their life to look like.

A dealmaker’s job is not to find and connect with founders, but to understand what matters to that person, determine whether a transaction could support those priorities and earn the right to continue the conversation. You cannot start that relationship with a “canned” email.

We saw this firsthand in a recent transaction involving a family-owned business. Different family members had different ownership stakes, leadership responsibilities and perspectives on what should happen next. They went from being unsure whether they should pursue a transaction to figuring out what a transaction would need to look like for everyone involved.

Earning this family’s trust began at our first email. Real people run businesses, and they want to work with other real people when making decisions that affect those businesses. Technology only gets you so far.

For example, a spreadsheet can show a founder what a transaction might be worth, but it can’t look them in the eye and answer what happens to their employees, walk the shop floor to understand why the business operates the way it does or build confidence between a founder and a potential investment partner by hosting an in-person meeting.

That’s why Charles Aris Transaction Services still operates in ways that can look old-fashioned.

We pick up the phone. We customize our outreach. We stay politely persistent. We use technology to improve our research and prepare for better conversations, not to remove people from those conversations.

At Charles Aris, we often say steady is smooth and smooth is fast. That mindset fits founder-led M&A particularly well. The goal is to move at the pace required to build trust, understand what matters and create a transaction both sides can stand behind.

For something as personal as selling a business, the path to a successful deal may still begin with something remarkably simple: a phone call and a handshake.