Confessions of an Investment Banker: I Thought I Was Selling Companies…Turns Out I Was Running Group Therapy
I went to school for engineering.
Then I got an MBA.
At no point did anyone suggest I might also need a minor in conflict resolution, hostage negotiation, or family therapy.
That was my first mistake.
Because somewhere between the first CIM draft and the final purchase agreement, I learned the truth:
Investment banking—particularly in the lower middle market—is less about selling companies and more about managing the deeply human, occasionally unhinged, and often spectacularly dysfunctional relationships behind them.
Let me offer a few exhibits.
Exhibit A: The Brothers Who Forgot They Were Brothers
Two brothers. Co-owners. Both in leadership roles.
On paper, a classic family business success story.
In reality? They hadn’t met face-to-face in years.
I didn’t know that when I scheduled the kickoff meeting.
Picture it: conference room, polite introductions, forced smiles…followed by a slow, unmistakable escalation into open hostility. Within minutes, we had gone from “strategic alternatives” to what I can only describe as pre-fisticuffs positioning.
At one point, I made a judgment call that probably wasn’t covered in my training: I physically removed one brother from the room and took him for a walk outside. Not metaphorically. Literally.
We walked. We talked. We cooled down.
Somewhere between the parking lot and the curb, I remember thinking:
I am definitely not billing for this correctly.
It got better.
I later learned these two communicated primarily through email—emails that were, let’s say, not written with publication in mind—and they cc’d employees.
Nothing builds organizational confidence like watching ownership exchange digital haymakers while looping in the finance team.
The twist?
One brother was staying post-transaction. The other was exiting.
Which meant I had to walk a very fine line—perfect neutrality, balanced communication, no perceived favoritism…
Even though, if I’m being honest (and this is a confession), I definitely had a favorite.
Exhibit B: The Two Families, One Company, and a Court Order
If the brothers were difficult, the families were…operatic.
Two families. Each owned 50%.
Also: multiple lawsuits against each other.
Eventually, the court did what courts do when adults refuse to act like adults—it ordered the company sold.
That’s where I came in.
My client wasn’t the company.
It wasn’t either family.
It was the court-appointed trustee.
Which meant:
- Both families wanted information
- Both families called constantly
- And I couldn’t tell either of them anything
Meanwhile, both families were also bidders to buy the company.
Let that sink in.
So here I am:
- Running a sale process
- Bringing in third-party buyers
- Coordinating meetings with management (Family #1)
- While knowing Family #2 is trying to buy the same business
And I cannot share pricing feedback.
I cannot signal bidder interest.
I cannot “read the room” out loud.
It’s like hosting a dinner party where half the guests are trying to buy the house and the other half are trying to burn it down—and you’re legally prohibited from acknowledging either objective.
But we’re not done.
Family #2—the non-operating side—decided they wanted to meet with employees to “share their vision.”
Sure. Reasonable.
Except for the small matter of active litigation, mutual distrust, and the ever-present risk of…influence.
So, every meeting required supervision.
Not casually. Formally.
An attorney and I sat in on these sessions like referees in a highly litigious cage match, making sure no one was:
- coercing
- incentivizing
- or otherwise “encouraging” employees to take sides
I distinctly remember sitting in one of those meetings thinking:
If anyone had told me this job would involve chaperoning family members around their own employees, I might have asked different questions during recruiting.
The Calls. So Many Calls.
Of course, throughout all of this, both families called me constantly.
“What’s going on?”
“What are you hearing?”
“Where do we stand?”
And my answers were consistently some version of:
“I understand the question.”
“I appreciate the interest.”
“I am not allowed to answer that.”
If patience is a virtue, investment banking is where it goes to die.
What They Don’t Teach You
No textbook covers this.
No valuation model accounts for it.
There is no line item in your engagement letter that reads:
“Emotional volatility management – billed hourly.”
But maybe there should be.
Because the reality is this:
Companies don’t get sold.
People sell them.
And people bring:
- history
- ego
- resentment
- pride
- and occasionally decades of unresolved issues
right into the middle of a high-stakes financial transaction.
Final Confession
Somewhere along the way, I realized I probably should have added another degree to the wall.
Engineering taught me how things work.
Business school taught me how deals get done.
But neither prepared me for:
- separating feuding siblings
- navigating courtroom-driven sales
- or refereeing multi-family standoffs while pretending everything is “on process”
If there’s a takeaway, it’s this:
Behind every polished deal announcement is a story no one prints.
And behind many of those stories is an investment banker quietly wondering if they accidentally signed up to become a therapist.
Preferably one with hazard pay.
