Tales From the Trenches: 9 Funny Stories I Couldn't Make Up

Sometimes you live through situations you simply can’t make up. They become the stories you tell over and over again.

During my career, I spent 14 years and an advisor and six in management. We give the best advice we can. Sometimes it has its funny side.

Here are a few highlights in the sales or prospecting process I will never forget.

My First Prospecting Call

I was new in the business. At the time, everyone cold called; there were few other prospecting alternatives. You built a list and started dialing, often working into the evening.

On my very first prospecting call, I gave my name and where I worked. The fellow replied: “I’m not interested and that’s the name of that tune!” Click.

Somehow I managed to pick up the phone again and again.

How I Realized Managed Money Was Perfect for This Client

When I got into the business, financial advisors still recommended individual stocks and municipal bonds paid returns in the double digits. I had a client who invested in individual stocks on my recommendations. He usually came into the office, and I would take him out to lunch from time to time. 

He owned a series of stores, so I decided to meet him at his main location, where he maintained his office. It was in a bad part of town. I noticed that the parking area had a high wall topped with razor wire. I also saw that the gates into the parking area were padlocked.

I parked the car within a line of sight to his office, so I could keep an eye on it.

After the portfolio review was done, I asked a few questions. “You are in a cash business. You are in an unsafe neighborhood. Have you ever been robbed?”

He thought a bit and in a relaxed, conversational voice said: “You know, I was robbed once. I had the days cash takings in a brown paper bag. This guy ran up to me, knocked me down, grabbed the bag and ran off. But he dropped the bag when I shot him!”

I paused for a moment, thought and then said: “Let me understand this right. You had money. This guy did something that caused you to have less money. Because you had less money and felt this guy was responsible, you shot him. Do I have that right?”

At that moment, this client became a prospect for managed money on our separately managed accounts program. If anything went wrong, I wanted to be on the same side of the table, or at least running alongside him.

The Hard-of-Hearing Client

Our branch office was located on the ground floor of an office building. I had inherited a client who owned a several apartment buildings, and our office was convenient for him because we were close to the Landlord/Tenant Court.

He was hard of hearing. He also bought municipal bonds. From time to time he would buy bonds, and when they matured he would come in to pick up a check for the proceeds. Sometimes the check was not ready because the cashier had other things to do. He would be standing by the cashier’s window yelling “Where is my money? I want my money!” in a loud voice.

You can see the obvious problem in a brokerage office when other people are sitting with advisors in an open floor plan discussing investments.

I learned to ask him to sit alongside my desk, and when he raised his voice too high, I would hold my hand out, smile and move my hand back and forth in a downward motion. He would lower his voice. I would send him to the window when his check was ready.

The Card-Cutting Client

I had a father and son pair of clients who were joint tenants on a brokerage account. The son liked to trade stocks. I would make suggestions but soon realized he picked his own stocks. That was fine with me.

We would talk on the phone. He would say he wanted to buy a stock, lets assume it was Ford. I would ask how many shares and the line would go quiet for a moment, and he would return, saying “Buy 300 shares.” 

This went on for quite some time until one day I asked him about the pauses. He explained: “I cut cards to determine how much I am going to buy. But if a black Jack comes up, we can’t buy Ford that day.”