Joe Saul-Sehy was a financial advisor for 16 years. His new website, Stacking Benjamins, launches today. What’s it like to be financial planner for people from diverse walks of life? Our guest blogger shares some “unique” stories…


What did I hate about being a financial advisor? That’s easy: Neurotic clients who knew nothing about the financial world and didn’t want a teacher…they just wanted someone to blame.

My second favorite question? What did you like best? That’s nearly as easy: I loved the diversity of people who walked into my office every day. One hour I’d be sharing my client’s vacation pictures of India or the Canadian Rockies, and an hour later, I’d be hours away from another client’s retirement, reviewing pension documents.

What I didn’t understand initially (but also why I loved the job) was just how absolutely diverse the job would become. Here are five of my favorite examples:

The Stripper

First of all, let’s get this out of the way: she was extremely attractive, even without makeup. When she walked in, she didn’t want to tell me what she did for a living. In fact, for the first several minutes, she lied about working for some machine shop. When she didn’t know anything about “tier 1, 2 or 3” or the major auto manufacturers in the area I knew it didn’t add up. That’s when she came clean: she worked as a dancer in a club and made uber amounts of money. Mondo money. Mucho money. She’d been wasting every dollar like every other dancer in the club but wanted out. She wanted to get her financial house in order.

A boyfriend came with her. They’d met at the club. He was a complete tool (surprised?), and in discussions with him later, he talked about trying to get his act together. Sadly, as part of this project to find himself, two years after we initially met he joined the army, was shipped out to Afghanistan and was killed in his second week. He and the stripper had already broken up long before. He had been heartbroken by the breakup, but she had moved on.

Her name was Sarah but she went by the stage name Alexa. She slept in every day and felt bad that she had to tan because she missed the sunlight. Most of the time, she said, she felt like a vampire because she finally opened the curtains just a few hours before the sun went down…and then only long enough to get ready for work.

One good story about Sarah and her boyfriend: we were reviewing their budget and trying to clean it up. One $400 line item said “entertainment.”

Me: What’s this, cable?

Sarah: (shifting in her seat) No. It’s just entertainment.

Me: Yeah, but it’s $400 and we might be able to lower that number. Let’s break it apart. What’s in that $400.

Dude: Should we tell him?

Sarah: (withering look to dude)

Me: Tell me what?

Sarah: I told him you’d wonder what that was.

Me: What is it?

Dude: Well….

Sarah: I don’t think….

Me: Is it like every subscription channel on earth plus XM Radio? What is it?

Sarah: It’s pot.

(I’m painfully slow. I shook my head. Clearly I was lost. What in the world was she talking about?)

Sarah: (Slower) It’s pot. We spend $400 a month on weed.

At least they’d budgeted the weed. I’d never seen that before.

The Goat-Hair Collectors

Speaking of pot….

“So, what do you do for a living?” I asked the absolutely bizarre couple sitting across the table from me. They wore Jamaican style afghan caps and he had on a brightly colored rock and roll tee shirt. The guy had an unkempt dark beard and the woman was frail and wore a flowery sun dress. I was sure they made a living following the Grateful Dead.

Boy was I wrong.

I was a new advisor. In those days we’d go into meetings with a trainer who’d been in the business for at least a year or two (VERY experienced). Initially they did all the talking. Later on, I talked and they only interjected when it was clear I was spinning my wheels.

Kelly was a good trainer who knew what she was doing in meetings. She was also absolutely hilarious and loved a good joke.

In this meeting I’d presented Kelly as “an associate” who’d be in the meeting because getting two opinions was better than one. I was pretty good at “the pitch.” Here’s the way it worked: you started by asking about them and their goals and then listening. I knew (from my training) that this was a competitive advantage of good advisors. Most of the hacks talked first, selling a bunch of stuff that the client had no interest in purchasing. First you asked questions and listened, then, when you made your pitch, it was shortened to only the parts clients were interested in hearing.

I still think it was a pretty brilliant approach, and it’s still the reason why I prefer to listen first whenever I’m pitching anything….ever.

Jamaican cap guy: We help make wigs. It’s a living.

I looked at the sheet he’d given me. It was a good, nearly six figure living. “Wow! I’ve never met anyone in the wig industry. How do you make a wig exactly?”

Flowery woman: We don’t make them. We just collect the stuff for them.

I looked up. I could feel the eyes of Kelly, sitting next to me, lift also.

Me: What do you do, go around to barber shops?

Jamaican: No, we go to fields and barns.

Kelly: (not able to control herself) For wigs? BARNS?

Flowery woman: Yeah. We collect goat hair.

Kelly: Not human hair?

Flowery woman: No, goat hair. We have a bunch of different farms we visit and get the goat hair for wigs.

I can’t really remember the rest of the story because Kelly kicked me hard under the table. She was trying hard not to laugh at these people’s career, but even more, she was hoping to make me laugh out loud. I know what you’re thinking. It was rude and I’m still embarrassed that we were acting like 15-year-olds. But the rest of the meeting as we talked, Kelly kept kicking me under the table, trying to get me to laugh.

Believe it or not we didn’t proceed very far with that couple.

The Farmers

I worked with a farming family that everyone in the area knew. Not only did they operate a working farm, but they had this huge retail operation, complete with a retail store, a tractor to ride on and pick your own pumpkin, a corn field maze, and petting zoo. Families and classes made field trips to this place. It was neat. I couldn’t believe they were in my office.

When I asked about their budget, they frowned.

Mrs. Farmer: Budget? We just spend money as we make it. We really don’t make much money.

Me: About how much do you spend?

Mr. Farmer: I play a little golf, especially in Florida.

(Florida? We were in Michigan. Golf? No money?)

Me: Florida? That’s nice.

Mr. Farmer, with a look at Mrs. Farmer: Well, we manage to scrape by and go. The golf is cheap.

Me: How about investments?

Mrs. Farmer: That’s why we’re here.

Mr. Farmer: We don’t have many investments.

Me (thoroughly confused): You have this huge operation at your house. Heck, I’ve taken my kids to your place every year for the last three Halloweens. You don’t have any money?

Mr. Farmer (glancing quickly toward Mrs. Farmer, who is obviously avoiding Mr. Farmer’s glance): You’ve heard the joke about the farmer who wins the Powerball?

Me: No.

Mr. Farmer: He farmed it until the Powerball money was all gone. We lose money every year.

I couldn’t understand it. How did they stay in business?

Oh, did I learn how they stayed in business. Never officially…but I soon realized they were living on hard, cold cash, scraped out of the till! These people made uber-amounts of money! They had cash all over the place! I soon figured out that money magically appeared whenever we needed it. New car? Cash (salesman’s dream). Florida? Cash. That swimming pool behind the house? Cash discount.

I never felt completely comfortable and was glad when they moved away after selling their farm a couple years later.

The IRS Negotiator

How’s this for a cool job?

Me: What do you do?

Client: I interface with the IRS every day for (major car manufacturer). We negotiate on taxes.

Me: Wow! Really? That’s gotta be fun.

Client: It actually is. We get to work in the grey area of the tax code. Most of our discussions end at, “I’m going to have to sue you to find out where the line is here”…so we spend a fair amount of time in court.

Me: With the same people at the IRS?

Client: With the same people. This isn’t like suing your neighbor. There’s no animosity. We’re just asking the court to figure out the line between what we owe and what we don’t.

I couldn’t figure out why in the world this client hired me. They were beyond competent with their money. Heck, I couldn’t figure out why many of my executive clients hired me…until I realized something I’m still proud of: they wanted a competent person in their corner because they didn’t have time. Sure, they had the expertise, but they couldn’t do everything…so they hired me.

The Television Anchor

During the nine years I was at the television station I made friends with many people there, and several of the personalities became clients. What I saw appalled me.

Me: How much is your lease payment for this (big nice car)

Anchor: $950 per month

Me: (cough)

Anchor: I know. They told me I was going to get a deal. I got sold.

Me: Yeah. Let’s get out of it.

Anchor: I’ve already tried. I’ll be upside down on the thing.

Me: That huge payment is mostly interest?

Anchor: Yeah. I was in a hurry. It’s awful. Take a look at my mortgage….

Me: (after reading the contract) Who sold you this thing?

Anchor: My brother-in-law.

Me: He socked it to you good. You have a prepayment penalty and a huge interest rate you can’t get out of.

In short, my anchor client was being used by incompetent family members and friends. Because the anchor was in a hurry but was famous, people agreed to “help” all the time. At some point, the anchor had to trust someone, right? Unfortunately, these “advisors” were cashing in at my new client’s expense. Even after we sorted out their financial situation, I still felt bad when I left financial planning…more than many, these people really needed my help. The IRS agent would do fine on their own. This celebrity? Not so much.

I’d hate to live in that world. You’re busy, making a ton of money, and because you’re a local celebrity you’re a target for every hack around. I started off in television wishing I could be that person and later realized just how miserable an existence this must be. You really do live in a fishbowl. I can’t imagine how film stars keep their sanity.

You Don’t Have It Bad!

I felt lucky to work with people from many, many walks of life. My job was a constantly revolving door of new, interesting situations. I never knew who was going to walk into my office next, and whether we were going to talk about pot, expensive leases, farming, or goat hair.

The next time you think you have something weird going on in your life remember these people…..maybe your stuff isn’t as messed up as you might think!

What’s your craziest money madness story?