From Hawaiian Shirt to Company Mission

How an incredibly embarrassing moment turned into an important realization in my career.

I may be an accountant, but I don’t dress like one.

Sure, I used to. When I first started out in my career, I wore Polo shirts and Dockers. While that may be considered common accountant garb now, believe me, it was frowned upon at the time. The expectation used to be suits and ties, but I bucked that right off the bat.

When my company became distributed, we became even more relaxed. Our accountants would even wear shorts — gasp! But we were working from home, who cares?

In 2014 I was invited to a seminar in San Diego where I met Carl Smith, owner of Bureau of Digital. Carl invited me to speak at another conference in New Orleans just a couple of weeks away. When I traveled to New Orleans, I arrived just fine however, my luggage did not. All I had for clothing was what I had worn on the plane, literally the clothes on my back — a t-shirt, shorts, and tennis shoes — and I was supposed to speak in front of a group of business owners the next day!

Fortunately, there happened to be a mall across the street from my hotel where cruise ships would come in. One of the only clothing stores there was a Tommy Bahamas where they had a lot of Hawaiian shirts on sale (at a very hefty price!). So, I picked out two Hawaiian shirts (since I wasn’t sure when my luggage would come in) and a pair of pants. The first credit card I tried to use got declined because I forgot to let the bank know I was going to be traveling, so I used another one without any issues.

$400 later I left Tommy Bahamas with my tail between my legs a bit. Next, I found a store where I could buy a pair of shoes. This time my second credit card got declined! I pulled out a third card, bought the shoes and went back to my hotel room to relax a bit before the conference geared up.

That night there was a meet-and-greet dinner for the conference attendees. I showed up a little anxious wearing my Hawaiian shirt, new pants and shoes. I wasn’t sure what everyone else was going to be wearing but it turned out that I blended in just fine. Everyone else was dressed casually and didn’t think anything of it. I was feeling great — I was comfortable and getting to know people. As everyone was paying for their meals, I thought I’d pick up the appetizer for everyone, being the finance guy and all.

Turned out, the third credit card…got declined. There I was — no cash and no credit cards left!

Red-faced, I turned to the guy next to me, who I’d never met before, and asked if he could pick up my meal and the appetizer I told everyone I’d get. I promised to pay him back and threw in, “Oh, and by the way, I’m the one doing the finance talk in the morning!”

I called all of the credit cards and got them all released that night, went to the ATM and brought my new hero cash for the meal he’d paid for. It worked out fine, but it was extremely embarrassing.

As I started my presentation that day, I told everyone the story. It ended up being a humorous way to introduce myself before going into my presentation about how to be profitable.

Despite the embarrassing snafu, Carl invited me to speak at another conference in Chicago in another couple of weeks. With Chicago being just a 3-hour drive from me, I didn’t have to worry about luggage this time. When I show up for my presentation in my usual Dockers and Polo, Carl was a bit surprised. “Dude, what are you doing? Where’s your Hawaiian shirt?” he asked me.

It was that moment when I realized it was the Hawaiian shirt that had set me apart. I wasn’t seen as a boring, stuffy accountant. I was on the same level as everyone else and I was relatable. To this day I continue to wear Hawaiian shirts almost daily. It’s a constant reminder to me and my team of our mission: Changing the way people think about accounting!

Summit CPA is a distributed accounting firm with a non-traditional approach to accounting. We have an amazing team of CPAs and accountants who provide professional Virtual CFO Services and 401(k) Audits for companies all over the United States — many of which are remote companies as well. We fully understand the accounting, bookkeeping, cash flow management, and business tax nuances that come with being distributed, and we love helping our clients overcome these challenges through our own experience and expertise.