As I write this, the Dow is crossing 30,000 for the first time in history. Since all meetings today are on Zoom, I’ve had the pleasure of working from home. I’ve tried to celebrate this market achievement with my kids, but they just don’t seem all that interested. My wife is exhausted from overseeing our youngest’s virtual learning experience and my social media streams are a cross current of current events and holiday memories. Many of the folks I’ve known in the business over the years are pursuing other interests and tonight’s dinner plans with friends have just been cancelled due to a positive COVID test of a friend of a friend.

I thought it worthwhile to sit down and pen some thoughts on this historic day which, let’s face it, doesn’t quite feel all that historic within the context of financial progress.

I apologize in advance if I’m reaching to try and find something, anything positive about this year that just doesn’t seem to want to end.

Here are just some musings I thought you may find interesting over my financial journey.


  • In 1987 I was 10 years old and my father had been a stockbroker since 1972 with Merrill Lynch. Earlier that year we had spent two weeks in Maui and by October the market was up over 30%. The gap between sipping on virgin daiquiris and October is a blur, but not Monday October 19th. That day I will never forget, as by week’s end we knew something in our lives was forever different. This was the first year we bought winter jackets at the secondhand store and my first experience with really understanding risk. The Dow’s low was 1,616.


  • In 1989 I was 12 and received my first shares of McDonalds stock. This was life changing for me and began my love affair with investing. I sure wish I held those shares today. That was a terrible early sell. The Dow was 2,500.


  • In 1996 I step foot on the Kentucky campus and by 1997 I was trading stocks between classes in my dorm. I would use my dial up service and had a brokerage account with Etrade. I would buy stocks posted on message boards I had no clue what they did. By the time I would come in from class I’d make a few hundred dollars. Trading was easy and what a great way to make a quick buck…or so I thought. I always chuckle when I hear people call today a bubble. They have no idea. The Dow was 6,700 and climbing fast.


  • In 1998 I was directly involved in a startup company that wanted to bring travel to the internet. We contracted with local restaurants and hotels to give them an internet presence, allowing people to book reservations and write reviews. I know…I know… we were 10 years early and in a matter of months after 2000, we were out of business. It was my first real lesson in just how much fundamentals eventually always matter. The Dow topped out just shy of 12,000.


  • By mid-2000 I was a stockbroker in my father’s office. If you didn’t get in early enough you didn’t get a desk and therefore didn’t get a phone. This only happened to me once and rather than go home, I spent the day dialing for clients from my car. It was the most trying year of my career and extremely humbling. I learned how to handle rejection and how to persevere. I loved the business but hated selling products. After a year I was determined to go into business for myself. The same person who taught me the business told me I’d never make it.


  • Late 2007 I appeared on CNBC, which kicked off a tenure that has now lasted 13 years. I wore a corduroy jacket that I’m still made fun of to this day. Still not sure why I did that. I’ll never forget sitting in the green room with the then CEO of Potash corporation whose stock had gone from a Canadian Municipality to many billions of market cap in a few short years. “How high do you think it can go?” I asked. “Higher” he replied. Later that night with trading buddies I relayed the story and how I was going to short the stock first thing in the morning. I thought I was a genius, taking a dozen or so points out of the name when it topped around $160. I believe it bottomed around $5 or $6. Another early exit. Sigh. In 2008 the Dow began its 15-month crash, declining more than 50% before settling around 6,000 in March of 2009.


  • Side note, this was around the time I began hearing that the world was truly over this time and never again would we see bull markets. By March of 2010, one year later, the Dow had regained 10,000.


  • From there we went through a Flash Crash, Greece Meltdown, Brexit and now a 35% crash from Covid, yet here we are, 30,0047.95 or the official close on the day we passed a new milestone.

There are volumes of lessons in each and every experience mentioned and countless others I chose to leave out or just don’t remember right now. The one moral of the story, however, is that it has never been profitable to bet against the American progress. While I realize the Dow is not America, it is one of the closest measurements we have of American ingenuity and fortitude. Despite all the challenges we face, I’m pleased to say it is still alive and well.

May you be blessed this Thanksgiving, safe and healthy wherever you may be.