This shouldn't be difficult.

Every time I get used to things, the things change. 

First it was the dot com boom. I was a few years out of college. Felt like everyone I knew was getting rich. I went to school with someone who joined the marketing department at Pets.com. He was rich. He was "bought a boat at 25" rich. I was a bit skeptical, sitting in a cubicle at a job that still required a tie. But looking around at the time it was pretty easy to make the case that things had changed. There was a new normal. It was different this time.

I wanted to be rich too. So, I rode the wave. Cisco, eToys, yes, even Pets.com. Anything that George Gilder wrote about. I won't bore you with details about how that worked out. Let's just say that neither my friend nor I had a boat at 30. I was only just beginning to accept the new normal when that new normal changed.

A decade later, my focus was mostly on banks and banking. Another friend (not the guy from Pets.com) was working for a little boutique investment firm. Nothing prestigious.  It wasn't even based in New York!

My friend and I used to talk markets a lot. He was hell-bent on this fringe conspiracy idea that what was going on at the banks was going to blow up. He talked about credit quality, liar loans, all sorts of crazy stuff. He tried to sit me down and tell me what was going on. I listened, at least a little. But he also seemed to be leaning hard on the past, making it sound like things don't change. He seemed to totally discount the idea that maybe this was the new normal. And his side was losing money at the time. 

I mostly ignored him and kept riding the wave. A couple of years later everything he was trying to tell me was chronicled by Michael Lewis. This friend still has his boat. He could probably afford two if he wants. I still don't have a boat.

(Not actually his boat.)

It is really hard to time the market: To know when to buy and when to sell. To make it work, you have to predict the future not once but twice. You need to know when to buy and when to sell. It's not impossible. There are surfers all over California that can read the waves better than most, and ride them better than most. There are probably people who can read markets better than most as well. But they are as rare, perhaps rarer, than championship surfers. For most of us investors, riding the wave is nothing more than a short-lived joy ride.

In June 2011, a guy named Brad Jacobs invested some money in an obscure freight and logistics company called Express-1 Expedited Solutions. No one cared. There was no reason they should. It was $150 million. In logistics. Later that year I randomly was connected to Jacobs to chat about his plans for the company. His plan wasn't glamorous at all. There wasn't anything to suggest he was going to pivot to some wild new tech like space trucks or flying cars or whatever and in doing so build the next Microsoft or next Apple. I had no premonition that this could turn into a fantastic wealth builder. But what Jacobs said, it just made sense. 

I bought a small piece of Jacobs' company, rebranded as XPO Logistics, first chance I got. Not expecting more than I was expecting from any other investment. I didn't even follow it all that closely, beyond professional responsibilities. There were many cooler, more clever stocks in my portfolio that took up most of my attention. 

As for Jacobs, the next 10 years or so went pretty well. And I am lucky to have gone along for the ride.

My name is Lou Whiteman. I have been involved in various ways with Wall Street, finance, private equity, and investment banking for the better part of 30 years. I'm nothing special. I went through half a dozen majors in my first three semesters of college, finally settling on one that required little to no memorization and therefore allowed for plenty of time for socializing. My senior year I was forced to get an internship, and the local business journal was the first interview I got. That was my introduction to high finance. I wasn't first in my class; I certainly wasn't a wizkid trader at 14. 

But what I've learned, and what the XPO story is a good reminder of, is that a lot of times less is more. The slacker individual investor who doesn't trade in and out of things at a rapid pace actually has a huge leg-up on the pro. Set it and forget it actually works better than overthinking. Brad Jacobs wasn't lazy. He had a lot of work to do. There are ups and downs on that chart. But for investors, the best thing to do was to find Brad Jacobs' company and be lazy: Do nothing. 

Today I'm riding out the end of my 40s semi-employed, with the luxury of doing fun stuff and saying no to things that don't look fun. I get to say no a lot. It's a good life. I'm not here because of my credentials. I'm not here because I have figured out the secret formula of investing success. I have no magic pill to sell you. 

I'm here because, for lack of a better word, I'm a lazy investor. A slacker. Boring. I don't want to work too hard. I want to find something good, put it on autopilot, and go do other things. And every person reading this has the ability to get there too. It is one part mindset, and one part finding the stocks that are doing more than just riding the waves. Not every one of the stocks in my portfolio will work out like XPO. But a few of those go a long way towards making nothing else matter.

I used to think that every time I got used to things, they changed. But it turns out I was just focused on the wrong things. The better plan is to try to recognize the waves, to realize that even when things look like they really are different this time and there really is a new normal, that's almost always not the case. If it isn't different this time, we are better off focusing on the things that are consistent at high tide and at low tide. 

Fits and Starts is an ongoing conversation with myself, and the markets, about the waves, and about finding things that will still be there when the wave has passed. The goal is to help me to not get caught out on the break trying to pretend that this time, I am an expert surfer. Hopefully by writing it all down it can be useful for others as well. 

Disclaimer: Fits and Starts DOES NOT provide financial advice. All content is for informational purposes only. Stocks mentioned are as reference only, and a mention should not be interpreted as a buy or sell recommendation. The author is not a registered advisor or a broker/dealer. DO YOUR OWN HOMEWORK.