During the first few years of investing, I learned some of the basics. The first is mutual funds are a collection of investments in multiple companies to reduce the risk of any single company going out of business. Remember Enron and WorldCom? While mutual funds are mathematically guaranteed to never have the best performance, they are also mathematically guaranteed to never have the worst performance. Mutual funds seek to provide the market return of their investment objective. For example, an S&P 500 mutual fund seeks to track the performance of the top 500 companies by net worth (i.e. market capitalization). When the news talks about the stock market going up or down, they are usually referring to the S&P 500.
The next thing I learned about is asset allocation. Asset allocation is the percentage of stocks / bonds / cash that you hold in your portfolio. The most important decision you can make that affects the outcome of your investment strategy is your asset allocation. A 100% stock portfolio provides the highest returns over time, however it has the possibility to lose the most amount of money. A 100% cash portfolio typically provides the lowest returns over time and has the least probability of losing money. A mixture of stocks and bonds provides the investor the capability to rebalance when your portfolio's actual asset allocation deviates from your target asset allocation. A 60% stock / 40% bond portfolio is a very popular asset allocation for getting good returns with lower volatility / risk.
In general, a younger person has more time to invest and should be invested more in stocks for growth, while an older person who has less time to invest should be invested more in bonds / cash for stability. This is a simplistic view of asset allocation and is sufficient for an investor who is just starting out.
Let's say you invest $1,000 each in stocks and bonds. After a year, your stocks are worth $1,100 and your bonds are worth $1,050. To rebalance, you take $25 from stocks and invest in more bonds, effectively forcing you to sell high and buy low. You can rebalance based on a certain time interval (e.g. on your birthday) or when your asset allocation deviates from your plan by a certain percentage. The optimal rebalancing strategy varies depending on your actual portfolio holdings. You can backtest different strategies to see what has worked well in the past.
Later in life, I learned there are better ways to look at asset allocation to create a risk adjusted portfolio to mitigate risk. This allows you the opportunity to outperform a 100% stock porfolio with less risk if you choose the correct bonds and rebalance at 1% deviation from 60/40.
After changing jobs in 1999, I was eligible to rollover my 401k to a traditional IRA (Individual Retirement Account). There was a local money matters radio show that I listened to on Saturday mornings. I had been listening to it for a couple of years and I thought the guy was a straight shooter because he said his company does not charge any "wrap account" fees that his competitors charged, and he doesn't use funds that charge 12b-1 marketing fees, so it made him look like a stand up guy that told the whole truth. Not knowing any better, he helped me rollover my 401k into loaded mutual funds with Massachusetts Investors Trust, the company that invented the mutual fund in 1924. The financial planner also opened taxable accounts in my name with other loaded mutual funds from several other companies. The financial planners were really nice people and filled out all of the investment forms for me, all I needed to do was sign where the stickers were and cough up the money. Looking back on this, I should have figured out that anyone who makes something really easy for you must really be benefiting from the transaction. A few years later, this financial planner also sold me a variable annuity product, which I later found out was a really profitable deal for the financial planner.
In December 1999, I created Portfolio Tracker to track my own portfolio. The tracker was private and it allowed me to enter stock symbols and shares. Every evening after the markets closed, I would fetch stock quotes off of Yahoo! Finance and update my database and send out a text message with my portfolio total and how much it changed that day. I shared the web page with my friends and they were able to track their portfolios too. It wasn't until 2014 that Portfolio Toolbox was created. In 2020, this web site got a major upgrade when COVID-19 hit and I had some time on my hands to learn responsive web design and Google Charts. Portfolio Tracker is now available to the public.
In March 2000, the dot com bubble burst and the NASDAQ lost 78% of its value through October 2002. This was my first real bear market. Luckily, I was in my accumulation phase and I got to buy stocks "on sale". September 11, 2001 was another catalyst to drive the market even lower. I stayed the course and was able to recover my portfolio because I didn't sell anything.
A major reason for the dot com crash was companies spent $2 trillion worldwide investing in technology companies to prevent the Y2K problem. The Y2K problem needed to be fixed because a number of computer programs used two digits to store the year instead of four, and it broke logic of programs when the year rolled over from 1999 to 2000. The Y2K problem was largely a non-event however. This is mainly due to the fact that $2 trillion was spent on new hardware and software to solve the problem, so what did you expect? In the five years following the year 2000 many companies were still depreciating the cost of new hardware in their environments and very little capital was spent on technology as a result.
As the years went by, I did my best to max out my 401k contributions at work and opened a Roth IRA and maxed it out as best I could. One of the recommendations my financial planner gave me was to always defer taxes. This meant maxing out my 401k to reduce taxes and invest more. This is a core tenet of my investing strategy to this day. While avoiding taxes completely is impossible, minimizing taxes is a simply a goal. If you are saddled with a huge tax bill because of investing, you should be happy because you actually made money. (just make sure you set aside some of your profits to pay taxes!)
After several years with multiple investment companies, account statements and dividend taxes to pay, I was thinking to myself, there has got to be a better way. Moving money between investments? Forget about it! My investing situation had become too complex. Even though I invested into loaded mutual funds, I avoided the front end fee because they put me in class B shares which had no upfront load to invest. There was a catch though, a CDSC (Contingent Deferred Sales Charge) is assessed if I withdrew money before seven years was up. I put together an expenses web page that visualizes the impact of sales charges and expense ratios in an attempt to disuade others from getting involved in loaded mutual funds. There are plenty of no-load mutual funds available which don't charge loads for the privilege of investing with their company. (and they typically outperform loaded mutual funds to boot!)