The Best and Worst Investment Decisions I’ve Made

Today, I’m going to share stories about my best and worst investment decisions. But don’t worry, this isn’t just a brag-and-cringe session about making or losing money. These stories are about the valuable lessons learned, and how these adventures in investing helped shape my current approach. 

The Best Investment Decision

In investing, you don’t get extra points for creativity or difficulty. A million dollars earned while you are smiling buys as many potatoes as a million dollars that cost you your marriage and hair.

However, from a personal, creative satisfaction perspective, our investment in Uber was one of our best. That’s not to say that it has been the most successful decision from a financial perspective, at least not yet.

Uber doesn’t fit into the traditional value stock category. Until 2023, the third year of our ownership, it never made money. It was a stock everyone hated. After we bought it, I had clients reach out to me asking if I had been kidnapped and someone else was making these purchases of Uber.

We bought more shares very opportunistically during and after the pandemic. I wrote a long research report on it, which you can read here.

On one hand, Uber’s switchboard is a digital business, but the company also has a physical presence in thousands of cities, which incurs costs (the analog side of the business). Additionally, the availability of cheap money caused the ride-share market to go crazy and act rationally irrational, as competitors jostled in a land grab.

My thesis consisted of several insights:

1. Unlike traditional-tech, digital-only companies, Uber is a hybrid, both digital and analog. Thus, its cost structure is much higher than that of other companies. This, in part, explains the higher losses.
2. It has a strong brand; its name has become a verb.
3. The rideshare market is inevitable and will only continue to grow. Uber is not just in competition with taxis, second cars, or seldomly used cars; it is also in competition with the favors we ask of friends and relatives, such as dropping us off at the mechanic or picking us up from the doctor’s office.
4. Uber has global scale, which its competitors lack, allowing it to spread R&D across more markets.
5. As its revenue grows, each incremental dollar comes with a very high margin, which directly drops to the bottom line. Therefore, at some point, its earnings will explode to the upside as fixed costs stop growing, allowing it to scale.

The Uber story is not over; we still own the stock. I don’t want to do a celebratory dance. But this idea came with a lot of creative satisfaction. There is another point of pride here. Despite our very tumultuous ownership of this stock, we remained rational (I have written about that here). We bought more when it became extremely undervalued, and I would be lying if I said that was psychologically easy – it was not, but we followed our research and process.

The Worst Investment Decision

My worst investments that resulted in losses had several things in common: They were low-quality companies; their financials were complex and not transparent (for instance, one-time items were labeled as “one-time” every quarter); and they had questionable management. 

However, they were all considered “cheap”… until they were not. Now, I hope you see why I am dogmatic about quality. 

However.

When you are wrong on an investment and you lose money, the most you can lose is 100%. I have learned a lot from those. But they were not my worst investments. Those were the ones where I left 300–400% on the table when I sold too soon. Let me detail two examples.

EA – Electronic Arts

We bought EA in the early 2010s. I wrote about it – you can read my investment case for it here. To sum up, games were moving from being sold in stores to being digital downloads, which would lead to higher margins (don’t have to pay for packaging and Best Buy to sell them). The market for games was exploding, as every adult and teenager had a gaming device in their hands – a smartphone. The market for video games was going to be much larger. EA was the largest player in that space, with great franchises.

The following two years of ownership were very painful. EA had a few big game flops, and the market did not care about improving fundamentals. The stock kept declining. We continued to buy more. Every time we bought more shares, the stock fell further. Fast-forward a year or two. The stock doubled from our original purchase, but I was mentally exhausted. I did a celebratory dance and sold the stock. The stock then went up another 4x within a few years after we sold it. It went up for the right reasons – its earnings exploded to the upside, in line with my original thesis.

The sale was a mistake, not because the price went up but because I let frustration over the stock-price decline (volatility) get to me. Investing is a mental game. I learned from this adventure that it is important to zoom out and not obsess over individual stocks in the portfolio. This is why we have a portfolio. It was a very costly but educational mistake. Our ownership of Uber was not a walk in the park, either – just look at the stock price over the last few years. But I had learned my lesson from EA and was able to do the analysis, update our model, and zoom out.

In investing, there is a big difference between intellectual and tactile knowledge. I am going to go PG-13 on you for a second and quote the irascible Charlie Munger: “Learning about investing through a model portfolio is like learning about sex through romantic novels.” A big part of investing is observing yourself as an investor – your thoughts and emotions as you ride the actual rollercoaster of owning a stock.

I also made an important modification to our process.

We always value every company in the portfolio on earnings (free cash flows) at least four years out. Why four years? Three seems too short. There is no magic in this number, other than it being longer than most analyst estimates. We do this for all stocks in the portfolio, and then the total return for each is calculated and annualized. If a company has strong growth potential, it may appear to be expensive based on current earnings; but in reality, it may actually be cheap based on earnings projected four years from now.

On the other side of the spectrum, a company that has no growth or dividends may seem “cheap” based on its current earnings multiple, but this cheapness may quickly dissipate once a total return is calculated using future earnings. Time is on the side of growing businesses and the enemy of the ones that stand still. Therefore, a non-growing or slow-growing business needs a much greater discount (margin of safety) to secure a spot in our portfolio.

I want to stress another point. We sometimes sell a stock and then it goes higher. If we sold it for the right fundamental reasons, this doesn’t bother me. There is very little to learn.

Twilio

I’ll give you another crazy example. We bought Twilio at $25 in 2017 or so. Our thesis was that they had built the largest digital telecommunications network, which gave them a brief competitive advantage. They were also spending 5x more on R&D than competitors to build applications around this network, which would give them long-term advantages.

The stock price went up to $60 in a few months without anything significantly changing, so we sold a third of our position. Then it went up to $90, and we sold some more. To our disbelief, we sold the rest at around $120, a bit before the pandemic.

During the pandemic, Twilio’s price hit $400. I had zero regret about not holding on to the shares. Absolutely none. Twilio’s profitability did not match the stock market’s opinion of its price. Twilio’s stock price was as crazy to me at $250 as it was at $300 or $400. After reviewing our models, we concluded that even $120 was at the extreme end of our optimistic assumptions. Fast-forward to today, where the stock is at $60 or so. We are currently sharpening our pencils, but we have not bought the stock – yet.

Selling EA was a mistake; selling Twilio was not.

Key takeaways

• My “best investment decision” with Uber wasn’t just about financial gains, but the creative satisfaction it brought. It taught me the value of sticking to our research and process, even when it’s psychologically challenging.
• The worst investments often share common traits: low-quality companies, complex financials, questionable management, and the illusion of being “cheap.” This reinforces my dogmatic stance on prioritizing quality.
• Sometimes, the costliest mistakes aren’t the ones where you lose money, but those where you leave significant gains on the table by selling too soon. My experience with EA taught me this lesson the hard way.
• There’s a crucial difference between intellectual and tactile knowledge in investing. Actually owning stocks and experiencing the emotional rollercoaster is invaluable for developing as an investor.
• Selling a stock that later increases in value isn’t always a mistake if the decision was based on sound fundamental reasons. My experience with Twilio illustrates this point – sometimes it’s right to sell even if the price continues to climb.