17 investing lessons learnt from managing my family's portfolio for 10 years

Nine years, seven months and six days . This is how much time has passed since I started managing my family’s investment portfolio of US stocks on October 26, 2010.

19.5 per cent versus 12.7 per cent. These are the respective annual returns of my family’s portfolio (without dividends) and the S&P 500 (with dividends) in that period.

I will soon have to say goodbye to the portfolio. Jeremy Chia (my blogging partner) and myself have co-founded a global equities investment fund.

As a result, the lion’s share of my family’s investment portfolio will soon be liquidated so that the cash can be invested in the fund.

The global equities investment fund will be investing with the same investment philosophy that underpins my family’s portfolio, so the journey continues.

But my heart’s still heavy at having to let the family portfolio go. It has been a huge part of my life for the past nine years, seven months and six days , and I’m proud of what I’ve achieved (I hope my parents are too!).

In the nearly-10 years managing the portfolio, I’ve learnt plenty of investing lessons. I want to share them here, to benefit those of you who are reading, and to mark the end of my personal journey and the beginning of a new adventure.

I did not specifically pick any number of lessons to share. I’m documenting everything that’s in my head after a long period of reflection.

Do note that my lessons may not be timeless, because things change in the markets. But for now, they are the key lessons I’ve picked up.

Lesson 1: Focus on business fundamentals, not macroeconomic or geopolitical developments – there are always things to worry about

My family’s portfolio has many stocks that have gone up multiple times in value.

A sample is given below:

Some of them are among the very first few stocks I bought; some were bought in more recent years. But what’s interesting is that these stocks produced their gains while the world experienced one crisis after another.

You see, there were always things to worry about in the geopolitical and macroeconomic landscape since I started investing.

Here’s a short and incomplete list (you may realise how inconsequential most of these events are today, even though they seemed to be huge when they occurred):

• 2010 – European debt crisis; BP oil spill; May 2010 Flash Crash
• 2011 – Japan earthquake; Middle East uprising
• 2012 – Potential Greek exit from Eurozone; Hurricane Sandy
• 2013 – Cyprus bank bailouts; US government shutdown; Thailand uprising
• 2014 – Oil price collapse
• 2015 – Crash in Euro dollar against the Swiss Franc; Greece debt crisis
• 2016 – Brexit; Italy banking crisis
• 2017 – Bank of England hikes interest rates for first time in 10 years
• 2018 – US-China trade war
• 2019 – Australia bushfires; US President impeachment; appearance of Covid-19 in China
• 2020 (thus far) – Covid-19 becomes global pandemic

The stocks mentioned in the table above produced strong business growth over the years I’ve owned them. This business growth has been a big factor in the returns they have delivered for my family’s portfolio.

When I was studying them, my focus was on their business fundamentals – and this focus has served me well.

In a 1998 lecture for MBA students, Warren Buffett was asked about his views on the then “tenuous economic situation and interest rates.“

He responded:

“I don’t think about the macro stuff. What you really want to do in investments is figure out what is important and knowable.

"If it is unimportant and unknowable, you forget about it. What you talk about is important but, in my view, it is not knowable.

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"Understanding Coca-Cola is knowable or Wrigley’s or Eastman Kodak. You can understand those businesses that are knowable.

"Whether it turns out to be important depends where your valuation leads you and the firm’s price and all that.

"But we have never not bought or bought a business because of any macro feeling of any kind because it doesn’t make any difference.

"Let’s say in 1972 when we bought See’s Candy, I think Nixon [referring to former US President, Richard Nixon] put on the price controls a little bit later, but so what!

"We would have missed a chance to buy something for US$25 million (S$35 million) that is producing US$60 million pre-tax now.

"We don’t want to pass up the chance to do something intelligent because of some prediction about something we are no good on anyway.”

Lesson 2: Adding to winners work

I’ve never shied away from adding to the winners in my portfolio, and this has worked out well.

Here’s a sample, using some of the same stocks shown in the table in Lesson 1.

Adding to winners is hard to achieve, psychologically. As humans, we tend to anchor to the price we first paid for a stock. After a stock has risen significantly, it’s hard to still see it as a bargain.

But I’ll argue that it is stocks that have risen significantly over a long period of time that are the good bargains. It’s counterintuitive, but hear me out.

The logic here rests on the idea that stocks do well over time if their underlying businesses do well.

So, the stocks in my portfolio that have risen significantly over a number of years are likely – though not always – the ones with businesses that are firing on all cylinders.

And stocks with businesses that are firing on all cylinders are exactly the ones I want to invest in.

Lesson 3: The next Amazon, is Amazon

When I first bought shares of Amazon in April 2014 at US$313, its share price was already more than 200 times higher than its IPO share price of US$1.50 in May 1997. That was an amazing annual return of around 37 per cent.

But from the time I first invested in Amazon in April 2014 to today, its share price has increased by an even more impressive annual rate of 40 per cent.

Of course, it is unrealistic to expect Amazon to grow by a further 200 times in value from its April 2014 level over a reasonable multi-year time frame.

But a stock that has done very well for a long period of time can continue delivering a great return. Winners often keep on winning.

Lesson 4: Focus on business quality and don’t obsess over valuation

It is possible to overpay for a company’s shares. This is why we need to think about the valuation of a business.

But I think it is far more important to focus on the quality of a business – such as its growth prospects and the capability of the management team – than on its valuation.

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If I use Amazon as an example, its shares carried a high price-to-free cash flow (P/FCF) ratio of 72 when I first invested in the company in April 2014.

But Amazon’s free cash flow per share has increased by 1,000 per cent in total (or 48 per cent annually) from US$4.37 back then to US$48.10 now, resulting in the overall gain of 681 per cent in its share price.

Great companies could grow into their high valuations. Amazon’s P/FCF ratio, using my April 2014 purchase price and the company’s current free cash flow per share, is just 6.5 (now that’s a value stock!).

But there’s no fixed formula that can tell you what valuation is too high for a stock. It boils down to subjective judgement that is sometimes even as squishy as an intuitive feeling.

This is one of the unfortunate realities of investing. Not everything can be quantified.

Lesson 5: The big can become bigger – don’t obsess over a company’s market capitalisation

I’ve yet to mention Mastercard, but I first invested in shares of the credit card company on December 3, 2014 at US$89 apiece.

Back then, it already had a huge market capitalisation of around U$100 billion, according to data from Ycharts. Today, Mastercard’s share price is US$301, up more than 200 per cent from my initial investment.

A company’s market capitalisation alone does not tell us much. It is the company’s (1) valuation, (2) size of the business, and (3) addressable market, that can give us clues on whether it could be a good investment opportunity.

In December 2014, Mastercard’s price-to-earnings (P/E) ratio and revenue were both reasonable at around 35 and US$9.2 billion, respectively.

Meanwhile, the company’s market opportunity still looked significant, since cashless transactions represented just 15 per cent of total transactions in the world back then.

Lesson 6: Don’t ignore “obvious” companies just because they’re well known

Sticking with Mastercard, it was an obvious company that was already well-known when I first invested in its shares.

In the first nine months of 2014, Mastercard had more than two billion credit cards in circulation and had processed more than 31.4 billion transactions.

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Everyone could see Mastercard and know that it was a great business. It was growing rapidly and consistently, and its profit and free cash flow margins were off the charts (nearly 40 per cent for both).

The company’s high quality was recognised by the market – its P/E ratio was high in late 2014 as I mentioned earlier. But Mastercard still delivered a fantastic annual return of around 25 per cent from my December 2014 investment.

I recently discovered a poetic quote by philosopher Arthur Schopenhauer: “The task is… not so much to see what no one has yet seen, but to think what nobody has yet thought, about that which everyone sees.” This is so applicable to investing.

Profitable investment opportunities can still be found by thinking differently about the data that everyone else has.

It was obvious to the market back in December 2014 that Mastercard was a great business and its shares were valued highly because of this.

But by thinking differently – with a longer-term point of view – I saw that Mastercard could grow at high rates for a very long period of time, making its shares a worthy long-term investment.

From December 2014 to today, Mastercard’s free cash flow per share has increased by 158 per cent in total, or 19 per cent per year. Not too shabby.

Lesson 7: Be willing to lose sometimes

We need to take risks when investing.

When I first invested in Shopify in September 2016, it had a price-to-sales (P/S) ratio of around 12, which is really high for a company with a long history of making losses and producing meagre cash flow.

But Shopify also had a visionary leader who dared to think and act long-term. Tobi Lütke, Shopify’s CEO and co-founder, penned the following in his letter to investors in the company’s 2015 IPO prospectus (emphases are mine):

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“Over the years we’ve also helped foster a large ecosystem that has grown up around Shopify. App developers, design agencies, and theme designers have built businesses of their own by creating value for merchants on the Shopify platform. 

"Instead of stifling this enthusiastic pool of talent and carving out the profits for ourselves, we’ve made a point of supporting our partners and aligning their interests with our own.

"In order to build long-term value, we decided to forgo short-term revenue opportunities and nurture the people who were putting their trust in Shopify. 

"As a result, today there are thousands of partners that have built businesses around Shopify by creating custom apps, custom themes, or any number of other services for Shopify merchants.

"This is a prime example of how we approach value and something that potential investors must understand: we do not chase revenue as the primary driver of our business. 

"Shopify has been about empowering merchants since it was founded, and we have always prioritized long term value over short-term revenue opportunities. We don’t see this changing…

"… I want Shopify to be a company that sees the next century. To get us there we not only have to correctly predict future commerce trends and technology, but be the ones that push the entire industry forward. 

"Shopify was initially built in a world where merchants were simply looking for a homepage for their business.

"By accurately predicting how the commerce world would be changing, and building what our merchants would need next, we taught them to expect so much more from their software.

"These underlying aspirations and values drive our mission: make commerce better for everyone. I hope you’ll join us.”   

Shopify was a risky proposition. But it paid off handsomely.

In investing, I think we have to be willing to take risks and accept that we can lose at times.

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But failing at risk-taking from time to time does not mean our portfolios have to be ruined. We can take intelligent risks by sizing our positions appropriately.

Tom Engle is part of The Motley Fool’s investing team in the US. He’s one of the best investors the world has never heard of.

When it comes to investing in risky stocks that have the potential for huge returns, Tom has a phrase I love: “If it works out, a little is all you need; if it doesn’t, a little is all you want.”

I also want to share a story I once heard from The Motley Fool’s co-founder Tom Gardner.

Once, a top-tier venture capital firm in the US wanted to improve the hit-rate of the investments it was making. So the VC firm’s leaders came up with a process for the analysts that could reduce investing errors.

The firm succeeded in improving its hit-rate (the percentage of investments that make money). But interestingly, its overall rate of return became lower.

That’s because the VC firm, in its quest to lower mistakes, also passed on investing in highly risky potential moonshots that could generate tremendous returns.

The success of one Shopify can make up for the mistakes of many other risky bets that flame out. To hit a home run, we must be willing to miss at times.

Lesson 8: The money is made on the holding, not the buying and selling

My family’s investment portfolio has over 50 stocks. It’s a collection that was built steadily over time, starting with the purchase of just six stocks on October 26, 2010.

In the nine years, seven months and six days since, I’ve only ever sold two stocks voluntarily: (1) Atwood Oceanics, an owner of oil rigs; and (2) National Oilwell Varco, a supplier of parts and equipment that keep oil rigs running. Both stocks were bought on 26 October 2010.

David Gardner is also one of the co-founders of The Motley Fool (Tom Gardner is his brother).

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There’s something profound David once said about portfolio management that resonates with me: “Make your portfolio reflect your best vision for our future.” 

The sales of Atwood Oceanics and National Oilwell Varco happened because of David’s words.

Part of the vision I have for the future is a world where our energy-needs are met entirely by renewable sources that do not harm the precious environment we live in.

For this reason, I made the rare decision to voluntarily part ways with Atwood Oceanics and National Oilwell Varco in September 2016 and June 2017, respectively.

My aversion to selling is by design – because I believe it strengthens my discipline in holding onto the winners in my family’s portfolio. Many investors tend to cut their winners and hold onto their losers.

Even in my earliest days as an investor, I recognised the importance of holding onto the winners in driving my family portfolio’s return.

Being very slow to sell stocks has helped me hone the discipline of holding onto the winners. And this discipline has been a very important contributor to the long run performance of my family’s portfolio.

The great Charlie Munger has a saying that one of the keys to investing success is “sitting on your ass.” I agree. Patience is a virtue. And talking about patience…

Lesson 9: Be patient – some great things take time

Some of my big winners needed only a short while before they took off. But there are some that needed significantly more time.

Activision Blizzard is one such example. As I mentioned earlier, I invested in its shares in October 2010. Then, Activision Blizzard’s share price went nowhere for more than two years before it started rocketing higher.

Peter Lynch once said: “In my investing career, the best gains usually have come in the third or fourth year, not in the third or fourth week or the third or fourth month.”

The stock market does not move according to our own clock. So patience is often needed.

Lesson 10: Management is the ultimate source of a company’s economic moat

In my early days as an investor, I looked for quantifiable economic moats.

These are traits in a company such as (1) having a network effect, (2) being a low-cost producer, (3) delivering a product or service that carries a high switching cost for customers, (4) possessing intangible assets such as intellectual property, and (5) having efficient scale in production.

But the more I thought about it, the more I realised that a company’s management team is the true source of its economic moat, or lack thereof.

Today, Netflix has the largest global streaming audience with a pool of 183 million subscribers around the world.

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Having this huge base of subscribers means that Netflix has an efficient scale in producing content, because the costs can be spread over many subscribers. Its streaming competitors do not have this luxury.

But this scale did not appear from thin air. It arose because of Netflix’s CEO and co-founder, Reed Hastings, and his leadership team.

The company was an early pioneer in the streaming business when it launched its streaming service in 2007. In fact, Netflix probably wanted to introduce streaming even from its earliest days.

Hastings said the following in a 2007 interview with Fortune magazine: “We named the company Netflix for a reason; we didn’t name it DVDs-by-mail.

"The opportunity for Netflix online arrives when we can deliver content to the TV without any intermediary device.”

When Netflix first started streaming, the content came from third-party producers.

In 2013, the company launched its first slate of original programming. Since then, Netflix has ramped up its original content budget significantly.

The spending has been done smartly, as Netflix has found plenty of success with its original programming.

For instance, in 2013, the company became the first streaming provider to be nominated for a primetime Emmy.

And in 2018 and 2019, the company snagged 23 and 27 Emmy wins, respectively.

A company’s current moat is the result of management’s past actions; a company’s future moat is the result of management’s current actions. Management is what creates the economic moat.

Lesson 11: Volatility in stocks is a feature, not a bug

Looking at the table in Lesson 1, you may think that my investment in Netflix was smooth-sailing. It’s actually the opposite.

I first invested in Netflix shares on September 15, 2011 at US$26 after the stock price had fallen by nearly 40 per cent from US$41 in July 2011.

But the stock price kept declining afterward, and I bought more shares at US$16 on March 20, 2012. More pain was to come.

In August 2012, Netflix’s share price bottomed at less than US$8, resulting in declines of more than 70 per cent from my first purchase, and 50 per cent from my second.

My Netflix investment was a trial by fire for a then-young investor – I had started investing barely a year ago before I bought my first Netflix shares.

But I did not panic and I was not emotionally affected. I already knew that stocks – even the best performing ones – are volatile over the short run.

But my experience with Netflix drove the point even deeper into my brain.

Lesson 12: Be humble – there’s so much we don’t know

My investment philosophy is built on the premise that a stock will do well over time if its business does well too. But how does this happen?

In the 1950s, lawmakers in the US commissioned an investigation to determine if the stock market back then was too richly priced.

The Dow (a major US stock market benchmark) had exceeded its peak seen in 1929 before the Great Depression tore up the US market and economy.

Ben Graham, the legendary father of value investing, was asked to participate as an expert on the stock market.

Here’s an exchange during the investigation that’s relevant to my discussion:

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“Question to Graham: When you find a special situation and you decide, just for illustration, that you can buy for 10 and it is worth 30, and you take a position, and then you cannot realise it until a lot of other people decide it is worth 30, how is that process brought about – by advertising, or what happens?

"Graham’s response: That is one of the mysteries of our business, and it is a mystery to me as well as to everybody else. We know from experience that eventually the market catches up with value. It realises it in one way or another.”   

More than 60 years ago, one of the most esteemed figures in the investment business had no idea how stock prices seemed to eventually reflect their underlying economic values. Today, I’m still unable to find any answer.

If you’ve seen any clues, please let me know!

This goes to show that there’s so much I don’t know about the stock market. It’s also a fantastic reminder for me to always remain humble and be constantly learning. Ego is the enemy.

Lesson 13: Knowledge compounds, and read outside of finance

Warren Buffett once told a bunch of students to “read 500 pages… every day.” He added, “That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.”

I definitely have not done it. I read every day, but I’m nowhere close to the 500 pages that Buffett mentioned. Nonetheless, I have experienced first hand how knowledge compounds. Over time, I’ve been able to connect the dots faster when I analyse a company. And for companies that I’ve owned shares of for years, I don’t need to spend much time to keep up with their developments because of the knowledge I’ve acquired over the years.

Reading outside of finance has also been really useful for me. I have a firm belief that investing is only 5per cent finance and 95per cent everything else. Reading about psychology, society, history, science etc. can make us even better investors than someone who’s buried neck-deep in only finance books. Having a broad knowledge base helps us think about issues from multiple angles. This brings me to Arthur Schopenhauer’s quote I mentioned earlier in Lesson 6:  “The task is… not so much to see what no one has yet seen, but to think what nobody has yet thought, about that which everyone sees.”

Lesson 14: The squishy things matter

Investing is part art and part science. But is it more art than science? I think so. The squishy, unquantifiable things matter. That’s because investing is about businesses, and building businesses involves squishy things.

Jeff Bezos said it best in his 2005 Amazon shareholders’ letter (emphases are mine):

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“As our shareholders know, we have made a decision to continuously and significantly lower prices for customers year after year as our efficiency and scale make it possible. This is an example of a very important decision that cannot be made in a math-based way.

"In fact, when we lower prices, we go against the math that we can do, which always says that the smart move is to raise prices. We have significant data related to price elasticity. With fair accuracy, we can predict that a price reduction of a certain percentage will result in an increase in units sold of a certain percentage. With rare exceptions, the volume increase in the short term is never enough to pay for the price decrease.

"However, our quantitative understanding of elasticity is short-term. We can estimate what a price reduction will do this week and this quarter.But we cannot numerically estimate the effect that consistently lowering prices will have on our business over five years or ten years or more.

"Our judgment is that relentlessly returning efficiency improvements and scale economies to customers in the form of lower prices creates a virtuous cycle that leads over the long term to a much larger dollar amount of free cash flow, and thereby to a much more valuable Amazon.com. 

"We’ve made similar judgments around Free Super Saver Shipping and Amazon Prime, both of which are expensive in the short term and—we believe—important and valuable in the long term.”

On a related note, I was also attracted to Shopify when I came across Tobi Lütke’s letter to investors that I referenced in Lesson 7.

I saw in Lütke the same ability to stomach short-term pain, and the drive toward producing long-term value, that I noticed in Bezos. This is also a great example of how knowledge compounds.

Lesson 15: I can never do it alone

Aaron Bush is one of the best investors I know of at The Motley Fool, and he recently created one of the best investing-related tweet-storms I have seen.

In one of his tweets, he said: “Collaboration can go too far. Surrounding yourself with a great team or community is critical, but the moment decision-making authority veers democratic your returns will begin to mean-revert.”

I agree with everything Aaron said. Investment decision-making should never involve large teams.

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But at the same time, having a community or team around us is incredibly important for our development; their presence enables us to view a problem from many angles, and it helps with information gathering and curation.

I joined one of The Motley Fool’s investment newsletter services in 2010 as a customer. The service had wonderful online forums and this dramatically accelerated my learning curve.

In 2013, I had the fortune to join an informal investment club in Singapore named Kairos Research.

It was founded by Stanley Lim, Cheong Mun Hong, and Willie Keng. They are also the founders of the excellent Asia-focused investment education website, Value Invest Asia.

I’ve been a part of Kairos since and have benefited greatly. I’ve made life-long friends and met countless thoughtful, kind, humble, and whip-smart people who have a deep passion for investing and knowledge.

The Motley Fool’s online forums and the people in Kairos have helped me become a better human being and investor over the years.

I’ve also noticed – in these group interactions – that the more I’m willing to give, the more I receive. Giving unconditionally and sincerely without expecting anything in return, paradoxically, results in us having more. Giving is a superpower.

Lesson 16: Be honest with myself about what I don’t know

When we taste success in the markets, it’s easy for ego to enter the picture.

We may look into the mirror and proclaim: “I’m a special investor! I’ve been great at picking growth stocks – this knowledge must definitely translate to trading options, shorting commodities, and underwriting exotic derivatives. They, just like growth stocks, are all a part of finance, isn’t it?”

This is where trouble comes. The entrance of ego is the seed of future failure.

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In the biography of Warren Buffett, The Snowball: Warren Buffett and the Business of Life, author Alice Schroeder shared this passage about Charlie Munger: “[Munger] dread falling prey to what a Harvard Law School classmate of his had called “the Shoe Button Complex."

“His father commuted daily with the same group of men,” Munger said.

“One of them had managed to corner the market in shoe buttons – a really small market, but he had it all. He pontificated on every subject, all subjects imaginable.

"Cornering the market on shoe buttons made him an expert on everything. Warren and I have always sensed it would be a big mistake to behave that way.”

The Shoe Button Complex can be applied in a narrower sense to investing too. Just because I know something about the market does not mean I know everything.

For example, a few years after I invested in Atwood Oceanics and National Oilwell Varco, I realised I was in over my head. I have no ability to predict commodity prices, but the business-health of the two companies depends on the price of oil.

Since I came to the realisation, I have stayed away from additional commodity-related companies.

In another instance, I know I can’t predict the movement of interest rates, so I’ve never made any investment decision that depended on interest rates as the main driver.

Lesson 17: Be rationally optimistic

In Lesson 1, I showed that the world had lurched from one crisis to another over the past decade. And of course, we’re currently battling Covid-19 now.

But I’m still optimistic about tomorrow. This is because one key thing I’ve learnt about humanity is that our progress has never happened smoothly.

It took us only 66 years to go from the first demonstration of manned flight by the Wright brothers at Kitty Hawk to putting a man on the moon.

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But in between was World War II, a brutal battle across the globe from 1939 to 1945 that killed an estimated 66 million, according to National Geographic.

This is how progress is made, through the broken pieces of the mess that Mother Nature and our own mistakes create. Morgan Housel has the best description of this form of rational optimism that I’ve come across:

“A real optimist wakes up every morning knowing lots of stuff is broken, and more stuff is about to break.

"Big stuff. Important stuff. Stuff that will make his life miserable. He’s 100 per cent sure of it.

"He starts his day knowing a chain of disappointments awaits him at work. Doomed projects. Products that will lose money. Coworkers quitting.

"He knows that he lives in an economy due for a recession, unemployment surely to rise. He invests his money in a stock market that will crash. Maybe soon. Maybe by a lot. This is his base case.

"He reads the news with angst. It’s a fragile world. Every generation has been hit with a defining shock. Wars, recessions, political crises. He knows his generation is no different.

"This is a real optimist. He’s an optimist because he knows all this stuff does not preclude eventual growth and improvement.

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"The bad stuff is a necessary and normal path that things getting better over time rides on. Progress happens when people learn something new. And they learn the most, as a group, when stuff breaks. It’s essential.

"So he expects the world around him to break all the time. But he knows – as a matter of faith – that if he can survive the day-to-day fractures, he’ll capture the up-and-to-the-right arc that learning and hard work produces over time.”

To me, investing in stocks is, at its core, the same as having faith in the long-term potential of humanity.

There are 7.8 billion individuals in the world today, and the vast majority of us will wake up every morning wanting to improve the world and our own lot in life – this is ultimately what fuels the global economy and financial markets.

Miscreants and Mother Nature will wreak havoc from time to time. But I have faith in the collective positivity of humanity. When there’s a mess, we can clean it up.

This has been the story of our long history – and the key driver of the return my family’s portfolio has enjoyed immensely over the past nine years, seven months, and six days.

My dear portfolio, goodbye.

This article was first published in The Good Investors.