The Paradox Of Buying Real Estate

In any growing and economically vibrant location with strong future prospects, real estate always seems very expensive and almost out of reach in the present moment.

However, in hindsight after multiple decades, the same asset looks dirt cheap.

Anyone living in a major and growing economic hub would have felt the pain while looking at home prices. From SF and Singapore to NY and Gurgaon, home prices always feel “out of reach” in the moment.

However, now that I have enough grey hair from living through multiple economic cycles, hearing stories from many generations in my family, and also personally going through various real estate deals both as a buyer and seller across the Bay Area and India, I have noticed an interesting paradox:

In any growing and economically vibrant location with strong future prospects, real estate always seems very expensive and almost out of reach in the present moment. However, in hindsight after multiple decades (or sometimes even as short as a decade in alpha zones like the Bay Area), the same asset looks dirt cheap.

Story #1 – the grandparents

As an example, in the 70s, my maternal grandfather built a house in Lucknow, the capital city of the Indian state of Uttar Pradesh. As a kid, I remember hearing stories from him and my grandmother about how they had to struggle to put together money each month to pay the contractors. They ultimately built an amazing house over many years of scraping and saving. Cut to today, 50 years later, the location of the house has become very central and extraordinarily scarce, organically driven by the growth of the Indian economy. Needless to say, its price today has exponentially appreciated.

Story #2 – the auction

Second story – while growing up, we stayed in a rented house in South Delhi for a few years. For those who don’t know, South Delhi is now one of the premium parts of the Indian capital, but when we used to live there, it was just about at the tipping point with the first-generation multiplexes and the first-ever McDonald’s store coming in.

Our landlord was a very senior army officer and a really nice gentleman. As a teenager, I remember him telling stories of how he bought the house. While he was away fighting on the border, his wife saw the ad for plots of land being auctioned in the area. Even though in his own words “this was the time when there was nothing here and one could even see foxes in the neighborhood”, these plots of land were still out of reach for a working-class army officer.

Gathering courage, his wife borrowed money from her parents to make the downpayment and ultimately, got allotted a plot of land in the auction. Through monthly savings, they ultimately built this house. Cut to today, this house is now in one of the most prime locations of the capital of the soon-to-be world’s 3rd largest economy. You don’t even want to know the current price of the asset. In hindsight, the prices in the original land auction look like a steal.

Story #3 – the parents

A similar story from my family. My parents purchased a home in the mid-90s again in South Delhi and much before its tipping point. As a kid, I remember how big of a stretch that was for the family back in the day. My parents borrowed from every source of capital – my dad’s employer, his old business associates, my dad’s brother, my mom’s sister. Servicing this debt required major financial discipline on a monthly basis, needing hard choices that both I and my sister remember to this day.

Cut to today, the location of that house has become super-premium, and again, those prices that stretched our family thin back in the day, now look like a steal.

Story #4 – the Bay Area

Over the last decade, I have observed similar trends in SF/ Bay Area at large, albeit on a significantly compressed timeline (heck, we are talking about Silicon Valley here where everything happens exponentially faster and rises exponentially higher):

  • Then, downtown SF ended at the Giants stadium. Once you crossed the creek, you felt unsafe. Now, that same area begins with Mission Bay (home to the Warriors and UCSF), moves on to Dogpatch (home to YC), and beyond.
  • Then, Potrero Hill was just starting to get premium, and Bernal Heights had those old SF single-family homes with weird layouts and stairwells. Now, Potrero Hill is beyond premium, and Bernal is now what Potrero was back then.
  • Then, we used to make fun of one of our colleagues who bought in San Ramon in 2013 (who lives in that jungle anyway?) and made the commute to Mountain View every day. Now, San Ramon is one of the most premium Bay Area locations, especially post the development of Bishop Ranch and City Center Mall.

Illiquidity is key to long-term compounding

As I reflect on these stories and experiences, I kind of see why people call the illiquidity of real estate a feature, not a bug (Btw, I say the same thing about venture capital as an asset class).

Of course, this doesn’t mean real estate is a free lunch. I know a few Indian diaspora tech folks who took a bet on Oakland back in 204/15, buying homes there driven by news at the time that the likes of Amazon and Uber would be moving there. Unfortunately, Oakland has become an even bigger sh*tshow since then. Governance and security have massively deteriorated, none of the tech giants have moved there, and major sports teams like the Warriors and the Raiders have ended up moving their home bases out of Oakland.

To make the illiquidity-led, long-term compounding in real estate work for you, I would like to refer you to the guiding principles that Bruce Flatt, CEO of Brookfield, lays out for any type of real asset investing:

  • Buy great assets – pay more, if one has to, for quality.
  • Invest assuming we will own the assets forever – even though we may not. Eg. Brookfield has owned marquee buildings in Manhattan for 20+ years.
  • Go against the trend and buy value, especially in times of distress.
  • Finance prudently, as surviving downturns is paramount.
  • Acquire when capital is scarce (in other words, when interest rates are high like in 2023-24), as it is the best indicator of the right time.
  • Never become too positive, or too negative.

If this is too much, I have a TLDR for you:

Outsized long-term compounding in real estate seems to happen in locations that are positively aligned for future economic growth over decades. If you can buy at the bottom of the cycle/ in times of distress, even better!

I don’t know if this post is helpful for you. It’s definitely a departure from my usual topics of startups and venture capital. Still, I felt like penning this down, more to document these stories and aggregate my observations around them. Hopefully, you found it interesting!

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When To Sell?

Be it venture capital, public markets or real estate, “when to sell?” is an important question that both individual and institutional investors face.

Is it better to keep taking chips off the table? Or is hold-forever the right mindset? The journeys of Sequoia, USV, Berkshire and Brookfield give us some clues.

Yesterday at Primary’s NYC Summit, Fred Wilson (Managing Partner at Union Square Ventures) said something really interesting (and controversial) about venture firms that held on to their winners post-IPO in the recent cycle:

Their limited partners should fire them. They should never give them another dime. It is irresponsible what they did in my opinion.

Fred Wilson

Reading this argument brought me back to a question I think about often as an operator-angel – when is the right time to sell? In fact, I am faced with this dilemma right now wherein I might have an opportunity to exit a 2014 vintage investment. So, I guess it’s timely for me to attempt a deep-dive into this question, and analyze what the best investors across asset classes have to say on this topic.

A. Venture Capital

Clearly, Fred Wilson believes that venture firms should keep taking chips off the table as and when opportunities arise during late-stage financing rounds, and then cash out completely post IPO. Here’s an interesting excerpt from one of his posts on this topic:

Taking money off the table is smart portfolio management. It is very different from selling your entire position, which could be brilliant but is equally likely to be a mistake. Selling a portion of your position, returning a multiple or two (or eight) of the fund, and holding on to the balance works out for you no matter which way the position goes in the future. If the position blows up, you got a lot out and booked a huge gain. If the position goes up significantly, you make even more money on the part of the investment you retained. If it goes sideway, you got a little bit out early. It is a win/win/win pretty much every way you look at it.

Taking Money “Off The Table” by Fred Wilson

However, another OG VC – Doug Leone of Sequoia, has a different view. This is what he said on this pod with Jason Calacanis (paraphrasing):

It’s way tougher to go from 0 to $5Bn market cap than it is to go from $5Bn to $20Bn market cap.

There was significant upside created post IPO in companies like Yahoo, Google, ServiceNow and Facebook.

By holding for the long term, it’s a win-win-win for founders, LPs and Sequoia.

Doug Leone (Sequoia)

In fact, Sequoia started an evergreen fund in 2021 where the goal is to partner with entrepreneurs for 25 years, from idea to IPO and beyond. Here’s the firm’s stated thinking around evergreen hold periods for generational companies:

Source: The Sequoia Capital Fund: Patient Capital for Building Enduring Companies

So while one OG believes in taking chips off the table at every opportunity, another believes in staying all-in for decades.

Let’s see if we can break this deadlock by studying public market investors.

B. Public Markets

The first thing that comes to my mind when I think about the topic of when to sell public equities is the following legendary quote from Peter Lynch, later re-phrased and popularized by Warren Buffet:

Selling your winners and holding your losers is like cutting the flowers and watering the weeds.

Peter Lynch/ Warren Buffet

The gold standard in public markets investing is inarguably Berkshire Hathaway. Let’s look at the hold periods of some of its top holdings as per the 2022 Annual Letter:

1/ Coca-Cola – first started buying in 1988, and completed its purchase in 1994. Since then, annual cash dividends from Coke have increased from $75Mn in 1994 to $704Mn in 2022. The value of Berkshire’s investment has grown from $1.3Bn in 1994 to $25Bn in 2022, accounting for ~5% of Berkshire’s net worth.

2/ American Express – completed its purchase of Amex shares in 1995. Since then, annual cash dividends from Amex have increased from $41Mn in 1994 to $302Mn in 2022. The value of Berkshire’s investment has grown from $1.3Bn in 1995 to $22Bn in 2022, also accounting for ~5% of Berkshire’s net worth.

3/ GEICO – As a Columbia University business student, Warren Buffett made his first purchase of GEICO stock in 1951. Then in 1996, he purchased all outstanding GEICO stock, making it a subsidiary of Berkshire Hathaway, Inc. Warren paid ~$2.35Bn in total over these years to completely buy out GEICO. By 2022, the business was doing ~$39Bn in annual revenue itself.

Berkshire holds winners for extraordinarily long time periods, and benefits from their compounding, like no other investor on the planet. The 2022 Letter has an interesting para on this philosophy:

Source: Berkshire Hathaway 2022 Annual Letter

So till now, Sequoia, Peter Lynch, and Warren Buffet all seem to be in the hold-forever camp. Intrigued enough? Wait till you see what the world’s best investor in real assets (real estate and infrastructure) has to say on this.

C. Real Assets

IMHO, one of the best investing talks of all time is ‘Durable Principles of Real Asset Investing’ delivered at Google by Bruce Flatt, CEO of Brookfield. In fact, if you look at the video, it’s a travesty that only about 20 people actually attended this talk. Over 5 years since then, it has had a mere 175k views on YouTube, compared to the Millions that random TikTokers get.

Anyway, one of the core principles that Bruce talks about is investing with a mindset to hold assets forever. He cites an example of investing $432Mn in a marquee downtown NYC office building in 1996. Brookfield held it for 21 years, over 4 business cycles including 9/11 and the ’08 financial crisis, ultimately selling it for ~$2.2Bn in 2017. Note that this doesn’t account for additional returns created via using leverage for this asset and rental income.

Brookfield held this marquee office building on Park Avenue for 21 years, even through multiple global crises (Source: Durable Principles for Real Asset Investing)

Bruce says that when you invest with a hold-forever mindset, you automatically start looking at the asset’s long-term fundamentals, rather than what will happen to it next year or who will pay up for it later.

Cool – so we now have multiple OGs across asset classes in the hold-forever camp. From Sequoia in venture capital, Warren Buffet and Peter Lynch in public markets to Bruce Flatt of Brookfield in real assets.

D. Where I Stand On This

Based on personal experience as well as observations, I firmly lean towards hold-forever as a default mindset. Here are the reasons:

1/ Motivates fundamental analysis – as Bruce rightly said, a cross-decade hold mindset ensures that in the beginning itself, an investor will be prompted to think deeply and rigorously about the long-term future of the asset. Otherwise, there is a risk of investing with a ‘passing-the-buck’ mindset (expecting someone will be willing to pay a higher price for it in a few years) without building a strong investment thesis.

2/ Be on the right side of Power Laws – business outcomes across most contexts are driven by Power Laws, wherein only a few assets end up becoming winners in any portfolio. Therefore, adequately compensating for all the losers, such that the overall portfolio drives superior returns, requires milking the few winners as much as possible.

Those who regularly read this blog know that I worship at the altar of Power laws (refer to my posts on Conviction vs Randomness in Venture Investing and Only Need to Get a Few Right!).

In this regard, the following extract from Berkshire’s 2022 Annual Letter really caught my eye:

Source: Berkshire Hathaway 2022 Annual Letter

3/ Room for compounding – it’s important to hold assets long enough for this 8th wonder of the world to do the work for you. Studying the journeys of the best investors in history across asset classes, it becomes clear that compounding is really the true force that drives superior returns. As Bill Miller says – “the key to returns in the market is Time and not Timing”.

Am seeing the power of compounding in my own angel portfolio where the 2014-16 vintage companies have now hit strong product-market-fit and I expect a bulk of returns in these companies to be rear-ended. Check out what Susa Ventures has to say about its learnings from winners across vintages:

Source: Chad Byers, Co-founder/ GP at Susa Ventures

E. A Framework for “When To Sell?” Decisions

While I am philosophically in the hold-forever camp, I do believe a framework is needed to ensure rigorous thinking on a deal-by-deal basis, especially to catch edge cases where applying the default philosophy might, in fact, be sub-optimal. These could include either (1) luck-driven/ speculative upside cases (eg. a previously unknown crypto token hits unjustified all-time highs) or (2) scenarios with potential Risk of Ruin (eg. having an inordinate concentration in a single stock).

Inspired by Nick Sleep’s** decision-making framework on when to sell (via Mohnish Pabrai), here’s a set of proposed questions an investor can look to answer while making a sell decision:

1/ What is the ultimate destination? – Is there enough growth runway still left in front of the business? What does the business look like in another 10/20/30 years?

2/ Is the business getting better? – How are the operating and financial metrics trending? In particular, is its competitive advantage getting stronger?

3/ Have any of the fundamental assumptions underlying the original investment thesis changed in any way? – Is the market shaping up differently than expected? Have new competitors entered the space? Is a new technology disruption around the corner?

4/ Is a sale going to serve any other strategic purpose besides the quest for returns? – Are there any time-critical professional or personal requirements that need this capital? Is there an opportunity cost case to be made?

5/ Is the valuation egregious? – Is the asset at the peak of a hype cycle? Is the price at crazy levels that are unlikely to be seen again for several years?

Rather than giving a binary yes/no answer (real-life deal situations are rarely binary anyway), this framework should help in figuring out which side to lean on and in what proportion. Ultimately, one has to use judgment to arrive at the final decision.

A disclaimer

My stance as outlined above applies more to the context of personal investments. In the case of managing other people’s money, various considerations related to fiduciary responsibilities kick in. My sense is Fred Wilson’s argument as outlined earlier is more focused on the latter.

F. Summarizing

Fred Wilson’s stance of de-risking via routinely taking chips off the table is a safe and conservative strategy that makes a lot of sense for most investors out there. But as many OG investors across asset classes have shown, generating outlier returns with generational impact requires going all-in and holding the winners for decades. Essentially, one has to become a smart gardener that only cuts the weeds and lets the flowers grow.

**If you enjoy reading investor letters, the Nomad Partnership Letters by Nick Sleep and Qais Zakaria are a must-read. FYI Nomad was one of the best-performing investment partnerships for 15 years starting in the early 2000s.

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to my weekly newsletter where in addition to my long-form posts, I will also share a weekly recap of all my social posts & writings, what I loved to read & watch that week + other useful insights & analysis exclusively for my subscribers.