Offtopic: How to start with cryptocurrency (75 minutes reading) Part 2

Part II: Investment Philosophy
Okay — now that you hopefully have a good grasp of what cryptocurrency is and why it’s interesting, we can move on to dipping your fingers in getting some.

We can all be honest — the reason the vast majority of you are reading this is probably because you’ve heard a lot about just how much money people have made investing in cryptocurrency. Many, if not all of you, are wondering how you, too, can get on the gravy train and start making millions.

This isn’t necessarily wrong, or inaccurate. This is the reason I first started paying attention to bitcoin. Countless people have made shocking amounts of money investing in cryptocurrency. I’ve personally made over $400,000 in less than two years. In fact, bitcoin has already proven to be the best investment in all of recorded history by a shocking margin for those who got in at its most early stages.

Here’s a story about a completely random Norwegian student who bought 5000 bitcoins for $27 back in 2009. Today, with a single bitcoin pushing past $2700, those 5000 bitcoins are worth over $13.5 million. That’s a gain of over 500,000X. No other investment in recorded history that I’ve been able to discover has ever come close to touching these sorts of gains.

Even the Dutch tulip bubble, which is classically regarded as one of the first instances of massive speculative market mania, saw increases only on the magnitude of 10–100X — not even remotely close to 100,000X+. And even the most successful of extremely risky angel investments in companies, such as Peter Thiel’s initial $500,000 seed investment in Facebook, see returns on the scale of 10,000X or so or less — Thiel’s $500,000 investment, had he held it all the way to the present day, would be worth $6.8 billion, or approximately a ~13,500X gain. More incredible than just about anything else, certainly, but still nowhere even near Bitcoin’s meteoric rise in price.

What’s also striking is that traditionally, these sorts of ‘angel or seed’ investments in new technologies have been closed off to all but an incredibly well connected inner circle of elite high net-worth individuals and institutions. Peter Thiel, for instance, was only approached to become Facebook’s first outside investor because he was already incredibly well known within Silicon Valley for having founded and sold PayPal for over a billion dollars. In contrast, with bitcoin, a random student in Norway was able to invest just $27 and make millions.

That said, just as with everything, there’s survivorship bias here. What you don’t hear about are the profusion of people who lost their entire fortunes investing in cryptocurrency. While there are a few ways you can beat all the odds and come out vastly ahead in cryptocurrency, there are infinitely more ways you can lose everything you put into it and end up in a much worse place than where you started.

Here, I’ll try to cover the most common ‘mistakes’ people have made. Do keep in mind that this is all entirely my own opinion. Please come to your own conclusions here.

The most common mistake people seem to make is investing solely based on the price alone and its short term historical trajectory, and nothing else. The second mistake is investing in assets that they don’t actually understand or believe in long term, are not planning to hold for at least 5 years, and will be tempted to sell if the price begins to fall in the short term. The third mistake is believing that they’ve already missed the boat on the most established and successful cryptocurrencies, like bitcoin and ethereum, and that consequently they should invest in much less established, much more speculative ‘altcoins’ to achieve truly outsized gains, for no truly good reason besides the fact that the price/market cap for the altcoin is a lot lower than bitcoin’s, and seems like it has more room to grow. The fourth mistake is day trading, and trying to capitalize on short term market movements. I’ll address each of these in turn, and why I believe them to be mistakes.

On the first mistake — I made this mistake myself when I first got into cryptocurrency. I first heard about bitcoin from a friend who was raving that we should all get into it just around the time the price of a single bitcoin reached $100. He had gotten in at $30, and was extremely pleased with his gains.

At the time, it was relatively big news that bitcoin had reached $100. I remember thinking to myself that it was clearly too late to get in, and promptly forgot all about bitcoin.

The next time I heard about bitcoin was in the fall of 2013, when it began its last truly meteoric price rise from $100 all the way up to $1200. This time around, I distinctly remembered thinking I’d missed the boat back when the price was just $100, and kicked myself for being totally wrong. I resolved to not make the same mistake again, and tried to get in before I missed out again.
I ended up wiring several thousand dollars to an incredibly sketchy Russian exchange, BTC-E.com, to purchase my first few bitcoins at around $1000 apiece. Before I knew it, I was addicted to constantly checking the price, and spent a full 48 hours doing nothing at the height of the November 2013 bubble doing nothing but refreshing BTC-E.com and seeing how my investments were doing.

I ended up making another big mistake here too, and figured that bitcoin had already gone up way too much, and that my best bet was to invest in some smaller altcoins as well. I made this decision after seeing litecoin (LTC) skyrocket from $4 to $40 in just a few days. The buzz at the time was that litecoin would be to silver what bitcoin was to gold. The price seemed incredibly low compared to bitcoin, and this made a superficial sort of sense (meaning, no sense at all), so I decided to jump in. For good measure, I also decided to jump into a few of the other most popular altcoins of the time — peercoin (PPC) and namecoin (NMC).

The 2013 cryptocurrency bubble burst just a few days later, brought on by the collapse of Mt Gox, the largest bitcoin trading exchange at the time. It was revealed that Mt Gox had either been hacked or embezzled from, and no longer had any funds left to honor customer withdrawals. As a result, anyone who had decided to keep their bitcoins in Mt Gox at the time instead of withdrawing them to their own wallets ended up losing all their money. How much the price of bitcoin rises doesn’t mean anything if you lose all your bitcoins, unfortunately.

The price of bitcoin cratered about 80%, falling all the way to about $200, before stabilizing at that price for much of 2014 and 2015. Litecoin, on the other hand, fell from over $45 to about $1, and consequently lost over 97.5% of its value. PPC and NMC suffered so badly that I didn’t even bother to calculate how much I had lost, because it was basically everything.

This is when I first saw the light, and realized that investing in altcoins that I didn’t really believe in, and that didn’t really have any truly compelling reasons they would ever overtake bitcoin or deserve any level of market share, was an incredibly foolish move. It was certainly true that these altcoins did often gain on bitcoin and appreciated far more rapidly in many cases while the bubble held strong, but the moment it began to collapse, the altcoins were the first to go, and often fell all the way to zero.

As a general rule, what goes up can come down, and what goes up particularly quickly is privy to come down just as quickly. This is not to say that things will come down if they go up, but merely that they can, and certainly have before. This is particularly noteworthy today, with ethereum having seen some truly wild gains this year, all the way up from $7 back in December of last year to over $350 presently — a gain of 50X in just about half a year. Again, this isn’t to say ethereum will fall, but merely that it very well might, for any host of reasons, and it’s very important to keep this fact in mind and not overextend yourself with investments you perceive to be less volatile than they truly are. I’ll get back to this more later.

What I ended up learning was something the smartest people in the investment world had learned a long time ago. Benjamin Graham, the mentor of Warren Buffett, who became the richest man in the world by practicing the principle of value investing, has a pretty wonderful analogy that I think is worth repeating here. You should buy your stocks (or any investment, generally) like you buy your groceries — not like you buy your perfume.
What he means by that is that for some reason, people tend to buy stocks when they’re going up in price, and sell them when they’re going down. At face value, this makes no sense. We wouldn’t buy a watermelon when it was $10, and sell it when it was $2. With groceries, it makes intrinsic sense to us to buy watermelons at $2, not $10, but seemingly not so with our investments.

The short term price movements of a stock shouldn’t concern a long term value investor in the slightest, as a value investor doesn’t care about what the market has valued the price of a stock at, but rather only about the intrinsic value of the business behind the stock, and its future potential value. Only after coming to a conclusion about the actual value of a company and its future potential value, should an investor then look to what price the market has assigned a stock, in ascertaining whether or not a stock is a good purchase.

In the case of a watermelon, what we intuitively grasp is that there is some fundamental, intrinsic value to the watermelon, and a ‘fair’ price for it. We have a general understanding of what this price should be, and are more than happy to buy watermelons when they are on discount relative to their fair price, and are reticent to do so when they are being sold at a premium to their fair price.

If we decide that a watermelon’s fair intrinsic value is $6, then we’d be happy to buy watermelons all day long at $2, and reticent to do so at $10.

With investments, it’s the same deal. If we decide that Company X is presently worth $100,000 dollars, and that it has strong growth potential in the future, and the market is presently valuing Company X at $50,000, that would probably be a good buy.

On the other hand, if we decide Company X is worth $100,000, and has ambiguous future potential, and the market is presently valuing it at $200,000, it might not be such a good buy.
In a third case, if we decide Company X is worth $100,000 today, and has extremely strong growth potential, and the market is valuing it at $100,000 today, it might still be a good buy to hold and capitalize on that future potential.

In all of these cases, however, a value investor first and foremost must decide, with rigorous analysis and thorough examination, what they believe the fair value of an investment to be, and what degree of future potential it has. Only from there do they then examine what value the market has assigned the investment, in order to ascertain whether or not the investment is a wise one likely to yield good returns. Under no circumstances should one ever buy into a stock without knowing much, or anything at all about the stock, save for the general market sentiment or hype surrounding it, and its short term price movements. Buying a stock merely because it has seen great gains in the past, without any understanding of why it saw those gains and what gains it might expect to see in the future based on fundamental analysis of the stock, is an inordinately risky and foundationally bereft strategy.

If you’re interested in learning more about value investing at large, I’d highly recommend The Intelligent Investor, by Benjamin Graham, who again was Warren Buffett’s personal mentor and a professor of economics at Columbia University. He pioneered a lot of the foundational concepts around value investing, and can give you much better and more nuanced advice than I ever could.

All of this said, while these principles can and should be kept in mind at large for just about any investment, cryptocurrencies are dramatically different from stocks, bonds, or any other sort of traditional investment vehicle. They’re also so early stage and so volatile that it’s a near-certainty that a value investor like Benjamin Graham wouldn’t even dream of labeling such opportunities as investments, rather than speculations (at best, they would be labeled growth investments, but I’m working with the Buffett philosophy that there is no difference between ‘value’ and ‘growth’ investing, and that good value investing appropriately takes into account growth).

Investments, under this distinction, would be clarified as things that could generally be safely assured not to suffer from dramatic, catastrophic losses in the absence of dramatic, catastrophic situations. Coca-Cola and Walmart might be considered investments. They’ve been around for well over a century and a half century respectively, are massive, mature companies with a healthy track record of stable, non-volatile growth, and show no general signs of turmoil that might portend a sudden collapse in value.

Speculations, on the other hand, are like the Wild West of opportunities. They’re extremely high risk, extremely volatile, and could on one hand multiply one’s principal manyfold, and on the other, dissipate it all into thin air. A seed ‘investment’ in Facebook, for instance, could be considered a speculation. In the vast majority of cases, such an investment is likely to fail outright and lose all of the money invested. In a few instances, however, that investment just might succeed, and return tens, hundreds, or even thousands of times the principal invested.

It’s important to note that the mere fact that something is speculative does not necessarily mean it can’t be a good investment, or that it is merely akin to blind gambling, dependent solely on the luck of the draw. Poker might be a suitable analogy. Poker can be played well or poorly, and skill and calculation lends an incredible degree of advantage to a player’s odds of success.

However, the game still fundamentally deals with an immense degree of unavoidable variation and unknowns, and even the best poker player is guaranteed to lose many of their games, even if they play each one ‘perfectly’. The goal, simply, is to win more than you lose, and with the right amount of skill, knowledge, and preparation, this is a possible feat in poker.

The same might be said of speculative investments such as those in cryptocurrency. You can and absolutely should do your part to learn as much as possible about this field, and come to your own personal conclusions on its current and future potential value. However, no matter how much research you do and how many calculations you make, there will always be a fundamental and inextricable degree of pure luck involved in determining the ultimate outcome of your speculation. Any number of future events could tip the scales for or against cryptocurrency, or more specifically, any one cryptocurrency, and a number of these will be ‘black swan’ events that are fundamentally unpredictable in their nature and timing, but in aggregate whole, almost certain to occur.

Just because there is this element of luck, however, does not mean that you necessarily shouldn’t play the odds, if you so believe with very good reason that those odds are in your favor. What you do have to make sure of, however, is that you have such good reason to believe that those odds are in your favor, and that you don’t put up more than you can afford to lose, given the odds.

The key takeaway and lesson to be learned, again, is to invest, both in speculations and in ‘safer’ investments, based on firm knowledge of the underlying asset and intrinsic analysis, to the extent possible, and never merely based on price movements.

In the case of bitcoin, my personal belief is that there is enough to justify the possibility of long term gain based on fundamentals and first mover advantage. If everything goes right, I do see a future in which it’s possible that bitcoin achieves a market cap similar to that of gold’s, given that so far as I can see, it provides all the benefits gold does, and a host of incredibly valuable advantages on top of those existing benefits. I even see a future where it just might be possible that bitcoin goes even further, and becomes a dominant leading global currency. It’s also possible that bitcoin’s blockchain is used to power many future technological innovations, such as smart contracts and even DAOs, and thereby creates and imbues itself with even more value.

At the same time, I also see a million and one ways where bitcoin fails to reach the promised land. Bitcoin has already experienced numerous growing pains, and at the present moment, is suffering most acutely from a huge backlog of transactions that can’t be fit on the blockchain. This is because blocks are presently limited to 1 MB in size, and can consequently fit only a small fraction of all the transactions that are trying to be propagated over the network. This forces those who want to have their transactions go through to pay inordinately high transaction fees in order to prioritize their transaction over other transactions.

There are already a number of proposed solutions to this issue, such as the implementation of the Lightning Network, but in order to implement these solutions, the majority of bitcoin miners must agree to update their bitcoin software. Many bitcoin miners are reluctant to do so, in large part because high transaction fees are good for miners, at least on a short term basis, as it means they earn far more per each block mined. The implementation of the Lightning Network and other solutions threatens to take away this extra revenue stream. Hence, users of bitcoin and miners of bitcoin find themselves at odds with a very understandable conflict of interest. It’s unclear as of yet how this will be resolved, though it seems the community is pushing forward towards a resolution, and I’m of the personal belief that they’ll get there eventually.

Similar problems like this are virtually guaranteed to occur in the future as well, and it’s simply impossible to predict right now how the bitcoin community might respond to and handle those problems, and if they’ll be successful in doing so.

At the same time, it’s entirely unclear how governments will respond to bitcoin as it continues to grow, and if they’ll attempt to crack down in a very strong way and prohibit the use of bitcoin, or the creation of bitcoin related service companies, such as exchanges. If exchanges were banned from operating, for instance, it could very well make it very difficult for most people to transact between fiat currencies and bitcoin, and render the latter far less useful than it otherwise might be.

On the flip side, if the world suffers a global financial meltdown on the scale of the Great Depression or something similar again, and fiat currencies start to crater, it very well may be such that governments are forced to resort to accepting bitcoin and other cryptocurrencies, if enough people simply flat out refuse to put their stock in fiat. This was exactly what the US government was forced to do just 13 years into their original experiment with Continental currency, when they agreed to promise to back all the currency they issued with hard gold and silver.

These are just a few of countless twists and turns and vicissitudes our much vaunted (and much derided) bitcoin will have to endure before its long journey comes to an end, either six feet under or as an indelible fixture in our global economy. There’s no telling which way it will go, and one must come to one’s own conclusion on how much faith and conviction one chooses to place in bitcoin.

That’s the case as I see it for bitcoin. In the case of most altcoins, however, I don’t see remotely enough to even begin to justify the possibility of long term gain in the first place. Even with speculations, or perhaps especially with speculations, it’s incredibly important to thoroughly analyze a given investment opportunity for at least the potential for long term gain and success, and assess the magnitude of that possible gain, and then to weigh that potential versus the likelihood of outright failure of the speculation. With most altcoins, their value over bitcoin or ethereum is far from clear, and generally superficial or minor at best.
Dogecoin is the most pure example of this. Dogecoin offers just about no fundamental innovations over bitcoin, and is in fact a self-deprecating cryptocurrency premised (initially, at least) entirely on poking fun at itself. The name itself is a reference to the doge meme, and offers little to no further justification for its existence.

Despite this fact, Dogecoin’s market cap is presently valued at over $300 million. Come to your own conclusions here.
Less immediately obvious examples include things like Litecoin. Litecoin, too, offers fundamentally no truly great innovations over bitcoin — in short, nothing that bitcoin itself couldn’t adopt over time. It uses a different hashing algorithm and just adopted Segregated Witness, the same update that bitcoin is debating adopting that would allow the implementation of layer two protocols such as the lightning network, but beyond this, doesn’t have much in the way of unique differentiation going for it. This said, Charlie Lee, the creator of Litecoin and previously the Director of Engineering at Coinbase, one of the most well respected and successful bitcoin exchanges, just announced his departure from Coinbase to focus solely on improving Litecoin. It remains to be seen what will come from this endeavor, as Charlie certainly is without question one of the most accomplished and formidable players in the cryptocurrency sphere, but largely litecoin appears to be a small hedge in the slight off chance that bitcoin doesn’t actually manage to resolve its scaling issues, and begins to catastrophically lose market adoption and faith and crumble into the ground. In a case like that, the notion is that litecoin would be able to quickly take over the ground lost by bitcoin, and become the dominant cryptocurrency.

There are a number of issues with this, however, and a lot of things would have to go right before this occurred. There are several cryptocurrencies, for instance, with ethereum being the most notable, that are already far larger than litecoin, and it would have to be demonstrated that there’s some reason something like ethereum couldn’t simply take the place of bitcoin, and that litecoin would have a better shot at doing so than the larger players that already exist in this space.

Litecoin would then have to deal with exactly the same issues bitcoin has faced at scale, and it’s not clear at all that litecoin would fare any better at resolving such conflicts if ever reaches the same scale as bitcoin presently has.

All of this said, it does seem extremely likely to me that there will inevitably be some true innovation in this space, and that some cryptocurrencies will be able to carve out niches of varying degrees of value. One might even prove to ultimately demonstrate so many more advantages as to overtake bitcoin one day — ethereum, for instance, is teetering remarkably close to doing just that, at least in terms of market cap, if not quite yet other markers such as developer activity and transaction volume. The true feat here will be discerning those few new technologies with true fundamental potential and innovative advantage (and an incredible execution strategy) behind them, from the vast swaths of similar looking yet ultimately worthless contenders almost certainly doomed to eventual failure.

Expected value is a useful concept frequently employed in poker that also serves to provide utility here. In short, expected value is a way to decide when an outcome is not certain, but a set of outcomes are probabilistically determinable, if a given action is going to be net positive or net negative, and to what degree.

The simplest example is flipping a coin. This will yield heads 50% of the time, and tails 50% of the time. Expected value of betting on the coin yielding heads, hence, is 0. This is because in any one given flip, the coin has exactly a 50% chance of coming up heads. Hence, if you bet $100 on the coin coming up heads an infinite number of times, your expected gain, or value, from such an action, is to be $0.

Conversely, if you bet at even odds that a six sided dice roll would come up 3 or higher, your expected value would be positive, as you would be correct 2/3 times. Hence, if you repeated this bet an infinite number of times, you would be guaranteed to be earning more money than you lost.
Similarly, if you were able to bet at 1:2 odds (meaning if you bet $100 and win, you get $200) that a coin would yield heads, this would also be very +EV (positive expected value). The coin would still yield heads half the time, but that half of the time, you would earn $200, and the other half of the time, you would only lose $100. Hence, repeating this bet an infinite number of times would allow you to dramatically earn more money than you lost yet again.

There are far too many variables and unknowns to take into consideration with most speculative bets, and cryptocurrency in particular, to be able to hope for anything so nice and clean as an exact mathematical probability of how + or -EV a given bet on a given cryptocurrency might turn out, just as there are far too many unknowns to calculate the precise fundamental present and future potential value of a cryptocurrency for the purpose of value investing analysis, but regardless, holding both principles at large as a general guiding strategy in determining one’s actions here and elsewhere is a good bet.

Personally, for myself, a quick back of the napkin calculation that I can do to estimate the possible future value of bitcoin is to see what the market has valued all of the gold in the world at, and use this as a rough guiding principle for seeing how much appetite the world currently has for something that can hedge against other currencies and holds similar characteristics to gold as a store of value. I can see that the total value of all the gold in the world is over 8 trillion dollars, and consequently, if bitcoin were to reach that same total valuation, each bitcoin, assuming 21 million eventual bitcoins, would be worth approximately $400,000. Dividing this by bitcoin’s current value, I can see that there’s still room for approximately 150X gains. This means that if I truly believe this is a possible outcome for bitcoin, then as long as I believe this outcome has more than a 0.66 percent chance of happening, or 1/150 chances of success, it would be an +EV bet to make.

That said, it’s extremely important to keep in mind that one doesn’t get infinite opportunities to keep playing this bet out over and over again. There is only one bitcoin in the world, and we only have one opportunity to play out this exact bet. Given this fact, it’s important to realize that if this were somehow to actually be a perfectly EV neutral bet, with a possibility of a 150X upside and a 0.66% chance of realizing that upside, it would still mean that we have a 99.33% chance of losing all our money that we place on this bet. It would be extremely foolish, therefore, to invest all our money into such a wildly speculative investment, even if it is technically EV neutral or even slightly EV positive. What might make sense, is to set aside a responsibly proportionate amount of money specifically earmarked for such wildly speculative investments as a part of a holistic investment portfolio, that one is fully willing and able to lose without significant impact to one’s well-being or quality of life, and to invest that amount of money in a +EV bet like this.

Returning to the question of calculating potential investment upside here, there are countless other ways to make projections on the future potential value of bitcoin, and I encourage you to try to make some depending on your personal beliefs regarding the level of success bitcoin might have, and the ultimate utility it might provide to the world. For instance, if you see bitcoin primarily as a way to simplify making international transactions and cut out inefficiencies there, you might look to see what the overall market size is for a solution that might solve that problem and capture that market. Western Union, as one example, is a company with a market cap of $9 billion. Consequently, it might be reasonable to expect that bitcoin’s true ultimate value would be something roughly in that order of magnitude, if this were to be bitcoin’s one true long term use case.
If you see bitcoin as most useful for its blockchain, you might calculate hence the value you think can be created through applications, contracts, and other technological innovations run on the blockchain, and use that to guide your estimation of bitcoin’s value.

If you think bitcoin will be used to primarily enable black market transactions, same deal. And so on.
I hope that this elucidation provides some insight into why I personally see it as suspect to invest in something based on price alone, and why I urge extreme caution particularly if one is exploring whether or not to invest in an altcoin, especially if one is at least partially motivated to do so because of the feeling that the ship has already sailed for bitcoin, and that there might be better potential for outsized gains with a smaller altcoin. Again, this certainly may be true, and often is true even for altcoins destined for eventual failure in the short term while a bubble/bull market continues, but risks are amplified just as much as the opportunity itself when it comes to altcoins, and oftentimes moreso in a bubble than otherwise.

It’s easy to be swept away in the fervor of a frenetic market, and the fear of missing out can be overwhelming especially when you see altcoins rising by wild amounts overnight, but my personal guiding philosophy is to always try to keep in mind fundamentals to the maximum extent possible, to never invest in anything I don’t actually understand or see long term value in, and to only invest in things I intend to hold very long term (for at least 5 years), especially in such a volatile market.

Speaking to that last point now (the ’second’ mistake I mentioned at the beginning of this part) I’m of the personal opinion that it is incredibly important to not only invest solely in things that I truly believe have the real potential to succeed in a big way long term, but to actually commit and hold to that investment, once I make it, no matter what happens with the price short term. If some fundamental fact underlying my investment changes, I can certainly re-evaluate it, but if the price drops 90% or even 95% in the short term for no particular reason except a collapse of a local maximum in price speculation (e.g., a bubble popping), I must never be tempted to sell and try to ‘time’ the market in any way. Instead, I have to hold that investment with firm conviction in what I believe the eventual price based on fundamentals is worth, regardless of how the market values it in the present moment.

This is critically important precisely for incredibly volatile speculative investments such as cryptocurrency, and plays into the fourth mistake I mentioned above, day trading, as well. More than possibly any other market I’ve seen, short term price movements for cryptocurrencies are oftentimes absolutely mystifying and nothing short of mind boggling. Highly anticipated events, such as halvings in bitcoin’s reward per block mined, come and go without any real perturbation in price. Other times, things rise when reason seems to suggest they should fall, and fall when they seem to have every reason to rise. For instance, bitcoin’s price collapsed to $200 after the bubble popped in 2013, and stayed stagnant at those levels, despite massive development in bitcoin infrastructure and significant growth in the adoption and usage of bitcoin over that same period of time.
More recently, the approval or rejection of a bitcoin ETF was widely touted as being the contributing factor to a bitcoin bull run from under $1000 to over $1200. It was speculated that if the ETF were to be rejected, that naturally the price would fall to where it was before the bull run began. Indeed, the moment the ETF was announced as rejected, the price did momentarily fall to almost $1000. However, it just as quickly recovered, and began an inexorable climb all the way up to over $2700, where it stands to this day.

Consequently, with the short term price movements of bitcoin and other cryptocurrencies being incredibly volatile and oftentimes nothing short of inexplicable, I highly caution anyone against making decisions such as selling their bitcoins on the way down in anticipation of a market crash, so as to either avoid the crash or to buy their coins back at a cheaper price at the bottom of the crash.

This goes hand in hand with mistake number four I mentioned above: day trading. This is absolutely number one the reason I see people who have gotten into bitcoin and cryptocurrency lose their money. If you at almost any point in the history of bitcoin (earlier than say, this month of June), merely bought bitcoin and held it to the present day, you would have made money. However, countless people have actually lost money in bitcoin, and this is because they ended up trading their bitcoin somewhere along the way.

I would venture to say that most people have far more confidence in their ability to predict short term market movements than is actually the case. I’ve seen plenty of instances of people who have thought that they could capitalize on short term volatility on the way up, and essentially ‘buy the dips and sell the tips’, and in every single instance I can recall, this strategy eventually fails, and often in a big way. At face value, this seems to make sense. If you think you can time when the dips will occur and when they will end, and similarly when the peaks will occur and when those will end, you can definitely make more profit along the way by selling high and buying low.

However, as I’ve mentioned before, this is far more difficult, if not impossible, to do with cryptocurrency, more than even normal investment vehicles like stocks. I’ve seen people who think that bitcoin has hit a peak and must necessarily stop going up sell, intending to wait until bitcoin falls again to buy in again and make maybe a 20% extra profit, miss out entirely because bitcoin kept going up and never came back down. There are numerous stories of those who bought into bitcoin at $1 or less, but sold well before it ever reached even $10, much less $2500.

With something as speculative as cryptocurrency in the first place, it makes no sense to invest in this space to begin with if your only goal is to make 20% profit. It almost certainly isn’t worth the risk at that level of gain. Hence, risking losing out on the long term upside of 10X+ that you’ve calculated and come to the conclusion does exist for a gain of less than 1X or .5X in most cases makes little to no sense at all. It only makes sense if it’s essentially a guaranteed gain with no risk, and that, again, is almost certainly not the case.

Indeed, some market movements are fundamentally unpredictable in their short term timing. Two very vivid examples of this were the collapse of Mt Gox for bitcoin, and the hacking of the DAO for ethereum. Both of these events absolutely cratered the price of bitcoin and ethereum respectively, and both of them were fundamentally unpredictable in their exact timing. These are examples of the black swan events I mentioned that are certain to continue playing a large role in short term price developments for bitcoin and all other cryptocurrencies at large, that make it doubly dangerous for those who day trade.

I’ve also seen plenty of people who intend to hold long term, but lose faith when they see their investment crater 30%, 50%, or even 70%. At this point, they lose faith, and decide to sell their investment to at least recoup some of their initial capital, and not lose everything outright. Thus, they end up buying high and selling low, and then having double regret when bitcoin eventually ended up rebounding even higher than the ‘high’ they bought at.

This illustrates even more vividly why it’s incredibly dangerous to invest in anything you don’t actually believe in, and aren’t willing to hold, long term. If you aren’t going to hold something long term, then generally you must believe that while the price will rise in the short term, it will not continue to rise in the long term. If you hold this belief, it generally means that there’s some reason that you believe what you are investing in won’t hold true value long term, but that there is enough speculative mania in the short term to make the price go up anyway. The thinking goes that if this is going to be true, you might as well profit from this speculative mania and buy in now, wait for a little bit for the price to rise, and then sell it for short term profit.

The problem with this is that just about everyone else investing in these things is thinking the same thing, and everyone involved is effectively playing the greater fool theory, expecting that they will be smarter than everyone else and be able to time the market better than everyone else, and get out before everyone else does, and before the price eventually collapses. By mere inviolable fact, most people who engage in this form of speculation are guaranteed to lose in a big way. Over enough iterations, the eventual likelihood of loss generally grows to become one, in my opinion, as one must continue to time a market correctly time and time again for this to work. While it may seem like the market will continue being bullish for you to get in and get out before things go south, this is true of every moment in time right up until things go south all at once. Inevitably, at some point, the gravy train will have to derail and explode in a rolling ball of fire.

I know for a fact that I’m certainly not remotely smart or knowledgeable enough to pull off this kind of short term investment that aims to profit from market sentiment alone, especially not in the turbulent, mercurial waters of cryptocurrency, and that’s all I can say about this here. On top of this, the existence of black swan events that can crater an entire market unpredictably short term introduces a variable that inherently is just about impossible to predict, and makes short term bets like this even more dangerous.

The most dangerous game of all, then, in my opinion, is day trading in altcoins that one doesn’t believe in long term. This is basically combining every ‘mistake’ I mention above: trading in something because of short term price movements, not holding it long term, day trading, and speculating in highly risky small cap altcoins. If you manage to survive doing this over any long period of time (5 years+, let’s say) and end up net profitable (particularly if you end up more profitable than just buying and holding over that same period of time), please do let me know, as I’d be extremely curious to hear just how you pulled it off.

Going back to my personal story, ultimately the crash from $1200 to $200 for bitcoin was the best thing that could have ever possibly happened to me. At the time, of course, it certainly didn’t feel that way. It felt like I had made an absolutely stupid, foolish decision, and had lost all my money. In fact, I did make a stupid, foolish decision, but not for the reason I thought at the time. I didn’t make a stupid, foolish decision because the price had cratered to $200. I made a stupid, foolish decision in deciding to invest in bitcoin and altcoins without actually having done my research and without really knowing anything about them.

Had I actually done my research and believed that it was a fair bet to make that one day bitcoins would be worth far more than even the height of the local maximum bubble at the time, it absolutely could have been the right decision to buy in then, even if it crashed later temporarily to $200. What wasn’t right was buying in simply because the price was going up and I had a fear of missing out.

The crash proved to be the best thing that could have happened, however, because it gave me time to actually do my research and learn about bitcoin, and have real reasons for believing in it long term, at a point in time where the price was unusually deflated. As a consequence, I was able to buy more bitcoin at the very bottom of the market, around $230 or so, when I became truly convinced of bitcoin’s long term potential. I was also lucky enough to decide not to sell the bitcoins I had originally purchased for $1000 or so, and ultimately saw even those return 250%+ in profit.

It was at this time, incidentally, that Coinbase, became worried about stagnant growth of their user base, and decided to offer a truly astounding proposition. They offered to pay anyone who referred a new customer to Coinbase $75 if the new customer purchased just $100 in bitcoin. Coinbase took a 1% transaction fee at the time, meaning that for every $100 in bitcoin a person purchased, Coinbase charged $1. In short, Coinbase would pay out $75 for every $1 a new customer paid them.
It didn’t take a genius to see a clear arbitrage opportunity here, and I wrote up a quick blog post detailing this opportunity and fired out a single Facebook post telling my friends about it. From that post and just a few hours of work, I ended up earning almost 17 bitcoins entirely for free — worth over $45,000 today. I had plans to scale this strategy en masse, but singlehandedly ended up killing the program almost as soon as it started, when Coinbase finally came to its senses and realized just how much money it was hemorrhaging here with no hope for eventual recoupment (at the time, the lifetime value of the average customer was only something like $25 to Coinbase — a far cry from the $75 they were offering).

Digression aside, that sums up most of the thoughts I have about the primary things to be cautious about when it comes to bitcoin investment. There are a few more practical matters to be extremely cautious about (namely, how you store your cryptocurrency), but I’ll address those in the next part, which will be an actual how-to guide showing actually actionable steps for those interested in getting into bitcoin investment.

The final point to make, then, are a few thoughts on how to correctly invest in bitcoin and other cryptocurrencies. I have no truly great pieces of wisdom to offer here, but do have a few ideas that primarily aid in being psychologically being resilient to the short term vicissitudes of cryptocurrency investment.

Once you’ve decided that you truly believe in a cryptocurrency long term, and are willing to commit to it for the long term and hold it no matter what the short term price movements might be, the next step is to decide how much to invest, and when to invest. One might be hesitant, with not bad reason, to invest at an all time high, even if one believes that that all time high will one day be exceeded.

The mere fact that the future potential is still huge doesn’t necessarily preclude the fact that cryptocurrency may be in a short term bubble, and that prices might crater any day by 30%, 50%, 80%, or even more.

Generally, the strategy suggested to average out such short term volatility for something that one is investing in long term is to practice dollar cost averaging. This preaches that one should set an exact time at regular time intervals to buy an exact amount in fiat currency of the investment one is looking to purchase — e.g., $1,000 worth of bitcoin on the 1st of every week, or every month. This means that over time, you’ll be able to take advantage of bitcoin’s general trajectory upwards, but balance out the relative short term volatile price movements both high and low, such that you experience a more linear growth trajectory over time of your principal.

I think that this is a great strategy, and personally practice it with a few modifications. While I’ll never sell at any price essentially (unlike other investments, bitcoin and cryptocurrencies are unique in that they are currencies, and consequently if they succeed, you won’t have to sell them to gain value from them. You can just use them directly, just as you might US dollars or any other form of currency. In the manner that I use the word sell here however, I mean that I likely won’t sell at any price under $100,000, as that’s where I personally see the moonshot value of bitcoin going towards, in the slight chance that it does succeed), no matter how high the price rises in the short term, if and when the price becomes particularly low as a result of a cratering market, I will look to buy more than I normally would, to double down on my investment here — all the while keeping in mind never to invest more than I’m perfectly willing to lose entirely.

Psychologically, if it’s helpful, I think it may be fine to sell off some small portion of your upside if you do realize upside over time, in order to recoup your initially invested principal. I don’t think that this is necessarily the most optimal actual move to make, but do think it likely makes a huge difference psychologically, such that it makes it far easier for you to hold your remaining investment with sangfroid in the case that it ends up cratering sometime in the future.

As for investing an initial lump sum to begin getting exposure in this space, my personal strategy would be to do a semi-timed dollar cost average, if one is particularly concerned that they might be investing just before a local minimum market crash, but also particularly concerned that the price may keep rapidly appreciating ad infinitum, and would like to get in before that happens. That is, I’d decide the total lump sum I’d be willing to set aside to invest here, say, $10,000, and invest 33% or 50% of it immediately. Then, if the market did crash, I’d be psychologically very happy, and be super excited to invest another 33% or 50%.

On the flip side, if the market continued to rise indefinitely and never fell again, I’d also be happy that at least I was able to get exposure to the market and didn’t miss out entirely. A 33–33–33 split would allow me to invest 3 times when I felt the market was at a particularly good time for investment, and a 50–50 split twice. Just random arbitrary examples of divisions I might do here, depending on how exactly wary I feel about the market at the present moment in time.

That about sums up my thoughts on cryptocurrency investment at large. There are some nuances, but I figure 8000+ words worth of a brain dump is a good enough place to start. If you’re still here, please feel free to read on to Part III if your constitution allows for further word consumption.