Bitcoin Stands between Me and Retirement

Why I won't sell my Bitcoin to retire


Forgive in advance any content below that may come across as boastful. That is absolutely not my intent. While I share some details that may seem braggadocious on the surface, I share them only because I think they provide context for my larger point, which is this: I refuse to be shortsighted with my Bitcoin investment, which if successful, will differ from literally every other investment I have ever made.

My Circumstance

Some of you know I am 51 years old. What some of you may not know is that I am a small business owner whose primary source of income comes via a contract with the US federal government. In fact, this contract is the reason for my relative anonymity on CryptoTwitter (CT). At the point I retire and/or no longer maintain an active role in my company, I will fully disclose my identity, share my LinkedIn profile, speak more openly about my investing experience, etc. But where I am in my career is the reason I decided to write this article: If I liquidated my Bitcoin position today, I could, quite literally, retire on the spot and still maintain my current lifestyle permanently. This is true even after paying US capital gains tax, putting the net proceeds in a non-interest bearing savings account, and supporting my family in perpetuity, which non-trivially includes two young boys, ages 10 and 8.

Again, I share these details not to boast, if they indeed come across that way. The reason I share them is because I hope they will not only illustrate my personal level of conviction about the future of Bitcoin, but also hopefully help younger investors in particular understand the importance of maintaining a long-term perspective when it comes to investments, especially in volatile growth assets like Bitcoin.

My preface notwithstanding, not a day goes when I don’t think to myself at least once, “The heck with it, just cash out and retire. Don’t get greedy. I mean, what if the recent all-time high is in fact the peak, never to be reached again, or at least not reached again for several years, despite the bullish narrative surrounding BTC? Why not just be grateful you’ve tripled your initial investment, a gain so substantial that you could now retire while maintaining the same standard of living?”

There is one reason and one reason alone I do not liquidate my entire position now. And no, it’s NOT greed. I wish for nothing more in life than I have now. I have an incredible wife, the love of my life, two amazing (if insane) boys, and a career that enables me to live literally anywhere in the world, which at the moment happens to be in East Asia. I want for nothing. But I do have one life regret, and it is Amazon.

By 2001, almost two full decades ago, I had been living overseas for five years, primarily in countries where English is not widely spoken. I therefore had limited access to long-form English reading materials, so Amazon had become my one and only means of accessing such materials. Even then, I was amazed by Amazon’s customer service and pricing, particularly for someone like me who lived half-a-world away. I was so impressed, in fact, that I decided to buy some of its stock (AMZN). The dot-com bubble had burst two years earlier, and while Amazon had survived, it was still on somewhat shaky ground. Nevertheless, it was such a great company, it seemed like it would succeed and therefore was wildly undervalued in my opinion.

At that point in my life, I was living what I’ll euphemistically describe as a carefree existence, so money in those days was primarily for maintaining my hedonistic lifestyle, not for saving. Nevertheless, because I really liked Amazon and believed in its potential as a game-changer, I scraped together $1100 to buy 100 shares. Yes, my purchase price was $11/share. It was November 2001.

You can probably guess where this story is headed.

Anyway, my investment was doing well when, in the summer of 2003, I moved to Hawaii to start graduate school. I was fortunate enough to receive a full scholarship, so I paid no tuition and was given free housing and a generous stipend to cover other living expenses. In short, all was well financially. But man, did that Kawasaki Vulcan look sweet sitting on the lot of that local motorcycle dealership. Sure, living in Hawaii, literally only one mile north of Waikiki Beach, was already paradise. But wouldn’t it be just that much cooler if I could explore the island on a motorcycle, especially given that it had no helmet laws? Wind jostling my rapidly receding hairline?

Of course it would. And heck, my Amazon shares had already quadrupled in value, so how much more could they grow? I didn’t want to be greedy. Why not lock in such amazing gains, especially with Hawaii’s roads beckoning so loudly?

So I did. I sold my shares at $43, netting about $2500 in profit after taxes on an initial investment of $1100. Not too bad, especially because it enabled the purchase of a vehicle that gave me immense pleasure for my two-plus years on the island. Having that motorcycle literally opened up possibilities that simply would not have been possible via public transport alone. I rode it everywhere: to Lanikai Beach to watch the sun rise, to Waianae to watch the sun set, over the mountains to the North Shore to watch world-class surfing competitions, down Kalakaua Avenue on Saturday nights to soak in the Waikiki atmosphere and to swim amidst the gently rolling waves on warm summer nights near Diamond Head, and then over to Chinatown for midnight dim sum. It was awesome, plain and simple. And none of this would have been possible without that sweet beast of a machine. Literally.

In this light, I do not regret selling my Amazon shares, even to this day. I derived innumerable pleasures from that purchase, a purchase that would otherwise not have been possible, save for the sale of my Amazon stock.

But what I do regret is my shortsightedness. Hard as it is to imagine now, Amazon seemed overvalued at the time I sold, in that summer of 2003. And, as it would happen, I wasn’t entirely wrong. AMZN peaked at about $60/share two months later (in October) before sliding all the way back to a low of $26/share in August 2006, 57% lower than its local peak in October 2003. To further justify my sale, AMZN didn’t permanently reclaim my sell price of $43/share until April 2007, nearly four years after the date I sold. So, in all these respects, my decision seemed - and arguably was - reasonable, perhaps even smart. But let’s have a look at just how shortsighted I really was. Below is a zoomed-in view of my trade with some other milestones marked:

At this level of magnification, it looks like I made a pretty good trade, buying near the local low and selling near the local top, a top that would remain in tact for three-plus years thereafter. But now let’s zoom out a bit:

I think the message is pretty clear, but to punctuate the point in words, Amazon stock has appreciated so much in the 17 years since my sale that you literally cannot see the price points where I bought and sold because they are masked by the volume bars on the horizontal axis. Heck, you can’t even see the 1999 dot-com peak when zooming out over this 20-year span.

The chart above succinctly encapsulates the reason I won’t sell my Bitcoin position today, despite having tripled my initial investment in nine months and despite the fact I could literally retire if I were to do so. Granted, the ability to retire is arguably far more significant than the purchase of a motorcycle, but in my opinion, it isn’t actually, at least relative to my lot in life at the time. Remember, at the time I sold my stock to buy the motorcycle, I was single, in my early 30s, had no debt and was entering grad school on a full ride. At that point in time, what seemed to make more sense? Keep an investment that could arguably implode - and in fact did, not long after my sale - or sell at a 300% gain so I could purchase a motorcycle that would not only give me the thrill of riding but also enable me to fully partake in all that my new tropical paradise of a home had to offer?

If this Amazon investment were the only shortsighted investment I had ever made, then perhaps I could indeed forgive myself. But it isn’t. Not even close.

To wit: I originally bought Sirius-XM stock at $0.25/share, Netflix at $42/share, Google when it IPOed at $100/share, Facebook at $40/share…the list goes on an on and on. And the worst part is, at no point did I ever need to liquidate my position when I did. Not once! I always and only did so to lock in profits, to “not get greedy,” because I saw a local top forming, or to satisfy some materialistic urge. But at what opportunity cost? Quite a large one, obviously. My original Amazon investment, that stupid $1,100, for which I grossed $4,300 when I sold it, would now be worth $312,000 today. And this is only one, if the most prominent, of all the investments I have made over thirty years that would be worth multiples more now than when I had sold them.

So what’s my point? Well, it is NOT to suggest that people should never sell any investment for any reason. Every financial decision, whatever it happens to be, is always most importantly a personal decision, and as I’ve said many times before, markets cease to exist without both buyers and sellers. I would never question or critique a person’s reason for buying or selling any asset, no matter how illogical or ill-timed it seems to me personally. To each their own, through and through.

But what I would suggest is this: If you really believe in the future of Bitcoin, whether “only” as a store of value, or perhaps eventually serving as the world’s reserve currency, and you do not need the money you invested for, e.g., an emergency or living expenses, then at least reflect upon my experience with Amazon stock (and countless other growth-oriented investments) before pushing the sell button, whether motivated to lock in profits, avoid seemingly being greedy, because you want to purchase a different asset, or for any other seemingly legitimate reason, including plain-old fear.

Note too that I am sharing my personal investing experience primarily with the kind of people in mind who both consider themselves investors (as opposed to traders) and who truly believe in Bitcoin’s potential, as I do. In other words, if you are ultimately a trader at heart and/or see some potential in Bitcoin but perhaps are not yet fully convinced of its game-changing destiny, then of course the basis of your buy and sell decisions will differ from my own. This is also true if you have perhaps overextended yourself to buy into your position, whether it be via leverage or even just at a larger percentage of your overall investment portfolio than you are fully comfortable with.

This latter point is really the only one I grapple with at the moment. Because of how much both Bitcoin and Etherium have appreciated since I initiated my positions, about 78% of my investable assets (excluding real estate and my business) are in cryptocurrencies, and about 80% of that amount is in Bitcoin. That allocation does give me a bit of a pause and has me toying with the idea of selling a bit to rebalance my portfolio. But I can assure you of one thing: I will not fully liquidate my Bitcoin position even though I could literally retire on the spot if I did.

Stated differently, I am truly going to HODL my investment, perhaps for the one and only time in my entire life. I am going to HODL through thick and thin, for better or worse, until/unless the Bitcoin network ever faces a fatal network threat. The fact is, and at the risk of sounding incontrovertibly pompous, I have never picked a loser. Literally every asset I have ever invested in has succeeded over the long term. Not because I am some sort of investing savant; simply because I never invest really early, instead choosing among investments that reach a near-certain probability of success but are still far enough out on the frontier that not everyone has already piled in.

In my opinion, that is Bitcoin today. It is also the reason I was on the sidelines during the 2017 cycle. At that point, Bitcoin was still too speculative in my opinion, still a playground for cypherpunks, libertarians, and speculators, still ultimately open to failing. Thus, despite the gobstopping gains it made over that 12-month stretch, and particularly during those four incredible weeks from 24 November to 17 December, I watched from the sidelines, intrigued and amused, but not enough to open a position.

But today is not 2017. In my opinion (and my opinion alone; not financial advice), I think Bitcoin is all but certain to succeed, just like I thought Amazon, Apple (version 2.0, post return of Steve Jobs), Sirius-XM, Google, Netflix, Facebook, Chipotle and countless others would, when they were still early in their growth lifecycle but no longer purely speculative plays. Nope. This one, I’m riding out. And given my age, this could quite literally be my last shot of getting in at the “right” time for an investment, that sweet spot between pure speculation and mass adoption, where asset success and appreciation seem all but inevitable.

Again, I cannot and do not offer financial advice, but in sum, this is how I am approaching my Bitcoin investment for the foreseeable future:

  1. Invest only money I do not anticipate needing any time soon. Note that I specifically did not write “only money I am willing to lose.” That ship has sailed, in my opinion. As I’ve mentioned, I no longer consider Bitcoin speculative. It just isn’t. Volatile? Of course. But not speculative. In my opinion, all speculative investments are volatile, but not all volatile investments are speculative. Bitcoin is in the latter camp at this point. Too many smart investors have endorsed and/or invested in Bitcoin for it to still be considered speculative. Now, does this mean it can’t drop 50%, 60%, even 70%, at some point in the future? Sure, it’s possible. But I’d argue that such a severe a drop is unlikely at this point, short of a global financial/economic meltdown. In my opinion, this cycle really is different than all previous cycles. But my larger point is this: I can no longer envision a scenario where Bitcoin flat-out fails, short of some fatal network flaw. But the risk of uncovering such a flaw at this point, in my opinion, is no more likely than, e.g., the likelihood Facebook will suddenly fail, and I make this statement without a trace of hyperbole. So in sum, my plan is to invest money I cannot foresee needing any time soon, but with nothing other than the tiniest hint of worry that my initial investment is at risk of going to zero due to the failure of Bitcoin.

  2. Pull out my initial investment at some point to completely de-risk my investment. I frankly hesitate doing even this given my near unshakeable belief in Bitcoin’s potential, but it really is the prudent financial decision to make. i.e., No matter how much conviction I have about Bitcoin’s future and no matter how many times my investment intuition has proven correct in the past, there are still no guarantees. Bitcoin could theoretically still fail, hard as that is for me to imagine. So, what does this mean in practice? I’m not sure yet, to be honest, but I do think I’ll pull out my initial investment soon. Ideally, I would do so during the next parabolic leg up (“sell when others are greedy,” à la Warren Buffett), but the other possibility is to do so once I quadruple my investment, meaning pull out 25% of my position when Bitcoin reaches $48K. That would leave 75% of my position in tact while still enabling me to get my initial investment back out, just in case...

  3. Leave the balance invested, theoretically forever. After pulling my initial investment out, I will likely leave the balance invested indefinitely, theoretically forever, or at least until/unless I need to make a future financial transaction where Bitcoin is not an acceptable medium of exchange. Hopefully that day will never come, but if it does, then I would cash out only what I need for the transaction and leave the balance invested in perpetuity, or rather, until I die.

  4. Donate the remainder of my long position to charity after my wife and I have passed. While I love my kids dearly, we are NOT leaving them a fat inheritance should we become fortunate enough to ever have to make such a decision. For better or worse, I grew up poor. Not figuratively; literally. My parents divorced when I was very young, my dad was all but nonexistent, and my mom was a secretary at a state prison, so I have been working to make ends meet in one way or another ever since I started delivering newspapers at the age of nine. Only now, over four decades later, am I in a position where I can even contemplate slowing down. While I will help ensure my kids are not saddled with an obscene amount of educational debt and might even provide them seed money to start a business of their own someday (if that’s a path they so choose), they will enter adulthood with nothing less than the bootstrapping blue-collar work ethic I developed over the years, even if mine evolved out of circumstance rather than philosophy. In short, I think I understand and appreciate the value of a dollar, and so too will they, even if the damned thing is being debased at 15% a year. So, donations it is if we are so lucky to have something remaining when knocking on death’s door.


Bitcoin is a volatile asset. Most enter its market with visions of life-changing wealth but many exit with a slice of humble pie and often less fiat than which they entered. I therefore consider myself insanely fortunate to have entered the market at such a fortuitous time, with my current investment now triple its original value. And I invested enough initially, perhaps foolishly so, such that I can now afford to retire, even at the relatively young age of 51 and despite still having two young boys smashing up my house at every turn. It has quite literally become a life-changing investment for me. And yet, as much I love the idea of retiring, I am determined, for perhaps the one and only time in my entire investing career, to water my flowers rather than cut them. I will not lock in profits, I will not try to predict local tops, and I will not worry about “getting too greedy.”

And if my decision backfires and I escape with “only” my original investment? So be it. I’ll keep working. But that is not Bitcoin’s fate, in my opinion. Quite the opposite, I think it is more like Amazon circa October 2009, when AMZN finally eclipsed its previous ATH of the dot-com bubble, at the staggering price of…wait for it…$107/share (split-adjusted). Yes, AMZN has still gone 30x after eclipsing its dot-com bubble ATH, despite the Great Financial Crisis, despite its sharp downturn in late 2018, despite its multitude of pullbacks all along the way. And I doubt very much Amazon’s growth has concluded even still.

Does this mean Bitcoin will also 30x after eclipsing its previous ATH of $20K this past December, eventually reaching the seemingly ludicrous price of $600K/coin? Who knows. But as I always say:

Bitcoin’s price history has shown that at any given moment, its price is not the highest it will ever be, but it could very well be its lowest.

This statement is literally true for all but the past 12 days (following its latest ATH high of $41.7K, reached on January 8). So with that in mind, I’m in this investment for the long haul, if for this one and only time in my entire investment career.

Good luck all, and go BTC.