Interesting discussion guys. I think indeed it takes discipline sticking to your strategy and don't frontload, even when bitcoin has a seemingly continuing upward momentum from its $3k bottom. Somehow over the years I lost being sensible when it comes to Bitcoin, while I am generally cautious buying individual stocks (VTI FTW). I admire being stubborn and sticking to the strategy.
It is a whole hell of a lot of work just to create a strategy, and many mere mortals have lots of difficulties really making an honest attempt to assess each of the relevant factors which bear repeating here: cash flow, other investments, view of bitcoin as compared with other investments, risk tolerance, timeline, and skills (limitations) and time available to research and tweak holdings/trades.
Those are not easy factors to figure out, even for ones self, and sometimes it can take years to just figure out the personalize parts like those above factors.
Feeling regret in retrospective to not have frontloaded makes little sense:
I don't know how you get around a "regret" inclination that almost everyone has, even when they have thoroughly thought through their plans and approach and attempted to tailorize their plans and approach to themselves. Second-guessing is almost inevitable, even for the strongest-minded people - even if they might not want to personally explore those monday morning quarterbacking considerations.
you have a strategy and need to stick to it, perhaps it helps in case you imagine for a moment the bitcoin price went into the other direction? Especially having little 'dry powder' while bitcoin, seemingly inevitably, comes down back to earth is terrible. Bitcoin is on fire sale and you can't buy any.
For sure, that remains part of the forgotten formula when people are feeling regrets. They see the BTC price go up 50% or 100% or 300%, and then they forget that they had NOT invested so much because they wanted to be prepared for DOWN. They have a tendency to see ONLY what happened rather than the preparation and insurance aspects regarding why they had decided (earlier) how they had decided.
It might have turned out very well for some, but that does not prove frontloading / going all in is a wise decision.
Personally, I proclaim to have profited quite well from a kind of frontloading. Of course, my frontloading has not gone to such extremes as "going all in", but I personally feel that there were several times that I purposefully invested quite well beyond my rational thinking about how much I should be investing, as a kind of gamble. Yeah, that inclination towards frontloading did not feel so good or feel as if it were paying off while the BTC price was going down, but it felt a lot better when the price started to go back up.. (two years later.. or some other seemingly extreme time, later).
I will give you a specific example: Through most of 2014, I did not disclose to anyone that I was investing in bitcoin, and I engaged in a kind of mild frontloading of my BTC investment, and throughout the year BTC prices were going down and they seemed to be kind of plateauing in the $600 range, so when BTC prices went into the upper $300s (something like $385 in about October 2014), I pretty much began to tell a lot of people about bitcoin and my tentative theory that the bottom was in, and proclamations like that.
I was considering putting in a portion of my 401k into BTC (but I ended up rejecting that consideration) and also, I ended up converting two of my index fund investments into bitcoin (which then constituted about an additional 10% injection of value into bitcoin). I was pretty sure that we were god damned close to the bottom, and yeah we know what happened after that, no? In December BTC prices dipped below $200 and even had a spike down to $150/$160 and thereafter until October 2015 the BTC price pretty much stayed in the mid $200s, and even dipped below $200 again in October 2015. Those were not times in which too many HODLers were able to retain their confidence in BTC or even to continue to buy. I had my own issues and reservations, and I continued to frontload "a tiny bit" into bitcoin, which surely did not feel good, and it surely made my stomach feel queazy and I kind of felt like I was going to get fucked if the BTC price continued to go down and I was adding a bit more dollar value to my BTC investment while I was about 50% in the negative and I surely was not splurging beyond bare budget necessities in other matters. I was NOT exactly eating ramen, but I was living relatively frugal and considering that I was continuing to "frontload" into BTC.
Sure, I had been frontloading the whole 2 years from 2013 through 2016, but my confidence about the frontloading never really started to see the light of day until about May 2016 when the BTC price shot above $500 (of course we had that little burst from $250 to $500 in late November 2015, but that had gone back to bouncing between $350 and $420, so it did not really begin to feel more solid until the May 2016-ish - and even the mid-2016 rise did not feel the best because we got the purported Bitfinex hack in late July/early August 2016 - which drug the BTC prices back to sub $600 prices for a couple of months).
In essence, what I am trying to say, is that even frontloading does not need to be considered as an all or nothing kind of practice. A person can frontload in a kind of incremental way... a way that leans in a kind of direction without necessarily going all in, but at the same time, in the guy's (or gal's) head, the amount of the investment feels like too much and is quite balanced in an uncomfortable direction.
(and thanks JJG for the honest previous response)
I am not trying to hide these kinds of matters from anyone, and of course, I account for various ways that money is lost along the way. Maybe Lazlo also could say that he got fucked by spending 10k BTC on two pizzas, but he surely does not consider his decision in that way.
Of course, there are risks with being an early adopter and exploring various kinds of ways to exchange coins or to keep coins on exchanges, and sim porting surely caught a lot of BTC HODLers by surprise, including yours truly. Sims porting is still a strategy used by hackers and remains quite effective. Hackers are also learning new and innovative ways to hack, so being your own bank is a fuck of a difficult thing to attempt to practice without getting robbed. Of course, the more that you experiment with a variety of tools, the more that you might learn, but sometimes you also might inadvertently open yourself up to one or more attack vectors.
At least, I feel that I did not get fucked by using some of the shady altcoin exchanges because I hardly dabbled in altcoins, so a lot of people (maybe more) got fucked because they experimented with various altcoins, but yeah, I did give BTC-e (that's and exchange) that transitioned into WEX too much benefit of the doubt by continuing to use their exchange/services while they were continuing to be attacked by the US Government. In retrospect, I probably should not have considered them to be able to prevail in the good fight, whether it was trying to continue to operate in a way that evaded getting shut down or they were not secretly planning an exit scam. In the end, coins were lost.. and I had opportunities to remove a decent amount of those coins, and I had even done it at one point to see if they would let me, and after they let me withdraw the vast majority of my coins, I ended up, through several months, putting back more than the amount of coins that I had initially withdrawn... which seems really stupid in hindsight... and as if I had not spent enough time really considering the amount of risk that I was putting on that part of my BTC holdings... which ended up going poof (even though there are some threads attempting to figure out if there are ways that people can get their coins back or a portion of their coins back, the odds seem to be quite on the low end, currently.. maybe less than the dumber dumber odds - eg. "there's a chance.")
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