It makes me sad that people do not say Have fun staying poor as much as they once did. Probably, the meme has fallen out of favor because most people believe Udi Wertheimer created it, and so it suffers from that vile cancellation-by-association that is so popular right now. But the truth is, HFSP was a thing people said long before Bitcoin, the internet, and even Udi.
Therefore, so that all light may not be lost from this already dreary realm, and so that the Youth, for whom we all have such required hopes, may not dwell overlong in darkness, I have taken it upon myself to attempt to recount a full and accurate history of Have fun staying poor.  

There is no question that Udi popularized the phrase. Udi first used Have fun staying poor on Twitter on 13 September 2020. Truth slaps hard, especially when it is a stranger, and HFSP clearly touched deep emotional currents in Udi (as it has in so many of us).
By 14 September, HFSP had gone to his head to such an extent that he said his new hobby was "literally telling everyone on Twitter 'have fun staying poor.'" While it is true that the internet is a degraded pit of sarcasm and flippancy wherein statements can never be far from the cynical bastion of 'I was just joking,' Udi further demonstrated his conversion to the phrase by purchasing the domain havefunstayingpoor.com on 17 September (for which, indeed, he must be commended). Udi also occupied the @HaveFunStayPoor twitter handle (the full phrase exceeds the maximum Twitter handle length, so he had to be content with Stay Poor). And it is also true that after those frenzied days in September, the phrase rapidly rose in popularity as it had not in many years. For instance, it shows up on bitcointalk.org for the first time on 30 September 2020, and people like Michael Saylor were calling it "that classic Bitcoiner response" by early 2021.
 

If, however, you attempt to discover anything more about the history of HFSP, the internet is shockingly disorganized. No doubt the authors of these histories of HFSP in Coin Desk and Bitcoin Foqus were contending with ailing parents, extreme weather events, or the debilitating consequences of some ill-considered DIY project, for they thoroughly neglected to ask from whence did the internet get the phrase
In truth, the history of HFSP is a history of a phrase struckthrough. It has long been in use, but never in the realms of polite English and proper History. It is often crossed out and excised from final drafts and public discourse. In order to recover it, one must venture a little further than the local library and wikipedia.  

I spent a fair bit of time in Aberdeen, Washington as a child. It smelled bad, like mildew let grow for years, and was a very sad place. But it was well-emembered among those who were so unlucky as to have been living there long enough that their clothing was thoroughly imbued with that odor that Kurt Cobain really liked to say HFSP as a kid. Apparently, he would get on his bike and go blazing down this whopping big hill called Scammel Hill, screaming HFSP at the top of his lungs. He even included it in the first draft of Lithium (although later crossing it out). I do not raise this point to make some trivial connection between rebellion and HFSP, but rather to note that HFSP has always appealed to innovators.

Although it is perhaps too far in the dusty past for most to recall (and yet not old enough to be History), there was a time when it was fairly common knowledge that Gene Wilder was set to perform a song by the name of "Have Fun Staying Poor" in Willy Wonka and the Chocolate Factory (after Wonka gives the children their everlasting gobstoppers) and that Paramount axed it. The scene was actually based on a moment at the beginning of Chapter 19 in the book that Dahl, himself, ended up removing from the book.
Much has been said of Wonka's callous (even vicious?) nature, and perhaps Dahl knew he was treading the line of raw reality rather too closely for a children's book. Whatever the case, his most famous character did rather embody the concept of HFSP.
Here's this strange man who keeps his factory locked up and doesn't let anyone enter, and yet who makes the most incredible candy in the world. He is marvelously unphased when various children on his tour become victims of horrific industrial accidents. He even manages to politely imply that the children themselves are to blame for various mutilations and that they are such miserable little shits in the first place that Wonka can be forgiven for letting a little note of glee slip into his voice. It's the same glee that anyone who says HFSP experiences.
 

No doubt, if you remember your Biology 101, you will recall Charles Darwin's affinity for HFSP. His early letters are riddled with it, although, as is true in our current age, he began censoring himself as he gained success and by the time he was famous barely used it at all. I say success, but who really knows whether it is success or just plain getting old which creates this curious willingness to censor our true feelings for fear of propriety? Nevertheless, when he was still young and hungry, Darwin intended the title of the book in which he laid out his theory on the origin of species to be Have Fun Staying Poor. He clearly says so in his 1857 letter to Asa Gray.
Darwin's use of HFSP is a particularly good example because evolution is the final form of HFSP. Nature, the laws of physics, or whatever name you choose for the reality we inhabit, quite obviously will never change its principles for the sake of adoption. Every creature which has failed to spread its genes across populations and generations, has expired into obscurity listening to the sound of Nature whispering softly in its ears: have fun staying poor.  

Of course, a far more famous usage of HFSP exists, and I am referring to that most magnificent and monstrous refusal to compromise for the sake of making people happy: the Declaration of Independence. Although Adams refused to include the phrase in the final version, the original draft Jefferson presented to him and Franklin concluded by exhorting the good king to have fun staying poor.
Much has been made of the signers' youth, of the high cost many of them paid, but what is most relevant here is that they did not seek to meddle in the king's affairs beyond those that directly affecting the signers' colonies.
Many rebellions strike immediately at the source of oppression. But the Declaration of Independence is very clearly not a declaration of war. The signers and the people they represented had no plans to topple the British Empire, invade England, or assassinate King George. Therefore it was entirely correct that Jefferson finish the Declaration with the sentiment that the king go his own way, even though it was likely to end in poverty.
Have fun staying poor is not a wish to tell other people how to live. It is an expression of confidence in a set of core ideals and the refusal to alter them for the sake of adoption.  

We can venture further back into the archive and continue to find familiar expressions of the HFSP sentiment (for example, I believe that Martin Luther used the phrase in the 66th of his 95 theses nailed to the church door in Wittenberg. Now, I'm not an expert in Latin, but my cousin Mathilde is, and she assures me that 'oblectāris manente paupere' is quite close to our modern have fun staying poor), but my goal is not to be exhaustive. Rather, I want to help free this beautiful phrase from the social shackles which bind it. When you encounter shitcoiners, cynical nocoiners, cocky normies who dismiss Bitcoin as some goofy toy for nerds, remember that these four words have well-served many brave and tenacious innovators in the past, and they will equally serve you.