Written September 2, 2025 by Past Brian. To Future Brian (that's you, September 3 Brian), I genuinely hope you're managing to survive whatever particular brand of chaos has unfolded today. Whether it's been a resignation scandal, some kind of medical crisis, or just Trump deciding to announce a trade war with household pets, I'm confident this essay will still hold up regardless of what broke at 2 PM. So here's the situation: Trump just released what can only be described as a self-congratulatory video about his "11 Life Lessons," and it's exactly the kind of performative theater you'd expect. The fundamental problem is that his entire life story contradicts virtually every single lesson he's trying to sell to the public. If this turns out to be his swan song, then it's nothing more than a hypocritical whimper from a man who never learned anything worth teaching. And if it's just more PR fluff designed to distract from whatever destructive plot he's cooking up next, then it's empty grandstanding from someone who's spent his whole life desperately seeking respect he never actually earned.

This is rich coming from someone who inherited an absolutely massive real estate portfolio directly from his father. The truth that Trump doesn't want you to know is that Fred Trump subsidized Donald's entire career through a combination of tax avoidance schemes and continuous family bailouts. We're talking about an estimated $413 million in today's dollars, according to extensive reporting and financial records. Without that silver spoon firmly lodged in his mouth from birth, Donald Trump would likely be just another struggling real estate wannabe from Queens, probably still trying to figure out how to make his comb-over look less obvious. The whole "self-made billionaire" narrative? That only exists in the marketing materials and his own imagination. The reality is that he started on third base and has spent his entire life pretending he hit a triple.

If Trump really loved what he did, you'd think at least some of his business ventures would have succeeded. Instead, his business empire reads like an encyclopedia of failures and abandoned projects. Remember Trump Steaks? That was supposed to revolutionize how America eats meat, but it collapsed faster than a house of cards in a hurricane. Trump Vodka was marketed as "success distilled," which is ironic considering it failed spectacularly. Trump Shuttle was going to transform air travel between major cities, but it never even got off the ground financially. And let's not forget Trump University, which turned out to be less of an educational institution and more of an elaborate scheme to separate desperate people from their money. In every single case, Trump walked away without an ounce of shame or responsibility, leaving behind a trail of disappointed students, burned investors, and consumers who bought into promises that were never going to be kept.

Sure, thinking big can be valuable, but in Trump's case, it's also how you end up declaring bankruptcy six separate times. His version of "thinking big" consistently meant overpromising, underdelivering, and then finding creative ways to avoid the consequences. Trump University stands as a perfect example of this pattern. It was marketed as a way for everyday Americans to learn Trump's supposed secrets to real estate success, charging students up to $35,000 for what turned out to be essentially worthless seminars. The whole operation eventually resulted in a $25 million fraud settlement, as documented by Congress.gov. Then there's the infamous border wall, which was supposed to stretch from sea to shining sea but ended up being half-built, riddled with cost overruns, and mired in accusations of graft and corruption. When Trump says "think big," what he really means is "create massive grifts that sound impressive but ultimately fail to deliver anything of value."

This might be the most laughable lesson of all. Trump's actual work ethic, as documented by numerous White House insiders and journalists, consisted primarily of what he called "executive time." According to leaked schedules and firsthand accounts from Vanity Fair, this meant hours upon hours spent watching Fox News, firing off tweets, and actively avoiding intelligence briefings that might have required actual mental effort. The man spent over 300 days golfing during his presidency, as meticulously documented by Wikipedia. That's nearly a full year out of four spent on the golf course, often at his own properties where taxpayers footed the bill for his entourage. This happened even as major crises unfolded, markets crashed, and Americans desperately needed leadership. If this is what Trump considers "working hard," then the phrase has lost all meaning.

The irony here is almost painful. Trump's administration had the highest staff turnover rate of any modern presidency, with churn rates approximately four times higher than his predecessors. His team didn't just lose momentum; it completely disintegrated in a spectacular revolving door of resignations, firings, and dramatic exits. Key positions went unfilled for months, policy initiatives stalled out before they even began, and the whole operation lurched from crisis to crisis without any coherent direction. In his post-presidency period, the pattern has continued with a series of failed startups, endless court battles, and no clear vision for what comes next. If maintaining momentum means anything, Trump never learned the lesson he's now trying to teach others.

This is perhaps the most disingenuous lesson of all. Trump was raised in extraordinary privilege, attended elite private schools, moved in wealthy Manhattan social circles his entire adult life, and built his fame on inherited wealth and media connections. His supposed "outsider" status is pure theater, carefully crafted to appeal to people who feel genuinely disconnected from power. Let's not forget that this is the same person who dodged the Vietnam draft with a dubious "bone spurs" diagnosis, spent decades cozying up to politicians of both parties when it suited his business interests, and cultivated relationships with autocrats and dictators around the world. Calling himself an outsider is like calling a wolf a vegetarian just because it occasionally eats grass. The reality is that Trump has always been the ultimate insider, just one who figured out how to profit from pretending otherwise. He's an entitled rich guy in an expensive but poorly tailored suit, playing dress-up as a populist.

Trump's instincts are precisely why we had a president who suggested that Americans could cure COVID by injecting bleach into their bodies. His instincts are why American farmers got hammered with retaliatory tariffs that destroyed their export markets. His instincts led him to keep Rudy Giuliani as his personal lawyer long after the man had clearly lost touch with reality, resulting in press conferences featuring hair dye streaming down Giuliani's face while spouting conspiracy theories. These same instincts have produced more bankruptcies, legal problems, and public relations disasters than any reasonable person could count. If Trump's instincts were a GPS system, they'd consistently lead you off a cliff while insisting you've arrived at your destination.

Trump's version of the American Dream seems to involve being born into extreme wealth, systematically exploiting workers, dodging taxes at every opportunity, and then congratulating yourself in the mirror while ordinary Americans lose their health care and struggle to make ends meet. Throughout his business career, he consistently outsourced labor to cheaper markets while claiming to champion American workers. He's notorious for stiffing contractors, many of them small business owners who did honest work and never got paid. His policies consistently favored the ultra-wealthy while increasing inequality for everyone else. The actual American Dream, where hard work and determination can lead to success regardless of your starting point, is about as far from Trump's reality as you can possibly get. His nightmare carnival of greed and self-promotion represents everything the American Dream was supposed to transcend.

This advice comes from someone who was impeached not once but twice, lost the popular vote in both presidential elections he participated in, and faced an absolutely crushing series of legal defeats. He lost 61 out of 62 court cases related to his claims about the 2020 election, a spectacular failure rate that would embarrass anyone with a functioning sense of shame. Multiple juries have found him liable for sexual abuse and defamation. His charitable foundation was dissolved by court order due to "shocking" illegality and fraud. His businesses have failed repeatedly, his marriages have collapsed publicly, and his reputation outside his core base is in tatters. If this is what "winning" looks like, then the word has been completely redefined.

The truth is that Trump isn't original in any meaningful way. His entire persona is a hodgepodge of borrowed and stolen elements from other sources. The reality TV star angle was pioneered by others long before Trump stumbled into it. His political playbook reads like it was copied directly from the strongman dictator handbook, complete with attacks on the press, scapegoating minorities, and claiming that only he can solve the nation's problems. Even his most famous slogan, "Make America Great Again," was lifted directly from Ronald Reagan's 1980 campaign. Trump is essentially a cosplay version of a successful businessman, complete with the fake tan, the elaborate comb-over that's arguably more synthetic than organic, and the oversized suits that he seems to think make him look powerful but actually just make him look like a child wearing his father's clothes.

In Trump's case, this translates to never giving up on lies, conspiracy theories, and scams, no matter how thoroughly they've been debunked. He continues to cling to false claims about the 2020 election despite overwhelming evidence and countless court rulings. He pushes pandemic conspiracies that have been definitively disproven by science. He maintains innocence in cases where he's been found liable or guilty. This isn't resilience or determination; it's stubborn corruption masquerading as resolve. There's nothing noble about refusing to give up when what you're refusing to give up is a commitment to falsehood, fraud, and the destruction of democratic norms. Real strength would involve admitting mistakes and learning from them, something Trump has proven himself completely incapable of doing.

Let's take a deeper dive into some of Trump's most spectacular failures and frauds, because the pattern here is impossible to ignore:

Trump University stands as perhaps the most egregious example of Trump's willingness to exploit desperate people for profit. Marketed as a path to real estate riches, it was described by prosecutors and former students as a "massive scam" that specifically targeted people who could least afford to lose money. The operation became entangled in multiple class action lawsuits, with students testifying that they were hustled for increasingly large sums of money for increasingly worthless information. Trump eventually settled for $25 million rather than face trial, though he naturally claimed this was not an admission of wrongdoing. The full details are documented extensively on Wikipedia.

The Trump Foundation was supposed to be a charitable organization, but it turned out to be more of a personal piggy bank for Trump and his family. The foundation broke virtually every rule governing nonprofits, engaging in self-dealing, conducting unregistered fundraising, and even using charitable funds for campaign purposes. After extensive investigation by the New York Attorney General, Trump was forced to pay $2 million in damages and the foundation was dissolved under court supervision. The level of corruption was so blatant that it shocked even seasoned investigators of nonprofit fraud. More information can be found on Wikipedia.

The Trump Organization Civil Fraud Case resulted in Trump being ordered to disgorge an astounding $354.8 million for systematically inflating property values to secure better loan terms while simultaneously deflating them for tax purposes. The judge in the case found that Trump and his organization had engaged in persistent fraud over many years. The penalties and oversight requirements are still playing out in courts, but the verdict was clear: Trump built his business empire on a foundation of lies. Detailed coverage is available on Wikipedia.

When you look at Trump's "11 Life Lessons" in the context of his actual life and career, what you see is a breathtaking buffet of hypocrisy. Every lesson is contradicted by documented facts, court records, and the testimonies of people who've had the misfortune of doing business with him. These aren't life lessons; they're the hollow platitudes of a man who's spent his entire life failing upward thanks to inherited wealth and a willingness to exploit others.

If this video represents his final attempt at reshaping his legacy, it's a ridiculous and hypocritical whimper from someone who never learned the actual lessons life was trying to teach him. And if it's just more PR fluff designed to distract from whatever destructive scheme he's planning next, it's still worthless pomposity floating over a graveyard of actual consequences that real people have had to suffer.

The truth is that behind every rehearsed quote and carefully crafted talking point is a lifetime of failures, frauds, and devastating harm packaged in fake wisdom and sold to people desperate enough to believe that a man born into wealth understands their struggles.

To Future Brian: I hope this gives you what you need. Get your red pen ready if needed, but make sure to keep those facts tight and those sources solid. Most importantly, keep reminding everyone that Trump's "wisdom" is worth exactly as much as a degree from Trump University: nothing, except maybe as evidence of how badly you've been scammed.