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In this episode, Chelsea dives into the most problematic cultural figures who have directly influenced our relationship with money. Click the "JOIN" button below to join our $4.99 Society tier to see our bonus episode on Dave Ramsey!

Join Chelsea for her first-ever 4-week live masterclass, How To Build A Real Business On YouTube, kicking off April 19th! *DISCOUNT: Get $49 off your ticker (regular price $199) before space fills up! Replays available for anyone who can’t join live!*


Ronald Reagan:

Shark Tank:,part%20of%20the%20American%20Dream

Dave Ramsey:

Suze Orman:

Winkelvoss twins:

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Hey, guys.

It's Chelsea from The Financial Diet and this week's video is brought to you by my own class. So I'm sponsoring my own video today because it's my house and I can do what I want.

So for those of you who don't know, at TFD we do tons of workshops and events and conferences and things like that. And we do every so often these longer four-week deep dive classes. We have one on investing.

We have one on building financial foundations. Those come around every couple of months. And we have a really qualified credentialed people who teach those and they're awesome.

But when I was thinking about-- because I wanted to do a class myself-- the subjects that I feel qualified to teach a four-week master class on, the only thing I could really think that I am truly qualified to teach is building a real and sustainable business on YouTube. There are a lot of classes and courses and videos out there about how to go viral and get a lot of subscribers. And those things are good, but I also know from my nearly seven years on YouTube that even consistently going viral or having a lot of subs does not translate into having a real, sustainable business.

And as you guys probably know, I'm also very, very passionate about operating that business in a way that is ethical and equitable to its staff and genuinely working to build something that you're actually proud of. So this class is for people who have a channel or are starting a channel that they are looking to build into a real, sustainable, profitable business, whether that's just supporting them as an individual or supporting a staff like we do here at TFD. It's a four-week class starting on April 19th and if you can't make classes live, there will be recordings available of everything.

I also have office hours where I work with my students and answer all of their questions. There's going to be live critiques and feedback for real channels of people in the class. There's going to be take-home activities and tools and resources for every single class to really help build your channel, diversify the revenue of your channel, and learn how to change just making videos that are cool into a business that works.

Tickets for this class are normally $199, but you can get yours for just $150, is $49 off using the code MasterClass49Off at the link in our description. I am incredibly excited to be teaching my own four-week class. It's the first of its kind.

And I hope you'll be there starting April 19th. Anyway, today we are here to talk about the people and the cultural figures and the phenomena that have really messed up our relationship to money. This is actually the longest script I've ever written, so first of all, buckle up, baby.

But second of all, I wanted to go along on it because I really do feel that these people and things deserve our individual attention and understanding. Ultimately, the way we look at personal finance and money, what we aspire to, what we expect from our government, all of these things do not exist in a vacuum and they don't come from nowhere. The lessons that we get about money, both on the personal level and on the macroeconomic level, are ideas that come from various cultural forces that we may be impacted by without even realizing it.

And it's not to say that these people and things have no redeeming qualities or can't be sources of good advice. In fact, many people who follow TFD and align with a lot of our views on sociopolitical and economic issues have been hugely helped by some of this stuff and there's no shame in that. I think when it comes to money and life and career advice, it should be very a la carte.

You can get good advice from imperfect sources. And as much as I'm loathe to admit it, I myself I'm an imperfect source. I know.

It's hard to believe. And even some of this stuff on this list, like my beloved Shark Tank, has provided some great insights for me over the years while still being overall quite problematique. And the point of this video is not to universally throw the baby out with its bathwater, but to be very conscientious about where these ideas are coming from, what we consider normal, what we consider aspirational, and what we consider sound advice when it comes to money, especially when it comes to things like political climates.

These things change. So it's important to be critical about the frameworks through which we're analyzing all of these things. So without further ado, let's break down the six key figures who lowkey torpedoed our relationship with money.

Also fun fact, it was initially supposed to be seven figures and Kris Jenner was one of them and the whole Kardashian-Jenner consumer panopticon, but the video was already so long that I had to move them to their own video. That will be coming out soon. So we're starting our list of cultural figures who destroyed our relationship with money.

We got to take it all the way back to the early 1980s. We got to hear a big round of applause for that big dog, the OG, the Don of drizzle down economics, the bootstrap big boy, the Hollywood Insider, Margaret Thatcher's friend with no benefits, the artist formerly known as The Gipper. That is right.

For those keeping score at home, I am talking about our 40th President, Ronald Wilson Reagan. Now it is really difficult to think of a president who did more damage to our overall economic climate as well as our personal relationship to finance than Ronald Reagan did. In fact, his own former Director of the Office of Management and Budget, David Stockman, wrote an entire op-ed in the New York Times on how his version of the GOP and their disastrous policies quote, "destroyed the US economy." And while it would take its own video to truly break down all of the damage that Ronald Reagan did, the overall picture is a very fundamental shift both in terms of what we think of as prosperity and who we think is entitled to that prosperity.

So Reagan's Club Sandwich of Fiscal Catastrophe that is historic financial deregulation, tax cuts for the wealthy, subsidies and welfare for corporations, starving public works, and the hard emphasis on a bootstrap mentality which demonizes any public assistance for the poor while practically throwing it at the wealthy and big business combined to create a new paradigm in our economy, which swiftly and mercilessly eroded the middle class over the subsequent decades. And to be clear, this is not to say that economic policies which dramatically favor corporations and the wealthy, or which allow Wall Street to run roughshod over the average citizen-- Clinton and Obama both did quite a bit in their own ways in this regard-- Reaganomics were definitely a new era in American life both in terms of the actual economic consequences and the perception shifts that may have felt subtle at the time, but which have culminated in a profoundly different relationship to what we feel society and the government owes its citizens, and vise versa. For example, robust government programs that helped Americans get jobs, buy homes, secure affordable education and training and have families used to be not just the norm, as it is in most of the developed world, but a demand in exchange for everything that Americans contribute both in terms of taxes and productivity, which has steadily been increasing since more or less the industrial era.

This was a kind of social contract, which especially after World War II was embedded in the idea of what it meant to be an American. Americans worked hard and America, through robust public programs, gave working and middle class Americans an ability to create a better life for themselves and their children. But Reagan did an incredible and unprecedented job in undermining that social contract and in eroding the trust of Americans have towards the value of these programs.

For example, his powerful welfare queen narrative which, despite having been thoroughly and frequently debunked in the years since-- which we'll link you guys to down below-- continues to this day to color how we feel about people who use social programs, despite most of those people statistically working a job of some kind. Meanwhile, during that same propaganda campaign about average citizens using public services, the financial services industry, big business, and the ultra-wealthy in this country were seeing a level of government support and favoritism that had previously been unheard of. In short, Reagan, through both his policies and his fantastic ability to communicate terrible ideas, completely shifted our idea of who the government fundamentally was there to help as well as who should expect to benefit from it.

And it is something that our economy has never truly recovered from nor, incidentally, has the middle class. Number two is my baby, Shark Tank as a show and also all of the shows like it. And this one really does hurt me because I love Shark Tank, I mean, to the extent that I can no longer say "and for that reason" without saying it like my beloved Lori Greiner.

And as I mentioned in the intro, I actually do believe that I've learned quite a bit from Shark Tank mostly in the form of what not to do, but also in some ways about how important it is to diversify your business for sustainability and growth because doing one thing well isn't going to be enough to make a business survive long term. (WHISPERS) We cover that in my class. But it is undeniable that the massive popularity of this show and the narratives that it pushes, aside from launching a somewhat credible political campaign for noted thumb Kevin O'Leary, has instilled an idea of entrepreneurship, business owning, and the American Dream, which is basically diametrically opposed to how all of those things have been trending over the past decades in this country. It is no secret if you watch this channel-- and why wouldn't you?

You're so chic-- that for as resilient as the American mythos actually is in terms of our rags to riches story, we actually have incredibly low class mobility for a developed economy. And aside from the actual amount of people who manage to ascend class strata through hard work and grit, the broader idea is that the generation which follows you will do better than your own and that this is the aspirational life promise of having children, giving them a better life than the one you knew. And to be fair, for many years this was more or less true in America.

Generations gained in wealth and opportunity and class mobility was competitive with comparable economies. But as many of us might know, the millennial generation kind of put an end to all of that Don Draper-style class reinvention and left us poorer and with fewer opportunities than our parents' generation enjoyed. And Gen Z so far appears to have it even worse.

But the continued success of shows like Shark Tank doesn't just contradict this reality by pushing the narrative in a passive way by its own popularity and the fact that some of the entrepreneurs on the show really do have rags to riches stories, especially products launched by, again, my beloved Lori Greiner, the show also reinforces these narratives explicitly with many of the hosts, even Mark Cuban, who everyone does love, talking about this unique opportunity to build something better for yourself and your family, being what makes America so great. The data just doesn't support this. But as far as a PR campaign for keeping the long-discredited myth of the American Dream alive, Shark Tank is actually pretty effective.

And as much as some of the individual stories can be powerful to watch in a vacuum, it's extremely important to remember that on aggregate, this is not the story of what it means to work hard in America, (SARCASTIC TONE) not even compared to some of those dreaded socialist regimes in Europe. Because for as much as the show stresses that the secret to success for these contestants is their hard work and determination, it has been years that things like productivity or hours spent at work are totally decoupled from how much a person can expect to earn, particularly in a gig-based economy where working multiple jobs to survive because your main job doesn't pay a living wage anymore is reframed as being your own boss. But I guess just not like the bosses that they feature on Shark Tank.

Number three is Dave Ramsey. Here we are. Hey, who would have thought?

Not me. We're finally talking about this dude on the channel without me referring to him as beep beep. We have been operating TFD since 2015 and despite our frequent but thinly veiled allusions to our many issues with the Dave Ramsey industrial complex, I've been extremely personally reticent to make a video that talks about this stuff directly, particularly as it pertains to his toxic influence on the culture or, allegedly, his own staff, which I do a deep dive into on our bonus video, but more on that later.

And the Ramsey Empire has actually in the past reached out to me personally about possibly collaborating on some stuff and it is something that I would never even consider doing, despite the huge boon it could possibly be to our business because of their undeniable massive reach as a company. But, and again. As I will get into more in the bonus video.

I've been pretty reticent to talk about this stuff because not only has the man sort of notoriously been quite litigious, the fandom that follows him can also be quite aggressive themselves. And frankly, I'm just not trying to start a flame war with a bunch of evangelical Christians in my comments. But also also, because this is the one where I need to be most clear, that if you have benefited from some of Dave Ramsey's advice over the years or have followed some of his instructions to your own personal financial empowerment, that is fine.

I don't think there's any one right or wrong way in which to improve your finances and many people who are big fans of this channel and don't like the dude personally have gotten some value out of some of his tips. That's OK. But at the end of the day, this man and his empire are massively popular and have influenced the culture in many ways beyond just the few people who may have actually, for example, been able to pay off 100% of their debt and yelled about it on his show.

And that's what we actually need to talk about, the pervasive and negative impact that Dave Ramsey has had on the financial culture. Because if you've taken even a passing interest in personal finance, you have definitely been exposed to at least one of his sizzling fajita [MUTED] hot takes on the subject. So it's important to understand that in addition to some of the actual tenets of his financial advice being a bit shaky, there's also a general tone of incredible shame, judgment, and moralization of poverty as a cornerstone of his brand and, in some ways, I think his success.

As far as the shakiness goes, his repeated claim of 12% average market returns on investments has been thoroughly debunked by people more qualified than myself, which we'll link you to below. But basically, even though investing in the market is important and basically essential for most people to retire comfortably, the average returns are way less than that and over-promising is part of what can lead people to get fed up with the slow and steady route to wealth building and try to find back doors to making money quickly. And similarly, his overall framing as Debt As Holy Enemy leads to a framework in which if you are a person in debt-- and there is debate here about the nuances of which kind of debt are acceptable-- you basically should be living the life of a medieval serf until you have crawled out of the hole into which your sinful and indulgent choices have led you, with Dave even going so far as to famously say on Twitter, "if you're working on paying off debt, the only time you should see the inside of a restaurant is if you're working there." And in fact, his relationship to debt is so extreme that he recommends people only have an emergency fund of $1,000 until they are out of debt, for which many Americans could be literal decades.

So I guess even though that is well under the recommended amount to buffer people from unexpected financial catastrophe, generally three to six months of living expenses, it is enough to keep someone in a life of absolute penance and precarity in order to erase the debts that our societal paradigms all but forced people to enter. See student debt. There's also the hypocrisy of it all, with Dave staunchly opposing government aid for individuals even during times like, for example, the height of the pandemic while happily taking millions in government incentives for his own business.

Link to all that stuff and more in the description. Dave's general outlook on money can sort of be summed up as the residue that would be left in a pot if you boiled the bootstrap narrative overnight for like 12 hours on high heat. It is just pure, uncut shaming and derision for people who are in poverty with almost no understanding of the cycles that keep people trapped in poverty even if they're making the right decisions or the incentive structures which all but oblige people to get into debt in the first place, like the fact that many entry level jobs now outright require master's degrees among many other things.

But all of this becomes even more complicated when you understand that the dynamics here of shame and judgment and ostracization don't just get applied to the callers who happen to call in for advice while committing the cardinal sin of being A Poor, but also allegedly to his own staff, about which there is an eye-searing amount to learn when it comes to how not to run an ethical business. So for our members, click on the link in our description to get and exclusive bonus video that is just a deep dive into the alleged insane employment practices and gender discrimination, amongst other things, that give the Ramsey Empire its secret blend of herbs and spices. And if you're not a member yet, you can go ahead and click that link or the Join button and just sign up for our society at TFD tier.

It's $4.99 a month and in addition to these bonus videos has tons of amazing benefits. Next up, let's all give a big round of applause to the stage for the Blazer-- I can't. I can't do this, guys.

Suze Orman is the next person on this list. And in some ways, it almost feels redundant to talk about Suze Orman after we just talked about Dave Ramsey because the Venn diagram of their badness so often just forms an awful circle. But Suze Orman, more than possibly any other figure in the financial media ecosystem, has really been responsible for creating that sort of Avocado Toast As Reason You're Not Able To Accrue Generational Wealth Paradigm that has become so anchored in our discourse that it's basically a meme at this point.

And while many thoughtful people have already gone through the trouble of cataloging her bad, outdated, and downright mean advice-- and we'll link you in the description-- I think it's worth drilling down on just how much her positioning in the culture led to years of otherwise smart people framing their financial situation through the prism of to what extent they were willing to forgo all conveniences. Or for example, accept her new paradigm of 70 as the correct retirement age. Or, for those happening to experience intergenerational poverty or financial struggles, her advice of helping to prioritize your parents through retirement at the expense of your own.

So I guess basically just to ensure that we're now trapping every subsequent generation in a cycle of not having enough to get by. Essentially, when you think of the problems that many adults currently face in our economy, being priced out of the housing market, not being able to retire with dignity and enough time to enjoy it, having parents struggling to make ends meet in older age, et cetera, the solutions that Suze consistently proposes are almost universally about the individual choices and often the ones that are so far into the margins, like having occasional conveniences like a Netflix subscription or getting a coffee at Starbucks, that even if you were to follow this advice to a T, mathematically there's just no way that these incremental changes would accumulate to the extent needed to fix the actual systemic problems. And when it comes to terrible redirected solutions to actual societal problems, next up, we have the sigma male grindset.

Now Suze Orman may be bringing it home for the ladies in terms of financial advice that takes their real grievances and turns them into unsustainable and self-punishing solutions, we've got to bring it up in the rear for the men here and talk about the Sigma Male/ Hustle Bro mindset that has taken over a lot of this type of financial media and advice on the internet. There has arisen an entire cottage industry of YouTube videos, instructional essays, e-books, classes, et cetera around the topic of how men can empower and enrich themselves by becoming a vaunted sigma male or following this hustle culture grindset. And while there doesn't seem to be a ton of internal cohesion around who is actually considered aspirational in the subgenre-- because we have everyone from Jordan Belfort, usually as portrayed by Leonardo DiCaprio, to Marvel superheroes to famous entrepreneurs to random stock images of handsome men in open space offices-- the overall message seems to be that the path forward for men is to disavow the interest in or approval of women, pursue total self-reliance, usually through the accumulation of substantial wealth, and escape the typical social hierarchy by, I guess, being extremely good at it.

This is often the type of financial, professional, and social advice being given to men who, in many ways, do rightfully feel kind of cut out of the normal order of things or are having a difficult time fitting into the typical standards of acceptance, especially when they center around money, which famously millennial and younger men on average don't typically have a lot of. So just as Suze Orman redirects a feeling of, hey, this society really isn't working out the way it's supposed to for huge numbers of working adults into well, I guess it's my fault for going to the movies and buying popcorn that one time. Better not agitate for any kind of systemic change.

The grindset accounts-- again, often with literally millions of followers. See my recent video with Big Joel on YouTube channel Alux-- funnels a general feeling of young, disenfranchised men being left out of a social order that used to be much better at supporting them through material benefits like accessible education, job training, family subsidies, affordable housing markets, et cetera, into a sense that they're better off aspiring to wear expensive watches and model their lives after men who went to prison for securities fraud. It also, as a lot of these particular phenomena are want to do, places a heavy amount of the blame on women because I guess we're just not attracted to them because we're just petty, vapid, hypergamous, superficial succubi.

And beyond that, because it's probably a lot easier to think that than to buy into the idea that we are being materially shut out of a sociopolitical and economic order which consistently favors the already wealthy and large corporations to leave the working and middle classes to fight each other for scraps of status or a vague chance at a dignified retirement. But that's probably a conspiracy. Lastly, we're keeping it fresh.

We're keeping it relevant. We're keeping it very 2022 in here with the Winklevoss twins, henceforth referred to as the Winklevii, who are in this case being used as a bit of a stand-in for the broader crypto crew. But as I'll explain, I feel are profoundly emblematic of a particular aspect of the entire phenomenon.

So I should say upfront here that while the Winklevoss twins are not the biggest players in the crypto space nor the most foundational nor the most important by any number of metrics, they do typify a very specific aspect of the crypto world that is very much worth unpacking. So I'm not going to waste time here talking about my negative opinions on the world of cryptocurrencies, decentralized/deregulated financial markets, speculative assets, NFTs, et cetera, but I will say that what makes the Winklevii so particularly interesting in this world is something that NFT Slayer and YouTuber Dan Olson said in his seminal video The Problem with NFTs, a video for which we recently interviewed him on an episode of The Financial Confessions-- please go watch both. They're both in the description-- but basically, he argues that a huge driver in the world of Web3 is that people who know that the previous systems did not make them the winners/oligarchs, whether that means the traditional financial system or the big emergent winners of Web2 like Facebook, Amazon, et cetera, Web3 is a concept-- and it's a dubious concept to begin with-- and the wild west financial system it entails, offers an opportunity for a new class of people to become the winners.

And while a sane person might argue that the Winklevii walked away from Web2 as big winners themselves, securing a $65 million settlement from Mark Zuckerberg for copying some of their social network ideas, enough to live on comfortably for two lifetimes and then some, they clearly felt incredibly slighted by what was perceived to be their owed glory in the era of social networking and massive platforms. So they were not comfortable just stopping there. And their most successful venture post-Facebook fracas has been their crypto empire Gemini, which recently raised $400 million to build a metaverse, which heavily leverages and features cryptocurrencies, of course, and has seen them become billionaires in their own right in part through their incredible bullishness on Bitcoin, of which they reportedly own so much that at one point they held 1% of all Bitcoin in circulation.

In many ways, their hyper-aggression as it pertains to making decentralized and financially deregulated technology the territory of the future has seemed specifically targeted at seeing the end of juggernauts like their former nemesis Mark Zuckerberg, whom they frequently criticize in the press and specifically position their ventures against, like their metaverse project, which is specifically being built to exist outside of and eventually hopefully render obsolete platforms like Facebook. We love it when the girls are fighting. Get each other.

And at the end of the day, if you believe like I do, or like the aforementioned Dan does, that this new and even more dangerous version of the intersection of technology and finance represents an existential threat to both worlds as well as all of the naive consumers who will be churned through this mercilessly to prop up pump and dump schemes for people like the Winklevii, you will see why their epic quest to slay the moist dragon that is Mark Zuckerberg and his Web2 victory they've clearly never gotten over is so particularly toxic to our current tech predicament. Also sorry, Winklevii, no matter how hard you try, you're never going to have cakes like this. Anyway, when it comes to figures that have seriously harmed our relationship to money, I could go on for another several hours because there are many.

But for different reasons and in different ways, these are six of the biggest. And again, it doesn't mean there's never been a piece of good advice or a useful tool out of any of this stuff. It just means we need to be a lot more critical about where our ideas are coming from and how we might be perpetuating them without realizing it.

As always, guys, thank you for watching and don't forget to hit the Subscribe and Join buttons and to come back every Monday, Tuesday, and Thursday for new and awesome videos. Bye-bye.