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From DC Spy Dreams to Substack

Amanda Claypool on Media, Money, and Meaning

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Richard Helppie

Hello. Welcome to The Common Bridge. I’m your host, Rich Helppie, and we’re continuing today with our series on Substack writers. I think Substack is a very important platform because we’ve all seen the decay in the legacy media. People now are treating it like Pravda, frankly. They read it, they wonder what was left out of the story this time. They wonder why something’s down in paragraph 47 when it really is the lead of the story. They have other ways of slanting, manipulating the news, manipulating reporting, robbing people of historical context and, frankly, just getting people angry. Well, today we’re going to feature a Substack writer, Amanda Claypool. I’ve never met her, don’t know much about her, but I do like the way she writes and she writes a lot. Amanda, welcome to The Common Bridge. So happy you’ve joined us today.

Amanda Claypool

Thanks so much for having me. I appreciate it.

Richard Helppie

Our audience likes to know a little bit about the folks that are on the show. Our audience will listen, they’ll read the transcript and, of course, they’ll watch this video, but tell us a little bit about yourself, maybe what your early years were and what your career arc has been, and what’s brought you to this point in life.

Amanda Claypool

Believe it or not, I actually had a completely separate career before I started writing on Substack. I was originally a defense contractor in Washington, DC. My dream job was to become a spy for the CIA. I actually came really close, it just never panned out, but I got to work on a couple different really cool projects in Washington, DC. I helped manage a counter nuclear smuggling program in the Middle East. Spent quite a bit of time traveling and living in the region as well. So spent a lot of time in the DC Circuit and living in that world. Right before COVID hit, I decided to hang up my hat, leave that career and move back home to upstate New York. Obviously, COVID happened so the plans I had to restart my life in upstate New York were on pause. I ended up spending the pandemic traveling the country, living in my car full time, just seeing what was out there. That started putting me on the trajectory to start writing because I was remote, and just doing a bunch of side hustles at the time. I’d originally started on Medium, publishing essays there. I started gaining traction on that platform. Then about a year or two ago, I switched over to starting publishing on Substack, recognizing that Substack was starting to become, I think, the alternative media platform that so many of us were craving, especially after the pandemic. We started learning more and more information about how the legacy media was shaping the narrative, withholding information, and all that stuff. I’ve been publishing weekly on Substack ever since then.

Richard Helppie

That’s a great story. You’ve been out there getting firsthand information from firsthand people. I do want to let our listeners, readers and viewers know that the writers on Substack don’t get paid unless you subscribe to them, others of us have a tip jar out - so to speak - a Venmo address, a Zelle address, a Buy Me a Coffee. So if you like what you’re hearing from Amanda, or you just think it’s important, I’d encourage you to subscribe or contribute to what she does. And of course, if you’ve got a few nickels left over for The Common Bridge, we’d sure appreciate your support as well. Amanda, what’s the name of your page and how can people find you?

Amanda Claypool

I publish under Tomorrow Today. It’s right on Substack. You can also Google me. I’ll come up in a Google search as well.

Richard Helppie

Tomorrow Today is the name of the Substack page. What are you writing about on Substack these days? I know you cover quite a breadth of topics, but if you had to pick out one, two or three of the most important things, what are they? Why did you pick them? And are there any that are being under covered or mis-covered by the existing legacy media ecosystem?

Amanda Claypool

The main thing I love to write about and I’m really passionate about is the economy from the perspective of Main Street. I think a lot of the legacy media really talks about economic issues from a really high level. It talks about it from the perspective of Wall Street, but it doesn’t really talk about it from a perspective of day to day Americans and what our lived experiences are like. I became really interested in the more economic realm of things and the intersection of economics with technology, AI, how our society is advancing. As a result of my career in Washington, DC, like so many other young people, I was struggling to make ends meet. I think now, with Gen-Z coming up, they’re starting to push back against a lot of things. I think we’re starting to see systemic breakdown with the cost of living and cost of education, all that stuff. I was going through this in the 2010s and I didn’t understand, from my perspective, why I had gone to college, did all the things I was supposed to do, got the degree, got all the awards and all that stuff, landed in Washington... My first full time paid job was analyzing open source intelligence information on Twitter, basically following Arabic language media accounts to cover the war in Syria. I was paid $16 an hour, and I just couldn’t wrap my head around like how that was possible. So I started first diving into personal finance and learning more about that. That was my entry point into writing online. I started a personal finance blog first, but eventually realized, no, there’s this entire economic system underpinning all of this. And even though I had studied international relations, political science, history, in college, I never learned about economics. I had one course on economics as an intro level course on economics, never had to read Adam Smith, never read Karl Marx, cover to cover. So didn’t actually know any of the stuff that was really behind the lives we’re living. The fact that we’re going to these jobs, having to make money, pay these bills, and there’s all this economic engine underpinning it. Then of course, there’s the political side and the monetary policy and all these other things beyond our control. I started diving deeper and deeper into that really trying to understand what exactly those of us on Main Street - your average day to day, Americans - what exactly are we doing with our lives. We’re spending so much time working these jobs, like, why are we doing it and what’s the purpose? And then, of course, ChatGPT came online in November 2023, and that changed everything. For me, I saw that as our generation’s Gutenberg Press moment. I still believe this to be true. I think it’s a foundational technology that really changes everything, and it changes the value proposition of work. It changes the economy and it changes how we see our own human existence. And so really trying to understand what it is, what it is we’re doing every single day participating in this economy, and what is the entire point of the economy and its existence. There’s so much nihilism, I think, today, and fatalism in the world. People are just anti-capitalist because it’s, I think, fashionable to do so, or pro-socialist because it’s fashionable to do so, but they don’t really understand the philosophies or the ideas underpinning those ideas. So I try to dive deeper into some of that stuff; the economic theory, the thought, but then also how it applies to the rest of us. How is AI going to shape the job market moving forward, and if we lose our jobs we’re going to lose social capital. It’s going to change our interactions with one another in our day to day lives. How is that going to change society? That’s the thing I’m really fascinated by, because I think that has the greatest impact on all of us.

Richard Helppie

You’ve hit on many of my favorite topics, and we’ll start at the end point that we have this media ecosystem - depending on who’s in office - that tells you, hey, you’re all fine, what are you talking about? What are you worrying about, these are the best of times. Then the presidential administration changes literally overnight; hey, it’s all not fine. By the way, this is not new at all, in that there were claims of horrible homeless camps prior to 1992 when there was a change in leadership, then all of a sudden, hey, we just don’t report or talk about those anymore. I know that was a very long time ago. The social contract that many of my generation came up with was hey, give me your labor hours and you can get back from the economy a reasonable standard of living, and part of that included an education. One of the great risks I see in all the AI engines - whether it’s ChatGPT or the one that I use often called Perplexity - if you don’t understand how that engine is being fed - and I have a long history in computers and data and personal information and the like - you don’t know what to believe. We need to get back to a grounding in education. Let’s start with physics, which is really important, mathematics, which is very important, and econ and accounting, because everything ends up in some of those buckets. Then ChatGPT can be a tool to enhance our lives, not the thing that can manipulate us faster than the current methods. I really applaud what you’re out there writing about. What type of reactions are you getting to some of the things that you’ve penned? If you want to talk about a recent column that you posted on Tomorrow Today, that our listeners, readers and viewers should be finding... and if I haven’t mentioned this, they should be subscribing to and contributing to the support of excellent writers like yourself.

Amanda Claypool

The reaction has been really good. I’m surprised at how good it’s been, I will say individuals really appreciate it and appreciate what I have to say. I’d say the institutions that still control a lot of the media ecosystem - not so much. I was doing a lot of freelance writing prior to publishing on my own on Substack and I found that’s a dead end at this point. There’s no use in pitching articles.

Richard Helppie

There’s an old saying - I can never remember the front part of it - the back part is, if they can’t take a joke. Innovation comes externally. That’s one of the things in economics, that all bureaucracies will ultimately start serving their own bureaucracy and if there is not a private sector to innovate, then we’re just going to be stuck in a bureaucracy that grinds very, very slowly and produces less and less, [a pattern we’ve seen] from the times of feudalism to today that we need to be battling constantly. And it’s hard, particularly in the economic condition where, what is the social contract? And you asked what does an economy exist for? We’re not here to serve the economy. The economy is about distributing goods and services and harnessing labor and materials to produce a better life. And so the ultimate question is, are we producing a better life for the most people in the best way possible? Not that hard.

Amanda Claypool

Exactly, exactly. And I find those questions are so important. I think I’m still maybe a little naive and hopeful that many of the legacy media would like to entertain those types of conversations, but I’ve just hit a complete brick wall with a lot of that. I’d say anyone who’s still subscribing to legacy outlets, definitely that has been a no go. But for the most part, definitely a lot of positive interactions. I know this past May, I started posting more video commentaries on YouTube and within a few months went from zero subscribers to almost 11,000 now, so definitely resonating with a lot of folks. Just a lot of the strife and struggle people are struggling with. But I write a lot of... it is a diversity of topics. The economy is obviously, I think the big one for me, because I think it impacts us the most. But also touching on political change, political events, just because I did live in Washington, DC and was part of the bureaucracy, and had a firsthand window into what that experience was like. And then also, I write a lot of social commentary as well about feminism and just the cultural and gender wars right now, because I’ve also made a shift in how I think about that.

Richard Helppie

You’ve got a great perspective and a terrific ability to articulate. I’d love to hear, if you don’t mind.

Amanda Claypool

Absolutely. I’ve written several different pieces about this and been talking a lot about it on YouTube, because this is a pretty salient issue. It does pertain to the economy, because at the end of the day, you’re going to need workers and we have to reproduce, and therefore they are odds with one another. It’s not going to end well for the rest of us. I was raised in an evangelical Baptist church, grew up with one foot in the conservative world but was public school educated, so another foot in that world. Went to college like everyone else. I can’t say that someone explicitly sat me down and said here is the feminist syllabi, this is what you must believe. But over the period of time I was in college, it was definitely ingrained in me that I was disadvantaged, the patriarchy was against me and all these systemic problems. I didn’t understand it as systemic oppression in the way that it’s being talked about today, but it was definitely being communicated as a structural disadvantage that affected me based on my gender. So for much of my early 20s I was definitely not a raging feminist in the social sense, but definitely from a career perspective I believed career is the most important thing in the world and I didn’t want anyone standing in my way. I definitely thought there was a meritocracy and I had done well in school and therefore I was owed something. It wasn’t until I left DC, traveled the country during COVID, that some of the rose colored glasses and my belief in the legacy media started coming undone during that period of time, I started to really critically question feminism. By the time I got to my early 30s, I realized, wow, I’m going to be one of these women who ends up childless and unmarried if I don’t reject this right off the bat. And so I made that transition, married and all that, and starting a family. I’m really excited about that. But I’m now seeing everything I was afraid of starting to play out where women my age and a little bit older are starting to acknowledge that, okay, this might not have panned out the way it was supposed to. And then, of course, you look at it from the context of the AI revolution that’s underway, and it’s like, okay, well, these jobs, they don’t really matter anyways. If you’ve staked your entire identity and your well being in a career that could go away at an instant, you’re living a very fragile existence. So starting to realize that there’s far more to our lives here on Earth than just a nine to five job and who we work for.

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Before we dive back into today’s enlightening discussion, we have a quick message for all you common bridge enthusiasts out there. Did that you can find this episode and over 300 more on Substack as part of The Common Bridge series. You can also find written columns and opinions as well. Subscribe at TheCommonBridge.substack.com for a full Common Bridge experience. There, you can comment and express your opinion on all the topics we cover on this and the past seven seasons of our podcasts. If you’d rather support the show without subscribing, you can do so with Zelle at Rich@RichardHelppie.com or using Venmo @Richard-CBridge. Thanks for listening. Now back to the episode.

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Richard Helppie

To be fair, women were discriminated against, they were denied the right to vote. I know that my beloved godmother, when she got married, was working for the telephone company and they said, oh, you got married, you no longer have a job because we don’t employ married women. I came through my business career when women were coming into corporate leadership and coming into the law profession, more into the medical profession. Title IX was a profound event in terms of leveling the literal playing field for women and girls. So there was a mission there and I think today perhaps that it’s been overshot in that if a young woman has the opportunity to go to law school or engineering school or medical school or what have you, become one of those professions and not be denied that opportunity - but you don’t get the job because you are female. In my career, I built a substantial consulting business, and when we were audited one time by the Department of Labor, amongst other accolades, they said, you realize you have 45% women in senior leadership? And I said, no, I didn’t know that. We just put the people in place that could do things. And frankly, in computing, it’s a binary, objective world that either works or it doesn’t work, and it doesn’t care if you’re man, woman, what race you are, what age you are; it does the same thing for everybody. But I understand that as you were coming up, you caught the tail end of that. It’s like the race industry; they need to keep beating that drum, even though they could easily declare victory and move to a more equal society.

Amanda Claypool

Absolutely. I like how you use the term overshot, I think that really describes it because I think there was a time and place for helping women achieve parity. But I think with my generation and moving forward, it really overshot, and it transformed from striving to help women succeed to creating a sense of entitlement. I definitely was horrible in my 20s, I felt incredibly entitled, and it definitely shaped my outlook on life and how I participated in the workforce.

Richard Helppie

It’s your interview today but I will only give you one anecdote about how easy it was to overlook this. This goes all the way back to the 1980s. I call somebody who’s very close to me, who’s an excellent attorney, and she is livid. And I’m like, well, what’s the matter? Well, the head of the litigation department had taken all of the litigation department to his house. I go, well, what are they doing there? Do you know? They’re playing video games? I said, well, do you want to play video games? No, but I’m the only woman in the litigation department, and they’re all over there doing that. It was like, oh, I doubt the guy gave it a second thought, but his upbringing, the way he was cultured, never saw the incredible insult he had just leveled. And so in my professional career, there has been a substantial amount of gain and I’m very happy that those women and girls near and dear to me have opportunity and choice. I hope that, like you, they lead a full life with higher values as well. Do whatever you want to do, let there be equality, opportunity and choice.

Amanda Claypool

Absolutely, absolutely, totally agree.

Richard Helppie

We’ve talked about economics, we’ve talked a little bit about social and then you hinted at the difference of the perspective between Washington, DC and the rest of us out here.

Amanda Claypool

Yeah. So if you’re familiar with the Hunger Games, I think it’s a really good metaphor. I know that that was like a young adult series that was popular several years ago, but this whole idea is that the Capital District is very different from all of the other districts in that world, and it’s very ostentatious. Everyone is just a higher level, see themselves as higher, holier than thou, holier than everyone else. I definitely observed this and noticed this when I lived in Washington, DC. Everyone is highly educated, yes - potentially over educated, in my opinion - but they definitely have this ethos where a lot of the people who work in DC believe that they are distinct and better than everyone else, that they have been anointed with some sort of mission, whether it’s a political mission, whether it’s a social justice mission - there’s a lot of nonprofit space in DC as well - they’ve been anointed to pursue some sort of mission, and they’re working on it for the benefit of humanity. A lot of these people really believe that, and they don’t really understand how they fit as a cog in the machine. I think the USAID scandal that broke last year really highlights this. You have a lot of really good people with good hearts and good intentions working in an organization that now we’ve come to find out, okay, well, maybe they weren’t exactly funding all humanitarian efforts. Maybe there was some other stuff going on here. That is definitely a part of it. But one thing I also noticed when I lived there is DC was really insulated during the 2008 financial crisis. The money kept flowing through government. The contracts kept coming. You say you worked in consulting, so I’m sure you’ve experienced that as well; as long as you sign the contract, a multi year contract, you’re good to go. A lot of people there have never really dealt with the economic consequences of the policies that are being passed by the institutions in the district because the government money keeps flowing. It’s only once the government money stops flowing that I think they start to realize, oh, wait a minute, we’re not as impervious to the outcomes of our policy choices as we thought we were. I personally believe much of the rest of us, much of Main Street America, has been living in a prolonged recession since 2008. I don’t actually think the recession actually ended. I think we’ve just been living under this illusion that everything was fine and dandy, and that’s because credit was cheap. It was very easily accessible to folks in Silicon Valley. They could create and manufacture jobs that weren’t necessarily needed, and it created this illusion of opportunities in tech, everyone was told to go code. They created all of this illusion of all of these opportunities, and then COVID hit, and the contraction started shortly after that. I think people started to realize, wait a minute, all this cheap, free money that we thought was circling around the economy doesn’t really exist anymore and I think the rest of us on Main Street have been aware of it. I’m from a rust belt town in upstate New York so I’ve had a front row seat to the consequences of de-industrialization, brain drain. Almost everyone I went to high school with, we’ve all left and moved elsewhere now. Baby Boomers, my parents generation, they’re starting to retire in their older age. A lot of mom and pop restaurants and diners I used to go to with my parents, they’re now gone. You have your strip malls and your retail private equity chain owned restaurants taking over so the character and the culture that I think really built a lot of communities on Main Street is starting to go away and fade away. I think we’ve lost a lot in the last almost two decades now, and folks in DC just, they don’t really leave the DC bubble. They might go into the Virginia countryside. They might go into West Virginia, but for the most part, they’ve never interacted with someone who lives in South Dakota or someone who lives in Nebraska. They just have no idea how other Americans live. And then, of course, the media ecosystem has created such an echo chamber where they’re just fed information that reinforces their pre-existing biases and assumptions and beliefs about how the rest of the country operates. And it’s just, it couldn’t be further from the truth. I think there’s just a complete divide between the people who have been put in charge to govern us - whether we elected them or whether they elected themselves - and the rest of us who are in the electorate who have to face the music of whatever choices they make on our behalf.

Richard Helppie

I think that’s a very excellent articulation. We used to have this thing called servant leadership coming from all levels of our government, our education systems and people took it seriously; we’re educating, preparing the next generation. And to your point, those making the rules are often insulated from the impact. Nihilism is, I think, an apt description. There was a time when an elected person would be embarrassed at the hint of personal enrichment or corruption and now it’s expected that, yeah, someone goes and serves in Washington, they’re going to make a lot of money. They don’t even try to hide it. If a tenth of what’s being alleged in Minnesota and California right now is true, it is corruption on a massive scale. The flip side of that corruption is that the people that our government agencies are supposed to serve are not only not getting served, they’re paying for it, and it’s another weight on them. But it’s turned into this tribal contest where, well, my party is less awful than yours. I’m just very encouraged by listening to your intellect and your analysis, it gives me great hope for the future. We’re also going to be featuring entrepreneurs on The Common Bridge. I’ve got a series coming up with people that have found a way to make a good living in this economy. The advice that I give people of your generation is this: find work. My generation was told find a job. Find a good job with benefits, with a future. And I’m saying, no, go find work. What can you do today that people will give you money for? If you get up every day saying, I’m going to find work that I get paid for, you’re going to be surprised by the great results. Amanda, you have been very generous with your time and I think we could probably go on for six or seven hours. Any final comments for the listeners, readers and viewers of The Common Bridge? I will again say, please consider subscribing to Amanda Claypool, Tomorrow Today, at Substack. We need more writers like her out there producing content, doing research, maybe - who knows - expanding. Maybe she becomes the daily newspaper some day, and you’ll say you were able to support her way back then, which is now. So please lean in. Amanda, please take us home here.

Amanda Claypool

I think we’re in this incredible transitional period in human history. I think it’s going to be very destabilizing. I think it’s very scary. I think there’s a lot of uncertainty, but I’m also hopeful for the future. I think there’s going to be unprecedented opportunities as well for people who are paying attention to what’s happening; they’re not just listening to the day to day hustle and bustle on X or whatever, although it is important to stay on top of things, but that they’re not getting lost in it. I think understanding where things are going, the changes that are going to be happening, and just keeping tabs on the bigger macro trends of what is going on, I think that will help a lot of folks be able to navigate what’s underway. And that’s my goal. That’s my goal, is to use the talents I’ve been given to write and share my thoughts and do the research and help folks understand, okay, this is where we’re at today. This is where we could be tomorrow, and this is how you need to start thinking about things and prepare. The best thing you can do is just focus on the things that you can control. The world’s a crazy place. You can’t control everything, but focus on what you can do. Focus on the work you can do, the skills you have, the family you have, the things you have. Be grateful for those things. And I think the people who can do that, I think they’ll come out ahead of this.

Richard Helppie

We’ve been talking today on The Common Bridge with Amanda Claypool of Tomorrow Today on Substack. This is Rich Helppie on The Common Bridge, encouraging you to support the program. If you’re one of our thousands of podcast listeners, please come to TheCommonBridge@substack.com or our Venmo or our Zelle. We’d sure appreciate your support there, and of course, a subscription or a contribution to Tomorrow Today with Amanda Claypool. With our guest, Amanda Claypool, this is your host, Rich Helppie, signing off on The Common Bridge.


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