What you're actually getting paid in, with Leila Clark
In this episode, Patrick McKenzie (patio11) is joined by Leila Clark, founder of Stardrift and formerly a software engineer at Jane Street, to discuss her essay "What Are You Getting Paid In?" They cover how a Jane Street manager staffed the firm's least lucrative corner by paying people in culture, why Ken Griffin is worth roughly fifty Taylor Swifts, and how a longtime Google product manager quietly ends up with Grammy-winner money. The conversation ranges from academia's brutal tournament structure and YC as a script to founderdom to the one currency Taylor Swift holds that Ken Griffin's $50 billion buys only awkwardly: a restaurant reservation anywhere in New York.
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Timestamps:
(00:00) Preview
(01:23) What are you getting paid in?
(03:16) Scripts, teacher figures, and hitting capitalism
(08:18) The academia trap
(11:08) Paying people in culture: Jane Street's back office
(14:03) Ken Griffin vs. Taylor Swift
(16:53) Learning about finance by osmosis (or not)
(20:44) Sponsors: Mercury | Chainguard
(23:46) Musician money vs. Google money
(30:03) Keeping up with the Joneses and the meritocratic ladder
(33:12) YC as a script to founderdom
(36:19) What entrepreneurship pays you in
(39:12) Gratitude, culture, and quirky preferences
(40:11) Sponsor: MongoDB
(43:48) Does winning this script look like winning to you?
(48:29) Don't end the week with nothing
(51:06) Fame and living in bubbles
(56:57) Restaurant reservations as a currency
(1:02:57) Where to find Leila
(01:03:35) Wrap
Transcript
Note: Below is the episode transcript. Patrick will be returning later to add in his signature transcript notes.
Patrick: Hideho, everybody. My name is Patrick McKenzie, better known as patio11 on the internet. I'm here with my buddy, Leila.
Leila: Hi, I'm Leila. I guess I would say I'm a software engineer, 'cause that's the class you're assigned when you graduate from college, and you're never allowed to change it again. In practice, most of my time nowadays is spent as the founder of Stardrift. We're an AI travel planner, YC and BCV-backed, and I'm also a big patio11 fan.
But I think predominantly for this podcast, we're gonna be talking about the first four years of my career, where I was working as a software engineer in finance. Not a trader β a software engineer, predominantly at Jane Street Capital.
What are you getting paid in?
Patrick: Awesome. So you wrote a blog post recently β I should say essay. One of my little tiny hobby horses: people ought not to commoditize their work by calling it something like "blog posts," because blog software does not necessarily encapsulate the value that something creates for the world. The word essay has a higher perceived value in many quarters, and so call them essays. And yet I occasionally slip up and call my own things blog posts too.
But your essay on the topic of what people choose to get compensated in in their career β that there are many currencies available. Can you walk people through some of the logic?
Leila: Yeah. I guess it's interesting that you say what people choose to get paid in, actually, 'cause the title of the essay is "What Are You Getting Paid In?" And part of the thesis β or part of why it's resonated with so many people β is that a lot of people don't realize what they're getting paid in, or haven't thought very hard about it. And I think this is one of those sleeper essays β I'm sure you've had some yourself β where I wrote it and it felt like no one read it for a year, and then suddenly lots of people came up to me and were like, "Oh, I really liked your essay on what are you getting paid in." I think part of what happened here is that Ricki Heicklen, who's also been on your podcast, sent it around to a bunch of our friends, and they all really liked it.
But yeah, having worked in finance β and especially working quant straight out of college β I saw a lot of people go through a job-hunting process and think about what jobs they wanted, and it felt a little bit like an extension of how you get into college, where everyone's like, "Let me get the highest grade" and "Let me optimize for the highest number." And especially in quant, it felt like the thing a lot of people were optimizing for was the highest salary.
I think one of the interesting things about being eight years out of college now is seeing how those various paths have diverged, and how much people who thought they wanted to get paid in money β including maybe me β actually didn't wanna get paid in only money, and how many other things there are that you can get paid in. Sorry, that's maybe the backdrop of the essay.
Scripts, teacher figures, and hitting capitalism
Patrick: I think that's a very reasonable starting point for it. I think people often kind of default into scripts that are socially acceptable in whatever milieu they find themselves in. And those scripts make a lot of decisions for us, where if we thought critically on what we actually wanted β what our actual preference set is β we might choose things that are different from the scripts.
I think that one of the β I don't know if it's wonderful or not wonderful, it is observationally true β things is that there is some class, for lack of a better word, of people who do very well in school and make a large portion of their identity doing very well in school. And this includes some amount of intellectualism and also some amount of pleasing a teacher figure and buying in on meritocracy very, very hard. And so the system will conspire to put meritocratic competitions in front of them. And people who are in this class β like, say, myself and perhaps yourself and perhaps many, many friends and family of ours β will just say, "Okay, I just got done crushing the last meritocratic competition, which is awesome, because there's another one coming up in just six months and I have to crunch to make it through that gate." And then you just keep going through the gates, and then eventually you hit capitalism.
And for a while, capitalism just dispensed with the notion. And then I think one of the creative, awesome, and terrible things it did is: well, if you need to have teacher figures in your life to feel happy, we will assign you surrogate teacher figures, and we will give you fake essay-writing competitions to track you into this opportunity or that, which will be compatible with the scripts that you've been living in previously.
But if you get trapped into high-status professions, some of them weight the compensation very much towards cash or equity or other dollar-denominated sorts of things. Other high-status professions somewhat notoriously weight it towards social status. But I don't necessarily know that the people at the point in their life where they are choosing "I would really like to do immigration law" are explicitly thinking, "Yes, I will go to sleep exhausted after having dealt with many, many problems that were the same as the problems that I've been dealing with for the last six months, with different names on the paperwork. But I will feel like there is some amount of social significance to this, and also I hope that there is someone paying for my living expenses in New York, because what they pay immigration lawyers will not let you rent an unsubsidized apartment in many places in New York."
Leila: Oh, I actually didn't know that. I thought immigration lawyers did all right.
Patrick: I'm willing to be wrong on this one, but I think the lower end of the immigration law stratum doesn't really do all that well β the ones who work for NGOs and similar. I think the immigration lawyers who work for, without loss of generality, tech companies doing paperwork for highly paid W-2 employees coming over do quite all right for themselves.
Leila: Hmm, that makes sense. I mean, even within immigration law β immigration law is actually a good example of what can you get paid in. Because yes, as you pointed out, you can get paid in sort of straightforward form-filling work, which doesn't require a lot of β I don't know β where you are helping people who are already doing pretty well in the world and getting paid a nice amount of dollars for it. And so you're getting paid well in dollars and predictability and some amount of stability. I'm sure you can β not easily, but it's straightforward to build a pipeline of such clients.
And then also, as an immigration lawyer, as you point out, you can choose to represent people who really need your help, who probably don't have the means to help you. And instead of getting paid in dollars, get paid in, yes, feeling good. I'm not sure you actually get paid in a lot of social status in that specific situation, actually, butβ
Patrick: I don't know. There's a legibility to being a lawyer in that it's a, quote-unquote, "rich and scary job." Everyone knows what a lawyer does for a living, whereas not everyone knows what a, I don't know, product marketing manager does for a living. Legendarily, in many ethnic groups and social classes, there is the mom-and-dad-approved list of occupations. And lawyer is on the list, and product marketing manager is not, as far as I am aware, on any of the commonly accepted lists.
Leila: Ah, yeah, that's true. And outside of America β and even, I think, within many groups within America β software engineer is also not on that list, even though it really should be. I think we're recording this in Silicon Valley, whereβ
Patrick: I think this is finally starting to change, although the McKenzie family still β so, I have one publication credit to my name in an actual academic journal. And when that came out, a great number of the McKenzie aunts and uncles said, "Finally, he's no longer unemployed. He's gotten an academic credit, and clearly he's going to stop wasting time and go get the PhD as he's always been meant to do and finally have a job."
Leila: Oh, academia's a great example of this.
Patrick: Yeah, please.
The academia trap
Leila: Oh, sorry, I was just β yeah, actually, now that I think about it: when I wrote this essay, I wrote it very much for the people who just came out of college. Life is so diverse and it brings people on so many paths. But a lot of people, especially those listening to the podcast, probably did go to a good university and went into kind of a PMC-type job β professional managerial class.
And yes, I do think academia for many people can be a bit of a trap in the what-are-you-getting-paid-in way, where I did see a lot of my classmates pick it because it seemed like a stable way to continue getting paid in approval from teacher figures. And then they did it and they were like, "Wow, this sucks. This is not set up for me to succeed. I'm on my own. There's no guidance. I'm not getting paid any money." Some of them, of course, succeeded and became professors and are having the times of their lives, and those people are absolutely getting paid in what they wanna get paid in, butβ
Patrick: And academia is a brutal tournament model right now, where the top of the distribution for PhDs do successfully achieve tenure, knock on wood. There might be, you know, a market for three tenured PhDs per year in the entire United States in a field. But β not to say that academia is a Ponzi scheme, but structurally, a field cannot graduate only three people per year and solve for the equilibrium. The vast majority of PhDs cannot get a tenure-track position, but the only jobs worth doing in academia β apologies to postdocs everywhere β the job everyone wants to get in academia is a tenure-track position. And so structurally, almost everyone will be disappointed.
I often think that because students have spent the entirety of their life optimizing for the academic career track at the point where they're making important life decisions, and they are supervised and coached by people who made the same set of decisions, largely have no understanding of what the job market ex academia looks like, and β very importantly β won the freaking tournamentβ
Leila: Oh, yeah.
Patrick: βthey have a blinkered perspective of: well, clearly, if I get a PhD in computer science or East Asian languages and literatures or similar, I will get to lead the life of the mind like my mentor figure does here, and I will have challenges similar to the challenges that they have. And unfortunately, this is just not the case. I think there has been more awareness among professors in the last couple of years that, ooh, if you are graduating right now, there are some harsh realities of the academic job market which I was not subject to 20 years ago, but you will definitely be subject to. And so there is some percolation of that to people making decisions, but maybe less than one would have hoped for.
Paying people in culture: Jane Street's back office
Leila: Yeah. I think the high level of the essay β it actually starts off with a story from a friend of mine. Or, it's actually based on the management philosophy of a friend of mine who was a sort of middle manager at Jane Street, and I think he managed the technical back office. He was very, very successful at it. Back office in finance means the reconciliation, operations, finance in the financial sense β which is not the trading, but managing how and where your money is. It's all boring stuff, basically, unfortunately. Super valuable, but very boring.
And my friend was obviously trying to run his business in a place like Jane Street, where everyone gets to work on exciting things like new trades and fast order engines and things like this. And so he had this problem of: how on earth do I get good people to come work for me in the most boring section of the technical part of this organization, but in a place which is very important to the business? And I think as a result, he developed this management philosophy of what can I pay people in.
And I think it is true β people who go into finance usually do it because they like money and they like getting paid money, and they think, like I did, that the thing they wanna get paid in is lots of money. Because they probably got into finance because they looked at the salary and they were like, "Wow, this salary is like twice the salary of the other job options I have available. What if I did that, and then I can have a nice apartment in New York City?" And I think one of the problems with back office in finance, structurally, is that it is really hard to pay people lots of money. It's almost very adverse, because your entire organization is composed of people who optimize for the most money, and now you're trying to convince them to join the part of the company that pays the least money. There's sort of a structural problem here.
But he was very successful, and I think one of the ways he did it was he actually built one of the best cultures in the organization β and it turns out culture is a way you can pay people. And then you can almost play this practical joke or trick on people, where you're like, "Ah, you thought you wanted to get paid in money. But here are two jobs. Here's one job that's miserable and will pay you twice the amount of money, and here's one job where you make enough money, you have a nice apartment, you are suffering no lifestyle constraints, you can still send your kid to private school or whatever." It turns out when you're making a good salary in New York, doubling it does get you some nicer things, but it's not β like, 10x-ing is a different story. Then you can buy yourself a plaque in a museum of your choice or something. But doubling it β I think many people get to this point in finance where they realize money's not gonna be a constraint.
And yes, the way he built this was: he picked out people, he made sure they worked really well together. He went out of his way to make sure people got fun things to work on, which is, I think, an underrated thing in technical disciplines. As I'm sure you're familiar with, if you're writing code, you can write very boring code, or you can write very fun, exciting code which has sort of dubious business value but is extremely fun to work on. And so he did a lot of that. And that was the motivating source of this essay.
Ken Griffin vs. Taylor Swift
Leila: And I think there's a second part, where I break into a more approachable analogy for most of us who haven't worked in financial back-office situations, which is comparing the lives of Ken Griffin and Taylor Swift. Ken Griffin is the CEO of Citadel, which is one of the most successful financial firms of all time. Maybe you've heard of him and maybe you haven't. Taylor Swift is the most successful musician of our generation, and Iβ
Patrick: Also occasionally gives excellent security advice on Twitter, which is literally how I found out who Taylor Swift was.
Leila: Are you serious?
Patrick: I am very serious.
Leila: Wow. Okay, I was gonna say, if you don't know who Taylor Swift is, you live under a rock.
Patrick: Yeah. I was firmly under a rock on the other side of the Pacific for a number of years. By the way, I'm blaming the Pacific too much. There were many Japanese people who knew who Taylor Swift was at the point where I did not.
Leila: On a fairly calm day, she probably sold out a stadium in Tokyo orβ
Patrick: Yep. Oh, certainly. SwiftOnSecurity introduced me to the Taylor Swift cinematic universe. And then, some years later, when my daughter came around, she became a great, great fan.
Leila: People are always like, "Are you a Swiftie?" And I'm like, "I'm definitely not a Swiftie." I mean, the Taylor Swift music's fine, but the Taylor Swift extended universe is fascinating. She's probably one of the women who has most successfully β I don't know β operated fame and capitalism in sort of a relationship. Maybe my cope for being a celebrity follower is that I'm fascinated by the way she uses fame as a way of living in the world.
Patrick: And importantly, this is a thing that Ken Griffin largely does not do, even though he has, like, $50 billion.
Leila: Right. Yeah.
Patrick: Well, does in some ways. But β so I did know who Ken Griffin was. And there are certain forms of social status you can buy if you are successful in trading that you can't buy if you are simply a multi-platinum, Grammy-winning artist who is one of the most celebrated songstresses of all time.
One thing that Ken Griffin did: if you live in Chicago and go to the Field Museum, there is a well-known skeleton named Sue, of a Tyrannosaurus rex. And if you just look on the wall, there's a little plaque that says funding for Sue was donated by Citadel Securities β and it might have Ken Griffin named explicitly there, it might not. I don't quite remember. But what can you do when you have $50 billion? Buy the world's most intact T. rex skeleton. And what do you do after you buy the most intact T. rex skeleton? Put it somewhere where everyone knows that you are the only person that was able to buy the T. rex skeleton.
Leila: It's true β where "everyone" is people who go to natural history museums. Perhaps some set of people you would like to know that. Wow. Is this the way you learned about Ken Griffin, primarily?
Learning about finance by osmosis (or not)
Patrick: Oh, no. I learned to read from my dad reading the Wall Street Journal growing up, and so he's in there a time or three. Another thing you can get paid in: if you are, say, a small businessman and the business is not making a lot of money, but you have an emotional investment with the notion of being a small businessman, you might have a subscription to the Wall Street Journal, because that is a talisman for the class that is people running a small business. And you might take it out every Saturday and inculcate your son in this ritual of the class that is people who read the Wall Street Journal β which is very different than the more conventionally understood social class that we were in at the time. But it does have some interesting knock-on effects. I knew who Ken Griffin was growing up, and β people might detect that I have something of an interest in this whole financial infrastructure thing over the years β I got my start on that very early.
Leila: Fair enough. Yeah, I was like, "Surely you didn't hear about Ken Griffin from the plaque." But I guess I was not reading the financial news when I was younger.
Patrick: Interestingly, most people in finance, I feel, don't β unless they are sort of heritage workers in the financial industry. There was a young lady who was in college with me β I went to Washington University in St. Louis β a very bright person, who had her interview with an investment bank. She knew I had something of an interest in all things finance, and she was very interested in getting a job at an investment bank. And 30 minutes prior to her interview, she came to me and said, "Patrick, can you explain to me the difference between a stock and a bond?" And I thought, "You're doomed. There is no possible way you will succeed at an interview for an investment bank not knowing that."
And this is something they do not teach you in the Wall Street Journal: most people, at the point where they join the financial industry, know nothing about anything. And then they get molded into the forms that they need as they get through their first couple of jobs.
Leila: I wonder if I'll regret saying this, but I did not know the difference between a stock and a bond. Or, I mean, I knew they were different, but I think all I knew was that a bond was the safe investment thing and a stock was the risky investment thing, and that at 21 my 401(k) should be 60% bonds and 40% stocks, or 60% stocks and 40% bonds. This is absolutely incorrect β don't do this. I did not really know what a bond was until about eight months into working at Jane Street. Does that make sense? I'm still not entirely sure I understand what a bond is, or how to price it, but maybe that's a knowing-what-you-don't-know thing.
Patrick: I still can't do bond math in my head, but luckily I'm not in a position in life where I have to be able to do bond math in my head. Another thing you can get paid in: not having to be able to do things.
Leila: I am reminded of an old Jane Street trader who said that when he started trading options in 2001, he had to memorize the 1/16 multiplication tables of everything, because that's how stocks were priced back then. We are all quite happy not to have to do that to get paid nowadays.
Patrick: Decimalization is wonderful. Decimalization also mechanically decreases the amount of money that gets leaked to market makers, so it's against the interests of firms that probably have that sort of business model, but it certainly makes thinking about it much easier.
Leila: I guess to go back to the essay a little bit β there are two other points I wanted to highlight. I brought up the Ken Griffin versus Taylor Swift thing because I think one fact that I was somewhat surprised by, and maybe your audience might find surprising as well, is: Ken Griffin is worth approximately $50 billion, and Taylor Swift is worth approximately... well, maybe you know the answer. How much do you think Taylor Swift, the most successful musician of all time, is worth?
Patrick: I would guess maybe two billion. But I know many musicians that everyone knows are far, far down the scale.
Musician money vs. Google money
Leila: I think Taylor Swift is β last time I checked, it was $1 billion. It might be two now, or higher. I probably should have fact-checked this before the podcast. But yeah, it's approximately 1/50 of Ken Griffin. And other major musicians β basically no other musician is worth as much as her, I think. Kendrick Lamar, I think, is worth like $400 million according to some sketchy websites on the internet, despite having performed in last year's Super Bowl and having huge cultural impact.
Patrick: I'm not sure how much I trust the sketchy websites on the internet for information on this. But a thing we learn in places like divorce filings and bankruptcy filings, et cetera, et cetera, is that after a multi-decade career, people profess in front of professionals and under oath that you have far less resources than one might naively expect β or far less resources than if you had simply gone and gotten a job at Googleβ
Leila: Oh, yeah.
Patrick: βand sung on the weekends. You would have done quite well for yourself, relative to even what seems like a superstar musical career.
The "Lemon Pound Cake" guy β Afroman. So, not my favorite musician. He's best known for the hit "Because I Got High" many, many years ago. It was a bit of a thing for people who remember the early 2000s very well. But he was raided by police for an unrelated reason, and dropped some hilarious diss tracks, which are simultaneously rap diss tracks and also some of the best encapsulations of the American political religion that have ever been recorded to any media.
There was a lawsuit about this, and he describes under oath in the lawsuit the microeconomics of being β again, he's been a performing musician for 20 years with one album which was hyper-successful, so not quite a one-hit wonder β and he has a lifestyle which is plus or minus that of a person with employment precarity. With some more cash than you might expect for that, and the capability to own a house, but certainly not a mansion in a guarded compound or anything.
And when you see other celebrity divorces and similar, they will say: decade-long career, multi-Grammy artist, house is $2 million, and they are $5 million in debt.
Leila: That part's not so great.
Patrick: Synthesizing a few things that happen here β I think one of the things that happens to artists, athletes, and other famous people is they seem to have an entourage of people, including a business manager, and often the entourage is a very large cash cost, and the business manager does not necessarily have their best interest at heart.
Leila: You know, I wrote this essay being like β I think some of the thesis is saying that you might be surprised that a product manager at Google who's worked there for 15 to 20 years might be worth more than your favorite musician.
Patrick: Yep. That's straightforwardly true. It's funny β the entire world conspires against people learning some of these obvious truths, I say only partially jokingly. We have a particular association with the words millionaire and billionaire in English. And so when I said out loud for the first time, "Someone who has worked at Google for 10 years in a software engineering role is a millionaire, period," I got surprising amounts of pushback from that. And they said, "Well, the definition of millionaire is not simply someone who has made more than a million dollars in salary." I'm like, "No. Do the math." This is an anecdote from many years ago, but do the math. A full-time engineer at Google makes bare minimum $200,000 a year. That ratchets over the course of their early years, up until the mid six figures. And then continue that for 10 years with some amount of saving, et cetera, et cetera β unless there is a health catastrophe or divorce in the interim, they invariably become millionaires, as a rule.
And so a product marketing manager that did it for 20 years β not quite as well compensated as engineers are, but quite well compensated β they do end up with Grammy-Award-winning-artist financial statuses. And that is probably not the thing that Google would say is the primary thing they are compensating product marketing managers with, but it's definitely one of the things.
Leila: Yeah. I mean, it is interesting that in our culture we have such a pull towards being a musician. If you ask a kid what they β maybe nowadays it's YouTube influencer, but I think it used to be musician.
Patrick: It used to be musician and astronaut, oddly enough.
Leila: That's a cool one.
Patrick: But I do worry about the surveys that say all American children want to become Minecraft YouTubers. It's partly the update on the old problem where the only job children were routinely exposed to was that of a teacher, and so too many kids wanted to become teachers. Now the only adult working in public that is not a teacher that they see routinely is a YouTuber, and they assume, "Ah, yes, I too would one day like to grow up and join the working economy as a YouTuber, as all people must."
Leila: Huh. Yeah, when I was in third grade, I also wanted to be a teacher. But I think I progressed out of that pretty quickly. I spoke to someone yesterday who actually advertises on Minecraft YouTube channels, which was fascinating.
Patrick: Well, I have to ask β what do they advertise?
Leila: They advertise their Lovable for Minecraft mods.
Patrick: Oh, okay.
Leila: It's creative mode. I don't intend for this to be a plug for them. It's just interesting to think about the other side of this economy.
Patrick: I have been somewhat enraged β not with respect to Minecraft, but with respect to Factorio β that it is not wall-to-wall ads for engineering recruiters. The world will eventually move in that direction. And there is at least one company that has sponsored Factorio videos, or the Factorio Seablock subreddit, if I recall correctly. Great ad copy, by the way: you play Seablock voluntarily, you'll do fine in AI engineering.
Keeping up with the Joneses and the meritocratic ladder
Leila: I've talked to some lawyers who get paid probably more than most product marketing managers, at least in cash up front or something. And I do think there's a very lucky thing about being a tech person in the South Bay, where you buy your house, you maybe buy a nice car, you send your kids to school, but there's not a lot of pressure to keep up with the Joneses. Whereas my understanding of the professional class is β you know, to be a lawyer, you're getting paid a lot, but you have to live in New York City, and it's expensive. And you don't have to send your kids to private school, but all your friends do. And you don't have to wear expensive suits, but maybe it helps you get more clients and be more respected. And so there certainly are professions where you get paid a lot of money, but it also sort of all goes out the door.
Patrick: Yep. I think that's also connected to the superstar cities with the agglomeration effect, and also just the social mores of being in a class like that. As you mentioned, there are public schools in New York City. You can send your children to them. But if you mention that among the other partners at the firm, they might not have questions, but they will have questions.
And then many of the most competitive professions to get into are gated by β you personally had to win 16, 20-plus years of meritocratic competitions to get into that. And as a parent myself, there is a tiny bit of terror that you are not setting your children up to win the same competitions. And so, given that there is the perception that there is a way to turn money into outcomes on the brutal meritocratic competition cycle, people will attempt to turn money into outcomes there.
Leila: Yeah. You know, it's interesting β I find myself kind of torn on the brutal meritocratic ladder, because I think it's sort of both over- and underrated.
Patrick: Yes.
Leila: I think it's underrated because β I am now about eight years into my career, but I just went to my husband's 10-year reunion. And the people who are doing the best are the people who bought this β you know, got a good job and just worked really hard at that job for 10 years. Some of them got really lucky and happened to get attached to generational startups. But they were not founding them. They were just kind of, I don't know, employee number 150 or something. So β someone like yourself.
Patrick: No worries. It's a true fact. I was employee number 600 or something at what is reasonably described as a generational startup.
Leila: So I do think there's some part of β the world is trying to sell you the message, like, "You should be Taylor Swift." And I think it's important for people to realize these competitions are β it really is winner-takes-all.
And I guess this is where I think the meritocratic paths may be overrated: because I think people can do a lot better in them than they expect, and the rewards can be a lot better than they expect. And it's really hard to see that until you've seen someone who did it and succeeded at it. This is where being in the Bay is actually really helpful, because you do meet founders and you're like, "Wow, this guy built a business to, you know, $10 million in annual revenue. He doesn't seem that smart" β or, it's a little mean, but, "he doesn't seem way smarter than me. Maybe I can do that too."
YC as a script to founderdom
Patrick: I remember there was a discussion around the dinner table about startups, and Ricki mentioned something which I think is kind of the orthodox opinion β that startup founders are a breed apart and like no one you would ever meet, et cetera, et cetera. And I said, I don't know, it was sort of my job to meet them for many years. And there are some founders who are smarter than I will ever be. But as a population, not too dissimilar from the people I went to school with, and mostly dissimilar in terms of risk-taking and willingness to do something that did not always have a clear script for it.
Although β and I mean this extremely positively with respect to YC β YC gave people who sort of need a script a script to founderdom, whereas they had a script available for going into finance or Google or similar, but did not have one to get into founderdom. And there was no legible way of making it happen by walking a social network and getting an introduction to a VC and similar.
Leila: Yeah, I do think YC is a good thing. And it's really having a moment now, interestingly, during the AI boom.
Patrick: One of the things YC does β and it's always a question of, is this a designed part of the system, or is this an emergent part of the system where it works and you double down on it β I think YC replicates a lot of the meritocratic experience that people have been experiencing prior to YC. There's an application. You fill it out. The YC application process is roughly meritocratic. One exceptional thing about the application is there are a number of questions on it, and then it doesn't ask some things. And it pointedly does not ask who your father is.
And that is a thing that is true about the upper echelons of the tech industry that is not true about the upper echelons of many industries. Many of them, you're quiet about it. But Hollywood definitely knows who your father is if you are in a casting call for something. Or, well β they know who it is if your father matters. And if your father doesn't matter, then minus 95% chance you get the position.
Leila: I didn't realize Hollywood was that.
Patrick: I think they basically invented the word nepo baby to describe Hollywood casting.
Leila: Oh, that's so sad.
Patrick: Yeah. So YC has this process, and then you get into YC, and they try to inform you: "Congratulations, you're about to meet capitalism and market realities in the harshest ways possible. But as we are ramping you up to that expectation, meet your partner. They're totally not your professor, wink, wink." And you get to meet them every week, and you can proxy satisfying-the-partner as satisfying-capitalism for at least the next couple of weeks, before capitalism is your only boss.
Leila: I will say it's a useful script, in that capitalism-your-boss is really harsh, and having any sort of feedback loop that shortens that cycle or tells you what you should be doing β I mean, people do spend years kind of in the wilderness, not realizing that they haven't even opened the gate to meet the boss or something. And YC at least is like, "No, you gotta go that way. It's over there. Stop doing this."
What entrepreneurship pays you in
Patrick: Yeah. I will say, one thing you get paid in as an entrepreneur is you are so much less worried about security when you get back into other jobs that you can do. My first manager after I joined Stripe β we were coming up on a performance evaluation, and he started to have the supervisor-talking-to-a-new-employee-about-performance-evaluations talk: "This is nothing you have to be worried about. It's just a normal process. Everything goes through it. You'll hear some things which are very positive, some things which are other than positive, but I don't mean that to crush you." And I said, "Not to interrupt you, but my performance evaluations for the last 10 years have been delivered by capitalism. What can you possibly say to me that would make me worried about life?"
Leila: Yeah. Entrepreneurs are interesting too, 'cause I think by and large, at least in the tech industry, they are usually selected from the same pool as the Google product managers. But as you point out, they wanna get paid in something very, very different.
I think when I was an employee, I was very effective, but I've also been told that I was very difficult to manage. It's kind of very standard for founders. It's like β well, you want to do lots of things, and sometimes you're frustrated about how slow the company is, and, like, "maybe you should be a little more patient," or something like this. Not quite the feedback I got, but the feedback that got back-channeled to me by the managers after I left. It's like, "Oh, man, I'm glad you seem to be doing well now," 'cause, like, oh boy.
Patrick: Yeah. I think many founders prize autonomy, and I think sometimes founders overrate how much being a founder is a single-player game. You no longer have a defined corporate structure above you which is telling you what to do and that you must make the 8:00 meeting. No β you must make the 8:00 meeting because you scheduled the 8:00 meeting.
Leila: Yeah. And if you don't, this once-in-a-lifetime option will slip out of your grasp.
Patrick: Right. And, you know: I hated having one boss, so instead I elected all the customers as my boss, also the investors as the co-boss, et cetera, et cetera. Although I think there are definitely different power dynamics after you have multiple bosses, versus having a single boss that could quasi-unilaterally decide to fire you.
Leila: I do think tech β I guess I've been privileged as a software engineer β the job market is sort of helpful here. As a software engineer, maybe this is why I was such a pain to manage. I was always like, "Well, you know, we're in a..." And, to be fair, I have this attitude with my employees a little bit too, where I'm like, "I feel like it's such a privilege to work with you" β and I felt like all my managers should be happy to work with me too, 'cause it's very hard to find good software engineers. And so, yes, if your manager doesn't like you, it's fairly easy: go find another one, whether within the company or in a different one.
Gratitude, culture, and quirky preferences
Patrick: Speaking of things that people value that they can get from an employer, and also things that should be very easy for employers to say β it's a line, and it is a line, it is a sincere line, but it is a line that I've deployed frequently with candidates and others: "I really appreciate you taking the time to talk to me today. I understand you have many other options, and I am honored that you would choose to spend time with us." And this is a thing that I would repeat frequently with coworkers and similar.
Gratitude is a thing that you can be paid in, and many people are starving for it, and this is frustrating to me on all sorts of aesthetic levels. One, that people are not getting a thing that they want and need. And two, people are not getting a thing that they want and need and is almost trivial to provide to them. Like, just say nice words occasionally. Organize your life to think that that is important. And so this is my pro tip to managers out there: tell your people that you like and appreciate them.
Leila: Yeah. I'm reminded that even within finance β I'll say, when I graduated from college, sometimes people would get offers from one financial firm or the other. Without saying which, let's say trading firm A and trading firm B. And trading firm A would offer 20% more in salary, but was known for being a place where you might get fired after a year, or it was just generally a very cutthroat environment. And trading firm B was like, yeah, you might get paid 20% less in your first year, but you will never get fired and you will always have a good working environment. And I was kind of surprised how many people chose trading firm A. I feel like if there was a big miss, it was that.
Now, some people think they will win the competition, or want to be part of that, and they're absolutely making the right choice. But I do think, on the margin, if there's one thing I kinda wanna get across in my essay, it's: think very carefully about the bundle of things you're getting paid in, other than just salary. Do not reverse-sort by salary and pick the top thing.
Patrick: Yep. When I've written about this before, I've used the term multidimensional preference β that there are some people whose preferences are sufficiently non-consensus with regards to one or two dimensions that they might even be a different sign than other people have. Like, there are some people who just thrive on stress β or maybe not even stress: the kind of environment where yelling angrily at a coworker at work is accepted. That environment would be absolutely toxic to me. I could not work in it. I would try to avoid it maximally. You could not pay me enough money to get yelled at every day by coworkers. There are some people who love that β and when I say love, their eyes light up the way my eyes light up when I look at my children.
And so, if you are aware that you have a quirky preference with respect to some dimensions, don't sort the opportunity set like everybody else in your class does. Go to the high-conflict place, or the low-conflict place.
Leila: Oh, yeah. I think this is a lesson that people-pleasers can take a little bit too. I assume you got decent grades in high school and college β and if you did get good grades in high school and college, I think there can be this temptation to be like, "Ah, in order to get the better grade, I should fit myself into the box that capitalism is providing for me, and then I will get paid 20% more if I'm okay with people yelling at me at work angrily."
And this is surprisingly true in high school and college, so I'm not gonna lie about that. But afterwards, in the three or four years afterwards, I learned there's a huge amount of value in learning how you work, what works for you β and you should just exploit that. And if you do that, the rewards will be surprisingly more than you could ever dream of.
Does winning this script look like winning to you?
Patrick: Mm-hmm. And being intentional about it. I did indeed get pretty decent grades in high school and collegeβ
Leila: It would've been embarrassing if I missed on that.
Patrick: No worries. Some portion of that is being very good at guessing the teacher's password. And there are environments in which guessing the teacher's password is very important for the operation of various firms, or not. But getting good at it doesn't really unlock surplus value for the person that is doing it, except for the feedback that: yes, you have correctly guessed the password. More passwords to guess tomorrow.
And so if you think, "Well, okay, this was always instrumental for me. I want to get the good performance evaluation so that I can rise in my career," et cetera, et cetera β you should spend at least a little thought on: am I on the right career track? Am I doing the thing I want to do? Does the script for winning in this industry look like winning to me?
There are people who get into big law β the slice of the legal profession that is: become a partner at a large firm, make a lot of money, and sacrifice all other goals in life on the altar of that. There is replete evidence available to lawyers β who are not selected because they are incapable of reading things on the internet β that the life of a big law partner is, for a period of minimally 15 years, but probably a lot longer than that, you're going to be expected to bill much more than 2,000 hours a year, and you will not cheat your clients, and so that implies working much more than 2,000 hours a year. And indeed, when working with lawyers, they have the level of availability that is predicted by that working schedule. And that's just really rough for everything in life.
And I talk to some people who want to become lawyers: "Great, what are you going to do about the work-life balance thing?" "Oh, I'm gonna become a lawyer that has work-life balance at big law." Like, hmm β that one isn't really on the table.
Leila: You can run your own firm and have work-life balance, is my understanding.
Patrick: Or, you know, join an NGO and work nine to five, hopefully.
Leila: Or be in-house counsel.
Patrick: Yeah, in-house counsel is another one that's different. I also think there was an over-rotation onto work-life balance, where many people want work-life balance, where what they really want is work that they would be happy to be doing. But contingent on them being happy to be doing it, they would draw the balance line very differently. That's true of myself, by the way. I was a big fan of the FIRE movementβ
Leila: Oh, yeah.
Patrick: βFinancial Independence, Retire Early β when I was a Japanese salaryman and hated life. It was like: happiness for me is making my working career as short as possible. If I had thought through that more deeply β even if one is thinking about this strictly in financial terms, one way to make the working career as short as possible is to continue in a job that makes $30,000 a year and optimize your investments aggressively. Another way is to stop working at the job that makes $30,000 a year. And that was not in my solution set at the time. And it probably should have been.
Leila: Was that realistic in Japan? I guess other than entrepreneurship, I don't think there were reallyβ
Patrick: I mean, I certainly could have decamped to Tokyo and gotten a job in either the financial industry or one of the outgrowths of the American tech industry that hire in Tokyo. But for various reasons, I didn't think I was likely to achieve that. Many people have the instinctive reaction of, "Well, can you actually choose? Isn't there a barrier in front of choosing?" β where there is often less of a barrier in front of choosing than there would be if people put some amount of directed effort into the thought.
I have, for example, friends who have worked in government continuously, and lament the fact that they are working in government. And I say, "Not to be an evil seducer with capitalism's blandishments, but have you ever considered not working in government?" They say, "Well, the private sector wouldn't hire me, because I have no marketable skills." I'm like, "False." I am a hiring manager.
Leila: I would hire you.
Patrick: Yeah β with regards to a particular person I'm thinking of, I could not licitly hire them. But many people could licitly hire them. And I said it in as many words: "Nah, I don't really believe it." One meta-strategy: talk to more people than life will naturally expose you to, and choose to believe the things that you hear from many independent people who say directionally similar things and have no particular reason to lie to you.
Don't end the week with nothing
Leila: I do think that one of the biggest downsides of working in a job, as far as I can tell, is that it becomes your whole world, and it's very hard to see the world outside of it. And there are some structural parts of jobs that make this very difficult. I think for me, and probably for you, Twitter β or X, I guess β has been a great way to meet people and to see life paths that are outside of what we thought, and maybe Hacker News as well, back in the day or still today. Certainly X and Hacker News have been great for me to meet people and see all the different life paths I could have had.
But it is very hard to have a social media presence if you're an employee, is something that's definitely true. This is actually one of the ways in which being a founder pays me in ways that I quite enjoy, because I'm almost incentivized to post a lot on social media. Whereas if you're an employee β it's interesting, because we're seeing a little bit more of a movement towards employees representing their companies as well. Like, Roon represents OpenAI somewhat on Twitter, though never officially.
Patrick: I have some amount of experience with that model myself. I wrote an essay a few years ago about "Don't End the Week with Nothing" β I'll drop a link in the show notes. One thing that working for a firm structurally discourages is the accumulation of capital outside the firm structure, including intellectual capital and social capital. And given that the internet age is changing this equation for people, I would suggest working in places where you can be seen doing the work, even if that isn't, quote-unquote, maintaining a social media presence. It could be as simple as writing an essay and hosting it on your own website. Working on things that you can keep, and working on things that you can show people.
And this is one of the things that the financial industry legendarily does not compensate employees with. The financial industry is a very broad brush, but trading firms are quite tight-lipped about what they are working on, and they do not send people out to conferences to say, "Hey, we built a cool thing recently. All of our competitors, please copy this one. It's working great. By the way, have you heard of the Indian options market? Extremely lucrative."
So you can choose to work in an industry β like, for example, tech β where people are allowed to build up some base of capital outside of the firm structure, which makes you more affordable in the future. Or you can choose to work in a position where structurally you get more face time with social media or real media or similar. There are a lot of people who wanna be famous. Becoming a tech founder is not a great way to be famous.
Leila: That's true.
Patrick: It worked out for, like, five people, and none of them really loved that outcome.
Fame and living in bubbles
Leila: I still remember the anecdote you told me about how you went on Conversations with Tyler, I think β or maybe you should retell it. You went to Chicago and you worked for Stripe, a well-known company, and the parents at the local kids' school were like, "There's Patrick. I guess he does some tech thing." And then you went on Conversations with Tyler, and suddenly they're like, "Oh my gosh, Patrick McKenzie. What a celebrity."
Patrick: Yeah. I have a dear friend of my family who is an academic, and of course academics pay attention to academics like no other, and there is no amount of Hacker News karma that would ever get me on this person's radar. But Tyler Cowen β well-respected US economist, and well followed by many academics and policy people. And when I was on a Tyler Cowen podcast and she became aware of that fact a year-plus later, it was like, "Wow, you have met a rock star."
Leila: I was mind-blown that even these Chicago suburban nice-neighborhood parents had never heard of Stripe, a $90 billion company. Well β every developer knows about Stripe. You do. It's excellent marketing. But it was a good reminder that we live in a bubble.
Patrick: An anecdote: back in 2016, in my sort of entering class at Stripe β again, we love using these metaphors to make it easier for people to join from college directly into the working world β in my entering class, there was a controversy among people on whether we were too late to the party, and whether all the interesting work had been done and all of the economic value had been created, and it was just riding out a payment processing business from now. And then if you look back on old Stripe annual letters, you will see that in fact there has been some growth in the business between 2016 and the present, including in β paid in a variety of currencies β processing volume, economic returns to shareholders of the business, interesting problems, international expansion, et cetera, et cetera.
People who were quite exposed to the startup ecosystem in 2016 might have reasonably thought, "Well, everybody knows who Stripe is." Where in fact: one, not the case β there are many intelligent people in the world who still don't. And two, even simultaneously, where many candidates think, "Well, everyone knows who Stripe is," the internal view from inside Stripe is it is so hard to hire people, because Google is legible β because people use YouTube on their phones, they have interacted with their product before. And when we get into conversations with candidates β not randomly selected Americans or Europeans, just candidates, people who are already in the tech industry looking for jobs β they have never heard of us and don't have any idea what we do for a living. And we have to get them over that hump before getting over the other humps of: there are smart people here, interesting problems, you should probably work for it. Hurdle number one is just: so, here's what a credit card processing company does.
Leila: I'm constantly amazed by how large the world is. One of the most surprising things to me about marketing is that you can sort of always 10x, at least at the startup level β maybe not if you're Coca-Cola. Stripe being a good example of this. Even Jane Street, to some extent: I first worked at Jane Street in 2016 β that was when I first interned β and at the time I would tell people, "Oh, I work at a small financial firm." In certain circles, I'd be like, "Oh, it's called Jane Street," and they'd be like, "Okay, cool," or, "Oh, I know Jane Street." And nowadays I'm kind of just shocked by how much their marketing has grown, and I'm sure it's very, very well known amongst college seniors and certain people in the financial world. But even so, most people know JPMorgan far more than they know Jane Street. I would not be surprised if that changes in the next 5 to 10 years again. But you can always sort of 10x β that's the thing I've been surprised about, even things that feel very large and behemoth-like.
I guess Anthropic's a good example of this too, where a year ago in the Bay Area it's like, "Oh, everyone's using Claude, it's so annoying," and you talk to normal people and they'd be like, "I've never heard of this."
Patrick: There was, not too long ago, a survey aimed at normal people. It's a classic brand survey β just, which of these brands are you aware of? And one of the things we've learned in doing brand surveys is you have to throw in a few non-brands β companies that you just made up β to defeat the Lizardman's Constant. And Anthropic had lower name recognition than the Lizardman's Constant brandsβ
Leila: Oh, no.
Patrick: βat one point in the not-too-distant past. Obviously I don't speak on behalf of Anthropic, and so I don't know whether that was either lamented or someone was like, "Yes."
Leila: It is sort of a weird name, I guess, even by the standards of tech company names, which are always very sort of strange.
Patrick: I think a lot of tech company names, you can date very precisely when the company was founded by idiosyncrasies in their name. Of course, that sometimes gets changed. I used to know what the Snap name was before Snap became Snap β I'll put a link to it in the show notes. Infamously, Facebook was not Facebook prior to becoming Facebook, and now Facebook denies that it is Facebook. It says it's Meta.
Leila: Oh, true.
Patrick: Facebook is lying. It's still Facebook.
Leila: It was "TheFacebook" before Facebook, or something else?
Patrick: It was TheFacebook before Facebook, and I think something before that too.
Leila: Ah, something else before that. This is where domain names have really β I mean, this is something that they give you advice on when you do a startup. And it's actually surprisingly driven by domain names, I think. The opening up of .ai as a domain name created new opportunities for people to have reasonable names again, whichβ
Patrick: We can use all the dictionary words again. I know. This will be awesome.
Leila: Well, they did get snapped up pretty quickly. But yeah, something like Stardrift is still available, as opposed to having to be Snoop, Snoopy, or something like that. Sorry.
Patrick: Snoopily.
Leila: Snoopily. Yeah.
Restaurant reservations as a currency
Leila: I guess there is one final thing about the Ken Griffin versus Taylor Swift thing that I wanted to mention, which is one way in which Taylor Swift gets paid that Ken Griffin doesn't: she can get a restaurant reservation anywhere in New York that she wants to.
Patrick: I think there is a way to turn money into restaurant reservations.
Leila: There is. I'm pretty sure of this. But it's sort of weird and awkward, and you have to, likeβ
Patrick: I think if you have a full-time executive assistant at that level, you can definitely get any reservation you want.
Leila: I suppose. This may be true for Ken Griffin. But yeah, this is the one downside of being a Google product manager instead of a Grammy-Award-winning artist.
Patrick: This is the thing that, in that social class and with their resources, they would genuinely have difficulty doing. And advancement into a social class is one thing you can get paid in β learning the metas and the tricks, and using the social permission to do it. In a different conversation about restaurant reservations specificallyβ
Leila: Oh, how many conversations about restaurant reservations have you had?
Patrick: I've had more than five, and far less than, say, Tyler Cowen has had.
Leila: Oh, interesting. Yeah, when I wrote this piece, there was some article going around about all the restaurants Taylor Swift had been at, and that was part of the motivation for this.
Patrick: One thing that β someone said that restaurant reservations are purely a matter of having social cachet with the people that control restaurant reservations. And I said, "I think this is untrue. I think there is a direct market in it, but we make that direct market other-than-legible to people outside of the market. But if you stay in the Four Seasons, which is a thing you can buy with money, the Four Seasons can get you reservations at a wide variety of places that don't have reservations available if you call them directly."
Leila: Ooh, I didn't know that.
Patrick: This is a thing that concierges specialize in.
Leila: Yeah. And so this is a very common travel tip for Tokyo, actually. If you stay at the top-tier hotels β I believe you probably know better than me, the Palace Hotel, the Imperial Hotel, I don't know if these are top-tier enough, maybe the Four Seasons, I don't know if they're well-connected enough β you can get the concierge to hook you up with a good restaurant in Tokyo, and this is actually one of the best ways to book good reservations in Tokyo. But as a source of alpha, I think this has degraded over time. I didn't realize it was true in New York as well, which actually feels to me like a more competitive restaurant reservation market in many ways than Tokyo. But I'll take your word for it.
Patrick: That would be a very fun essay for somebody β comparing American reservation culture versus Japanese reservation culture.
Leila: Ooh, but then β you tell me more.
Patrick: Ooh, okay. So, notoriously to Japanese restaurateurs: in the culture that is Japanese patrons, making a reservation means that reservation will definitely happen, at that time, with the stated number of people. And Americans feel like it's more of a guideline than a rule in many circumstances. And because the business of restauranting is inextricably tied up with table turns and similar, reserving for eight but then coming with five and saying, "But we still get the table, right?" is something that restaurateurs hate pretty much the world over. But you are priced into dealing with it in America. And Japan has not historically needed to price that in, because nobody did it. But now foreigners are a very large portion of the market for some restaurants, and the restaurateurs are banging their heads against this new user behavior of not coming to reservations promptly.
Leila: Oh, no.
Patrick: And so this has resulted in quite a bit of griping, but β neither here nor there.
Leila: I'm actually shocked at the rise of online reservations. I think in the US this used to be more true as well, but something about the online reservation market made it feel much more transactional. And in return, now, if you don't show up to your OpenTable reservation, they'll charge you $25 or something. And I'm a little bit surprised that this didn't happen within Japan while companies like Tabelog were growing in Japan. I don't know if you have any thoughts on that.
Patrick: No developed thoughts on Tabelog as the reservation product. I do know that Tock took a whack at selling tickets to dinner in the same way that you would sell tickets to a Broadway show β and if you don't show up for the Broadway show, well, obviously you have full freedom in your life to attend the screening that you paid for or not attend the screening you paid for, but you pay for it either way. And that failure-to-show fee has been somewhat popularized in the United States, and largely not popularized in Japan yet. But the prepay-for-dinner thing has not yet been popularized in the United States, to at least my ability to detect this. Although there are some places in the super-high-end restaurant market which work in a very different fashion.
Leila: Yeah, I think some of the very expensive restaurants in New York work this way. I've never really thought about what motivated them to do this. I sort of just assumed they had the market power to do it, so they did it, but I'm now wondering if it was in response to someβ
Patrick: I'll drop a link or two in the show notes to the entrepreneur behind Tock, who previously was an owner at Alinea, which is one of the best restaurants in β I'm not sure I'm pronouncing that right. I learned the word by reading it. Alinea? Alinea?
Leila: Alinea.
Patrick: Alinea. Okay. They dealt with exactly this sort of breakage problem. And there is no good way to maintain customer relations when the person in front of you, who you are not happy with, is not the one that flaked. And they feel it's very unreasonable for you to hold them responsible for their business associate or customer or similar who didn't come. And you do not care who is responsible for it β you just have three seats that are now unsold. And so this is an economic response to that.
Where to find Leila
Patrick: But β where can people follow you on the internet?
Leila: I am on X @leilavclark β L-E-I-L-A-V-C-L-A-R-K. I also have a blog called Approach with Alacrity, which you're welcome to follow. I think we now write on Substack β oh, I wish we had time to talk about why Substack is better than a personal blog, but not today. That's also where you'll find blog posts. And again, if you are planning vacation travel this summer, try out our AI travel planner, stardrift.ai. As you can tell, a totally reasonable name, which we got through being able to buy a .ai domain name instead of something like, you know, Snoopily.
Patrick: Mm-hmm. Well, thanks very much for coming on the program, Leila. And for everybody else, thank you very much for listening to Complex Systems, and we'll see you next week.
Leila: Thanks, Patrick.
Patrick: Thanks for tuning in to this week's episode of Complex Systems. If you have comments, drop me an email or hit me up @patio11 on Twitter. Ratings and reviews are the lifeblood of new podcasts, for SEO reasons and also because they let me know what you like.