How I Live On $25,000/Month In New York City

So I'm gonna have a child November 1st. That's the due date. We'll see a little girl. What Um, so in preparation of having this baby, I was like freaking out about like just the actual, uh, like the physical, her physical wellbeing of raising her. And so I read the biography of Lewis and Clark because I remember that Sacagawea had a kid like on that journey or something like that. And so I wanted to read the book. And so it turns out she had a 3-month-old that she carried like in a little sack across America for 2 years in like, you know, in the winter. And, um, that kind of like encouraged me, like, I'm not going to hurt this baby. So I'm not too worried about that. I would say the biggest thing, though, that I am freaked out about is raising a spoiled kid and raising a kid that's going to be a drug addict. I'm very like, like that. Like, I genuinely have like a deep fear in me. And so I've been trying to figure out how do I, like, in a very healthy way, withhold things from her? Like, how do I not give her what she wants? Just in order to instill some types of grit, because this sounds kind of douchey, but I can give her anything she wants, like in terms of like physical stuff. And I'm really freaking out about how do I stay strong and not give her what she wants in order to create grit? And how do I make sure that she's not spoiled and works hard? But my biggest fear is raising like a kid who is freaking out over that or who like just feels like she doesn't need to work. And so My current thinking, this has not been settled, but my thinking, this is just me, not my family. Me is the only thing that I'll pay for is free tuition and free medical for life. And beyond that, give her nothing. Um, that's kind of like my current thinking. Um, that's what I had growing up. My parents paid for my school and I never had to worry about getting braces or anything like that. And that's kind of like where I am now. I read Titan by John Rockefeller, and he was the richest person in the world. And his wife has this famous quote where she says something like, the biggest joy that I have in life right now is withholding from my children things that they want because I know it's going to make them stronger. And I'm kind of in that camp at the moment on how to do that. But I, I don't feel very confident on the right way that I'm going to do that. But my fear is the outcome of a drug-addicted, indulgent child who won't work hard. That's my biggest fear at the moment. And so I'm preparing by like getting my mind right on how to like withhold things from her and not give in, because I do give in to a lot of things. Is that a good answer? You have kids. Am I—

I have nothing to do with picking these questions. I just wanna say that I hate talking. I, I don't like that topic, but I will discuss it. So basically before I sold my first company, I, my 4 years of salary leading up to it was $20,000 a year, $20,000 a year. I think I paid myself $150,000 a year. And then the last year I think I paid myself $350,000 a year. So for the first while, I didn't have a lot of money. I was, I was, I, I didn't have much. And then all of a sudden I sold a business and I, I had enough. Uh, at first I did something that I advise everyone not to do, which is I bought a few things. I bought some real estate. I think that I bought a fancy car. I think that That brings close to no happiness. And might be one of those things that you have to go through in order to, to truly appreciate. But I think that if you do have a windfall, you likely shouldn't buy anything crazy fancy for the first year or two and just get used to it. But I've also learned there's this like, story about a, the study about these people who have studied amputees. And they found that after 6 months, the level of happiness went back to where they were when they had both legs. So you, you get hurt, you lose your leg, you're bummed for a little while. After 6 months, you go right back to feeling as good as you did with 2 legs. That kind of happens. Um, when I think when you make some money, um, but the biggest thing that it did was not what it could purchase you, but the biggest change is my confidence. My confidence went through the roof. I'm incredibly confident in my ability to start something and to see it through to be a success. I don't think that I have the confidence where I think everything I'm going to do is going to be a success. I think I still have paranoia that I'm going to lose everything and I still have massive fears about going broke. Um, that is something that my therapist and I are working through still. Um, but it hasn't changed significantly. I think that someone had asked a question about monthly expenses before I sold. I think I was spending anywhere between $10,000 and $15,000 a month. My apartment at the time was $4,000 a month. I thought that was astronomical. I had a girlfriend, my wife now, we live together, so it was $2,000 each. And I was like, that is insane. $2,000 in rent. I can't. That is just like, that's evil. I thought, um, now when I rent the place, it's a bit more. It, I, you know, $10,000 or $12,000 or $13,000 sometimes when I go to New York for the summer. And so I increased my rent price, my home that I live in, in Austin. I paid $900,000 for it. So my monthly nut or my monthly mortgage and taxes, I think it's $5,000 or, or $6,000, somewhere in between that with taxes. And so I think I increased my spend from like $10,000 to $15,000 a month to like $20,000 to $25,000 a month, maybe $20,000 a month when I'm not in New York. So I don't spend what I think is a significant amount of money. I don't have any car payments. I have two cars, a Tesla and a Mercedes. Those are paid off. I have a cleaning lady who comes once a week. That's $120 a week. I do some health stuff, so I have a fancy gym and I go to fancy doctors. Collectively, that's $1,000 a month. I don't own any jewelry. I'm, I wear, I'm wearing a fresh clean tee. It's a $10 t-shirt. I wear those constantly. So I don't buy a lot of fancy things. So my burn, I think, is relatively low. When I go out to eat, I don't look at prices. And when I go to Whole Foods, I buy the fanciest stuff. And that's basically besides that, I budget everything else out. And so like, I have a, My wife is like insane about this stuff. She has a drawer full of coupons. So we went to Costco this weekend because we had a $20 off or something like that coupon. So we still use coupons or coupons. Um, but it has not changed significantly. I guess one significant thing, I hate flying. I do not like to fly at all. So typically if I have to go somewhere, even if it's like 12 hours away, I tend to drive. I do not like to fly. When I fly now, I fly business class. And so that makes a $300 flight $800, something like that. But my increased expenses— rent went up, business class, but I don't fly often. And then my home doesn't have fancy furnishing. My whole house cost $30,000 to furnish. So it hasn't really changed significantly other than my confidence. My confidence has changed significantly. The idea of like creating something from nothing, that changed significantly. How was that? Did that answer those two questions?

So I, um, I'm, I think I mentioned this last podcast. There's this thing called ikigai that I'm totally bought into. I'm very fascinated with Japanese culture. Japan has this like, this philosophy where I think I said it last time, it was like a Venn diagram of like what the world wants, what the world wants to pay for, what you're good at, what you love doing. I try to find something in the middle. One thing that I'm obsessed about is data and numbers. I really am. Um, like I, if you search, if you go to my personal blog, which don't judge. I started when I was 21 and I quit blogging there, but I used to have this document called the CEO document and I tracked hundreds and hundreds of people. I read lots of biographies and I tracked when they're born, when they started their apprenticeship, when they found success, and then like what the success was. And I made these like in-depth databases. I'm obsessed with databases. I'm obsessed with researching things, so I have hundreds of pages, pages of my Notion document where I deconstruct how different companies work. So I thought about creating a research company or a database company. The, the, the reason I didn't start it was because I couldn't find an appropriate problem to solve for. So I have all these databases of information and I like to analyze them and figure out what they mean, but I couldn't find a good use case. Or I couldn't find a reason why people would pay money for it other than it's interesting. But I sought out like for 6 months, like different companies in the space, and I couldn't figure out the right, like, go-to-market strategy. So I wanted to start a database company or a research company because I love it. I thought about starting a media company. I do have a non-compete, so I can't start like a business news email for another 1 year, I think. And so I couldn't do that. And so I kind of fell into Hampton because I thought it was a— it was perfect in my little ikigai. It was like what I'm good at, what the world wants. But I was really obsessed with research businesses. We just had Jason Yanowitz on the pod. This episode will go live, but he came the episode before this and I asked him a lot about research businesses. I think they could be really big. I also think that there's not a lot of like youngish entrepreneurs attacking that space because it's a pretty stodgy old space. That hasn't had a significant amount of innovation, and I'm very— but I'm very fascinated by it. So research in data-based businesses is what I wanted to do. One of my favorite examples is CB Insights. I love CB Insights. I love PitchBook. I love those companies, and I wanted to build something like that.

Okay, I saw that question and I was trying to think of a good answer. My answer is boring. So my best friend, his name's Neville Medhora, I met him because he had a great blog on copywriting. And one year in 2013, I think it was '14, I cold emailed him and I said, Neville, my name's Sam, I'm gonna host this conference and I want you to come speak and I'm gonna pay for your flight and I'm gonna take care of your accommodation. Well, the conference was really like 15 of my friends hanging out talking, and I bought him a $250 Southwest flight and he slept on my couch and we became best friends after that. And when he was there at my— in my couch, I gave him a towel to like take a shower and it was like a moldy towel. And he was like, dude, you are disgusting. You're acting like this bachelor 23-year-old, which you are, but like, you need to be a man. You need to get your act together. This is disgusting. And I remember that changed my life when he— and so I like got together some of my, like, my, uh, my domestic skillset. I also like, I was like, I need to act like a man. I need to dress better. I need to like be more appropriate. Like I had to get, I gotta get my act together. So that helped me a ton. He also, he, Neville does this a lot. He criticizes me all the time, but in a really nice way where he is like, I'm gonna tell you this because I love you, but I'm gonna give you feedback. And another thing was when I, met this woman that he was like dating, or maybe one of his friends, I think it was one of his friends. He was like, you're asking way too many intense questions the first time you meet someone. You need to chill and quit talking about work. And that was like painful to hear because that was my identity. And so that changed how I had conversations. And so he's done a good job. Neville's 6 years older than me, so he's kind of done a good job of like being my brother a little bit and like teaching me how to like act like a man. So that was like a good thing. I remember when I started my first company, The Hustle, and this CEO of a large multi-billion dollar media startup that everyone knows, I'm not gonna call him out. He told me, I go, I'm gonna start this thing called The Hustle. I think it could become a huge thing. He said, this will never make more than a million dollars a year. Just come and join my company. And I was so hurt because I admired this guy so much. So much, and my admiration for him turned to hatred. Not really hatred, but like rage. I was like, I want to like, I want to destroy you now. And the reason I thought that was because I was so hurt. My feelings were so hurt that this guy that I admired just totally shit on me. And he was wrong, but I believed him for like 6 months. I like doubted everything. I was like, this is stupid. But he told me that. He won't even remember saying this, this guy, by the way. He probably made— he thought it was like an offhanded comment or that something like that. But it hurt my feelings so badly that I remember that, uh, like terribly. And then the last thing was like, anytime a girlfriend has ever like broken up with me, that like, that has always like stung me. I'll remember that for, for decades. Like, I'm still like trying to like prove them wrong. So like, I'm pretty sensitive, uh, to like rejection.

Um, I think the NFT and Web3 stuff. Is just complete nonsense. I think it's inferior entrepreneurs slapping their Web3 name on crap that no one wants and hoping that it's gonna work. So, but everyone knows that now. I think what's overhyped, I think starting a newsletter is really popular right now. Most people don't realize it is a treadmill. It is very challenging to create new content just like this podcast. It's hard. This is a hard job. I like it because I think I'm good at it or I'm decent, but it is very challenging. Any type of content business, very, very, very, very hard to do for like 2 or 3 years. And newsletter, the newsletter space, significantly different than when I started. It is way more competitive, way more challenging. So I think that is a bit overhyped, although I would still start one because I like it. I think that most of the people in the space are not going to work and it's pretty bad. Their content stinks because it's just a rinse and repeat of what already has existed. So I think that's quite overhyped. I would say getting popular on the internet can be awesome because you get an audience. But, um, in general, I think that creating businesses based off your, or like getting popular on Twitter and Instagram and things like that, I think it's incredibly empty feeling for most people. And I think it's complete nonsense and your time would be spent building a company or focusing on your family than getting popular on social media. I think it's empty. I think that it's like small boy stuff. I just, and I find it incredibly uninteresting and there's many days that I regret trying to like become popular on the internet.

Moving to a big city when you are young and have no family, I think is Absolutely awesome. My time, I lived in SF for 8 years. I got angry at the government and I left because it was dangerous. Otherwise I would still be there in a heartbeat. I have no problem paying the high taxes in order to live there. I think it's a beautiful place. I would still even go back there today if my wife wanted to, maybe. So 100% worth it. I loved it. Um, what I did when I got there was I went to meetup.com and I went to crazy amounts of meetups. I also did, uh, I started an event, so I created— it's so funny— Siava Kazitsky. So Siava is one of my best friends. Siava has a business that does like close to $100 million a year in revenue. We've had him on the pod. You guys maybe have heard of him. Um, he— so I created this book club called The Anti-MBA, and the idea was we're going to read one book per month and we're going to break it up into quarters. So week 1, we're going to read a quarter. And discuss it week 2, the second half or whatever. And I would have an expert come in on the book's topic and we would just shoot the shit with like 30 or 20 people on this book. And I posted ads on Craigslist, on meetup.com, and where else? I think I bought an ad in the newspaper for like $200. Like I just posted these ads and Sieva was one of the people who replied. And after doing that for every week for about a year, I had an email list of like 2,000 people. Who were like following this book club online because I would write out my notes from the meeting. And doing that book club changed my life. So I just hosted a book club and it was awesome. It was so good. It was such a fun way to meet interesting people. And so that's what I did in order to meet interesting people is we just read cool books and we brainstormed and talked about them. Most people, by the way, didn't even read the book. They just wanted to talk about it because I wrote notes ahead of time on, like, I wrote a summary on the book. So that changed my life. The way that I met Sean was I had this event called HustleCon, and there was this article in TechCrunch about Monkey Inferno, which was this incubator that Sean ran. And I saw a picture of the, his office, and it was magnificent. And I cold emailed Sean and I said, hey man, um, I'm hosting this event. Can I host the pre-dinner at your office? We'll, we'll take care of all the food. I'll even hire someone to clean it up., but can I just like host it at your sick office? And in exchange, you can come to the dinner and meet all these wonderful speakers and attendees. And he said yes. And that's how I met Sean. And so I think what I did, what I think more people should do, is you just reach out to tons of people. And I would say, don't even reach out to like ballers or people who are like ahead of you. Find other peers who seem like they got the juice, who got the, the charisma, or who have, who seem like they're going someplace like, For me, it was Ryan Hoover. Ryan Hoover started this thing called Product Hunt. We were buddies before he even started it. And I've got lots of friends that are now incredibly successful, um, where we were just all like losers who were ambitious, but we had nothing. And we, and I did a good job of like cold emailing those types of people and we hung out a lot and we just, I, I became wonderful friends with them and it was through my book club. It was through cold emailing. Twitter wasn't popular. I didn't even have a Twitter back then. So I just cold emailed tons of people and I would highly recommend that's what you do is find peers who you think are gonna go places and you guys all try to succeed together and you try to be pretty selfless in the sense of like, like when I hosted my events, they all volunteered to help me out. When they needed something, I helped them. And so just like succeeding together, I think was a really big deal. Now the issue is that takes like 10 years or 15 years, but it's worth it. Um, and you're not doing it just because someone's gonna be successful. Like, I had friends who were artists and like, they financially weren't successful, but it was just people who were like kicking their dent in the universe. And that was addicting to be around that. And we all kind of did it together. And that's what, what I did. I, I had a book club, The Anti-MBA is what it was called, cuz I was so jealous of the— I, I didn't go to a fancy school. I remember when I moved to San Francisco, I took a bus out or a train out to Stanford because I was like, I want to see what this shit's about. Like, what's, what's so special about this place? And I felt like in awe and I was like so jealous that I didn't know what Stanford even was when I was in high school. So I was like, I need to create my own Stanford because I'm jealous of all these people that went here. And so that was kind of the idea. It was the anti-MBA. It was free and I organized it. So I would suggest book clubs, meetup.com. I don't know, is meetup.com still a thing? I bet you it is. Right now, when I was in San Francisco, I went there like 6 months ago, and there was, and someone, someone like recognized me and they go, Sam, I love the pod. We're hosting an AI meetup and a hackathon right now. Do you want to come? And my wife and I were like, yeah, let's go. And so we just, you got a car here? We were like at the farmer's market and they're like, yeah. I was like, all right, come on. I'm going with you. And so we went to this guy's meetup and it was magical. I met all these AI people who I knew nothing about, and it was magical to be in those meetups at these places where you have like, a homogenous group of people working on something that is not mainstream, it felt really magical. So I would say go to those events.