My First Million: How I Live On $25,000/Month In New York City

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.

All right. What's going on? This is Sam. Sean's out with some surgery.

I've been telling people he's getting a nose job. I don't know if that's true,

but let's just pretend it is. But anyway, we are doing a quick 10 or 15 minute Q&A session.

I asked some of the listeners and some of my Twitter fans what type of questions they had

for me. And we'll talk about it. Let's get into it. So, Ari, what's the first question? What do we

got? Let's start with one that's really timely. You're about to be a dad. Someone's asking,

what is top of mind as you become a dad? So I'm going to have a child November 1.

That's the due date. We'll see. A little girl. What? So in preparation of having this baby,

I was freaking out about just the actual physical, her physical well-being of raising her. And so I

read the biography of Lewis and Clark because I remember that Sacajawea had a kid on that journey

or something like that. And so I wanted to read the book. And so it turns out she had a three-month

old that she carried in a little sack across America for two years in the winter. And

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 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 the sound's going to do she, 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. That's kind of like my current thinking. 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 the 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 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 given, because I do give in to a lot of things.

Is that a good answer? You have kids, am I? I'm a very withholding mother, so I totally get.

And speaking of you being f-ing rich, this is a next question that I personally am curious about.

It's, what's the biggest difference in your lifestyle now that you're f-ing rich?

I have nothing to do with picking these questions. I just want to say that. I hate

talking about, I don't like that topic, but I will discuss it. So basically, before I sold my first

company, my four 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 didn't have much. And then all of a

sudden I sold the business and I had enough. 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 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 story about the study about these people who

have studied amputees. And they found that after six months, the level of happiness went back to

where they were when they had both legs. So you get hurt, you lose your leg, you're bummed for a

little while. After six months, you go right back to feeling as good as you did with two legs.

That kind of happens. I think when you make some money. 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. That is something that my therapist and I are

working through still. 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. That is just like, that's evil, I thought. Now, when I rent a place,

it's a bit more. 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 mortgage and taxes, I think it's $5,000 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 wear, I'm wearing a fresh clean tea. That's

a $10 t-shirt. I wear those constantly. So I don't buy a lot of fancy things. So my burn,

I think it's 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. 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 costs $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? Love loved every minute of it. So now you can get out of the hot seat of

your personal life. And I'm going to throw it to you tonight. This was the most liked question. So

what were your alternative business ideas if you didn't do Hampton?

So 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 like, 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 of my Notion document where I deconstruct

how different companies work. So I thought about creating a research company or a database company.

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 six 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 one 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 icky guy. 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 of 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

young-ish 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 and database businesses is what I wanted to do. One of my favorite examples

is CB Insights. I love CB Insights. I love Pitch Book. I love those companies and I wanted to

build something like that. So you may know this but my beginning in business was being a copywriter.

It just basically means figuring out what motivates someone and how to use the written word to take

an action, get them to take an action or to think a certain way. And the way that I learned how to

copyright was I did this thing called copy work. And copy work is this famous technique that's

not really popular anymore but it used to be really really popular and you basically take

writing that is great writing that you love and you write it out by hand and you copy it and you

make notes of what particular thing that that writer is doing that makes it special. That's

how I learned how to write. I locked myself in a room for six months and I just did this for many

hours a day. I created a program to make it easy so you can do that. It's called copy that. Copy

that.com. You can go there and you can check it out. It's a 10-day exercise to make it really easy

to learn how to write. If you want you can just go do this on your own. You can find great writing

and just literally copy it by hand. I know it sounds crazy but it works really effectively

but I made something that makes it a little bit easier so check it out copy that.com

and back to the pod. Okay this next question I love although it's painful for me even to ask

it because it's really it cuts deep. This comes from Omar. What was the most painful thing someone

told you and how did it change you? 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 is Neville Medora. I met him

because he had a great blog on copywriting and one year in 2013 I think it was 14 I called the

email them and I said Neville my name is Sam. I'm going to host this conference and I want you to

come speak and I'm going to pay for your flight. I'm going to take care of your accommodation.

Well the conference was really like 15 of my friends hanging out talking and I bought them 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 my domestic

skill set 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 gotta get my act together so that helped me a ton he also Neville

does this a lot he criticizes me all the time but in a really nice way where he's 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 a six 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 and my admiration

for him turned to hatred not really hatred but like rage I was like I want to like I wanted 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

six 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 off-handed

comment or that something like that but it hurt my feeling so badly that I remember that 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 to like rejection

yeah for sure the most painful moments always come from high school I think everyone can agree

with that yeah like high school and college girlfriends where you're still trying to figure

out yourself a little bit and they like and you get and and they're right like you're not doing

things the right way but and they're rejecting you it's like it's the most painful thing ever

girls are so brutal okay this next question is from Caitlyn what is one trendy business model

you think is over height 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 um I think um what's over a height 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 two or three years um and newsletter the the newsletter

space significantly different than when I started it is way more competitive way more challenging

so I think that is a bit over hyped 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 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 then 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 okay are you up to do one more

we'll do one more okay this one comes from Jared Seidel he is moving to San Francisco he's curious

about this idea of proximity to power so he's moving to SF with the clear intention to start a company

and surround himself with high achievers his question is what did you do when you arrived

or what did Sean do when he arrived in SF to start laying the foundation to meet interesting people

and business builders 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 eight 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 what I did when I got there

was I went to meetup.com and I went to crazy amounts of meetups I also did I started an event

so I created it's so funny Sieva Kaczynski so Sieva is one of my best friends Sieva 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 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 one we're going to

read a quarter and discuss it week two the second half or whatever and I would have an expert come

in on the books 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 2000 people

who were like following this book club online because I would write out my notes from the

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 hustle con and there was this article in tech crunch

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 email Sean and I said hey man um I'm hosting this event

can I host the pre-dinner at your office 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 and I

did a good job of like cold emailing those types of people and we hung out a lot and we just 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 going to go places

and you guys all try to succeed together and you try to be pretty selfless in the sense of like

um 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 going to be successful like I had friends who are 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 I did

I had a book club the anti-MBA is what it was called because I was so jealous of the 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 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 six months

ago and there was and someone someone like recognized me and they go Sam I love the pod we're hosting a

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. Great awesome book club another thing that

you and Oprah have in common I love it yes we have a lot in common me and Oprah so there were a lot

of other questions we didn't get to but we'll do another one a little later let me know if you

guys like this stuff peace

Machine-generated transcript that may contain inaccuracies.