Sam hosts a solo Q&A episode while Shaan is out recovering from surgery. He answers listener questions on fatherhood and his fears about raising a spoiled child, what actually changed after selling his company (confidence more than spending), his monthly expenses breakdown, the business ideas he considered before Hampton, the most painful criticism he’s received, overhyped business trends, and how he built his network when he moved to San Francisco by hosting a book club called the Anti-MBA.
Speakers: Sam Parr (host, co-founder of The Hustle)
Introduction — Solo Q&A Episode [00:00:00]
Sam: My wife is insane about this stuff. She has a drawer full of coupons, so we went to Costco this weekend because we had a $20 off coupon. We still use coupons.
Sam: All right, what’s going on? This is Sam. Shaan’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. 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.
Becoming a Dad — Fears About Raising a Spoiled Kid [00:00:30]
Sam: All right, what’s the first question?
Sam: 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.
Sam: So I’m going to have a child November 1st. That’s the due date. We’ll see. A little girl. In preparation for having this baby, I was freaking out about just the physical — her physical wellbeing, raising her. So I read the biography of Lewis and Clark, because I remembered that Sacagawea had a kid on that journey or something like that, and I wanted to read the book. It turns out she had a three-month-old that she carried in a little sack across America for two years, in the winter. That kind of encouraged me — I’m not going to hurt this baby. So I’m not too worried about that.
Sam: I would say the biggest thing I am freaked out about is raising a spoiled kid and raising a kid who’s going to be a drug addict. I genuinely have a deep fear about that. So I’ve been trying to figure out how do I — in a very healthy way — withhold things from her? How do I not give her what she wants just in order to instill some grit? This sounds kind of douchey, but I can give her anything she wants in terms of 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 that grit? How do I make sure she’s not spoiled and works hard?
Sam: My biggest fear is raising a kid who feels like she doesn’t need to work. My current thinking — and this has not been settled, this is just me, not my family — is that the only thing I’ll pay for is free tuition and free medical for life. Beyond that, give her nothing. That’s kind of 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.
Sam: I read Titan — the John Rockefeller biography — and his wife has this famous quote where she says something like, “The biggest joy 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.” I’m kind of in that camp at the moment. But I don’t feel very confident about the right way to do that. My fear is the outcome of a drug-addicted, indulgent child who won’t work hard. That’s my biggest fear right now, and I’m preparing by getting my mind right on how to withhold things from her and not give in — because I do give in to a lot of things.
Sam: Is that a good answer? You have kids — am I on track?
Sam: I’m a very withholding father, so I totally get it.
Lifestyle After Wealth — What Actually Changed [00:04:30]
Sam: Speaking of you being rich — this is the next question, and I personally am curious about it. What’s the biggest difference in your lifestyle now that you’re wealthy?
Sam: I have nothing to do with picking these questions, I just want to say that. I hate talking about this topic, but I will discuss it.
Sam: Before I sold my first company, my salary for those four years leading up to it was $20,000 a year. Then I think I paid myself $150,000 a year, and then the last year I think I paid myself $350,000. So for the first while, I didn’t have much money. And then all of a sudden I sold the business and had enough.
Sam: At first, I did something I advise everyone not to do, which is I bought a few things — some real estate, a fancy car. I think that brings close to no happiness, and it might be one of those things you have to go through in order to truly appreciate. But I think if you do have a windfall, you likely shouldn’t buy anything crazy fancy for the first year or two. Just get used to it.
Sam: I’ve also learned there’s this study about amputees. They found that after six months, the level of happiness went back to where it was when they had both legs. You get hurt, you lose your leg, you’re bummed for a little while, and after six months you go right back to feeling as good as you did with two legs. That kind of happens when you make some money.
Sam: But the biggest thing it did was not what it could purchase. The biggest change is my confidence. My confidence went through the roof. I’m incredibly confident in my ability to start something and see it through to success. I don’t think I have the confidence where I believe everything I’m going to do is going to succeed — I still have paranoia that I’m going to lose everything, and I still have massive fears about going broke. That is something my therapist and I are still working through. But overall, my confidence changed significantly.
Monthly Expenses Breakdown [00:07:30]
Sam: 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 — and we lived together, so it was $2,000 each. I was like, that is insane. $2,000 in rent. I thought that was just evil.
Sam: Now when I rent a place in New York for the summer, it’s 10, 12, sometimes $13,000 a month. My home that I live in in Austin — I paid $900,000 for it. My monthly mortgage and taxes is $5,000 to $6,000 somewhere in between. So 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.
Sam: 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: a fancy gym, fancy doctors. Collectively that’s $1,000 a month. I don’t own any jewelry. I’m wearing a $10 t-shirt. I wear those constantly.
Sam: When I go out to eat, I don’t look at prices. When I go to Whole Foods I buy the fanciest stuff. But besides that, I budget everything else. My wife is insane about this stuff — she has a drawer full of coupons. We went to Costco this weekend because we had a $20 off coupon. We still use coupons.
Sam: One significant thing — I hate flying. I do not like to fly at all. Typically, if I have to go somewhere even if it’s 12 hours away, I tend to drive. When I do fly now, I fly business class, so that makes a $300 flight $800. But I don’t fly often.
Sam: My home doesn’t have fancy furnishings. My whole house cost $30,000 to furnish. So it hasn’t really changed significantly other than my confidence. The idea of creating something from nothing — that changed significantly.
Sam: How was that? Did that answer those two questions?
Sam: Loved every minute of it. Now you can get out of the hot seat on your personal life, and I’m going to throw to you — this was the most-liked question — what were your alternative business ideas if you didn’t do Hampton?
Alternative Business Ideas Before Hampton [00:12:00]
Sam: 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 philosophy where it’s like a Venn diagram of what the world wants, what the world wants to pay for, what you’re good at, and what you love doing. I try to find something in the middle.
Sam: One thing I’m obsessed about is data and numbers. If you go to my personal blog — don’t judge, I started it when I was 21 — I used to have this document called the CEO Document where I tracked hundreds and hundreds of people. I read lots of biographies and tracked when they were born, when they started their apprenticeship, when they found success, and what the success was. I made these in-depth databases. I’m obsessed with databases, I’m obsessed with researching things.
Sam: I have hundreds of pages in 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. I had all these databases of information and I liked analyzing them and figuring out what they meant, but I couldn’t find a good use case. I couldn’t find a reason why people would pay money for it other than it being interesting. I sought out for like six months different companies in the space and I couldn’t figure out the right go-to-market strategy.
Sam: I also thought about starting a media company. I do have a non-compete, so I can’t start a business news email for another year. So I kind of fell into Hampton because I thought it was perfect for my ikigai — what I’m good at, what the world wants.
Sam: But I was really obsessed with research businesses. We just had Jason Yanowitz in the pod — I asked him a lot about research businesses. I think they could be really big. I also think there aren’t a lot of younger entrepreneurs attacking that space because it’s a pretty stodgy, old space that hasn’t had a significant amount of innovation. I’m very fascinated by it. Research and database 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. I wanted to build something like that.
Most Painful Criticism That Changed You [00:16:00]
Sam: This next question I love, although it’s painful for me to even ask. It comes from Omar: what was the most painful thing someone told you, and how did it change you?
Sam: I saw that question and I was trying to think of a good answer. My answer is boring, so bear with me.
Sam: My best friend — his name’s Neville Medhora — I met him because he had a great blog on copywriting. In 2013 or 2014, I cold-emailed him and said, “Neville, my name is Sam. I’m going to host this conference and I want you to come speak. I’ll pay for your flight and take care of your accommodation.” Well, the conference was really like 15 of my friends hanging out and talking. I bought him a $250 Southwest flight and he slept on my couch. We became best friends after that.
Sam: When he was there on my couch, I gave him a towel to take a shower, and it was a moldy towel. He was like, “Dude, you are disgusting. You’re acting like this bachelor 23-year-old, which you are, but you need to be a man. You need to get your act together. This is disgusting.” I remember that changed my life. I got together my domestic skill set. I was like, I need to act like a man. I need to dress better. I need to be more appropriate. I got to get my act together. That helped me a ton.
Sam: Neville does this a lot — he criticizes me all the time, but in a really nice way where he’s like, “I’m going to tell you this because I love you.” Another thing was when I met 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.” That was painful to hear because that was my identity. That changed how I had conversations. He’s six years older than me, so he’s kind of been like my brother a little bit — teaching me how to act like a man.
Sam: I remember when I started my first company, The Hustle. The CEO of a large multi-billion dollar media startup told me — I said I’m going to start this thing called The Hustle and I think it could become a huge thing — and he said, “This will never make more than a million dollars a year. Just come and join my company.” I was so hurt because I admired this guy so much, and my admiration for him turned to rage. I was like, I want to destroy you now. The reason I thought that was because my feelings were so hurt that this guy I admired just totally crapped on me.
Sam: And he was wrong. But I believed him for like six months. I doubted everything. I was like, this is stupid. By the way, he probably thought it was an offhand comment, but it hurt my feelings so badly that I remember it terribly.
Sam: And then the last thing was anytime a girlfriend has ever broken up with me. That has always stung. I’ll remember that for decades. I’m still trying to prove them wrong. I’m pretty sensitive to rejection.
Sam: Yeah, for sure. The most painful moments always come from high school.
Sam: Yeah — high school and college girlfriends, where you’re still figuring out yourself, and they’re right, you’re not doing things the right way, but they’re rejecting you. It’s the most painful thing ever. Girls are so brutal.
Overhyped Business Models [00:22:00]
Sam: This next question is from Caitlyn. What is one trendy business model you think is overhyped?
Sam: 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 going to work. But everyone knows that now.
Sam: What else is 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. This is a hard job. I like it because I think I’m good at it, or at least decent. But it is very challenging. Any type of content business is very, very hard to do for two or three years. The newsletter space is significantly different from when I started. It’s way more competitive, way more challenging. So I think that is a bit overhyped — although I would still start one because I like it. Most of the people in the space are not going to make it, and their content stinks because it’s just a rinse-and-repeat of what already exists.
Sam: I would also say getting popular on the internet. It can be awesome because you get an audience. But in general, creating businesses based off getting popular on Twitter and Instagram — I think it’s incredibly empty-feeling for most people. It’s complete nonsense. Your time would be better spent building a company or focusing on your family than getting popular on social media. I think it’s empty. Many days I regret trying to become popular on the internet.
Moving to a New City and Building a Network [00:25:30]
Sam: Okay, are you up to do one more? We’ll do one more.
Sam: This one comes from Jared Seed. He is moving to San Francisco. He’s curious about this idea of proximity to power. He’s moving to SF with the clear intention of starting a company and surrounding himself with high achievers. His question is: what did you do when you arrived in SF to start laying the foundation to meet interesting people and business builders?
Sam: Moving to a big city when you are young and have no family — I think is absolutely awesome. My time in SF, I lived there for 8 years. I got angry at the government and 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. 100% worth it. I loved it.
Sam: What I did when I got there was I went to Meetup.com and went to crazy amounts of meetups. I also started an event. So I created this book club called the Anti-MBA. The idea was we’re going to read one book per month and break it up into quarters — week one we’re going to read a quarter and discuss it, and I would have an expert come in on the book’s topic and we would just shoot the breeze with like 20 or 30 people.
Sam: I posted ads on Craigslist, on Meetup.com, and I think I bought an ad in the newspaper for like $200. Case — who has a business that does close to $100 million a year in revenue, you guys have heard of him — he was one of the people who replied to those ads. After doing that for about a year, I had an email list of like 2,000 people who were following this book club online because I would write out my notes from each meeting. Doing that book club changed my life. It was such a fun way to meet interesting people. We just read cool books and 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 a summary ahead of time.
Sam: The way I met Shaan was I had this event called Hustle Con. There was an article in TechCrunch about Monkey Inferno, which was this incubator that Shaan ran. I saw a picture of his office and it was magnificent. I cold-emailed Shaan and said, “Hey man, 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 host it at your sick office? In exchange, you can come to the dinner and meet all these wonderful speakers and attendees.” He said yes. That’s how I met Shaan.
Sam: So I think what more people should do is you just reach out to tons of people. And I would say — don’t even reach out to ballers or people who are ahead of you. Find other peers who seem like they got the juice, who have the charisma, who seem like they’re going somewhere. For me, it was Ryan Hoover. Ryan Hoover started Product Hunt. We were buddies before he even started it. I’ve got lots of friends who are now incredibly successful, where we were all just losers who were ambitious but had nothing. I did a good job of cold-emailing those types of people and we hung out a lot. I became wonderful friends with them.
Sam: 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. I would highly recommend that — find peers who you think are going to go places, and you all try to succeed together and try to be pretty selfless. When I hosted my events, they all volunteered to help me out. When they needed something, I helped them. Just succeeding together — I think that was a really big deal.
Sam: The issue is that takes like 10 or 15 years, but it’s worth it. And you’re not doing it just because someone’s going to be successful. I had friends who are artists — they financially weren’t successful, but they were just people who were kicking their dent in the universe. That was addicting to be around. We all kind of did it together.
Sam: The Anti-MBA — that’s what my book club was called. I was so jealous. I didn’t go to a fancy school. I remember when I moved to San Francisco, I took a train out to Stanford because I was like, I want to see what this is about. What’s so special about this place? I felt in awe and I was so jealous that I didn’t even know what Stanford was when I was in high school. So I was like, I need to create my own Stanford. I’m jealous of all these people who went here. That was the idea — the Anti-MBA.
Sam: For going to a new city, I would suggest book clubs, Meetup.com. When I was in San Francisco a few months ago, someone recognized me and said, “Sam, I love the pod. We’re hosting an AI meetup and a hackathon right now — do you want to come?” My wife and I were like, yeah, let’s go. We just got in a car and went. We went to this guy’s meetup and it was magical. I met all these AI people who I knew nothing about. It was magical to be in those meetups, with this homogeneous group of people working on something that is not mainstream. It felt really magical. So I would say go to those events.
Sam: Awesome. Book clubs — another thing you and Oprah have in common.
Sam: Yes, Oprah and I have a lot in common.
Sam: 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.