Interview with John Catsimatidis Jr.
John Catsimatidis Jr. is an American businessman.
New Yorker
Contents
Max Raskin: I want to talk about New York. How important is being a New Yorker to your identity?
John Catsimatidis Jr.: It's fairly ingrained in my identity — I was born here; I grew up here. I went to preschool, middle school, high school, and college in the island of Manhattan, which wasn't originally my plan.
MR: Do you know how to drive?
JC: Yeah, of course.
MR: A lot of people who grew up in New York don't know how to drive. Where did you learn?
JC: I learned how to drive in New York City and Long Island.
MR: Who taught you?
JC: My mom and dad.
MR: Where in the city do you think you’ve eaten the most meals?
JC: Smith & Wollensky. Easy.
MR: And what do you get there?
JC: I started by getting the steak, but there's only so many times you can have steak at lunch before you start falling asleep. So I get the mixed green salad and the salmon.
MR: Where is the best Greek restaurant in the five boroughs?
JC: I'm going to get in trouble by answering this question.
MR: How about top three?
JC: Milos and Avra and Stamatis in Astoria.
MR: What about Italian?
JC: Nicola's on the Upper East Side, it's very good.
MR: Where did you take your wife on your first date?
JC: There's a handroll place, Mari, unreal.
MR: If you were giving recommendations to a young lad who lives in New York and wants to impress a young dame, what's a good date that you would suggest?
JC: I think if you're looking for high end, The Grill is a very romantic spot.
MR: And what are you doing after or before? Show? Standup?
JC: I love Hamilton.
MR: Really?
JC: Yes. I know every word.
MR: Do you go to Broadway?
JC: I only like Hamilton. I've seen it like eight times. I'll go on to say I really don't enjoy Broadway other than Hamilton.
MR: Are there any hidden gems in the city that people don’t know about?
JC: I think New York actually has some of the best hiking — within a one- to two-hour drive you have some really stunning hiking.
MR: Do you have a favorite hike?
JC: My favorite trail, which has been closed for a while for construction, is called Breakneck Ridge.
MR: What do you do for exercise?
JC: Carry the newborn, and I run and I lift.
MR: Are you religious about it?
JC: I was very religious about it before the baby.
MR: What kind of music do you listen to?
JC: A lot of classic rock — Jimi Hendrix and Pink Floyd, and also some newer stuff like Green Day.
MR: What is the last song you listened to?
JC: That is not baby music?
MR: Not baby music.
JC: Metallica, “Enter Sandman.”
Inbox Zero
MR: You do a lot — between politics, media, real estate, venture, and public market investing — how do you actually divide your time work-wise?
JC: I think about splitting work between operations and investing/creation — building new platforms, creating new business lines, or finding new investments and optimization. I enjoy the creation and investing more, but operations and execution is extremely important, and I think many people would argue more important.
MR: How do you keep track of your to-dos?
JC: I zero out my email inbox every day. So I always make sure that there's nothing outstanding that I don't know about. And then I have a to-do list.
MR: Is it physical or is it online?
JC: Just on my Notes app.
I've tried all the complicated tools. I just find a Notes app with the checkmarks works best. And then for email that I know is going to take longer than five to 10 minutes to respond to, I move it to my calendar.
More recently I've set a recurring time for my last meeting on Fridays for a weekly review where I think about what I accomplished the week before and I make sure to follow up with folks about outstanding items for the next week. I also audit my calendar for the following week and try to see what I can delegate. And you're trying to think about which meetings add energy and which meetings take away energy? There are some days where you could have just a few meetings, but you go home wiped. And then there are other days where you're back-to-back every 15 minutes and you feel energized when you get home. I find it just depends on the person. I've started to get to know the things that make me energized versus tired.
MR: Would you say the creative work makes you energized and the operations make you tired?
JC: For sure.
Dad Quotes
MR: You’re the son of a very successful businessman. How many of his habits and routines did you copy versus develop yourself?
JC: At least on the operations side, he's made an incredible impact. And I'd say it is the foundation of my operational and my strategic thinking.
MR: What did you pick up from him?
JC: It was a funny one that we just talked about today, and this is not when you're running a conglomerate, but when you're running an individual operating business. He has a line: People do what you inspect, not what you expect.
MR: I like that.
JC: I don't believe in being a micromanager, but when you're running a very thin margin business that is a lot of blocking and tackling, you have to make sure that all the balls are getting moved forward. People tend to have an increased focus on doing what they know you're going to follow up and ask questions on.
MR: Of all your dad’s sayings, which one do you think sticks with you the most?
JC: I mean, from a business context, that one's pretty good. I actually have a Notes app of dad quotes.
MR: That’s so good.
JC: “Don't complain about wakes. It's better to be the visitor than the guest of honor.”
Can't read that one.
This is a really good one about life, “Just avoid one bad hour and you'll live to be 100.” It’s an old Greek saying —try to foresee how something you're about to do is going to go badly.
MR: Other than your to-do list and dad’s quotes, what else do you have?
JC: I'll have different projects or products or companies that I'm incubating, and I try to have mental cycles around these different things. If I have a free moment, I’ll ask myself — what problem am I going to solve? I’ll pull that “off the shelf” and work through it. Then if I solve a problem, I'll immediately put it down in the Notes app, because as much as you think you can hold it in suspension for two weeks, by the time you get around to working on it's very hard to remember the fidelity of detail. So each major project has a note.
MR: What do you think you got from your mom business-wise?
JC: Empathy. Very strong empathy.
MR: What does that mean to you?
JC: I think it's really trying to think about how the person you're speaking to is going to react to a decision you make or the way you say something.
Context Switching
MR: How do you divide your thinking between different business lines? Do you think about real estate for 20 minutes and then venture for 20 minutes or is there a real estate day and a venture day?
JC: There's a huge amount of context switching. I would say we basically have one to two staff meetings a day, which are just a general weekly check-in for one of our businesses.
Say we have 14 companies in six or seven industries. We try to get through each industry every week just to have a touch point — generally what's going on in the business? What are the areas where, if elevated to our level, we could help fix things? Are there major strategic decisions or capital decisions? Refinancings? Personnel issues?
MR: How do you keep track of people? You meet hundreds and hundreds of people. Do you write notes about them? Do you create a new contact when you meet every new person?
JC: Basically the first thing I do as soon as I add someone to my contacts is write five to ten words into the notes section from our conversation.
MR: In their contact, right?
JC: Yeah. Met at this place, on this date, interests, et cetera. And then usually if I go back three years later and I haven’t talked to the person, I’ll go look at the notes.
MR: Are you religious about that?
JC: Very.
MR: What did mine say?
JC: So you actually have the honor of not having one.
I got this from my dad, actually. It will also say who introduced me to that person.
MR: That’s great.
JC: So if I type in “Raskin” in my book, ten people come up.
MR: I like that.
Desk
MR: I want to talk about your desk. What's all the stuff on your desk?
JC: I really love the American West. This is a replica of Frederic Remington’s Bronco Buster statue. Behind there is a Lego version of Barad-dûr from Lord of the Rings.
JC: Yeah.
This is a letter of marque.
MR: Like marque and reprisal?
JC: Yes — so it's a letter of marque that was given to me with my name and information. It’s from the Museum of the American Revolution.
Vices
MR: Do you have any vices?
JC: Ribeye.
If I wouldn't have a heart attack, I would eat ribeye for every meal.
MR: And where would you get it from?
JC: I have a three-axis rating system: consistency, price, and taste. So, I think this is a non-consensus view, but Bobby Van’s at 230 Park is really good and Wolfgang's on Park Ave. is really good. It’s hard not to like Smith & Wollensky’s too.
JC: Ray-Ban.
MR: Oh. Do you have any hobbies?
JC: Programming.
I recently made a video game. The way I actually relax is I build things. I built a robot last year and I program.
MR: Do you use ChatGPT?
JC: I do. And with Cursor and all these programming tools, my output has increased by 10x. It's crazy. I made a game in a few hours and it just passed 500,000 plays and I released it mid-last year.
MR: I get a sense from you that you wish you could just do one thing —— do you wish you could just work on one thing?
JC: Actually, no.
MR: Really?
JC: I just talked about this with my wife. I recently was presented with an opportunity that would require me to move to a different city and do one thing for three years.
MR: I feel like someone could put you in a dungeon and ask you to work on a new Grand Theft Auto and ask you to come out 7 years later.
JC: I would love it. If I felt the mission big enough, a hundred percent.
Greek
MR: You are Greek. I just want to talk about religion.
JC: Greek Orthodox.
MR: What does your religious practice look like? Is there a daily mass?
JC: We try to get to church as often as we can.
MR: What language is it in?
JC: It's a mix of English and Greek.
MR: Do you speak Greek?
JC: A little bit.
MR: Where's your favorite place in Greece to go?
JC: The island where my dad was born called Nisyros. There’s a little bit of tourism, but it has a population of 600 people in the off season. Most people wouldn't have heard of it but it’s wonderful. It's an active volcano off the coast of Turkey.
MR: What is that like for you to go there?
JC: It's nice because I'm tangentially related to a big chunk of the island. I think the last mayor there was a Catsimatidis, which is funny.
MR: Do you pray every day? What does your prayer look like?
JC: Yes, and I do gratitude exercises and meditations. I thank God a lot for how blessed I am and for my family and my baby and my wife, and allowing me to be able to experience everything that I'm experiencing. To quote Tommy Wiseau, "if a lot of people love each other, the world would be a better place to live"
MR: What’s the first piece of media that you consume in the morning?
JC: I wait an hour before checking my phone.
MR: Wow.
JC: And same with caffeine. I wait an hour.
But the first thing I open is X. I’ll look at the For You feed — I'd say if I had another vice, it would probably be X.
MR: Are there any apps on your phone that you use that people might not have heard of?
JC: There’s an interesting app called Clay Earth. Basically you can sync all of your contacts and it puts all your friends on a map. So if I’m traveling to LA I know who lives there and can reach out.
MR: What I’ll do is just search by contacts by area code.
JC: Smart.
MR: But it doesn't work great because people move.
JC: It’s still a good idea.
MR: What about any websites or Substacks?
JC: I have some finance and tech-specific reads. I have a lot of investing Substacks. I really like Stratechery. I think he's a really clear thinker.
MR: Do you watch TV?
JC: When everything is all settled, but I don't have enough time to commit to anything in particular.
MR: At the end of the day, what's your way of just turning your brain off and checking out?
JC: I'm building go-to-market tools for my company.
MR: And what language do you write in?
JC: PHP, which is an older language…don’t judge me.
MR: And where'd you learn how to do this?
JC: Mostly self-taught.