The Exchanges

Q Yeah, totally. Uh, Billy Joel, Allentown, growing up in Allentown. Um, so what were you like as a kid? Like, you know, is there anything, like, any, any little glimmers of the future not boring empire that were popping up when you were growing up?

A Yeah. So I, I think probably they're, they're a bunch of glimpses. I used to make these little books or newspapers on post-it notes. So one of my dad's, my dad was a consultant, uh, at Arthur Anderson, uh, and luckily got out before Enron, thank God. Um, but one of his early clients was the Miami Herald. And so when I was like, you know, six years old, I would make these little post-it note versions of the Miami Herald. I also have this one Which is creepy, and maybe we cut this part, but it was called Golden Memories of a Young Boy's Life. And so I had all these au pairs, and they would take me in like, you know, the women's locker room at the pool or something like that. And I was like a five-year-old kid, and I would come home and draw stick figures of boobs in this little book called Golden Memories of a Young Boy's Life. So that was probably the earliest version of Not Boring.

AI assessment note: “I used to make these little books or newspapers on post-it notes.”

Q sent out a tweet in February that you wanted not boring to make one million dollars this year, which as David has in the notes, uh, sounds effing crazy. And I, I'm curious, like, how, how did you, what happened in your brain as you formulated that tweet? Was it that the sponsored posts had been going well? Were you already contemplating Not Boring Capital? What was that moment like?

A Yeah. So I probably, I mean, like I'd been thinking a little bit about Not Boring Capital, uh, and so that was there, but really was talking about just purely making a million dollars off of the newsletter. A couple of things that happened around that time, like me and Ben from Composer wrote this piece on Excel that got picked up, I think, by two separate New York Times articles and got to the top of Hacker News and all of that kind of stuff. So I was like, whoa, that was my first taste of like this thing really going kind of, kind of mainstream. Uh, had written a sponsored post. I think probably, you know, either that week or was in the middle of writing the post. Um, and the company was really happy with it. It's like, and I was in Miami and the weather was nice and I could have been in, in, uh, New York in the middle of February and I probably wouldn't have tweeted the same thing, but I woke up and the sun was shining and I was like, you know what? Life is pretty good. Like I'm probably making at this point, call it 10 or 15,000 dollars a month or something like that. So like not close, maybe 20, I, I don't know. Um, But I just woke up feeling, like, really good, and I was like, you know, I'm just gonna, I'm just gonna say this, and, like, I'll probably, people will probably think I'm an asshole, but, you know, I, I've, I've, like, struggled on zero dollars for the past X n…

AI assessment note: “I just woke up feeling, like, really good, and I was like”

Q Did your parents like expect you to get A's or was that, was that you?

A My parents definitely expected me to, to get A's because they saw that I could get A's, right? Like I, I don't think it was any, any like undue pressure. It was just that they saw that if I applied myself, I could get A's. And if I didn't, which was also often the case, and then I didn't. So in fifth grade, I had told my parents everything was going really, really well. I was probably going to get straight A's, maybe like a B plus, maybe, but probably not. And then I got my report card and I remember my dad was coming home from a business trip and you know, he was a fancy consultant. So he had a cell phone way back in the day in his car. We got a report card, and my mom made me call my dad and tell him the grades that I got, and so I was like, science, A, English, A, French, C plus, blah, blah, blah, A. And he was like, alright, Paki, I'm gonna be home in an hour. By the time that I get home, I want all of your certificates, all of your trophies, anything that would suggest that you might be a winner, I want them in a box in the attic. We're calling that box the loser box because you're a loser. What? And my mom said that my dad went to like the, the Mo Mark Addafi school of parenting for this. I actually think it was awesome because what he was mad about wasn't that I got a C plus, like that wasn't the big deal. It was that I lied all semester and said that I was doing really …

AI assessment note: “My parents definitely expected me to, to get A's because they saw that I could”

Q So you apply to business school, right? And astute readers of not boring will know, and, and trollers of your LinkedIn profile will note that you do not have an MBA. Uh, Walk us through that and what happens.

A One other thing to add was while I was in finance, I started a company called Throgo, which was a terrible name. I had bought the site for something else and then I applied it to, uh, building this company that essentially took people from New York down to the Jersey shore and to the Hamptons every weekend. Uh, so the party bus ride, it was so much fun, paid for my summers. I took it You know, way too seriously and thought that this was going to be my ticket to a great business school, applied to Stanford, got summarily rejected, uh, from, from GSB. Um, ended up getting into Chicago, had my deposit down, was going to go. And then one, I kind of visited and it was snowing and it was like May or something, you know, April or May. And I also found a company called Breather on AngelList and had just started a conversation with the founder of Breather. Uh, where there was no guarantee of even an interview or anything, but I asked Chicago if I could defer. They told me, no, I couldn't defer. Your deposit's already in. If it were Harvard or Stanford, they would have let me defer. But Chicago wants to, you know, they know that people might try to say they want to defer so they can go to Harvard or Stanford. So they wouldn't let me defer. And so I just said, all right, cool. Not going to business school, uh, had already quit my job. And so really spent, uh, kind of the next four months,…

AI assessment note: “asked Chicago if I could defer. They told me, no... Not going to business school”

Q of the two posts that I do is going to be pure unadulterated. I'm getting paid by the subject to write this. I am doing the thing that is going to make classically trained journalists like freak out. And I'm just going to own that. How did you come to this and, and how did you, what were your fears around it? How did it come to be all that?

A Totally. So I'm going to get the origin story somewhat wrong. I'd started talking to Nick Abazita at That main street. And if you use Twitter, you've probably gotten a sponsored tweet from him about using main street also happens to be a phenomenal guy. Love Nick. Thank you. And he was like, by the way, like these posts that you write on companies, like you could write those on startups and I bet people would be willing to pay. And he had just come over from shrug capital to run marketing at main street. And he's like, you know, we'll be the first ones who, who do this. And I was like, all right, cool. Let's try it. Like I'm going to caveat the hell out of it and tell everybody right up front that it's sponsored. But like, I think Main Street is really cool, so I would actually love to write about Main Street and explain, and like, my audience is a bunch, a bunch of entrepreneurs and founders, and I bet my entrepreneur and founder audience would love to make money back from the government that otherwise they might not have, and Main Street will get you, kind of, your tax credits back in, in an easy way.

AI assessment note: “I'd started talking to Nick Abazita at That main street”

Q like cut down on something that, that is sort of at an inflection point right now? Or do you want to stay the course and hope that what you're building now has way more risk, but what you're building can Eclipse even what the greatest upside would be from becoming a general partner at a big firm. Am I thinking about that sort of right in the set of trade-offs?

A I think that you're thinking about it right in the set of trade-offs. I think the tricky part is that, and Schrodinger's cat is not right here, but maybe you'll understand the right version of what I'm saying is that as soon as I go in-house somewhere, Like I lose half of my value or, you know, X percent of my value as soon as I go in-house somewhere. Um, and that is kind of one, even though, you know, I do do sponsored posts and all of that, there is like this independent voice that I have that obviously goes away. Everything that I write would go through a legal team and a compliance team and all of those types of things. Probably wouldn't be able to even do it at the cadence or, you know, even the schedule that I do now where it's like, I'm making my last kind of edit, or writing my last sentence, 30 minutes before the piece goes out, or even a minute before the piece goes out, so I think it would lose a little bit of that flavor. Uh, and so I think probably, you know, you need to add, like, a time dimension on this, which is, when does it make sense to do this? And there's probably, like, when I'm deeply in that S-curve, if I've, like, gotten big enough that, like, somehow, just because I'm backing McCormick, people, like, now think that I'm smart, where, like, now I kind of need to prove that That I can add value every week. Like, maybe at some point in the future when the…

AI assessment note: “I think that you're thinking about it right in the set of trade-offs.”

Q This is the NYC debate club, right? Which you can go read about in the per my last email archive.

A Yes, you can. Um, but it was, I mean, like all of this stuff is a blast and I think it all comes from the same spot is, you know, the name not boring comes from, which is I had dinner with my mom and her business partner one night in New York while I was still at breather and her business partner asked me what I like to do outside of work. And I like just did not have an answer. Like, you know, other than I like traveling and I like hanging out with my friends. Like I had no passions, which is crazy because in college, like that was All I did. I spent a lot more time doing other things than, than I did actually probably studying. Uh, and so, you know, I think that kind of just like put a, put a bug in my head that I wanted to figure out how to get some of that back. And then I talked to a bunch of other people and they realized that they had kind of the same thing going on that once you kind of got out of school, it was work. And then it was your tight group of friends and whoever became your significant other, and then your family, but you didn't have those like kind of small Groups that were bonded around a particular kind of passion or hobby. So I was like, oh, cool. Like that plus Soho house. That sounds like the coolest thing in the world. Let me go start that.

AI assessment note: “Yes, you can. Um, but it was, I mean, like all of this stuff”

Q What, what would you have put the percentage chance at when you sent that tweet?

A I would have put the percentage chance that we got to a million dollar run rate pretty high. I thought probably, given that I kind of like knew what my sponsorship calendar was for the next couple months at that point, and that wasn't the, the right run rate to get me there, I probably would have put it at like 20% that I actually hit a million this year. But it is, I mean, like you really, it's, it is the power of compounding kind of happening where like it just keeps getting like The numbers just keep getting bigger to the point where it's like, you know, what would have taken me 10 sponsored deep dives I can now do in one sponsored deep dive. And so that, like, just kind of all grows and, and compounds, I guess. But it's still absolutely crazy.

AI assessment note: “I probably would have put it at like 20% that I actually hit a million”

Q I mean, you are, obviously there's some things you're, you're, That the companies don't want you sharing. But other than that, it's a pretty, it's a remarkably transparent way of going about venture investing. And it's also super different than, you know, classic venture capital. Like, did you lead a single round? Did you write any term sheets? Were you the biggest check in any one of those 91 investments?

A Never. And that's, that's all part of the strategy, right? Like, I mean, we all love talking about strategy and, and strategy isn't doing Everything. Well, it's picking what things you want to do well and taking advantage of those things. And so even like, you know, figuring out how to price the round and figuring out what should go into the term sheet and spending time negotiating that and then being on a board, God forbid, like it actually just doesn't work with my strategy because like it is a house of cards already where you move one thing and like the whole thing breaks. And so if I'm doing kind of the more deeply time consuming parts of a venture, It, at least as I'm currently constructed, doesn't work, but it really works very well when, you know, I can talk to a founder and we have the specific area, either kind of internally or externally where I can be helpful.

AI assessment note: “Never. And that's, that's all part of the strategy, right?”

Q not ones to judge whether it is or isn't. But if it is, and continues to be, Do you need all the other stuff? Do you need more shows? Do you need more content or on the internet? Can it just get big? And then when you add the capital piece too, then that is very scalable and directly related to, uh, to the content as well. So it's interesting.

A I think it can scale with this one thing pretty well. And like everything also kind of continues to feed off each other where if I have a bigger portfolio of companies, but each time I mentioned a company in a newsletter, it has a bigger impact because the audience has gotten bigger. It all kind of scales with each other, which I think is, is really nice. And yeah, I don't know. I mean, if this ends up being a thing where I do, you know, one sponsored post a month instead of two and get a little bit more time to like, you know, take a weekend off every once in a while, like that would be great. But you know, there's a path to this being a million person newsletter at some point in the next five years. And that's like, I'd be very psyched about that.

AI assessment note: “I think it can scale with this one thing pretty well.”

Q I'm curious how you would describe the most powerful aspect of the flywheel. Like, what is the thing where you are like, oh, these mutually reinforcing aspects are, are, are strongly tied?

A That's a really good question. Um, cause I mean, I think as we talked about a little bit before, like audience at the center of the flywheel is maybe not exactly the thing. Like if I had a million person audience of people who didn't care about startups or whatever, like it wouldn't be kind of as powerful. I think it's really just kind of the alignment between the content, the particular people who are in the audience, uh, and then the investing and like those three just, I think really work well together because they all kind of feed each other. So that's a cop-out answer where I think I pretty much just named the whole flywheel, but I don't think there's any one particularly strong link. I really think that it is that the con the content has attracted a certain type of audience member who's both more valuable. Two companies, uh, and who also include people who are starting companies and running companies and all of that, and it all just kind of feeds back into each other. But I think maybe the, the core part is that the content itself is so aligned with the venture business. I think that's, that's the magic.

AI assessment note: “the core part is that the content itself is so aligned with the venture business”

Q Not particularly venture-backable. What are your emotions like right now? Are you just like, I'm happy-go-lucky, it's all gonna work out, or are you like, kind of tearing your hair out?

A I'm to a fault and like, you know, everybody has their double-edged sword and mine is optimism. Um, and so, you know, like never, never once was there a time when I was like, uh, my life is absolutely over. You know, like when I joined breather and took a lower salary and it was a risky thing, my mindset was like, you know, my absolute worst case scenario here is that I moved back to my parents' house and I can still eat meals and I can still sleep in a bed and there's a roof over my head. So like, The floor is not that low. Certainly this time around, you know, there's, there's a hundred percent ego piece of this. Cause I have a bunch of friends who are doing really, really great things. And I was, you know, when I tried to bring not boring club online, I was sitting there, I had trivia nights that I like spent all day writing trivia questions and making slides and seven people showed up. And I was like, this is with my Duke education, my expensive high school education, all my experience, like this is what I'm doing with my, this is incredibly embarrassing. And so, you know, I decided to kind of just let Not Boring Club, the digital version, uh, fall by the wayside. In, uh, you know, February, early February, Pooja and I decided or learned that we were, uh, learned that we were pregnant. Um, and then really, you know, COVID, COVID kind of hit. And I remember just probably Apr…

AI assessment note: “everybody has their double-edged sword and mine is optimism.”

Q Uh, what about, um, Redfin is still in the market, another great Seattle company. Are you concerned about them as a competitor?

A Are they, are they, Above or below a billion dollar valuation right now. No, I, I think, I think, I think actually the mistake I made last time was I did a basket of these, these real estate stocks. It is a massive market that is awful to operate in right now, as, as a lot of people who bought a house over the past year, uh, have realized. I think that Redfin's gonna do really well. I think that Zillow, now that it's kind of back to its, uh, original focus is gonna continue to do really well. I, I still love Zillow. Uh, and I think that Opendoor is gonna do the, the best. I think they have the biggest lead in, in iBuying, and I think that's a huge, huge opportunity Particularly because they have the best company value in all of the world, which is bips for breakfast. Like, they pull every basis point out of operating these houses, and that is a really, really valuable thing. Like, it does remind you of another Seattle company, Amazon, uh, in that, like, that you really need to get your costs right, and they're the best by far at doing that.

AI assessment note: “I think that Redfin's gonna do really well. I think that Zillow...”