Music, Entrepreneurship & Embracing Non-Work - Paul Canetti

[01:38] Paul: Today I'm talking with Paul Canetti, welcoming another Paul to the, uh, podcast. He describes himself as an entrepreneur, educator, and futurist, but I wanted to reach out to him because I recognized somebody that was just deeply curious across a number of, or across a wide range of interests, past experiences, and I thought it'd be fun to dive in. He's currently an adjunct at Columbia Business School. He's running a podcast covering tech news for MBAs, writes at Hypothetically Great, and he's recently taken a shift towards a more intentional path, and we're gonna explore that. We're gonna dive into a lot of his interests, and see what emerges. Welcome to the podcast, Paul.

[02:29] Paul Canetti: Thank you very much. I'm very happy to be talking to another Paul. We're a rare breed.

[02:35] Paul: So I want to talk about just growing up. I like to start and ask people how, like, what were you like as a kid? How were you thinking about life? How were you thinking about your path in life as you grew up?

[02:51] Paul Canetti: That's a good, good line of questioning. I mean, as a young kid, you know, Ghostbusters was my favorite movie. Let's, you know, go way back. But I was Egon, so I don't know what that tells you about me. And I didn't know that he was like the sciencey nerdy one. I thought he was the cool one.

Um, I also thought it was a drama, uh, and had no idea it was a comedy. So, um, You know, as Egon going through life, uh, I remember going over to friends' houses and like, you know, disassembling alarm clocks and trying to build time machines, and always just sort of curious about how things worked and, and how you could sort of rearrange them into new things. And, um, I was really into music and played music and still play music. Um, at one point pursued that professionally for for a few years. And so yeah, I was a curious kind of nerdy kid. And in high school, which was— this is like late '90s— was getting into early web programming, which is how I ended up befriending my eventual co-founder of a few of my startups named Simon Baumer.

We went to high school together, and we were basically the two kids that were into HTML and CSS and like, you know, we would spend the evenings in each of our respective homes on our family computer, you know, IMing about like HTML. And so that, you know, was some foreshadowing of what was to come. I didn't know that was gonna be most of my career at that point. But, but that's sort of where my head was at.

[04:43] Paul: Yeah, that's fascinating. I think a lot of people I'm talking to who are doing stuff online creating were these people. I was one of these people that would kind of go home and then like all the cool stuff I'd get to work on on the computer, I'd hang out like I'd do like proggies on AOL.

[05:02] Paul Canetti: Oh yeah.

[05:04] Paul: GeoCities pages, Tripod, like all GeoCities.

[05:07] Paul Canetti: Definitely. Or like You know, I mentioned I was a musician. Like I would, I remember saving up money and buying this software called Cubase, which was like, you know, what today we'd call digital audio workstation kind of software. But the instruction manual and the interface were all in German. So like there was no like English language recording software, you know, and I was like in middle school trying to like figure out, and there was no Google or Google Translate, you know, and just trying to like figure out how to use the software. And like, there was a being into computers sort of implied that you had to have an unusual level of curiosity because it, the barrier to entry on a lot of these tools was high.

Um, and I'm sure we'll get into it, but there's a lot of things happening on the internet today that feel like that to me. Where it's like, you know, there's— we all got comfortable, and my parents can use all sorts of software today easily without asking me, which is really the mark of like how mature internet software has become. But then there's a lot of new stuff on the horizon that feels like it has that similarly high barrier to entry, um, which I find, you know, like that feels familiar to me.

[06:28] Paul: So you tinkered a lot as a kid. You had a good word, science, scientist, engineering mind. Uh, did that carry on through college? And, uh, how were you thinking about, I guess, entering the quote unquote real world?

[06:44] Paul Canetti: Music was really my main focus through college. I played in bands and Simon, again, my, my co-founder, but at the time, uh, we were also college roommates. We founded an a cappella group. And that was kind of like, you know, my life. I studied philosophy undergrad, not with an intention of career prospects there, but just found it fascinating. And then on the tech side, I quickly learned that my coding skills were pretty bad.

And design was definitely more what I had to contribute. And my father was a graphic designer, industrial designer. So like, Growing up, our basement, like his office was old school kind of graphic design, like Letra Press, like, which is, you know, like, like basically sheets of letters in a particular font where you had to rub off like one letter at a time onto a piece of paper to create, you know, a typographical graphic and, and a lot of rulers and compasses and, and that kind of thing. So like old school graphic design was just sort of like part of my upbringing. So Simon and I sort of became a tag team where he was good at coding, I was good at design. At the beginning, that was just like, can we make a webpage for our band?

Or, you know, little projects like that. And less career oriented there. So we continued to tinker, I guess you would say, but it didn't really occur to me It sounds weird now, especially, you know, I graduated high school in 2001. So this is like right after the dot-com bubble. Like I just sort of didn't know that people made software for a living. I don't know, like no one, it sounds so silly now, but like as a kid and even as a young adult, like I just like didn't, I didn't know that was a thing.

I don't know why. It's just no one in my life did that. None of my friends' parents were. Building software, like it just, I didn't know that was a profession.

[08:52] Paul: Yeah, I think similar thing for me. I was reflecting a couple years ago how I'm like building these, I, I'm hosting a podcast. I'm, I have these websites I control and update and code and doing all these experiments online. And I realized that it was basically just continuing what I did as a kid. So it sounds like we were pretty similar. And really now looking at it, I left the consulting career about 5 years ago.

That seems like the aberration.

[09:25] Paul Canetti: Huh, that's interesting, right?

[09:27] Paul: But, but when I was growing up, everyone just had kind of these corporate jobs, and yeah, me, that was what life was like.

[09:35] Paul Canetti: That's what a job was, right?

[09:37] Paul: You work for the rest of your life. Like, nobody had this sense that like technology was something I should do go do, even while I was interested in the whole time these things were happening, it just somehow never occurred to me that maybe I should go to San Francisco and work for some of these companies.

[09:53] Paul Canetti: Yeah, exactly. And I don't know if maybe I'd been a few years older, if I would've understood that better. Like I can remember in, I don't know, let's say 7th or 8th grade, maybe like on AOL Instant Messenger and they had a like a test feature, you know, a beta feature. I don't know if they called it that, where you could have live streaming audio, essentially a phone call through AIM. And I remember like messing around with it and being like, oh, like imagine if people made phone calls through the internet, but no part of me was like, that should be a company and I should found it and I should do a start— I was a teenager. I didn't— it just— these were things that just sort of came from on high.

There was no difference between McDonald's and AOL. These are just companies that some grownups did. And I think it's different today. I think a teenager might think, ooh, I could do a startup. And like, and actually like participate. But it didn't feel like that to me and my friends.

Like we didn't know that, that we could potentially participate in that world. That was the thing that like corporations were doing or something. And, and we were just on the receiving end of—

[11:20] Paul: well, that probably made sense too, because it was literally just way harder and more expensive to start a company.

[11:28] Paul Canetti: Yeah. Fair enough.

[11:28] Paul: Right now you can spin something up automatically online within a day. Yeah.

[11:34] Paul Canetti: Yeah. It's, it's, it's very, very true. And, and I, I think, yes, it's easier to get going, but also there are more stories in the culture of people having done that where, you know, like I had heard of plenty of bands that had emerged from high schoolers in their garage. Like, that was sort of the meme of the day for me, and I was like, that's gonna be me. Um, but the, the sort of cultural meme of the teenager hacking away, you know, which is funny because of course like Apple had already happened and Microsoft had already happened, but those stories weren't like the stories that we were telling ourselves as, as teenagers.

[12:24] Paul: Yeah, the— and I think what I write about, like people exploring different paths, I think we're just seeing the edges of what's going to emerge downstream from this. Because even when I left in 2017, there, there were some stories, but there's been an exponential increase in the number of people sharing different stories, different paths. And these are what people look to now, right? You go on social media and you see somebody doing van life, and all of a sudden in your mind that means it's possible and you can work towards that and you can message that person and ask them for advice. I think we're only in the early days of people actually grappling with this, which, which might be an interesting segue. Right now you're an adjunct at Columbia Business School.

I went to business school at MIT Sloan and I graduated in 2012. And although the tech revolution was happening, people were still taking very traditional safe paths: investment banking, consulting, corporate strategy, and then like a couple of people that were pursuing startups, but they were kind of seen as like, oh, they're different entrepreneurial type anyway. What's the energy and mindset of people now?

[13:46] Paul Canetti: Yeah, it's, it's interesting. So dirty little secret, I didn't go to business school. Myself. And but I've been teaching at Columbia Business School now going on 6 years.

[13:56] Paul: Cheaper way to get that.

[13:58] Paul Canetti: But yeah, you know, I went to the school of hard knocks. And, and I've always loved teaching. And to me, sort of doing startups and teaching about startup methodologies and, and like, they've always gone hand in hand. And And whether that's sort of informally or formally, but I started teaching at Columbia in 2016. So this summer, the summer of whatever, next summer, '22, will be 6 years. And, you know, I remember sort of informally polling my classes at the time, and I teach big sort of lecture hall style classes.

I currently teach 2 courses, Introduction to Product Management, an introduction to user experience. But again, these are for MBA students, right? So most of them are not designers. So they're taking UX, but not necessarily to become a UX designer, but instead to understand sort of the ethos of user experience. And product management sort of started like that too. So I would sort of poll the class and say, who here is interested in a career in product management?

And maybe, maybe 10% of the class would raise their hand as even just being interested. They were all in the class, right? So they'd enrolled in this elective for some reason, but it, but it was still sort of like consulting, finance, you know, like these, these sort of mainstream career paths. But with each passing year, I would say now when I take a poll at the beginning of my PM course, it's like maybe a third of the class are 100% like recruiting for PM jobs. Like, that's why I'm in business school, to become a product manager. Another third are considering it, or, you know, sort of like, it's one of a few options, maybe they're pursuing, you know, sort of like, I was working at McKinsey, maybe I'll go back there.

But maybe I'll be a PM at Amazon. And then there's still some that are really just sort of curious, but even that third, they know that they will be somehow interfacing with technical teams. Like maybe I'm going to be on the marketing side, but I'm going to do this. Maybe I'm going to be on the investment side, but I need to understand how the sausage gets made. Like everyone is at least adjacent to it. And again, only in 5 years I've seen that sort of shift.

And if you just sort of draw the trend lines out, you know, there's some major shifts. And at Columbia, I'm working, we're working on creating like a new sort of lab for product management and And we've expanded the curriculum, now added sort of like a level 2 PM course. We're introducing a growth hacking course. Like I'm working on a new metaverse course. There's a crypto course that's being taught now. Like things are sort of blossoming out of what was considered sort of almost like hobby-level electives into what is really shaping up to be a proper track.

Columbia doesn't do tracks, but, but, um, so my word, not theirs. Yeah, it's like you're going to business school because you want to build software products. Um, and some of those people are on the entrepreneurial path and some want to just land a job at Google, Amazon, Facebook, whatever, Meta, uh, Apple, et cetera. And it's funny because I think if you go to most PMs that work at Google today, a very, very small percentage of them studied that or anything like that when they were in school, because those subjects weren't available in academia. And now it's different. You know, if, if this is a graduate program, but you can go to an undergrad, uh, you can get an undergrad degree like in UX research, and that's going to look like a very different career path.

Than someone who, let's say, is, you know, 10 or 15 years into a UX career today, they definitely did not study that 10 years ago. And so we're seeing sort of the formalization of a lot of these like careers.

[18:19] Paul: Yeah. I always think of the MBA as the best search function for like the high-paid jobs that are also high status and interesting. And as soon as those paths become legible, like MBAs know exactly how to like prepare, exploit. And to be honest, it's probably a good thing. I think MBAs get a bad rap sometimes. Like I think MBAs can bring a sort of like rigor and standardization to the job.

And the people that were probably PMs 10 years ago are not going to want to do that job. 10 years from now, they're going to be on to the next.

[19:00] Paul Canetti: I think, I think that's a really, a really smart and charitable kind of interpretation, but, but not, but in a truthful way, where as industries mature, as job functions mature, they need to become standardized. You need to know how to evaluate them, you need to know how to hire for those roles at scale. And all of that means more rigor and standardization. And the other thing that I think is cool about MBA students is, you know, you said high status, and I think there's kind of a negative connotation built into that. Not necessarily that you had a negative connotation, but just societally.

But I think these are people that are essentially self-selecting as leaders or people that believe that they have the potential to be leaders, whatever that might mean in each case, and that they're sort of coming out of the crowd and saying, like, I want to lead in this space, but in a relatively safe way.

[20:05] Paul: So I'd love to shift gears and talk about your own journey. So you spent several years working at startups, as you said, Many of those failed, 2 succeeded. You've recently had what you told me was kind of a life-changing or a mindset-shifting exit from 2 of those companies. And you're starting to think about what the next chapter for your path is. I'd love to explore that. I think it sounds like you're at a similar stage I was probably 4 or 5 years ago.

But yeah, Where are you right now? Like what, what is the one or two questions you're thinking about?

[20:47] Paul Canetti: Yeah. I'm, I'm at the stage where when I meet other dads at the playground and they say, what do you do? I say, I have no idea.

[20:59] Paul: I was just talking about this with my last podcast guest. Um, he, he took some time off and he, he was, he was actually saying there were two other dads in his similar spot, but they always get made fun of.

[21:11] Paul Canetti: Yeah.

[21:12] Paul: Yeah.

[21:12] Paul Canetti: You need an answer, you know?

[21:14] Paul: Thank you. But why, why? Well, let's explore that.

[21:17] Paul Canetti: Well, that's interesting.

[21:18] Paul: Why, why do you say we need an answer?

[21:22] Paul Canetti: I think, I mean, you don't need an answer. You need an answer in the same way that people say good when you say, how are you?

[21:28] Paul: Right. Right.

[21:29] Paul Canetti: Like it's just cleaner to say that than to, you know, be like, well, my elbow hurts a little bit today. But I think it's because I worked out yesterday and I might like, you know, so it depends on who the audience is. Sometimes you just need the one-line answer. And of course my one-line answer is I'm a professor and then that's that. But it's interesting because I've been teaching for, for a long time, but I've never identified myself that way and forget what other people think of that answer. When I hear it myself, You know, it's interesting how much of one's identity is tied up in their work, in their profession, especially when you found a company and, you know, you have to sort of create hype from nothing.

As if you go join a well-known company, the hype already exists and you're just kind of getting on the train. When you are building a company from scratch, by definition, there's no hype at the beginning, so you have to be the hype man or woman. And a big part of that is staking your personal identity and your social capital on that project. This is what I'm doing now. This is why it's going to be the biggest thing ever. And it's funny looking back on my myself, we founded MAS in 2010.

You know, there was just so much like bluster. And, and now, in my old age, I almost can't imagine like doing that. It wasn't, it wasn't fake.

[23:11] Paul: Well, I think that's like, that's like 2010.

[23:15] Paul Canetti: Yeah.

[23:16] Paul: Time period.

[23:17] Paul Canetti: Yeah. Well, right.

[23:18] Paul: We've now had 10 years of social media on our mobile phones, which is radically transformed like how we see things as authentic, right? In 2010, I mean, you— like, the language of like marketing and like professionalism was so much heavier than it is now.

[23:36] Paul Canetti: Yeah, it's true, it's true. Things had to be more polished and there were a lot of like launch parties.

[23:42] Paul: And I think what you're saying is that like, as a founder, you have to believe that stuff, and inevitably your identity is going to get tied up with that.

[23:52] Paul Canetti: Well, exactly. And that no one on earth is going to believe in what you're doing if you don't genuinely believe it yourself. It's not that you're bullshitting, it's that you actually do believe it, and that is infectious, and that is attractive, and that's how you recruit a team, and that's how you recruit investors and customers. And it's all genuine, but Exactly. And of course, when a project doesn't work, it really stings because again, it's so synonymous with yourself that you say, hey, that thing that I've been talking about nonstop that I fully believed in, it didn't work. And of course, when it does work, it feels great.

But having seen failures and successes, I'm the same person and did mostly the same stuff. So it wasn't really me in either case. So that's actually been a helpful lens for me to look at. There are so many different factors when building a business and now having exited. So long story short, I had two exits in the last year, but not by pure coincidence. So Maz, which we've been running for over 10 years, my third co-founder, I mentioned Simon, who was one of my co-founders, our third co-founder, Shikha Arora, who was our longtime CTO and third co-founder, she took over as CEO at the beginning of 2020.

And I was still on the board. But Simon and I were working on a new project called Bounce House. And that was still fairly early in its trajectory. But when a deal started to form on the MAS side, Simon and I, we hadn't raised any significant capital for Bounce House yet, and we thought, well, what if we could find a buyer for this business, which was an unusual time to sell a business? We'd only launched a few months earlier, and we were lucky that we found a viable buyer there, but we said, It was purposeful because we knew that the MAS deal was going to be a financial windfall and we didn't actually have to go with the deal because we were already out of the day-to-day. And now we thought, okay, well, instead of signing an extended odyssey, what if we just got off the ride?

And we were very lucky because probably if we already raised money for Bounce House, which we didn't because of COVID and whatever, but in another scenario, we would've already been too far along with that project, but here it was still pretty nascent and we were able to offload it in a way that was acceptable to us and our investors within a couple of months of Mazz. And so all of a sudden we sold two companies and didn't have to go with either of them. And so we found ourselves without without a job, without a company.

[27:01] Paul: And what month was that?

[27:03] Paul Canetti: We closed the MAS deal, which was the second on August 31st. So now it's November 29th. So I'm just about 3 months deep into this.

[27:13] Paul: Yeah, how's it feel?

[27:16] Paul Canetti: Feels longer than 3 months. You know, it's funny, I imagined that my days would all be sort of sitting on a bench with a notebook just ruminating on the world and exploring different neighborhoods of New York City. And, um, it's not like that at all. I'm, I'm busy. I'm slammed. I can't keep up with my emails.

I have a million meetings all the time. Um, I, I'm doing it wrong. Uh, but what's interesting is that those—

[27:48] Paul: have you had any days like that?

[27:50] Paul Canetti: The first couple of weeks. Like the first day after closing, I like went to Chinatown and just like ate dumplings by myself. And I was like, this is a luxury that for whatever reason I have not afforded myself for 11 years. Um, and that was symbolic for me. I just— nowhere to be, no one to I see nothing, nothing on the agenda. But what's interesting, and I, you know, at first I was sort of fighting this, but now I've sort of embraced it.

I think I am the sort of person that likes to get coffees and lunches and Zooms and hear what people are working on. But what's very different about these past couple of months versus all the other time in my life is that I don't have an angle. Like, I'm not trying to sell something. I'm not trying to figure out, hey, do you know this person that maybe then I could meet as a result of our meet? Like, I'm just genuinely curious. I'm meeting with a ton of startups and hearing what they're working on.

And, and just like—

[29:01] Paul: I have a phrase for you.

[29:02] Paul Canetti: Yeah, yeah, tell me.

[29:03] Paul: So, I mean, I call this like networking 1.0, right? And it's this mindset, like, you're a worker, right? And The whole point of networking is for a future potential connection, right? Maybe you like each other too, but like really everyone kind of knows the subtext that it's all for future potential connections. Now, like on my path, like I don't really care about any of that. I don't want a job.

I don't, I'm not looking for a payoff. I kind of like what I'm doing. So I just call them curiosity conversations.

[29:34] Paul Canetti: Yeah, I love that.

[29:35] Paul: That seems to transcend things enough for people That it triggers the people who are like, ooh, yeah, let's just talk about random stuff. Yeah.

[29:45] Paul Canetti: Well, I have this framework I call 1,000 Coffees, and that's what I think it takes to basically bootstrap a professional network. And it almost doesn't matter who the coffees are with. I mean, they can't be too random, but at some point along the way, you start getting coffees with people that know other people you've already gotten coffee with. And the network starts, like those connections start to be made. You don't need to be particularly savvy at doing it. And if you end every conversation with, who else do you know that I should be talking to?

And it just kind of spreads and spreads from there and a single coffee or these days, even a single Zoom, but like a real human conversation can last you a lifetime, right? Years later, you can get in touch with that person. Say, hey, I noticed that you know so-and-so, would you mind introducing me? Or, hey, I'm interested in this area, you know, I know we haven't seen each other a couple years, but it's sort of, it's amazing just the power of sharing a coffee with someone. But you're totally right that, and I've been talking about this idea of 1,000 coffees for years, but it's in service of some future need, of some future favor, essentially, on both sides typically. Even though usually a conversation at a given time is weighted one way or the other, but sometimes in the future, you know, it can flip.

But it is interesting to at least attempt— I love this idea of a curiosity conversation where it's almost like reading a book or an article just to sort of jumpstart your own thought process, but instead of reading something on the page, you're just reading what someone's telling you. And it's like, what I'm hoping to get out of a lot of these conversations is just inspiration. It's just cool to hear what people are working on. And when you are building a company, the blinders are on. That's one thing I've really realized.

Again, it's only been 3 months, but you are so concerned with the problem you're solving and the customer you're addressing and your local challenges And once you aren't focusing on a single problem all day, every day, you realize how big the world is and how many different sorts of problems people are trying to solve and how many different sorts of customers people are trying to serve and, and how many different types of careers people have. And like, everything just opens up where you're not— when you're not concerned with your own thing. You know? Um, and so that's been, that's been great. Like just, just, just, just learning about what, how do other people spend their day, you know? Um, and that's been really fun and I'm hoping to sort of synthesize all that into some new life for myself at some point.

Um, but, uh, I'm in a very luxurious moment that I'm certainly treating like this will be the only time it'll happen to me. And for a lot of people, it never happens, which is just, I'm not in any financial rush. And so I don't have retire-forever money, but I have take-as-long-as-you-need money. And if talking about money is another sort of topic, which is socially embarrassing, because that's the other thing. When you tell someone you just sold your company, there's sort of this implication, "Oh, okay.

[33:29] Paul: So that has some financial inference there." When you founded it, did you have this idea like, "Hopefully we have an exit one day," or you just like starting companies with your friend?

[33:44] Paul Canetti: We didn't even know we were starting a company. Like, we didn't even know we were. If you were like, hey, are you working on a startup? I would have been like, what's a startup? Like, we were just futzing around, you know, and one thing led to another. And as we educated ourselves over time, we figured out, oh, we are building a company, and oh, we should raise money, and oh, we have to hire people, and oh, we need a board.

And like, we We pieced it together, like, as we went. But it was— it's funny, like, compare that to a lot of my students who are like, I want to do a startup, I just don't know what it is yet.

[34:21] Paul: Yeah.

[34:21] Paul Canetti: And we were basically the exact inverse, where we were actually doing the thing and serving a real need in the market before we realized that we were building a company at all, which, unfortunately, I don't think I'll ever be able to do again because it only came out of us being so naive. And once you've lost that, you know, you can't like, you can't get it back, which is a shame.

[34:48] Paul: Well, I think that's also a trap. I call it a hustle trap, which is they're actually aiming at an identity, right? They want to be the person that describes themselves as a founder, right? Rather than finding things they actually want to do. And it's kind of like one layer of abstraction, a little too much. And a lot of— I mean, some people can accidentally stumble upon their path on that, but a lot of people end up getting lost too.

[35:15] Paul Canetti: Totally. Or, you know, I know doctors, for instance, just to pick a totally different profession, that, right, when you ask like, why did you become a doctor? It's like, because I knew it would be— it would provide a good lifestyle. And it's like, oh, that was not the answer I was expecting. You know, like I thought it was because you want to help people or because whatever. And I'm sure there's some of that.

I'm not, you know, these people aren't like cold-blooded, like sociopaths, but it's, that's never the answer I'm expecting, which is I knew that if I had this type of profession, I would have a certain type of salary and a certain type of job security and certain type of whatever. It's just not the way I've ever really thought about my own career. Um, and there's no right or wrong there in my opinion, but it's always striking when you realize, oh, people are approaching these things in different ways than I do, or I would.

[36:15] Paul: Yeah. It's something I'm writing about in my book and I think is a difficulty with people taking their own paths is Almost everyone lies about why they're doing what they're doing. If it's for the money, no one will ever tell you, which is extremely unhelpful to the people that don't prioritize money because they don't see the potential money they could make, right? If people are doing it for like deeper reasons, like insecurity, needing to prove themselves, they may not even be aware that they're doing that. So they can't communicate it. We all have these kind of like surface-level stories about why we're doing what we're doing, um, and they're hard to understand ourselves.

And then we look to what other people are doing and we're just totally confused.

[37:00] Paul Canetti: Yes, or you piece together that story again, sometimes for yourself retroactively, to sort of make sense of what— why have I been doing these things, right? And, and We like it to fit, you know? Um, but in my experience, my own career has been so twisty and turny and unintentional. Um, but, but again, for clarity's sake or cleanness sake, you end up creating the bio that makes it sound like it was all purposeful.

[37:37] Paul: I'm just curious how your relationship to how you're thinking about work has shifted. In the last few months?

[37:44] Paul Canetti: Yeah. Well, you know, in all honesty, I'm, I'm trying to figure that out. So, you know, these are unpolished thoughts, but I think one thing that I've always believed that I'm surprised that most people in my life never seem to understand is, is that What you are working on and how you make money don't need to be the same thing. And when I was pursuing my music career, most of that time I had a full-time job, which had nothing to do with music. When I was building my first company, MAS, the way that I paid the rent was I had another business called Paul the Wizard, where I would go to people's homes and hook up their Wi-Fi routers or their printers or teach them how to use iPhoto or whatever. And they paid me $75 an hour.

And in the evenings and some days I was working on Maz, other days I was working on my band, and some hours of some days I was doing Paul the Wizard. Those were 3 different activities. One of them made me money and 2 of them were other pursuits. And so I was always comfortable with the idea that those things could be from different places. I think a lot of people get that wrong when they think, "Well, I don't want to leave my job to do X because then my income will go to zero." I just, I don't really understand that. Well, I do understand actually why people think that, because it's kind of what we're taught to understand, that either you have a salary or you have zero.

And that I always try to tell people, I mean, just in my personal life, there is something that you know how to do that someone else on this planet will pay you to do. And can you sit on a couch? Great. You get paid to be a babysitter. Like, it doesn't even need to be something highly skilled.

[40:00] Paul: People intellectually know this, but you don't actually know it in your body. And I think I experienced this in a very weird way. I left my job and I had comfort to leave my job because I had actually gone through a health crisis and gone several months without work. And that was the thing that told me, oh, I could be okay even if I don't make money for a few months. But what I totally unexpected was, or what I didn't expect, was that as soon as I didn't have an income, I awoke in this, like, motivation inside me to make money, right? Like, what people are underestimating is that your income will go to zero, but you will also realize it went to zero.

[40:44] Paul Canetti: Yeah, you get hungry, you know. Um, I'm, I'm sorry to hear that you had this, uh, this, you know, health issue. But, um, but I think what you just described is something that people don't give themselves enough credit for. Like, you will figure it out because you have to figure it out.

[41:04] Paul: And right, exactly, there's no choice.

[41:07] Paul Canetti: And I do think, you know, in all candor, something that I worry about now is that I might not have that same hunger. I worry that—

[41:21] Paul: interesting—

[41:22] Paul Canetti: that, um, you know, the only way to feel hungry is really to not know where your next meal is coming from, and then you just, you just sort of make it happen. Um, and trying to sort of synthetically create that urgency, uh, it remains to be seen how effective that can be. Now, of course, you see all sorts of insanely rich people that are still very, very ambitious, much, much wealthier than me. And so obviously it can be done, but I think a lot of it comes down to your personality and how much you are driven by different things. For me, I've never been driven by money That's not why I did any of the things that I've done, including these startups that ended up making me money. But again, you can't go back and sort of recreate those conditions moving into the future.

And so right now, the way I'm thinking of it is, what is sort of the The way that you can do the things you like to do, I think a lot about optimizing for the average day as opposed to kind of suffering through your normal life because you have a sick vacation planned or because one day there'll be some big payday or anything like that. But instead, just like most of your life is spent on just a normal day. For me, wake up, get the kids dressed, get them to school, work on something, have dinner, clean up toys from the living room, have a little time with my wife in the evening and go to bed. And so what does that day look like if you just pick a random day from my life is that day a good day? And I think about that a lot, of that actually being a better way to optimize than for some sort of financial outcome or some sort of lottery ticket or something like that.

And again, I'm not perfect at it. You can't help but sort of have multiple considerations, but I do try to really, when I'm when I'm mindful to do so, to think about that optimizing for the average day. I don't know if that resonates with you at all, but, but I think that's a much better way to approach one's work and just how one designs their, their life.

[44:07] Paul: Yeah, it's interesting. I think the day is a good starting point. So I went through this shift where I, I went like 2 or 3 months without making any income, and then I finally landed some freelance gigs, and I kind of figured out I could make it work. But in that space that it opened up, I kind of had this question of like, well, what do I really want to do? I, I realized I wanted to stay on this path long term. I didn't have enough money to, to make it without work for more than a year, but after about 6 months, I had made enough to kind of like give myself permission to not work for a while.

And I basically just asked my asking myself that question, I started with, if I could wake up every day and just do stuff I wanted to do, what will I end up doing? And what I ended up doing was nothing I could have planned, aimed at, or predicted. I started experimenting with like writing online and doing podcasting and literally just riding around on a bike in the middle of the day, which felt so bad to do at first. Like, who am I to be riding a bike on a Tuesday?

[45:14] Paul Canetti: It's just so funny you say that because really the only thing I've like splurged on is a bike and I've done a lot of these random daytime bike rides and you're totally right. There's like a guilt almost like what sort of person just rides around. Um, but it's incredibly liberating. I remember the first day I picked up my bike from the bike store and was riding to the West Side and along the way I just passed. A restaurant that had some nice outdoor seating and it was a beautiful day and I was hungry and I was like, I think I'm going to stop here and like get lunch. And just like, you know, again, these are such like sort of mundane luxuries.

But it was like so crazy to me that I was just going to, I was going to park my bike and then sit here and eat the, you know, $13, like Sushi lunch special at this restaurant and, and then get back on my bike and go about my merry way unplanned, unexpectedly. Uh, and yeah, it was honestly, it was really fun.

[46:20] Paul: Even the way you're describing it, you're kind of like, I shouldn't be appreciating this that much, but I think there's actually something hidden in that, in that these simple spontaneous spontaneous moments that are not scripted, they're not planned, actually are these portals to appreciating like the mystery of the universe, which to me is just beautiful and actually worth pursuing. Um, so the way I think about a day now is actually the potential to have that kind of day as many days as possible. And what I've discovered is that it doesn't actually require tons of money. It requires tons of time.

[47:07] Paul Canetti: Exactly.

[47:08] Paul: Which is much harder, especially if you're an interested and driven person, to carve out because there's infinite things you could work on.

[47:16] Paul Canetti: It's impossible. Well, even for you, though, you know, you're writing a book, you're trying to write online, you want to have a social presence, you're doing the podcast, like That's a lot of time right there to make progress on those projects. Do you set blocks? Like, I'm going to write in the morning and explore in the afternoon, or is it more sort of just, you know, feeling your way through the week?

[47:37] Paul: Yeah. So I think— so I was saying like the day is a good starting point. I've now scaled up where I think about it in kind of like chunks of time. So like I'm in New York for 2 months and my priority while I'm here is personal connections and these curiosity conversations. So, I'll pretty much drop the ball on everything except finishing up the book to do that. That is a learned skill because it requires literally dropping the ball or screwing up on things, not following up.

It involves not pursuing paid projects, but to me, it's It's not this 1,000 coffees to build a network. It's 1,000 coffees to build a life. So what is the most interesting life possible? Like, that to me is a crazy question worth actually pursuing. So after this call, I'm going to meet somebody for coffee, and we connected like 4 years ago talking about paths and careers. And I don't know what's going to happen, but to me, like, that's worth happening because I don't have an expectation or where it's going to go.

[48:52] Paul Canetti: Yeah. Not having the expectation, I think, is a luxury in itself. Um, and, and there's a, a real sort of openness that is hard to channel. And, you know, as you just even spoke the words dropping the ball, I'm like starting to sweat.

[49:14] Paul: It feels stressful, right?

[49:16] Paul Canetti: Well, because Nobody likes to feel like they're failing or feel like they're whatever, but you know, even in just like personal task management, like I learned a long time ago that I can pretty much only do one thing per day. Like even though my list is dozens of things, um, if I just choose one thing and I'm like, this is, if I get this done, then I can feel good about today and to sort of, and, and that means dropping the ball on all the other things. At least for a day. Again, we're talking about a day versus a couple of months, but like giving yourself permission, because if you feel bad about everything that you thought you were gonna do or supposed to do, but then you aren't able to do, you'll just feel bad all the time.

[49:59] Paul: Well, what are you gonna drop the ball on in the next month so you can come have a curiosity conversation with me?

[50:07] Paul Canetti: You know, like, Let's, let's say not your kids' stuff.

[50:11] Paul: Like, what was I going to say? Prioritize that. But you could drop the ball on something.

[50:15] Paul Canetti: But for instance, the easiest thing for me to drop the ball on is my own work, meaning writing, podcasting, you know, just sort of like giving myself time to read and think and whatever. Because that, when I, even if I try to block that off on my calendar, it's the first thing to go. Right. So if we have this podcast scheduled at 1 and someone says, hey, can you come get a coffee with me at 1? I'm like, well, no, I have a meeting at 1. Like that's official on the calendar.

Um, or obviously a family obligation or whatever. But even if I try blocking off like me time, which is, you know, again, like structured writing time, for instance, as a tangible example, it's easy to eat away at that. Um, by no one else's fault. I mean, they don't even know about it. I'm the one that's eating away at it because it's like, well, I could always just do that a different time. And those are the balls that end up getting dropped, I find, is my own work, because that's the thing that I am willing to sacrifice because it doesn't impact anyone else.

Whereas things that impact other people, I'm much less likely to to drop?

[51:27] Paul: Yeah, I think I'm— so my entire, like, approach has been only find stuff that I'm going to do without needing to overcome friction. So the writing will happen. Like, the writing, I love it. It's so much fun. It just happens, right? So I don't even think about scheduling that in the day.

I just make sure I kind of keep open space, and I know it happen. Meeting people is also the same thing. And then like running my like online course and coaching and consulting business, that stuff does require effort, right? But like my ambitions are not to maximize success. I'm probably targeting like 40% of what I'm capable of, and that's where the tension of like dropping the ball comes from. But I know in the long run, I'll feel better if I'm doing the things that continue to bring me alive.

[52:29] Paul Canetti: Yeah. Yeah. I mean, there, there is this— there's a chase that we're all sort of in, chasing whatever that next accomplishment is, and it doesn't really matter what level you're at because there's some other level, you know? Um, and, and I think, you know, I don't know how into like mindfulness and, and that kind of stuff you are, but as over the years, as I got deeper into that, it was very hard to square that with ambition, for instance. Um, And I think what you just said, something as explicit as, "I'm going for 40%," right? And just sort of calling your shot as opposed to, "I'm calling my shot, which is infinite." Like, I'm trying to be infinitely successful, the asymmetric upside, whatever, however people talk about it, because you'll never catch that.

I mean, by definition, you can't catch it, you know.

[53:41] Paul: I'm not wired for it either. Some people actually are wired for it.

[53:46] Paul Canetti: I think a lot of people aren't intentional one way or the other, and you're in that job and you're up for that promotion, or you're— whatever that next natural step is, you just sort of march towards it because that's what you're supposed to do. Like, for instance, right now Everyone I talk to is like, "So when are you starting your next company? What's your next startup going to be?" As if that's just a given. And it might be. It's hard for me not to think in those terms too, but I don't like that sort of fatalist view where there's just sort of one place that you're marching to. And I think that life has the potential to be much more interesting than that.

And so even thinking about your own experience, like a couple of years from now, let's say some amazing opportunity presents itself, feels great, and it's like a full-time job in an office. I don't know. I would imagine that if you're not dogmatic about anything, then it really is about just sort of going where life takes you. And not having it all sort of mapped out. And then you're constantly being disappointed because it's not lining up with that exact expectation, that exact plan.

[55:05] Paul: I think this would be an interesting place to pause. And I say pause. I think it would be interesting to reconnect and have another similar conversation in like 6 months.

[55:16] Paul Canetti: Yeah, that would be—