#145 Capitalist by Day, Spiritual by Night - Alex Hardy on achievement, Wall Street, tech startups, exiting his company, pride & suffering, his sabbatical, suppressing his curiosity and rediscovering his passions

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today, I am really excited to be talking with my good friend Alex Hardy. I am going to explore his journey from prestige-chasing overachiever like myself to wandering underemployed vagabond. Alex has not shared a ton of his story, but I think he's super interesting because he's one of the people that I think does a better job than many people of making friends through the internet despite not sharing a ton of content. And I think there's really interesting things to explore there.

You've also explored Buddhism. You've just taken a sabbatical. You've had an exit from a startup. So many things to explore. Welcome to The Pathless Path, Alex. Thank you, Paul.

[02:01] Alex Hardy: I mean, that's the best hype man job I think anyone's ever done for me. So thank you.

[02:06] Paul: Question I start with on all my podcasts is what are the stories and scripts you grew up with as a kid that told you as an adult, these are the things I'm supposed to do to be a good person in the world?

[02:23] Alex Hardy: The one that comes to mind is anything worthwhile requires suffering. That was one that was really, really engraved in just the culture that I grew up in. I went to a very competitive high school. Even the middle school was competitive. Everyone was trying to get into the most prestigious college, maximize the number of extracurricular activities, get the best grades. And that was really drilled into me, kind of like hard work and striving and achievement from a very, very young age.

And that kind of achievement was put on a pedestal and the kind of buy-in price that you paid for that was to outwork other people and to tolerate a lot of unpleasant times in order to achieve that.

[03:23] Paul: It seems like you internalized that though pretty young. I mean, talking with you, it wasn't as much your parents kind of forcing that onto you.

[03:32] Alex Hardy: Yeah. Yeah. Uh, my parents, thank you in advance for that mea culpa. Um, yes, it was definitely not my parents. It was really almost like the water that, um, that we were swimming in, honestly, in, in my hometown and just in that, um, yeah, in, in that space, it was really like, uh, memetic almost that everyone else, all the other kids were kind of doing it. And so you couldn't help but just get wrapped up in it.

And it carried through to college as well with prestigious jobs there. And graduate school. And it was really, I kind of very much fell into these, into wanting to play and win these games that I was basically, you know, flung into.

[04:16] Paul: What was the goal? Like when you're in middle school feeling these things, did you have a sense of what people were aiming at or why anyone was so caught up in the doing?

[04:26] Alex Hardy: You know, it was, we never really, and I never really stopped to ask the question like why or what for. It was really only like, You know, you would get some type of, um, you would get lauded in some way or kind of like shone upon in some way if you got such and such a GPA or got this many extracurricular activities or got into an Ivy League school or things like that. It was this thing that kind of everyone was talking about all the time. And that was always the ultimate goal. It was like a very finite game, if you will, but, um, it was always very clear along the way, like, oh, if you're, you know, a worthy person, you'll end up doing this. And so you kind of wanted to go after that at any cost.

[05:14] Paul: Did you have role models?

[05:15] Alex Hardy: Hmm. I think that there were like, I guess, kids, you know, that were able to— kids in years ahead of me that were able to like, you know, balance, you know, doing athletics but also achieving a lot academically. I think those were kind of the people I looked up to. My sister was able to do that. She was, you know, captain of like the soccer team, but also went to Berkeley and was like very studious and kind of the like jock, the jock nerd hybrid, I would say, was kind of like the, the, um, the aspirational model.

[05:52] Paul: But you were pretty good at this game too.

[05:56] Alex Hardy: I, I was a little too good, you might say.

[05:58] Paul: What do you mean? Why? What does too good mean?

[06:01] Alex Hardy: Um, I think that, that I was able to win a lot of, to win these games, and I was able to be like singularly, maniacally focused, ruthlessly focused almost on, um, winning. Like if you put an objective in front of me, I will basically stop at nothing to achieve it. It's just kind of how my brain is wired. And I did everything in my power to win these games. And along the way, I would kind of, once I reached the top or achieved it, I would kind of wonder why I even had done it to begin with, like question whether the cost of admission was, was worth like this ultimate, this goal.

[06:49] Paul: So you, you would question winning after winning even younger?

[06:54] Alex Hardy: Mm. I think that I regularly got a taste that success wasn't really as sweet as I had, I had thought it was going to be. Yeah. Even, even in middle school, high school.

[07:13] Paul: Is there a scenario that stands out?

[07:18] Alex Hardy: Um, you know, I don't know. I mean, one that jumps to mind was like when I got into, when I got into college, I went to Duke and I worked, obviously worked very, very hard to get the grades and all the credentials and stuff. And I just remember like getting accepted, early admission, felt really great for like 2 days. And then it like, and then it kind of faded. And that was maybe the first like real taste where I was like, huh, this is, this, this thing that I had really, really put a lot of time, sweat, tears, etc., into. And it felt good.

And other people were like congratulating me. On it and there was some status associated with it. But the feeling, that feeling wearing off was definitely something that, that stuck with me.

[08:10] Paul: It's not really something you can talk about in open too, right? If you say, is it really worth like this chase? People will be like, what are you talking about? You got into Duke.

[08:21] Alex Hardy: Yeah.

[08:21] Paul: Right.

[08:22] Alex Hardy: Yeah. It's, yeah, you almost, it's tough to, I mean, I am worried that I would come across as ungrateful or something if I, if I, if I dared to question it.

[08:31] Paul: Yeah, my— I run into this a lot when I talk with like my mother and I'll say, I just feel like that wasn't worth it, right? How can you say that? You have all these experiences, you did all these things, all of that is leading to this. And it's like, we're so conditioned to— like, even people who are saying, I went there, I achieved the success and it's not worth it, people will not trust that, or they'll like push it down And they'll still just go after it despite people saying that.

[09:03] Alex Hardy: Yeah. I mean, in my defense, I suppose, or in defense of that, all along the way I had people that told me, you know, there is no— you'll never arrive. You'll never be a certain dollar in your bank account or career achievement or anything that will be ultimately fulfilling. And yet, as I think back, even if I could have told my younger self that, yeah, I probably wouldn't have believed that. I would have said, you know, you need to go. Like, I am a person that learned, for better or for worse, I learned through direct experience.

And I need to really, like, do the thing myself to have trust, to evaluate whether it's worth it or not.

[09:47] Paul: Who is telling you it's like, it's about the journey, not arriving?

[09:53] Alex Hardy: I think that I don't know that a specific person comes to mind, but there was definitely— I don't know, there was just this like kind of wisdom, you know, in the air of older people that I had kind of looked up to. Some people even that had like left, you know, either left finance or left the law or left. It was usually coming from someone who had had like some career experience and then kind of wisened up. That was, that was kind of like you know, looking upon me and sharing that wisdom.

[10:26] Paul: I ask because I feel like I didn't have those people. Yeah. Like everyone around me was like, just nobody wanted to hear questioning. I remember being in my, one of my first internships and being like, what is everyone doing? You should be grateful you have an internship. This is the goal.

Like the goal is to make a lot of money, right? When was the first time you became just absorbed with achieving one of these goals? Do you remember it took you over? This was kind of what happened with me with strategy consulting. I'm wondering if a similar thing happened with you with Wall Street.

[11:06] Alex Hardy: Yeah, a couple of times come to mind for when I first got absorbed. First one was definitely law school. Law school is really a fascinating game because—

[11:18] Paul: It's like the ultimate game to break into.

[11:21] Alex Hardy: It is. It's one of the older ones that we have in our society. You know, it's hundreds of years old, this model, or at least over 100. Basically, the way that law school works is that there are a fixed number of prestigious law jobs for any given year of students, like only the top 10% or something get them. And the only thing that determines whether you get one of these jobs is your grades, your GPA, that's it. And the only thing that determines your GPA for a class is a single exam.

One exam for every, you know, you take 8 classes your first year. So 8 exams basically determine like, or at least what you're told, determine your entire trajectory of your career. And so I—

[12:09] Paul: it's, it's even crazier than that. Yeah, right. Because to get into law school, it's basically just two scores, your GPA and LSAT score, right? And then you just— people just sort down the rankings. Yeah, right.

[12:22] Alex Hardy: Yeah, yeah. But once you're, once you're there, so GPA and LSAT, that's kind of accumulated over the course of years of school, and you can take the LSAT multiple times. This is like this is 8 exams, 8 hours determine like your, determine your entire career trajectory.

[12:42] Paul: Crazy.

[12:42] Alex Hardy: And I went to, I mean, I went to Vanderbilt, which is relatively not like non-competitive by law school standards, non-cutthroat. And even then it was still very much people, you know, people were in the library super late and treated it like a, like a job or more than a job. And that was for the first time I remember it kind of, it kind of felt that you were competing in an Olympic sport or something. That was your, that was your job was to be the best at it. And I have, I was very good at it. And, um, there was, it was competitive, but it was also, there was a bit of a thrill because you were good at it.

That feedback loop of validating you. And if you're, you know, you're tying up your identity and your status in something and it's reinforcing it because it is, you're getting positive validation from it. And so it was, you know, kind of intoxicating, um, in a way.

[13:42] Paul: Yeah. What, what does that feel like? The intoxication?

[13:46] Alex Hardy: It's really, it was really thrilling. It was really, you, you feel like you have a purpose. It almost, it feels like you're having a purpose, like you are you have pride, you feel like you matter, you're worthy, you are, you know, you rightfully have a place at the table or rightfully can point to a credential and feel like you, like you belong and have some status in society almost.

[14:15] Paul: I love that you use thrilling. That's literally the same word I used to describe what it felt like when I landed at McKinsey. It's kind of like you're, you're chosen, right?

[14:25] Alex Hardy: Yeah.

[14:25] Paul: Um, and I really did like working there as well, but there was this sense of like, oh, I'm headed somewhere, right? I'm, I'm on my way. I've made it into the inner ring. Yes. Right. And it's like, once you like understand these secrets, there's like— but it never lasts, right?

[14:46] Alex Hardy: It never lasts. It never lasts. No, there's always— yeah, there's always some even more inner ring that you are trying to get to be a part of.

[14:53] Paul: Yeah. At McKinsey, I was sort— I got so confused there because I really liked working there and I loved my work, but everyone was leaving all the time to go to business schools, law schools, fancier NGOs to level up on social impact and things like that. And it's like, well, like, what am I doing? I can't just stay. Yeah, right. I think that's like the only regret of my career is like I should just stay there a couple more years and then just went on my own.

But you learn the hard way. Yeah.

[15:25] Alex Hardy: There was also, there was also kind of a thing, at least in Wall Street, where there was this perception that only the mediocre people actually stayed and that anyone that was smart enough, you know, cunning enough, driven enough would get in and get out and move on to greener pastures that had a better work-life balance or that was somehow more desirable game to play doing private equity or, you know, moving on in kind of the ways that you were talking about?

[15:52] Paul: Yeah, it's like you're a sucker, right? It's a— you're a sucker if you're not continually moving, right? I think this is one of the things about the modern career world is like there's more opportunities than ever. And in the educated world of knowledge work, people are making more than ever. But there's no home.

[16:13] Alex Hardy: You—

[16:13] Paul: it's so hard to find a place and you always need to keep moving, right? Yeah. So let's go back to you. You're in law school and you decide to expand your options and enroll in business school as well.

[16:27] Alex Hardy: Yes. Yeah, yeah. I went to law school during the Great Recession because I couldn't get an actual job when I was a senior in college and I had no idea what a lawyer did. My dad did it. It seemed interesting. It seemed a safe route.

And so I went and very quickly—

[16:46] Paul: It's the most prestigious way to, to, to like not know what you're doing.

[16:51] Alex Hardy: Exactly. Yes, that's exactly right. That's exactly right. It's a very prestigious— it's a very prestigious and expensive insurance policy, basically, to being unemployed. So I got to law school and I very quickly learned what lawyers do. And I was like, oh boy, I do not want— I don't think I could really do this.

And so yeah, I took the GMAT. I've always had a bit of like a math brain, played a lot of poker and have— and gaming and stuff. And so I did pretty well on the GMAT. And so yes, I got into the business school program. I also love a good deal. And if you do the JD and the MBA, you can do it in 4 years, whereas it would take 5 if you did it separately.

So, and at that point I was all about maximizing optionality. And so that was the ultimate optionality.

[17:41] Paul: Were you, what were you curious about while you were in school?

[17:46] Alex Hardy: Um, I think I suppressed a lot of my curiosities at the, uh, because they were really impractical, impractical. They weren't employable. Like, like my favorite class at law school Um, my two favorite ones and ones that I did the best in were criminal law and constitutional law. And there's just no— and I was fascinated by theories of justice and the background of the Constitution. And none of that stuff really means much or has any value in the employment market of being a— you can't be a high-paying white-shoe corporate lawyer, like, you know, arguing about the merits of the Constitution or the merits of, criminal justice reform or anything like that. So yeah, I was, I was really, um, I had some curiosities and I think they were just very much suppressed because they weren't really practical in from like earning an income out of.

[18:44] Paul: Yeah, I find this so often and we'll get to you taking the sabbatical. I think that's so interesting too, because having met you, I think I met you last January or February. You're one of the most curious people I know.

[18:59] Alex Hardy: Thank you. Thank you.

[19:01] Paul: Does it shock you looking back that you kind of let go of that creative, curious spark?

[19:08] Alex Hardy: In some ways, yes. I think in some ways a lot of my creativity was channeled towards fulfilling my resume. So I played saxophone and played musical instrument growing up, but it was often in order to have a good resume item to point at, to be in the jazz band or to be in the orchestra or things like that. And so some of the joy of that particular piece of creativity was really kind of sucked out of it. And I actually didn't— I totally stopped and developed an aversion towards really music and playing instruments until very, very recently. I've rediscovered it.

Or similarly with language and speaking Spanish. I loved, loved, loved, and still do love speaking Spanish. And I just, um, really doubled and tripled down on it for reasons of, um, having it be a really important resume item. I minored in Spanish and it became like an academic and, uh, resume building pursuit. And I like stopped speaking Spanish for like 10 or 12 years until Very recently again. And yeah, I've never thought of that, but I think that, um, the creativity, I was often channeling it towards how, you know, I was using it very, um, kind of like strategically and not just being creative to be creative.

That didn't compute for me. That was just wasting time. Why would I do that? And so I think that took some of the joy out of, out of maybe the more creative pursuits that I, that I enjoyed.

[20:46] Paul: Yeah, I imagine you also became interested in just the business world in general. I think sometimes the business world gets a bad rap. It can actually be pretty interesting.

[20:56] Alex Hardy: Yeah.

[20:56] Paul: To learn about how businesses are run. Like, I remember being genuinely interested and I still get joy out of it now. I just get to spend like 20% of my time, like tinkering on the business side of all the things I'm doing.

[21:09] Alex Hardy: Yes.

[21:09] Paul: I don't want to do that with 100% of my time anymore. Yeah.

[21:12] Alex Hardy: Yeah, yeah, I definitely found it extremely interesting, and especially in tech and startups, um, I really found a lot of the writing there extremely, um, yeah, like extremely profound, and, and you can see that, um, how some of these, like, you know, leaders and, uh, these thought leaders and, and kind of startup and tech icons, how they were able to change the world, whether it's, you know, Bezos and his letters or Marc Andreessen, Paul Graham, all of these people that we have a very rich history of their quarter by quarter or month by month thought process. It was, it was really interesting to kind of see, to see how they think and to see the, the impact of them on, on the business world and all of the problems that they were able to solve.

[22:08] Paul: Was there a portal into that world, a specific writer or author or any specific topic?

[22:16] Alex Hardy: I think when I was trying to play the finance game, I went really, really deep on Buffett value investing, Benjamin Graham, Nassim Taleb, and Seth Klarman, like all of these hedge fund guys that would write their quarterly and annual letters. Um, and then as I got into tech, there's kind of the tech canon of blogs that you're supposed to read that I think were actually really valuable of how to build a company. Paul Graham, Sam Altman, Mark Andreessen, Keith Rabois, um, the, the, the tech, you know, the typical leaders who have kind of had laid out a blueprint of this is how you successfully build a company that can leverage software in the modern era.

[23:02] Paul: Yeah. So how did you end up in Wall Street?

[23:06] Alex Hardy: Basically, I, so I did first year of law school, worked for a judge, did first year of B-school, worked in real estate. And then the third summer that I had was kind of make or break. It was going to be either that third summer determines where you work. And I was thinking about doing law, but I will never forget this. A guy in my gym, in my building in grad school was a— I was friendly with him. We were, you know, drinking buddies.

And he, he had just completed his investment banking internship and he was just raving about it, about how much he learned and how exciting and high-powered it was. And I kind of started drinking his Kool-Aid. I like attended a meeting of the Investment Banking Club, which is so cringe to even say, but I went to that and yeah, again, it was kind of like intoxicating when everyone in that room or in that environment is achieving for something you mimetically want to get it because it is highly coveted by everyone else. And so I knew, I knew very little about finance.

I never really worked in finance and I'd taken a couple of finance classes, but I became an expert on corporate valuation and discounted cash flows and took Excel modeling classes on the weekends and was trying to go from someone with zero work or life experience really at that point to a desirable candidate for, for a Wall Street bank. And somehow I got there.

[24:45] Paul: It's funny how powerful they can be in these environments, especially business school. I'm sure you had this happen where people would just suddenly show up and I think I'm going to interview for consulting. And everyone knows, including that person, that they shouldn't do it.

[25:02] Alex Hardy: Yes.

[25:03] Paul: Right. And then 10 months later, you hear from that friend, I quit.

[25:07] Alex Hardy: Like, I had to leave.

[25:09] Paul: It was so funny. Like, a year after business school, I'd say 50% of my friends had changed jobs.

[25:15] Alex Hardy: Wow.

[25:16] Paul: Because people put so much emphasis on what they thought they should be doing or what they thought they wanted, and then they go— are actually in the labor force. And they're like, oh, I need to actually find things I want to do.

[25:27] Alex Hardy: Yeah, there is almost this like masochistic element to it of who can endure the most suffering, specifically for investment banking. You know, in that world, a lot of the—

[25:38] Paul: I think banking is much, much more hardcore than consulting recruiting.

[25:42] Alex Hardy: They prided themselves and it was a point of pride. They would, you know, often compare themselves to like parts of the military of like we are able to endure the most suffering, the most bad stuff. It's going to be, you know, hell on earth. Worth for, you know, some amount of time, but it's going to be your, you know, golden ticket for the rest of your life from status and a financial perspective. And that was how it was framed. And that was— and just like in, you know, the Navy SEALs, 98% of the people end up dropping out.

There was a similar kind of attrition along the way of getting into banking. But if you stayed and got through it, it was, it was viewed as like a point of, point of pride.

[26:21] Paul: Yeah. And how How long did the glow last when you got accepted?

[26:27] Alex Hardy: Um, that is a good question. So I got, I actually, my summer internship, I got a job at Goldman Sachs, which was like the crème de la crème, still is the crème de la crème. And that glow lasted for some time, even into the internship. And then this, this was typical of Goldman, not, not really any of the other banks, but I actually didn't get an offer to return. And that absolutely just shattered my world. I was, I was like devastated.

I was like, wow, I didn't get an offer to go back. My life is over. I'm not going to be able, you know, I'm, I'm like a failure, all of these things. That was really the first time that I had put my all into trying to win a game. And and I failed. You know, that was really my first taste of like achievement, of a failure to achieve a goal.

And it was really, really rough.

[27:26] Paul: What did you want to do in that moment?

[27:31] Alex Hardy: Crawl under a rock. Yeah, I just wanted to, I mean, I was angry. I went back and thought about every, like, every micro decision I made throughout the entire summer, all the miniature mess-ups I had, and second-guessed each one and was like, if I had only worked a little bit harder at this one or that one, would it have changed the outcome? And it really made me like double down on perfectionism and intolerance for any type of mistake. And I think it made me a better, a better worker in some ways. But, um, it, uh, I would say what it made me do, I mean, it kind of made me want to prove them wrong, honestly, and show them that they had made a mistake.

And it put, it put, I had somewhat of a chip on my shoulder, but it put an even bigger one once I was past the kind of initial, like, mourning and shock of not getting the job. I didn't even consider that to be an option.

[28:33] Paul: It's funny, I had a similar experience which was incredibly embarrassing in business school. So I worked for McKinsey before business school. Yeah. And I think I realized what was happening now is that I was just not— my heart was not in the path, right? And I was competing against all these business school people that were gung-ho. I was competing against the Alex Hardys.

[28:53] Alex Hardy: Yeah.

[28:54] Paul: After the Goldman rejection.

[28:55] Alex Hardy: Good luck.

[28:57] Paul: And I actually did not get an offer. To go back to McKinsey. Like, I interviewed— I thought I wasn't going to work there, so I interviewed on campus, got rejected. I remember where I was, and I just felt like a loser. Um, and all the other firms rejected me because they're like, what's wrong with this kid? Yeah, he worked at McKinsey, why would he apply at our firm?

Yes, right. So, um, from that moment, I remember like, I need to take myself seriously. As a person and like, stop bullshitting, like start actually communicating what I care about. And I think a lot of things opened up for me from there. But I remember that it was, it was terrible.

[29:39] Alex Hardy: Yeah.

[29:40] Paul: But it was like the first, first like poke in that like identity of like the worker.

[29:45] Alex Hardy: Yes.

[29:46] Paul: But it took me like 5 more years to actually like think a little deeper about it. Me too. Me too.

[29:51] Alex Hardy: I mean, the other tough part about it was that like that whole— I had, you know, getting a job at Goldman is, is really for Western capitalists. That's kind of like the top of the heap for investment banking. And so I had, of course, told everyone and broadcast it and was like so proud of it and flaunting it. And I had just like this massive tail between my legs moment where, you know, when anyone asked me about the summer or what I was going to do next, which of course is the question that you always have with everyone. Yeah, it was, it was, that was really, really tough. Yeah.

[30:26] Paul: So you end up going and getting another job in banking.

[30:30] Alex Hardy: Yeah.

[30:32] Paul: And how long did you spend in banking after school?

[30:35] Alex Hardy: So I went to Credit Suisse right after school. I got a job there and I was there for almost 2 years. I was there for, yeah, I think 20 months or something like that. Just through the, through the first bonus site.

[30:49] Paul: What's your favorite Excel formula?

[30:51] Alex Hardy: Uh, I think we had, uh, some kind of index, an INDEXMATCH one that was pretty good. That was better than VLOOKUP.

[30:59] Paul: That's how you know you're hardcore. Yeah. If you know how to do that just like off your head.

[31:03] Alex Hardy: Yeah. We, we weren't, we weren't allowed to use like mouses. That was like a, that was like you, you were like laughed at if you used a mouse.

[31:10] Paul: Nice. Yeah. And so you, you stayed there 2 years. Um, when did you catch the tech startup bug?

[31:16] Alex Hardy: Um, So I, I, I mean, I caught the bug primarily because, well, one, I was just so miserable. I was desperate for anything else. But I remember I actually read a blog post that Packy McCormick put up.

[31:32] Paul: No way. Yeah. Shout out Packy.

[31:34] Alex Hardy: Shout out Packy.

[31:35] Paul: Yeah.

[31:36] Alex Hardy: Fellow Philly guy, fellow Duke guy.

[31:38] Paul: He was very—

[31:38] Alex Hardy: has been very inspiring to me. I was at my desk at like midnight on a Wednesday, hating life and super depressed. And I was going to be there for another few hours. And I somehow stumbled upon his post that he wrote about how he got his job at Breather after, like he wrote, he basically blogged his whole journey. This was, I don't know, 2014 or something. This is a long time ago.

Um, before he was on Twitter, literally before he was on Twitter, before he was writing online, I don't even know how or why he published this, but, um, I was like, wow, he seems like he has found something so much more fulfilling and he was coming from a finance background. And so I was like, okay, I think that there, there might be something here. And that was really like the initial thread that I kept pulling.

[32:24] Paul: Awesome. What kept emerging?

[32:26] Alex Hardy: So I at first started trying to interview, so I was very nervous and my parents basically refused to allow me to quit Wall Street without another job lined up, or they strongly discouraged me from doing it. So I, was kind of, you know, desperately interviewing in every spare moment that I had. I interviewed at a whole bunch of different companies. I got— I was interviewing at, at a— at that point, a small crypto company that I ultimately didn't get the offer for. But that was like Coinbase in 2015.

[33:05] Paul: It was Coinbase.

[33:06] Alex Hardy: It was Coinbase.

[33:07] Paul: Yeah.

[33:08] Alex Hardy: I totally bombed the interview, even though I had— even though I took like several days of vacation to prepare for it and flew out to San Francisco. And I just didn't understand Bitcoin at the time, which is ironic given my current interest in it. But, but yeah, that was— I went— I was basically going full bore on trying to interview at any software company that would have me. I, I ultimately ended up getting an offer from a very small company that was paying me very little even at that point. Like, they were willing to start me on a, on a trial for like 3 months at, I don't know, $50K a year annualized or something. And that was— I had an offer.

I didn't really— it wasn't really excited about it. But for me, that was good enough to quit banking. I was like, okay, if I can get— if I can trick these people to hire me, you know, with, with little tech bona fides whatsoever, I— my only qualifications to work in tech tech where I was a millennial that knew how to use a smartphone. I had no idea what any, anything about software, but it just, I felt like I could, you know, I self-taught myself corporate valuation and investment banking. I figured I could do the same for, for tech.

[34:20] Paul: Did you tell, uh, your parents?

[34:22] Alex Hardy: I told them. I did tell them. I think I communicated. I think I was, um, I made it seem like it was more likely that I would take this, this mediocre tech job than was, was reality. Like I told them, I was like, yeah, I'm noodling over it. It seems really cool, really compelling opportunity.

I feel good enough that I can quit Wall Street. And so they kind of like, were like, okay, whatever. Um, that gave me the COVID I would say, that I needed for that.

[34:51] Paul: And what'd you tell your coworkers when you decided to leave?

[34:54] Alex Hardy: Oh, I told them that I had found like the job of a lifetime and this incredibly compelling tech opportunity that I couldn't say no to.

[35:00] Paul: Why?

[35:02] Alex Hardy: Uh, I was extremely embarrassed at, to pos— to not have a coherent narrative as to why I was leaving, like leaving this high-paying, high-status, um, job that was clearly giving them a lot of meaning. I mean, all my older coworkers who I kind of looked up to were, you know, had been there, had been in the industry for 5 or 10 years. and so I just, the thought of trying to like explain my dissatisfaction with it and go against the grain and rock the boat seemed totally, uh, impossible.

[35:36] Paul: Yeah. Because successful people are always moving to something better and better and higher paying, right?

[35:42] Alex Hardy: Up and to the right. That's the trajectory.

[35:45] Paul: Um, which is really interesting because a lot of these tech jobs were not the best paying in the mid and early 2010s, right?

[35:54] Alex Hardy: Yeah.

[35:55] Paul: We didn't really see the flood of people flocking to tech until the late 2010s when the salaries started spiking like crazy.

[36:02] Alex Hardy: Yes.

[36:03] Paul: It was still not an obvious thing around 2015 to move into tech.

[36:09] Alex Hardy: Yeah. Yeah. I mean, when I was in B-school, I was in B-school in— yeah, I graduated in 2013. Nobody in my class worked at Google or Facebook. I mean, there were some people that went to Amazon, but those people were like from Seattle or something. And so it was very— the by far the high prestigious opportunities were consulting and banking.

[36:30] Paul: Yeah, it was the same for us in 2012. I think we had some friends that went to— we had some people that went to work for Zynga. We had some like random tech employees that had made some money and were just going to business school to hang out.

[36:43] Alex Hardy: Yeah.

[36:44] Paul: Nobody was like trying to break into tech.

[36:47] Alex Hardy: Yeah, I mean, it was really early in the tech days. I remember when I was in B-school, I think that was during the Facebook IPO. So they were—

[36:54] Paul: 2013.

[36:55] Alex Hardy: Yeah. And that was before they figured out their mobile strategy and the IPO was a complete disaster and they like the pricing got all screwed up and that was like a huge thing and a huge— it was like emblematic that tech as a whole, I would say, was, was pretty immature and was not, you know, didn't have its kind of rightful place at like the prestigious capitalist table.

[37:13] Paul: I remember buying Facebook, but I didn't really have any money, so I'm not like rich from it now. But I was like, I'm holding this. I still have it.

[37:23] Alex Hardy: Oh, nice.

[37:24] Paul: But I remember looking around and seeing everyone addicted to Facebook. I was like, I feel like this is something there. And then like studying Warren Buffett, he's like, well, everyone's addicted to Coke, so you should just buy this. And I was trying to apply the same principle.

[37:37] Alex Hardy: Not a bad—

[37:38] Paul: worked out. I just didn't have more than like $2,000 to put into it.

[37:42] Alex Hardy: Compounding.

[37:44] Paul: So talk to me about the next step. You decide you want to shift into tech. I think you got involved with an incubator type thing.

[37:53] Alex Hardy: Yes. So this was— so I was out of Wall Street, seeing my bank account go in one direction, which was down.

[38:02] Paul: In New York.

[38:03] Alex Hardy: In New York. Not a cheap place to live.

[38:05] Paul: Yeah, I made the same stupid mistake, quitting my job without a plan in New York. I'm like, what am I doing?

[38:11] Alex Hardy: So I, so I went into hyper, hyper networking mode. I made a massive spreadsheet as, as a recovering investment banker does. And I basically set up, I think the exact number was like 112 coffee chats over the course of 2 months.

[38:29] Paul: You did, you did all of that? Oh my God. Yeah. And This, so this is like so important. Like, people do not really, people are so afraid to quit their job. But what they don't know is as soon as you step off the paycheck ladder, you will have this like force of nature fill your body to take action.

[38:51] Alex Hardy: Yes.

[38:51] Paul: Right? Did that surprise you?

[38:53] Alex Hardy: It's what I imagine parents feel. I'm not a parent, but I imagine parents feel like this when they're protecting their children or something. It was like this primal instinct of like, okay, I now am responsible for myself, I need to like make sure that the bread is won.

[39:06] Paul: It's less urgent because they mostly just sleep all day. I have a 6-week-old, so you would— but yeah.

[39:15] Alex Hardy: Yeah. So I, so I did, I did, you know, made that massive spreadsheet. What was drinking so much coffee every day because I was going to, you know, 4 coffees a day, picking people's brains.

[39:27] Paul: You would get a coffee at each of these I mean, I would switch to decaf in the afternoon, but yeah, I was reasonable.

[39:33] Alex Hardy: Yeah, yeah. I wanted to fit in. And yeah, I kind of— I had no real idea what I was doing. These— the agenda was pretty, was pretty ambiguous. It was basically like, hey, can you help me? Or do you know anyone that can help me?

I'm kind of desperate looking for a job in tech. I don't really know what that means, but maybe you can help. So I learned about— I, for some reason, was focused on business development, which kind of doesn't even really mean anything. It means a million different things depending on who you ask. Ask, but I had this notion in my head that, yeah, I was a finance guy, I should do business development. That sounds cool and official.

[40:07] Paul: It does sound cool. I still have no idea what business development means.

[40:11] Alex Hardy: Yeah, I mean, yeah, I couldn't really tell you. It can mean partnerships, it can mean reselling, it can mean, you know, acquisitions. It can mean a million different things. So I did— I was kind of, you know, pounding the pavement for that. And people, I think, had sympathy on me and I'm likable enough. So they would like the way that you would— I remember this so vividly.

You're like bringing up some PTSD. The way that you would know if it was a successful meeting was if the person offered to intro you to another person. And so the only goal of the meeting, it wasn't even to get a job, it was to get the next conversation with someone else. And if the trail went dead, that means that you had kind of like messed it up and you wouldn't, uh, you know, you could, you could cross them off your leads list.

[40:54] Paul: So you were in a coffee chat Ponzi scheme.

[40:56] Alex Hardy: Basically, basically a lot, a lot of good coffee. Gregory's Coffee. It was a Great spot in New York.

[41:01] Paul: Gregory's very good.

[41:02] Alex Hardy: Solid, solid cold brew. But yes, so I did— the way that I got involved in the accelerator was with Techstars. I read about them in The Wall Street Journal. I read about that Techstars and Barclays was doing a fintech accelerator in New York, and the woman who ran it, Jenny Fielding— hey, Jenny, if you're listening— she was interviewed in it. And so I Googled her and found her email and asked her for an email or asked her for a meeting, and she didn't respond. And then a couple of weeks later, I was like, or maybe a month later, I was kind of getting pretty desperate.

Funds were running low. I'd been unemployed for 4 or 5 months at this point. And so followed up and emailed her and persistence paid off. I ended up ended up meeting with her, with her, you know, the person below her who ran the, ran the program, had one coffee, and the final coffee chat resulted in a job offer. And I started the following Monday with that salary. Yeah.

[42:09] Paul: So you had 4 or 5 months without work. And it's interesting. I think you just took what I would call a non-work sabbatical. But you were unemployed and you had the freedom to do many things. Do you look back at that and you're like, wow, I really should have done X, Y, or Z? Or really just tried to be a little more present in the moment?

[42:28] Alex Hardy: Totally. Yeah. I was not, I was definitely not present at all. I was extremely high strung and filled with angst over and caffeine and caffeine. Yeah. That probably didn't help, but I had, yeah, there was kind of like, you know, the sword of Damocles, that thing of like the king that has a sword hanging over his head by a, by a hair.

That's what it felt like. It felt like I was, you know, really, really, uh, up against it with needing to find something else ASAP or else, you know, catastrophe.

[43:00] Paul: Yeah. So you, so you end up working at Techstars for Techstars for Techstars and through them you end up meeting some people that you eventually found a company with.

[43:11] Alex Hardy: Yes.

[43:11] Paul: And for the most part, this seems like this was a very positive experience for you.

[43:16] Alex Hardy: For sure. Yeah, it was amazing. I mean, I owe my entire, you know, break into the tech world to, to Techstars. And Jenny has been amazingly an amazing mentor to me. Um, yeah, basically it was a 10-week, like, mutual interview process where Techstars invested in these 10 companies and I was able to kind of float between each of them. They were companies of various sizes and different, all in fintech, but various, you know, had various different needs.

And I did a little bit of consulting work for each of them. I mean, it wasn't particular. I wasn't an expert really in anything. I was kind of helping with just some menial stuff, but I got to— you get a vibe for someone when you're sitting in the same coworking space with them for 2 and a half months. And basically these two other guys, um, Andy and Pete, who later hired me and became my co-founders, um, I just loved their, um, their personalities and their integrity first and foremost. And secondly, the, the product that they had been hacking on was getting incredible reception by VCs and by, um, and by customers.

And I, I sat in on all of the investor and all of the customer meetings for all the companies, and they were getting, from what I could see and sitting in 100 meetings or something, um, definitely the most traction. And I was like, okay, these guys are, seem to be onto something. So it seemed like a good risk-adjusted bet to, uh, to jump in with them.

[44:52] Paul: Yeah. Was your goal at the time like, I want to find my lottery ticket?

[44:57] Alex Hardy: Yeah, I definitely went into the program with a, with a goal at the end to have, assuming that there was a company there that checked enough boxes that I wanted to end up working for one. I mean, that end of the program would have been, you know, month 7 of unemployment, basically. So yeah, that I was getting more and more desperate, I would say, as it kind of went along.

[45:21] Paul: Yeah. So you enter Techstars, you start working for this company, you eventually become a co-founder. Talk to me about the transformation from finance bro to tech bro.

[45:32] Alex Hardy: I feel like I'm a little bit of, of kind of the, um, like capitalist Forrest Gump in a sense. You know, I went to law school in the year 2008, had the highest law school applications in the history of law school that year that I applied. Did the law school thing, was doing Wall Street when that was super popular and the thing to do. And then I rode the tech zeitgeist, you know, at that point. And I think in New York at that point, the prestige and status around tech was really becoming a thing. Like New York was first, was becoming kind of putting its mark on the map as a tech hub.

This was— there was a lot of Twitter beef between New York and San Francisco at that point of, you know, could a billion— could billion-dollar companies be founded out of New York and New York New York was kind of having its moment of success stories. And, you know, this was when Fred Wilson and Union Square Ventures was getting really big. They had made a lot of really big and successful investments, and New York was kind of flexing its, its muscles as like a media and fintech hub, if you will. And so I feel like I just kind of embodied that and was drinking the New York Kool-Aid. It's the best city in the world. I'm a New Yorker.

I'm so important. And you have this additional status badge of working in tech on the cutting edge and frontier of this life-changing technology. Yeah.

[46:57] Paul: And now are you feeling pulled to start an AI company?

[47:02] Alex Hardy: Not on Twitter. I did tweet for the first time in like 5 months today, but generally not on Twitter. So I don't even know what ChatGPT is.

[47:10] Paul: Oh, you got to try it. Actually, don't try it. You might get sucked in.

[47:14] Alex Hardy: I know. I know. I've entered, I think, 4 queries total ever in ChatGPT. So I've managed to stay, stay away.

[47:23] Paul: So you're somebody that is very, I think, curious, and you collect a diverse set of viewpoints, writing. You're always sending me interesting things. Talk to me about how that was shaping your ideas. You got sucked into the ideas of like like Marc Andreessen and all these people, um, Paul Graham. Um, funny thing, I, I was always reading these, but I never thought to myself I should work in tech. I was so just an oblivious Northeastern person.

[47:54] Alex Hardy: Yeah.

[47:55] Paul: Um, but yeah, talk to me about like your information diet and how like the drive to like find interesting ideas.

[48:03] Alex Hardy: Yeah, I think Twitter was kind of Twitter was amazing for me, just the density of interesting people, interesting ideas, and the fact that there was kind of always— I mean, you know, it's easy to get addicted to the refresh button. There's always something interesting happening in your feed and always an interesting, um, you know, blog post or book or concept you know, seemingly coming out. And so I think I just, I did develop, um, that was a curiosity that I would say I did follow from kind of cultivating my, uh, Twitter feed well. And just, yeah, the, the information diet was a lot, a lot of tech stuff, a lot of crypto stuff, and it was intellectually interesting to me, but it was also, um, living and working in it felt very aligned. Like, it felt like it was a productive use of my time to also follow the intellectual interest because I was working in tech.

And so reading about tech all the time is kind of, you know, doubly, doubly good and important.

[49:15] Paul: It seems like you do a good job of also just connecting with people through the internet. Maybe you extended those coffee chats, but actually just reach out to people you actually want to meet.

[49:26] Alex Hardy: Yeah. Yeah. My mom is extremely, uh, she's amazingly social. She ran, um, a business all around networking. And so it's, it's literally in my DNA. And for whatever reason, I think authentically connecting with people and networking just came kind of naturally to me.

And I found it pretty easy to, to, um, follow basic social etiquette in circumstances, which maybe is challenging for certain people in the, in the tech world. Um, so yeah, when you have, uh, some intelligence paired with like a modicum of social grace, I guess it can be, uh, can be easier to endear yourself to people. But thank you for that.

[50:12] Paul: Yeah. And who are some of the people you were meeting early on that inspired you?

[50:17] Alex Hardy: Um, I mean, I met David Perel very early on, on, um, tech Twitter. Um, and he and I have become really good friends, roommates. I was just with him before this. Um, Kay Hee, for sure. Rad Reads felt like a very— Kay was a very kindred spirit of mine, and he was, you know, the older, wiser mentor who figured out that Wall Street sucked 10 years before I did. And so I look— I still do look up to him a lot, but I looked up to him a lot then.

Um, Tiago Forte, for sure. Um, Yeah, I think those were some of the big names that come to mind of like early internet people. Taylor Pearson, Chris Sparks. These were people that by and large were like living in New York. Nat, I met Nat pretty early on. Curious, smart, hardworking people that were either in crypto or entrepreneurs or tech, but were kind of not satisfied with, with the default path.

We didn't have that word for it back then, but they were kind of in some way blazing their own trail. And in New York, it's really easy to just meet up with people. And I think a point that you've hit on is that these types of people are craving connection because it feels so lonely. And so I found it pretty easy to like to link up with those types of folks.

[51:32] Paul: Yeah, it's funny. I was in New York 2015 to 2017, but didn't know like the other people were there. I didn't really use Twitter at the time. I was using LinkedIn. Boy. I was actually meeting people on LinkedIn.

LinkedIn was solid. Was it 2015, 2016?

[51:49] Alex Hardy: Okay.

[51:50] Paul: I was meeting more like corporate career types, but yes, there are a number of people that I'm still good friends with that I did meet through LinkedIn. Now, meeting people through LinkedIn is like— I can't remember the last time I met somebody through LinkedIn. But yeah, that— it seems like that early Twitter was such a magical space and I mean, even until maybe the last, like, year or two, it's just become kind of just insane and so much hustle posting.

[52:18] Alex Hardy: But yeah, I've been thinking about that. I think it's part— part of it is that the platform has changed for sure. But I think part of it is that for me, I think I was much more— are you familiar with the, like, explore versus exploit kind of framework? I think I was at that point in my career when I was kind of like aimless, friendless in many ways. I was casting a very wide net at the top. Um, and so I was much more open and, uh, got a lot more value out of kind of saying yes to everything.

Whereas as time has gone on, as my career has gone on, et cetera, I think there's a lot more value in kind of saying no. And there's just not as much of a need to cast that wide of a, of a top of net, like Twitter was great when I felt lonely and like didn't have that many tech friends. Now I have many. And so there's just like a higher cost, I would say, of kind of being that unambiguously open, uh, top of funnel mode.

[53:17] Paul: Friendless is such an interesting word because that's exactly how I felt after I left my job, which seems weird. I had friends, but I didn't feel— I felt like I was on an island. And you're sort of desperate for people that are seeing the world in a new way. Why do you think it's like this when you shift identities? And do you think this is kind of what drives the fear of changing identities?

[53:40] Alex Hardy: Yeah, I mean, I think it's like it in that work is, in just modern society, is the water that we swim in. It's how you define yourself. And when you're on something that's easily legible to your peer group, it is there's no, you know, it speaks for itself. If you tell someone I work at McKinsey or I work on Wall Street, there's a whole set of assumptions, values, status, etc. that is communicated along with it that I think just makes it, um, you feel like you fit in a lot easier. Whereas if you're on one of these less conventional paths where you have to like explain to someone what your no-name startup does or what, or God forbid that you don't have a job and that you're still exploring it.

These things just don't compute a lot of times with those people. And so the conversation can kind of die, you know, when you're— if you meet— if one, you know, if one iBanker meets another iBanker, they can talk to each other for like 8 hours about stuff that would be so boring to any other person. But when you explain like, oh yeah, I'm, you know, in business development at this no-name startup that works on cloud hosting, the conversation just like dies to most normies. And so that can also feel very lonely.

[54:58] Paul: I've said that on the default path, people sort by income and on The Pathless Path they sort by interest. And I think more and more of the world is actually becoming like this. Yeah, I think this is why the internet is so powerful to find the people actually interested. And I think even just a handful of people can change everything. Yeah, because if you're comfortable talking about things you're actually interested in, you feel safe, you feel connected, and you can take chances. Yes.

On things that feel silly. I think moving to Austin has been this for me, even though I've been on a path for like this for years. It's even more helpful to find people that are literally just like physically in the room with me that like don't laugh at what I'm doing.

[55:41] Alex Hardy: Yeah.

[55:41] Paul: Like hosting a podcast. People still laugh at this.

[55:44] Alex Hardy: Wow. Really? Not in Austin.

[55:46] Paul: Not in Austin. No, this is like— we're— because this is where we all come. But, um, I mean, The New York Times publishes a piece like every 6 months that's like, how are so many people still starting podcasts? People should have credentials to do this. And like, most people just think it's weird.

[56:03] Alex Hardy: Yeah.

[56:04] Paul: Um, so it's so powerful to have, um, those people that just don't laugh.

[56:10] Alex Hardy: Yeah, right.

[56:11] Paul: When you're trying something interesting. And I think the tech world has been that for many people, although now it's sort of just becoming the corporate world.

[56:20] Alex Hardy: Yeah.

[56:20] Paul: I saw Google is like limiting the number of staplers people are having, which is like they're just like IBM or GE. Yeah, it's the same thing.

[56:31] Alex Hardy: Yeah. Yeah.

[56:31] Paul: It's another big company putting—

[56:33] Alex Hardy: Yeah. Putting a nice, like, glossier finishing coat of paint on it. But yeah, it's the same thing.

[56:38] Paul: So the goal for you, the mountain you were climbing in tech was the exit. Was that the goal? Yeah, that's—

[56:48] Alex Hardy: yeah, that was, that was the— that's the final chapter of the hero's journey in tech, I would say.

[56:54] Paul: And that's somewhat useful because it's a long journey, right? And you— it seems like you did enjoy it too. Yeah, for sure. So it's kind of a useful goal to aim at. It's not like you arrive there and then it's super quick and then you have to find the next thing. Yes.

[57:11] Alex Hardy: Yeah.

[57:12] Paul: At least if there is an exit of sizable proportions, it might buy you some time to reflect. Yeah. The socially acceptable script.

[57:21] Alex Hardy: Yes.

[57:22] Paul: So, yeah, I mean, talk to me about that. I know it was kind of a rocky road toward the end of 2019 and into the pandemic when you guys were finally approaching that exit.

[57:33] Alex Hardy: Yeah. Yeah. So we had been building for about over 5 years. Um, and we were, the company was in, was in video conferencing, secure video conferencing. And, um, 2020 was a good time to be in the video conferencing business. As I think we all know.

I mean, when we started to give you an idea, we started when the company was started, nobody used Zoom. No, no, no. Corporation use Zoom? Everyone used—

[58:01] Paul: 2015?

[58:02] Alex Hardy: Yeah, they used Webex. And so bad. That was, that was probably it. I'm trying to think. There was some GoToMeeting here or there. I kind of had to memorize that whole landscape at some point, but, um, I've, I've blocked it out.

Um, but yeah, so this was like way before Zoom was a thing, way before, um, big, uh, companies were comfortable with like the cloud. Moving into the cloud was still kind of, you know, taboo. So a lot changed over that time. And 2020 was just the perfect storm, if you will, of, of video, you know, being like going from a nice-to-have to an absolutely must-have. You cannot get business done without a video solution because people were not allowed to meet in person. And so beginning of 2020 was that we started, uh, having, you know, dialogue with DocuSign, who is the company that eventually bought us.

But, um, yeah, there was a very open question of, do we— we ended up getting an acquisition offer from them. And the question was, do we go with DocuSign, which, which has, you know, this specific monetary value certainty, kind of, um, is a good story, obviously. Or do we go it alone, raise some more money, maybe try and grow the business 10x or something, and, you know, aim for more of like a grand slam outcome. And at that point in the world, nobody knew what was going to happen with the, with the pandemic. We didn't know if people— I mean, this was, we're talking like April 2020. We didn't know if anyone was ever going to be allowed to meet in a physical location, like ever again.

That was you know, people were talking about the permanence of this remote thing. Is this the new way of life? So there was a lot of uncertainty there. And yeah, we kind of did our, our best to, uh, make an assessment. We ultimately ended up choosing to sell the company, which I think in hindsight was the right move. But, um, yeah, it was, uh, things that now look obvious in hindsight.

There was a lot of uncertainty and chaos, I would say, um, in our decision making at the time.

[01:00:13] Paul: And how did it feel when you signed?

[01:00:16] Alex Hardy: Um, very anticlimactic. Uh, I mean, it felt good in a sense, in the sense of like going to your bank account when you receive like a nice IRS tax refund or something feels nice. But, um, we were, we were, this was still peak lockdown. So none of us were allowed to meet in person when we signed. I think we signed in sometime in May or June and I was like alone in my apartment when we, when the, like midnight when the lawyers officially signed and there was, you know, in Wall Street, interestingly, uh, anytime a deal closes, you go to like a closing dinner. There's all of this fanfare.

You go out to nightclubs and you spend thousands, you waste thousands of, you know, company dollars on this, um, or the bank's dollars. But with this, it was just me sitting alone in my apartment without having had like human contact in several days because of pandemic lockdown. And, uh, yeah, it felt, it felt, um, a bit like, huh, is this really as good as it gets? This is like supposedly a peak experience, peak moment in my life. And I'm just like sitting here alone feeling the exact same. Nothing has changed.

[01:01:29] Paul: Have you celebrated it?

[01:01:31] Alex Hardy: We did. We did a closing dinner, uh, a year later with all the investors and the execs and everything. Um, and that was, a little weird, but definitely felt like more appropriate.

[01:01:41] Paul: So yes. And you kept working at the company too, right? And this is pretty normal. I mean, not always, but sometimes the companies have the lead people come on to the company and there's a certain earnout period, right? Yeah. So you ended up staying 2 years?

[01:01:58] Alex Hardy: 2 and a half.

[01:01:59] Paul: 2 and a half years. And so I met you about a year into that.

[01:02:04] Alex Hardy: Yeah.

[01:02:05] Paul: And the first time we talked, like, I had been writing about leaving your job and taking breaks. It's very clear to me you were leaving. It was only a question of like how long that would take. I remember talking with my wife Angie and it's like, Alex is going to leave. Like the whole last year was just like, well, when is he going to leave? He says he thinks it's going to happen now.

And then your job got easier and you started staying longer.

[01:02:32] Alex Hardy: Mm-hmm.

[01:02:33] Paul: So it was very, very fun for me to watch from the sidelines. I mean, not at your expense or anything, but just kind of validated a lot of the things I'd been writing about, about like what people are craving deep down. Talk to me about that, like, deeper pull.

[01:02:51] Alex Hardy: So I— the first year— so I was there for 2 and a half years. The first year after the acquisition, we had very, um, very high, like, sales targets and other targets that we were trying to hit. And there was a lot of financial incentive for us to do it, a lot of money tied to that. And so we were grinding really, really hard, and we ultimately didn't end up hitting them, which is its own separate thing, which caused a lot of consternation and dissatisfaction. But once that carrot was gone, the job got to be like very easy, very enjoyable. I was like, oh, this is why people like working at a big tech company so much.

Like, it's not that hard. I mean, it's, you know, you're, you're, you're, you're working, but it's primarily just like Zoom meetings, status check-ins, things move at an infinitely slower pace than they do in the startup world. Like what's measured in what needs to be measured in days at a startup is measured in quarters at a, at a public tech company. And so I was kind of like, well, this is like pretty easy and pretty frictionless to enjoy. And so I just kind of coasted into it and it was, it was really nice. I was traveling a lot last summer and was kind of had just the best work-life balance that I've ever had in my life.

And so it was easy to, yeah, it was easy to kind of like relax into that and feel wanting to soak it up for a little bit.

[01:04:29] Paul: But what?

[01:04:31] Alex Hardy: I definitely felt that I was not aligned with my sole purpose to the extent that such a thing exists. It felt like I was wearing my capitalist mask by day and my spiritual mask at night. There was this whole spiritual exploration that I had been doing for the last 8 or 9 years. And it felt like what I was doing for the 8 or 4 or 2 hours in a working day, uh, was very divorced from that. It was very, it was just, there was just no relation whatsoever. I, it was like, you know, a very, very rigid kind of line drawn in between the two.

And so there was that nagging sense of like disharmony or that I was not being kind of authentic, but I was getting paid really well. It was really easy. It was frictionless. It allowed me to enjoy other parts of my life. So I was kind of content with it. Um, and then they did a massive round of layoffs and everyone, there were 5 of us at my level in a single day.

The other 4 people were fired. And so here I am just inheriting the job responsibility team, all of it, of the other 4 people, um, 2 of whom are my co-founders, 2 of whom were people that I had worked with for, you know, 5 years. And so there was that emotional toll and also just the practical toll of like, you know, imagine that, um, a peer colleague of yours is let go and in a single day, basically all of their email project deliverables to-dos are just getting totally redirected to you. You're the, the new kind of like lightning rod for literally any question in the company related to this. And that was very, very painful to deal with, shall we say.

[01:06:20] Paul: Yeah. And slight detour here. So I know Andrew Taggart is somebody that has influenced me and you both. I think his, his writing about work is very powerful, right? He identifies this idea of total work. As work is like the soup we're in, right?

This is water in the David Foster Wallace sense. And like, once you realize this, right, it's hard to unsee that.

[01:06:49] Alex Hardy: Yeah.

[01:06:50] Paul: How was this sort of influencing how you were thinking of yourself? Like, do you think his ideas and like, oh, maybe I'll just like do these 2 hours, it's still worth it. Like, how were his ideas kind of playing with your experience of that?

[01:07:04] Alex Hardy: Yeah, I mean, he's been really influential on me. I work with him, no pun intended. I philosophize with him. He's, he's a huge spiritual mentor of mine. I think that I was very— I was clearly seeing where in my life I was over-identifying as a worker. And I think where, what he, so that was definitely something to pay attention to, but I think what he, um, maybe like the point of balance that he would emphasize is that, you know, you shouldn't tie up your entire identity in work, but you also should, you don't need to like totally eschew it and say, I hate capitalism and I'm just going to go live in the woods.

Like work is kind of a necessary, uh, can be like earning income and providing for yourself can be a fine and necessary part of life, just like doing the dishes or showering or something can be. It's just not something to take so seriously. That was— that I think is really his message. And I was taking myself so seriously as a total worker that it was everything that I was doing. And I had this kind of nagging feeling that I really wanted to see what it was like to exist in the world with my identity not wrapped up in, in work.

[01:08:34] Paul: Yeah, I think one of his ebooks, How an Artist Can Hack a Living. Have you read this one? I haven't read it in 2018. It was just like on his site and it was very much about the relationship to work. So how do you show up to work with a lightness, a playfulness, a generous, generous spirit, like a right relationship to work? Work.

Like, how do you turn down money if it doesn't feel right?

[01:08:58] Alex Hardy: Right?

[01:08:59] Paul: Been super powerful and useful for me. Um, but when I first read his ideas, I sort of realized I need a period of time where I am not actively still in the machine, on the default path. Even if you're not working, you might still be on the default path because of how you're thinking about, I need that next thing, that next you're sort of like in the grind and it's a different lived experience to disconnect from that.

[01:09:27] Alex Hardy: Yes.

[01:09:29] Paul: It seems like that's what you were being pulled toward. Yes. Yeah.

[01:09:33] Alex Hardy: I think to rewind to the New York experience post-investment banking before tech, even though I wasn't working, I was very much in a total work mindset. I mean, that spreadsheet and how I was treating my day-to-day lived experience was like I was treating it like a job.

[01:09:50] Paul: I need to go. Total coffee.

[01:09:52] Alex Hardy: Total caffeine. Yeah. Caffeine maxing. But yeah, I felt, I mean, in many ways the pain, the challenges that I endured towards the end of the time at DocuSign was a huge blessing because it, like, I mean, things got so challenging that it really forced the issue. It was kind of like a, You know, coasting is fine, but sometimes you kind of need that crucible to make things so difficult that it forces you to leave and to seek something else.

[01:10:31] Paul: But you wanted them to make the decision for you.

[01:10:34] Alex Hardy: Yeah, I'm a people pleaser. So I have trouble saying no and disappointing people and setting boundaries. And so Yes, I, I was— I wanted to be able to leave guilt-free. And so I had voiced my concern about the new amount of work that I had to take on, that I was doing 5 people's jobs and not getting paid anymore for it. And they said, oh, Alex, you're so valuable. We, we really want to keep you.

We'll reduce your scope and we'll pay you more money. I was like, okay, I'll hear them out. And they came back to me with an offer for more money. And it was okay, but it didn't feel like it was worth the mental cost that I was enduring of working, doing 5 people's jobs. So I was going to quit. And then this little nagging voice in the back of my head was like, well, if you're going to quit anyway, why not make them a Hail Mary offer that they'll never say yes to?

And that way they can be the ones that disappoint you instead of you having to disappoint them. So I went back to them and I countered with triple the offer that they had offered me. I somehow arrived at that would be, you know, the price that I thought was worthy to sell my soul for a year if they said yes. I thought there was zero chance they said yes. I thought I was gonna get laughed out of the room. I bring it up to my boss's boss.

And he's like, okay, sounds reasonable. I'll see what I can do with it. I was like, oh boy. So he takes it to his boss, takes it to their boss, it gets escalated to the number 2 person at the company. And this is over the course of a week or 2.

[01:12:29] Paul: And I remember talking to you during this time and you were extremely stressed.

[01:12:34] Alex Hardy: Yes. Yeah.

[01:12:36] Paul: And I was like, I was talking with Angie again. I'm like, Alex is definitely leaving. It doesn't matter how big this number is. Like, the bigger, like, the bigger the number, it almost makes it easier because then it realizes you're just trading something that means a lot to you for money.

[01:12:52] Alex Hardy: Yeah. Yeah, exactly. Exactly. It felt I mean, it was going to be like over $1 million worth of value. Um, and over the course of these, of this week or two, I just remember every day waking up with this pit in my stomach being like, I really hope they say no. I really hope they just reject me.

I don't want to have to sign up for this for another year. And it felt, I mean, it felt very much like I was selling my soul, um, for for some amount of money. It felt very transactional and yeah, just like, like a sellout move. And so, um, ultimately I got word that this number 2 woman was supportive of it and that they just needed to have one final interview to finalize it. And I was like, oh God. Um, so this was the old, this was the universe testing me.

Like, do you, you know, how much do you really value your independence and mission and sole purpose. And basically I went back to them and said, I really appreciated that you're going to, you know, meet me on all my terms, but this is just not aligned for me. And I, I can't, I can't do it. It's just not, not, not in my future. I appreciate it all, but I'm leaving.

[01:14:10] Paul: And I think this is one of the challenges with a success or achievement-driven path is you will literally always be offered more and more money.

[01:14:19] Alex Hardy: Yeah.

[01:14:20] Paul: And more and more opportunity. Yeah. And nobody ever sits down and sets a price for their, like, non-working time. I actually have, like, created a price. My price per hour is $1,000,000 per hour of, like, my leisure time. I sort of just mentally do this as an exercise of, like, reminding myself that it is expensive to give up my time.

[01:14:43] Alex Hardy: Yeah.

[01:14:44] Paul: So you end up leaving and you end up basically creating like a mini sabbatical for yourself in Costa Rica.

[01:14:52] Alex Hardy: Yes.

[01:14:53] Paul: Um, what did you miss, Price?

[01:14:56] Alex Hardy: Hmm. I think if I knew how alive this sabbatical has made me feel, I would have left much sooner. I would have done it much sooner.

[01:15:07] Paul: How much sooner?

[01:15:08] Alex Hardy: Probably like right after the company had sold, I would say. Um, Yeah, I think, I think that for me, it was important for me to climb that mountain, that startup mountain and get the win and have that experience. But yeah, I feel like, I mean, there was, I was almost, I mean, just being in Costa Rica for 2 weeks, I was like, oh my God, I can't believe that I've put this off for this long, this reconnecting with myself, this living a simpler life, this stopping to be a worker and just being and existing and waking up with no set schedule and waking up and just being able to follow activities and curiosities that I want to do, or some days doing nothing and some days just taking a nap at like 11 AM and having no agenda, no schedule, not having to perform anymore.

[01:15:58] Paul: And we treat taking these breaks as such an unreasonable thing.

[01:16:02] Alex Hardy: Yeah.

[01:16:03] Paul: In adulthood.

[01:16:04] Alex Hardy: Yeah.

[01:16:04] Paul: Like the way I frame it is if that was the most important thing in life. Like, a lot of people buy really expensive houses and they decide that is the most expensive thing in life.

[01:16:13] Alex Hardy: Yeah, right.

[01:16:14] Paul: And then they orient their entire life to make that happen. A lot of people pull this off every year, right? If we treated this space in our lives as the most important thing and just created 3 months in our adulthood, I think most people could do it. Like, but sell it for me. Like, why is this so powerful?

[01:16:33] Alex Hardy: I mean, for me, it allowed me to just reconnect deeply with my emotions, with my sense of play, with, you know, things from my childhood that brought me joy that I had just totally forgotten about, like yoga and singing. And just, I was able to capture this, um, yeah, this like childlike sense of joy on a day-to-day basis that it was the happiest I've been in my adult life. By far, um, for— and not for any particular activity. There was— it wasn't like I was, you know, doing some kind of extravagant— living some kind of extravagant life. I was waking up, doing yoga, watching— and watching the sunset. Those were like my three main activities that I was engaging in.

But it was just— it just felt so liberating that, um, yeah, that it was— it was very special.

[01:17:29] Paul: Yeah, I, I've experienced a a very similar thing on this path, and it, it sort of shakes your understanding of everything. Yeah, right. I look back on my path now and people will say to me, well, you did all these things to get to this point, and you're like, knowing what I know now, like, these feelings are so powerful. And the more I've read, you find them throughout all of history, different cultures, different religions. Everyone writes about these aliveness feelings. Feelings, right?

Like yoga is a, like, practice to arrive at many of these feelings, but nobody believes it.

[01:18:08] Alex Hardy: Yeah, you're, um, for me it felt like I was like in my worker mode, I was kind of like hearing through like a very narrow keyhole as to what experience and living a good life and all of these things could be. And then when you kind of remove the shackling or the scaffolding of the work 9 to 5, you know, way of being in the world, you just start to have this vast opening and expansion into the possibilities. The possibilities are literally endless and limitless of how you can construct a day and how you can spend your time.

[01:18:39] Paul: Are you less stressed about finding work worth doing now than before you left?

[01:18:45] Alex Hardy: Um, yeah, much, much so. Um, I think my bar is higher as well for who, what types of people and companies that I want to work with. I mean, I was, I had to give myself a rule to like not do anything, to not try and start another company or to not start, go back into worker mode for 2 months. I made my, I forced myself to not like write anything down, not take notes, not take meetings, not do any of that. I didn't do a Zoom call for like 2 and a half months. It was amazing.

Um, and I've slowly started to dip my toe back in the water, but I've had a very high bar and intentionally I'm almost like anti-marketing myself when I'm talking to people that I might potentially work with. I'm prefacing myself as I don't want to work very much. I'm, I'm going to be extremely expensive. I'm going to be extremely concierge. I'm not looking for something full-time and I want to work with people that I actually enjoy. And that's like a good enough filter.

And the people that can get through that, I'm happy to work with. But setting that filter very high up front has been, has been nice.

[01:19:47] Paul: You sound like me in 2018. We would have gotten along well. Basically just like code for I don't want to work right now and I want to lean into this.

[01:19:55] Alex Hardy: Yeah.

[01:19:55] Paul: Talk to me about the American mind. I think a big shift for me was moving to Taiwan and realizing I had an American mind.

[01:20:03] Alex Hardy: Yeah.

[01:20:03] Paul: I thought I was like more chill than people.

[01:20:06] Alex Hardy: Yeah.

[01:20:07] Paul: And more relaxed, taking my career less seriously.

[01:20:10] Alex Hardy: Yeah.

[01:20:10] Paul: Arrive in Taiwan. Oh my gosh. I had a lot of American wiring I didn't realize.

[01:20:17] Alex Hardy: Yeah, in Costa Rica, I think I had conversations about my job and what I did for a living maybe 3 times in 3 and a half months, something like that. It just— the question, what do you do? Or what is your job? Or any of that, it just never comes up in any kind of, you know, casual conversation. So that was definitely a big one. I think also the kind of needing to cram as much stuff into as little of a time as possible, like this kind of like relaxation via checklist or something is very, very American.

And in Costa Rica and in other places too, there's just a lot more ease and flow and chaos in a good way. And not this orderliness of having to like do a certain amount of stuff. Things are just slower, more relaxed. There's less of an edge, you know, needing to be on edge or like performing. I would say if it rains, you stop working, internet goes out, you're going to do it.

[01:21:26] Paul: Exactly. So talk to me about some of the forgotten childhood hobbies. I know you got into music, singing. Do you now see those as like fundamental and important elements of like what a bundle of activities you want to be doing in the future?

[01:21:43] Alex Hardy: Yeah, definitely. I think the way I've thought about it is instead of having these things— so in, in law school, one of my favorite teachers like had this metaphor of there's like, you can have like, picture like a big jug and you can have, if you're trying to fill the jug, you can put in like boulders and then you can put in sand and then you can put in water. And like the boulder should be the most important thing because they take up the most amount of space. And that's like your family, your parents, your kids, et cetera, your job maybe. And then the sand is like the stuff that is important and nice to have, but just kind of fits in between the boulders where you can, which is like maybe, I don't know, friendship or something. And then water is the stuff that's like not that important.

It just fills in all the final cracks. And that's like, hobbies or these childlike pursuits that bring you joy. And so I think the American conception of that is your boulders are your job and the sand is maybe your friendship and the water is like some of your hobbies or some of these things that don't have any economic value. And I feel like I've just totally flipped that on its, on its, on its face.

[01:22:51] Paul: Like there, I will, I think the American would be to get a second jar. Yeah. Right. And fill it with your side boulders.

[01:23:00] Alex Hardy: Yes. Yes, exactly. So I think for me, whereas old Alex would gladly forsake doing yoga or doing, you know, playing instruments in order to hit up his boulders of, of a job, I think now it's the exact reverse. Like yoga is my boulder or, or, you know, do it, you know, playing the— I've been taking harmonium lessons. And so playing the harmonium and doing mantra chanting is something that I'm not willing to compromise on, or meditation. And the other stuff, the job stuff, can fall— is the water now that's filling between the cracks.

[01:23:39] Paul: That's a big thing where I differ from a lot of people. I kind of have this phrase called the work worth doing, right? The real work of your life. I think the American conception is like this silly ikigai chart that is basically made up. It's like work you can get paid for, right? But I think the work worth doing, the stuff that feeds our soul, we can't actually expect to get paid for that.

But we also need to be crazy enough. And it's not even crazy. It's really just having faith that leaning into these things is what gives our life richness. Yeah. Does that resonate with you? Yeah.

[01:24:17] Alex Hardy: Yeah, for sure. I think, yeah, I've never been much of a fan of that ikigai chart because I think it puts work on too much of a pedestal. Honestly, that's my main, you know, it's, it's hopes and prayers in a chart. Yeah.

[01:24:30] Paul: It's like, I hope the economy aligns with my interests.

[01:24:34] Alex Hardy: Yeah. I mean, I guess where I'm at now is like capitalism is fine, but why would I give my most precious gifts to it? You know?

[01:24:43] Paul: Yeah, it's just, it's an emergent set of conditions, incentives, and like a current state that exists. Right. And I think people think there's some like group in charge of like the capitalism. No, it's just changing.

[01:24:57] Alex Hardy: And like World Economic Forum.

[01:24:59] Paul: And I think for us, both of us have benefited from being very analytical people who do like connecting with other people. And that has benefited us with the current economic paradigm.

[01:25:08] Alex Hardy: Yeah.

[01:25:08] Paul: But if we grew up in a more agrarian era, maybe we would have sucked.

[01:25:13] Alex Hardy: I think I would have been a good farmer. I don't know.

[01:25:15] Paul: I don't know if I would have been. But yeah, it's, it's really hard, right? And it can be extremely frustrating too, because most people do just sort of cede purpose to the capitalistic machine.

[01:25:29] Alex Hardy: Yeah.

[01:25:30] Paul: Why is Jocko Willink like Jocko Willink's speeches, why are they close to Vedantic texts?

[01:25:39] Alex Hardy: Oh yeah. So in Costa Rica, I was really— I was going very deep down this spiritual rabbit hole, but also very into the Navy SEALs and David Goggins and Jocko stuff. And I couldn't really figure out why those two things were resonating for me, but they really were. And I think they both have this love for the present moment exactly how it is and a reverence for it. And Jocko has this famous quote, I think it's called Good, where he basically talks about, he goes down this long list of things that go wrong. The mission gets screwed up, your weapons jam, the weather sucks.

And after each one, he says, good, good. And it's basically like this, you know, amor fati, if you will, of loving the present moment, that things are perfect exactly as they are because they teach you something. And each, you know, each present moment is a chance to get better and improved. And I would say, you know, wisdom, Eastern wisdom traditions have a similar love and reverence for the present moment. Like, there are no problems. There's only a problem if there's an ego.

That's really like a very bumper sticker way of boiling down a lot of these wisdom traditions that there is no such thing as a problem. It's just your interpretation of it because you are an ego or you have an ego. Like sickness or a death in the family or anything that we give this negative valence to is not actually bad. There is no— there is no— it's not possible for anything to be bad. Each moment is just happening.

[01:27:21] Paul: Happening.

[01:27:21] Alex Hardy: There's no good, there is no bad. It's, it's— that's non-duality in a nutshell.

[01:27:25] Paul: Yeah. And I always think one of the challenges with people like Jocko and David Goggins— like, I agree with you, there's something deeper with both of them, and I think they're misunderstood. I think the challenges— they often communicate in this, like, sort of American hustle language that then gets co-opted by very similar people. Yeah. That don't have that deeper pull. Yeah, right.

And I often say, like, it's hard to figure out who to follow because a lot of people are communicating in this hustle language. And really, like, these people just need to read more poetry and literature to, like, use different language to communicate what they're saying. But you can see it once you've had these experiences. You've had this now, these many experiences, these shifting experiences, and you can see these people and you can sort of see, oh, they've had this shift too. They're looking at things in this deeper game.

[01:28:21] Alex Hardy: Yeah, yeah, exactly.

[01:28:23] Paul: What's the deeper game for you now?

[01:28:25] Alex Hardy: I'm going to dispute the premise a little and say that—

[01:28:29] Paul: Perfect. Yeah, I didn't love the question.

[01:28:31] Alex Hardy: I'm focused on more being and less planning, more or less doing and just more flowing. Like, it feels like things have really been flowing since being in Costa Rica. And I think a lot of that has been a resistance to thinking too far ahead. And, you know, my parents and my friends and all these people always ask me, what's next? What are you— what's the next company you're going to do? What's the next job you're going to do?

What's your— what's your 5-year plan? And I just say, I don't know. And I'm getting more and more comfortable saying that. And it's been very fun to see people's brains kind of break when you say that, because that's not an answer they're used to hearing all the time. But I am, uh, I mean, what's next is that I'm cultivating a trust that when I jump, the universe will provide the net.

[01:29:23] Paul: Yeah, I think we get tied to these abstract notions of doing, right? We need to be doing X with a label, with an identity. I've really detached from a lot of that and really been trying to focus on like people in place. So like, what is the environment?

[01:29:38] Alex Hardy: Yeah.

[01:29:39] Paul: How can we put ourselves in an environment where we can sort of cultivate the things we want in life? I think this is how we ended up in Austin. I think you leaving the US, that's really opened up this like curiosity around like, okay, what other places can I kind of lean into that unknown, that uncertainty? Is that kind of what's driving you right now?

[01:30:00] Alex Hardy: Yeah, I'm in my, I'm in my Eat, Pray, Love season for sure. I loved living in Costa Rica. I loved speaking Spanish.

[01:30:09] Paul: It was—

[01:30:09] Alex Hardy: and I just loved the whole getting out of kind of the American matrix. It was very much a rewiring of my brain in the best possible way. And I am feeling called in some ways inspired by you to go to Bali. So that is the next stop on the world tour. I'm going to be doing a yoga teacher training there, cliché as it might sound, but I'm really, really excited for it. And yeah, that's, that's, that's the next, the next stop that I'm, that I'm really excited about.

I love that.

[01:30:42] Paul: And yeah, I think I've really appreciated just how present you are and like, thank you. I can see the, like, I call it the post-work glow after your sabbatical, but I'm really excited about your journey right now. And you don't really have stuff to like hype. But if people did want to like reach out and connect with you, I think you're, you're open to that.

[01:31:06] Alex Hardy: Yes.