Good Life Project - How to Craft a Multi-Passion Career Path | Jason Mendelson

Episode Date: July 13, 2023

Discover the power of a multi-passionate career in our latest podcast episode featuring Jason Mendelson, a creative dynamo who's seamlessly integrated a spectrum of pursuits into an inspiring, joy-filled journey.Key highlights include:Debunking the myth that success equals singular focus, and exploring how a diversified "portfolio of pursuits" can enhance career satisfaction.Jason's incredible journey from passionate musician to tech engineer, law practitioner, entrepreneur, venture capitalist, philanthropist, writer, and back to music again, a testament to the magic of diversified career-building.Insight into his latest book, How to Be a Lawyer: The Path from Law School to Success, a must-read that bridges the gap between academia and real-world legal practice.The remarkable comeback to music after a life-altering injury, illustrating that passion transcends obstacles, and even opens doors to other interests.Join us as we unpack Jason's 'yes, and' approach to career progression, and learn how intertwining multiple passions can lead to a fulfilling, joyful, and successful career. Tune in, get inspired, and rethink the way you perceive success.You can find Jason at: Website | Spotify | Episode TranscriptIf you LOVED this episode you’ll also love the conversations we had with Adam Grant on rethinking beliefs and the power of motivation and creativity at work.Check out our offerings & partners: My New Book SparkedMy New Podcast SPARKED. To submit your “moment & question” for consideration to be on the show go to sparketype.com/submit. Visit Our Sponsor Page For Great Resources & Discount Codes Hosted on Acast. See acast.com/privacy for more information.

I never understood the concept of work-life balance. In fact, ironically, I've always thought, look, there's a certain amount of hours in the day I have. There's a certain amount of hours in my life. I've got to figure out how to allocate them in a way that I'm passionate and I care about. It's a little easier to do that as you get older and more successful. It's harder to do when you're younger, but it doesn't mean you shouldn't strive to be deliberate about how you allocate time and setting boundaries. And it's not about work-life. It's about life, which is life. Some things do you get paid for some things you don't, but you know, hopefully

the things you're getting paid for, you like enough that you want to put some effort toward that life is just life. So we're often told the only way to succeed in work and in no small part in life is to pick one or two things, focus intensively, go all in and say really no to anything that distracts you from that path. But is it true? Is the only real way to be both happy and successful that all in on one or two things or nothing approach? Or is there a place for a multi-passionate, diversified portfolio of pursuits approach to career building that can lead not just to never having FOMO, but also to joy and meaning and success? Well, it turns out the answer to that last question is yes,

but the bigger question is how. And the choices made and actions taken by my guest today, Jason Mendelsohn, show just how the pieces can sometimes come together to create a near magical puzzle of paths that let you pursue multiple passions while still building an true inspiration, and just someone who radiates life. With an early passion for music, he thought his recording and performing and composing would be his career. But an injury to his hand put an abrupt end to not just his vision and passion, but his very identity as a musician. And Jason mourned that loss, but soon also realized the space created when music took a backseat, let other passions and interests bubble up, leading him first into the world of tech as an engineer, and then the practice of law, then entrepreneurship, venture capital, philanthropy with in and out of nearly every stage. In fact, Jason's latest book, How to Be a Lawyer, bridges the gap between law school and practice, explaining what professors won't tell their students in law school and what employers and clients will actually expect from them. Now, while this was all going on, an incredible later in life twist also dropped into Jason's path. The unexpected healing of his music career ending injury led Jason back to music, where he now writes, performs, and records pretty much full

time running his own studio and also championing voices and causes he cares deeply about along the way. And for him, when it comes to his career path, it's never been about one and only, but rather yes and. Trusting that his passion for any given endeavor will infuse the others with the energy and joy and even insights needed to allow all pursuits to rise. And Jason to travel a career path filled with variety and joy and yes, success. So excited to share this conversation with you. I'm Jonathan Fields, and this is Good Life Project. how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're gonna die. Don't shoot him, we need him! Y'all need a pilot? Flight risk.

The Apple Watch Series 10 is here. It has the biggest display ever. It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch,

getting you eight hours of charge in just 15 minutes. The Apple Watch Series 10, available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. I want to say a little over a decade ago, when we began in the podcast world, we actually

weren't podcasting. We were shooting video. So we dropped into Boulder a little over a decade ago with a three-camera crew and found ourselves up at Bradfeld's place in Keystone. We had a great conversation, a great time, become friendly since then. But he shared this really interesting statement when we were talking. And we were talking about this early, like the ideas of what goes into success and happiness and fulfillment.

And he shared that when he was a kid, his dad said something to him that has stayed with him for life. And his dad told him, basically, you pick your 2% and you put everything against it. And that's largely what he credits towards a lot of what he's done. And you hear a lot of similar advice in the world of work, in the world of careers, like pick a lane, go all in. And then I look at you. You know where I'm going with this.

I do. You seem to have taken a very different path, a consultant, software engineer, practicing law, being a founder, VC, author, advisor, professor, guitarist, singer, drummer, songwriter, producer, philanthropist. What's happening here? You know, I am just not able to only do one thing. And when I think about what my life, what I want it to be, it's about fulfilling the potential that I have. And I have been lucky along the way for people to give me opportunities to do something. And I've said, why not? I love taking risks. I love change. And sometimes it works out and sometimes it doesn't. And what I've sort of done, if I look at back everything I've done, music is always my North

Star. Music has always been the only consistent thing in my life since I've been three years old. And I feel like everything else is a diversion from that for a short period of time. Although my venture career lasted 20 years, I've just always found that I am better at whatever I'm doing if I'm doing other things. Every time I've tried to do just one thing, and maybe that's the 2%, I find myself getting bored, frustrated. I lose my creativity, which to me is my greatest strength. With every career I've had, creativity has been the way I've gotten ahead. And as long

as I'm balancing what I'm doing with other things that are completely different, I seem to be able to keep the creativity and the enthusiasm for all the things that I'm doing. So music is the common thread then. Let's take a step back in time. You said it touches down in your life when you're three-ish years old. What does it look like back then? It looks like government subsidized housing with a single mom who is an alcoholic in a really, really bad situation. We were food and money insecure. And I had very little toys, if any. And the motorcycle gang guy across the hall stole a drum set off the loading dock at Toys R Us and brought it to me.

That was my indoctrination in music. And then my mother managed to get a record player and we had five albums. It was like disco duck. There was an Elton John album. There was a Paul Williams album, Age of Aquarius and something else. And she would put them on and I basically started to teach myself drums playing to those albums. And that was it. So for you as you're like three, four, five, middle school, high school, younger years, teens, what does music become for you? Because it seems like in the sort of like the early days that you're describing, it's probably a lot of struggle, you know, like in your mom's life, in your life, either directly or indirectly. And I'm always interested in when somebody turns to an expressive or performance or artistic pursuit, especially at a really young age,

when there's some level of strife or suffering in the family unit, what job that particular pursuit plays? What was the role that it played in your early life? Well, in some ways, music was my parent. I didn't really have a lot of supervision or a sense of home. My mother eventually got remarried and we moved in with him and we were no longer food insecure, but I didn't have a particular close relationship with him in the beginning, although I do have a wonderful relationship now. But I used to try to escape my family by going and listening to records and playing in them. I had the great fortune meeting Stuart Copeland from The Police a few years ago. My favorite album as a kid growing up was Outlander's Demour by The Police.

And I would play that thing so I could play every note and dream and fantasize that one day I was on stage playing these songs. And I got to meet him once and I said, look, I know this is completely lame, but I almost feel like you're a surrogate parent. I used to listen, escape my family, escape the fighting, escape the noise. I was always able to say, hey, I got to go practice drums because I was this special drummer and that was acceptable. I could leave the family to practice because they saw that as acceptable. And I told him, I said, man, I feel like you're sort of like a dad to me. And I told him the story about escaping all this bad stuff and

playing his records. And I said, I know this is totally lame. Can I get a picture with you? And he said, Hey man, after that story, I want a picture of us. And then I got a picture with him, but it was sort of a parental sort of situation. The other thing is I wasn't particularly smart. I had a lisp. I wasn't doing particularly well in school, but man, drumming, I was crushing. By the time I was nine, I was pretty special, and by the time I was 15, I was playing professionally, and the richest I ever felt was my senior year in high school, and I made over $30,000 playing drums, which back in the late 80s, I might as well have been a trillionaire. So it's had a lot of different roles, unfortunately. And then I went to school for music.

And then unfortunately I got injured and I was told I was never going to play again. So I had to make a left turn at that point. But while I don't play quite at a professional level anymore, it's always been the, you know, like I said, the guiding force of my life, even today. What's that like for you? It seems like your life is sort of like, it's kind of directed, you're focused, you're developing mad skills. You're literally earning money doing this at a really young age. And by the way, 30 grand in the eighties in music is probably time adjusted more than most professional musicians

make today full time. So that's tremendous, right? This is a trajectory that was just course and it's passion driven. Talk to me about this moment around the injury and what happens, not just physically in terms of like the change, but psychologically and emotionally. Well, I mean, at the time I'm in undergrad, my mother's passed away. My father, my adoptive father, who I wasn't super close with at the time, he's in Michigan. I'm at the University of Michigan on a music scholarship and I'm playing intramural football with some friends and we're way up, but I decide to keep playing. And I landed weirdly after trying to tackle a quarterback or get the flag. And I hear this woman go, oh my gosh, look at his hand. And I look behind me and there was nobody behind me. And I looked down at my arm and it was just,

I don't even want to describe what I was seeing, but parts were not where they were supposed to be. So you go to the emergency room there and the surgeon makes this joke. He says, look, as long as you're not a piano player, you're going to be fine. And I said, well, uh-oh, because yeah, I do play piano, but also drumming is, you're going to be fine. And I said, well, uh-oh, because yeah, I do play piano, but also drumming is you do use your independent fingers. And I was like, oh my God, what am I going to do? And at this point, I'm still not, I don't identify as intelligent. I don't identify as anything but a musician as a drummer. That's all my entire identity is there. Also my entire livelihood.

I've never had a real job. I made it like four weeks at an office max once. And I was like, okay, I can make 295 and get yelled at all the time. Or I can make 45 bucks an hour as a union musician. I'm out. It was the scariest part of my life. I had to drop out of school because I was no longer able to write. I moved in with my adoptive father and that's when we became best of friends. So in some ways I look at that as a turning point in my life and it forced me to go a different direction. And that direction ended up being a software engineer. I was a self-trained hacker. I did that on the side. I unfortunately got hit by a car when I was 13 and spent some time in a wheelchair. And my father was nice enough to buy me an Apple too. And I went to town. So, you know, it from there, after that, it's been sort of a career hodgepodge of there was no plan.

Music was always the only plan. And so everything from there has sort of been like, well, what is the opportunity cost of me not taking that opportunity? And Hey, that sounds pretty good. Let's give that a shot, but always keeping music. And ironically, four or five years ago, it took me close to 30 years, my hands back a hundred percent and I can play pretty well and playing with some artists that I never thought I would play with at age 52. I mean, it's insane. So I just feel really fortunate to be frank with you. I mean, it sounds sort of traumatic and it was terrible at the time, but looking back, I wouldn't change a thing. It sounds like there was a lot of power that came out of it. It's interesting also that the next

moved after that, because I imagine there's like this season of reckoning. It's like, well, like if this was literally not just my pursuit, my passion, but my identity, it's not just about like, what am I going to do moving forward? It's like, who am I moving forward? It's a complete re-imagining. Right. Like one of the things I had to figure out was like, when you're a drummer and you're in a band, you get done with the show and people come up and they talk to you and you can say anything you want and it's funny and it's a whole different thing. And then suddenly it's like, you're a software engineer. No offense to my software engineer friends out there. And I'm like, I don't even know how to interact with women. Like I can't go up and talk to somebody in a bar. I have no idea. I mean, it was 170 degree

of my life. I went from being cool and attractive to, you know, invisible. It does sound like you had this, there was like an undercurrent, there was a sub-passion for computers. And we're similar age. I remember remember back in the day like the radio shack trs80s and then like the really early apple it's like the cassette decks and you're trying to like adjust the volume level so you can record like this stuff right but so when you step into that world you know what occurs to me also is what seems from the outside looking in as an entirely different pursuit there's actually a lot of overlap. It's not performative or it's not performance driven the way it would be if you're literally like a musician

on stage in a band. But on the creative side, on the maker side, on actually putting together code versus putting together notes and rhythm and beats, there's actually a lot of overlap there. Yeah. I've found that math is a huge overlap, especially as a drummer. In fact, my first drum teacher, he used to make me sight read music. And while I'm sight reading it, he would ask me algebra questions. And if I got either a math answer wrong or the drumming, I screw up the drumming, he'd make me go to the beginning of the piece. And it was all about multitasking and math. So there's a ton of math. The creativity, I quickly became, I was at

Anderson Consulting, which is now Accenture. I quickly got up to manager probably faster than anybody I'd known because of my ability to just take a step back and say, wait a minute, this is the way everybody's done in the past, but is there a different way? And we were doing some multi-billion dollar engagements for banks, which by the way, later in life would do all of the automated loan processing for the mortgage crisis in 2008. So I get a small piece of blame for that, but I was shocked how much overlap there was. And I was shocked as a manager, how performative that is and how having empathy and being able to listen that is. And if you want to get somebody's confidence, it's not much different than being on stage.

I always had to sell myself as a drummer, even though drummer, you're in the background, you're not singing. What people don't realize is they get that gig, you got to be one hell of a salesperson, right? I got to go sell that artist or I got to sell that manager of who I am. I'm responsible. I'm well-spoken. I'm a good project manager. I have a good framework I'm going to bring to these shows. And it was shocking how much that poured it over to corporate America. I might've been wearing a tie and a suit that looked terrible, but the job wasn't actually that different. Yeah. That's so interesting. Especially when you think about the fact, a lot of people probably look at a band and they're like, oh, the front person is sort of like the lead person in

the band. It's the drummer. The drummer creates the beat that everybody else plays to. And if the drummer's off, everybody's off. The drummer's on sync doesn't mean everybody else is going to be on. But that's sort of like, that's the core. It's the heartbeat of it. In a similar way that a leader of a, that's the core. It's the heartbeat of it in a similar way

that a leader of a team in an organization would be playing a really similar role. So it does make sense that there would be that crossover. Yeah. I was shocked. I mean, the thing I always like to say is, you know, I treat every band I'm in like a rental car, you know, I respect it to an extent, but like, I also kind of don't. And as a drummer, I think one of the coolest things I love about it is especially when you're playing, you know, like one off or two off gigs with artists is I'm able to give audio cues that you and the audience may not recognize. But I've made a major decision. We're going somewhere else in the song or whatnot. And everybody's got to follow me. And, you know, if you follow me, great. If you don't, it's going to look bad on you, not on me. So, yeah, the drummers are, we're not just back there hitting stuff. It's, it's, you're the real-time band leader in real time because you're the only person who can make these cues that the audience, you know, you don't want to say, go to the chorus, go to the bridge. Like, that's no fun if you're a lead singer.

Just listen to the drummer and we'll get you there. Yeah. Mayday, mayday. We've been compromised. The pilot's a hitman. I knew you were going to be fun. January 24th. Tell me how to fly this thing.

Mark Wahlberg. You know what the difference between me and you is? You're going to die. Don't shoot him, we need him. Y'all need a pilot. Flight risk. The Apple Watch Series 10 is here. It has the biggest display ever.

It's also the thinnest Apple Watch ever, making it even more comfortable on your wrist, whether you're running, swimming, or sleeping. And it's the fastest-charging Apple Watch, getting you eight hours of charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations,

iPhone Xs are later required. Charge time and actual jet black aluminum. Compared to previous generations, iPhone XS or later required, charge time and actual results will vary. So you're dropping into that world. It sounds like you're really doing extraordinarily well. And then you make this really interesting left turn into the world of law. Yeah. Or I guess there was like a founding, there was a business endeavor in the middle of that. No, actually that was after law. So I was at Anderson Consulting. I was doing great. The best partner of all time, one of my best mentors came to me and said, hey, you know how much I

love you and you're incredible. I'm like, yeah. He says, but I just want you to know you're never going to be a partner here because you don't have a computer science degree, even though you're better than all these other folks. They've changed it since then. At the time, that was how it worked. And he said, look, I just want you to always keep your head open for other opportunities. And I was like, that's amazing. And then my arms started getting better and I started playing more guitar and I was playing bass and singing and songwriting.

And I started to get this stupid idea that I was going to become an entertainment lawyer and go work in LA and be like that guy who could empathize with the musicians because I'd been one of them and I would be special. And who knows, maybe I'd get to sit in on a couple of records and everything would be great. There's a problem. I went to LA, I interviewed at all these entertainment law firms. They took me out, they took me to shows. And I quickly realized that I wasn't wired as an entertainment lawyer. I hate the stereotype, but entertainment lawyers go out every night. There's a lot of drinking. There's some, in my experience, some questionable ethical dealings with their clients. And I was like, whoa, I can't do this. So I go back to law school and I think I'm going to drop

out because the whole plan was go to law school, become an entertainment lawyer. And I met a woman who was from the Bay Area and she told me about this thing called adventure capital. At least that's how I heard it. And I was like, never heard of adventure capital. What is it? She's like, I'm not really sure my ex-boyfriend was into it or dad was, but you can keep your long hair and wear blue jeans. And I was like, well, that's intriguing. So I started doing some research, you know, this was, you know, 1995. So this was pre-internet blow up, but the venture capital was existing. It existed and there were certainly a lot of good law firms. And I was lucky enough to get an internship one summer. And I realized, oh my gosh,

this is my software engineering coming back with the performative aspect of being able to convince clients and partners that at me as a young age, you should listen to them for my advice. And I fell in love with it. I was like, oh my God, this is what I'm doing. So that led to the legal career. The company I started later, we can talk about that if you want or not. This is where we have a really interesting parallel. I find myself, I was the weirdo in the world of law. I was a musician as a kid, similar to you. I was an artist. That was a big part of my identity. I went to college and I took this really weird left turn also. And I went to law school. I didn't ever know if I'd practice, but I thought it would be interesting and it would teach me some valuable skills. I end up around the same time, mid nineties, I end up

graduating, developing a fascination in securities markets and M&A, going to the SEC as an enforcement attorney, and then working in a large firm in private equity and VC on the law side for a relatively short time in New York City. My experience was radically different though, and it actually sent me out of the practice of law. And it was 100-hour weeks and I wasn't enjoying the process. And it's interesting because I'm asked occasionally, do you regret that time? And would you do it differently? And the answer is no, I don't regret that time. But to the question, would I do it differently? And I've asked myself over the years, had I known then what I know now in a lot of different domains of life and work, would I have found a way to stay?

And my answer is I may well have actually found a way to stay, but I didn't have the context or the understanding of what was possible back then. And I was so burned out and stressed and suffering that I didn't even have the bandwidth to conceive of what was possible. So I checked out. I basically entirely walked away from the career rather than saying, is there a way for me to step into this differently, even very unconventionally, that would allow me to actually be the person I need to be and stay in this path. So I'm fascinated because you found that way. And I think a lot of people, whether it's law, whether it's banking, whether it's sales, whatever it may be,

we kind of assume that there's a set of constraints, there's guardrails, and we're either in it or we're completely out of the entire profession. And I love how you really push up against the fundamental assumptions of that. Well, I appreciate you saying that. I'll tell you two things. One is I've also been an adjunct professor at the University of Colorado Law School for 11 years. And I've seen my former students go through the same sort of situation that most people have like you had. I'd also say the Bureau of Labor Statistics recently published a list of the most unhappy careers in the world. And accountants and lawyers were dead last except they said lawyers had higher incidences of substance abuse. So I guess

lawyers win. I was really frustrated. And it's a quick plug. I've recently released a book called How to Be a Lawyer, which is specifically targeted toward some of this, right? It's how to be a lawyer. It's not just how to be a lawyer and what are the nuts and bolts, but how to be a happy lawyer and how to step outside of what your biases and assumptions might be of what the legal practice is. when I got to Cooley, which I'll mention them because they supported me or amazing, have been a great partner my entire life, was I brought music into my practice pretty much immediately. One of my secret weapons, and I did this at Accenture as well, was get in there. You're the low person on the totem pole. I like this concept of what I call flattened hierarchies. And what I mean is let people above you in your professional world,

see you as an equal or a superior in other areas of life. So maybe you're a great tennis player and you take out a partner and you give them a tennis lesson and they say, wow, this person's been excellent at something and can teach me something. In my case, I would always go to a big company and put a band together of senior partners who used to play in high school and they're missing those glory days and really want to get out for one more show or two more shows. And I would basically put the band together and be the musical director. And then these partners would see me as the partner, as somebody who was taking a leadership role, project managing.

And it would flatten the hierarchy to some extent because they would see that I had excellence in something. And unlike the 2% rule, like focus everything on 2% or a lot of times you hear, well, everybody's excellent at one thing. I actually tend to think that if you're excellent at one thing, maybe you can be excellent at something else because you've developed a discipline and a framework to get there. It doesn't mean I can ever play basketball or be a great fisherman or a great cook. It's not happening. But there are some things I have found that I'm like, I can be excellent at that and excellent at that and excellent at that using the same framework.

And it was sort of that experience where, you know, especially in the Bay area at the time, the late nineties, if you could do, there were no rules about, well, you're only a first year or second year lawyer. If you could do it, they're like, go do it. And it was such a wonderful experience. I still had the hundred hour days as you did too. And man, those were brutal. I used to sleep in my office. I once woke up after passing out at work from a seizure because I'd literally been working that much. But the intellectual curiosity,

the support I got, and just, it was such a crazy time. I mean, it felt like we were changing the world. It was pretty amazing, but I wasn't there that long. I got stolen away by a client and that was another turn in my life. Yeah. But the notion that, I mean, what you're talking about, I love the idea of flattening hierarchies, right? Because you're using it in the context of as a first year, like as a young associate in the law firm, this is just a generalized concept where we can apply that to anybody who's young in their career, or even if you're not young in your career, if it's a second act, you're showing up or a third act or fourth act as many people have these days. And you're just the new person in the organization, in the culture.

People don't know you. They don't trust you. And maybe they look at you as being, especially if it's a new industry or like job for you, they'll look at you as some people look at you as lesser than not on a humanity level, but on a skill and experience level. Which makes no sense. Yeah.

But the fact that you can tap something different to flatten the hierarchy in a different context, and then that sort of reverse engineered its way back into the more generalized nature of the relationship and the assumptions around status. It's kind of a fascinating approach. Yeah. Every time I'm teaching at CU, I talk a long story about flattening hierarchies and asking every person in the class, what is the one thing that they identify as? What do they identify as doing something outside of law school? And how do we take that and show the world how special you are in that? Because nobody's special in law school. As a lawyer, you're in law school. So what else got you there? You didn't get to law school being a schlub. You're special at something. And how do we always make sure that's part of your core

and that you're wearing that on your sleeve as you enter the workforce, no matter if it's law or anything else? Because frankly, people like interesting people. And there's a natural bias. If you find somebody nice and interesting, you start trusting them and believing them and you do get ahead because people, you know, they feel like they know you. And that is really important breaking down those walls. Like you say, when you're the new person in the block. Yeah, I love that. So you're sharing these ideas when you're teaching people in law school.

The book you just mentioned, How to Be a Lawyer, your most recent, it's really interesting because you introduce ideas like this, but you also say, okay, so this is not the Jason show. I'm gonna bring in a whole bunch of other voices, a whole bunch of other people to share their experience. And I thought that was incredibly valuable. And again, you did this in the context of law, but I was thinking to myself as I'm like moving through it,

what if something like this existed for nearly every major profession where you may not have direct access to mentors who've been there and done that, who are willing to actually be transparent and really share the experience. But if there was some sort of basic guide where you've got 20 people who've been out there saying, okay, so whatever you learned in school, this is the reality. And there are a whole bunch of different ways to step into this. Don't box yourself in just because you think it's the way you have to be.

And don't assume that you have to be the person that they want you to be because you have no idea who they want you to be. And it's more important to be you and understand, find a path for that to come out. So having all these voices, basically sharing how that manifested, just extraordinarily powerful. So I'm curious, you've written a lot of books. You could have put this book together in a lot of different ways to step into it that way. Well, if I think about Venture Deals, which is my most widely read book, we just wrote that book because we knew what we were doing and we wanted to blow up the industry and let

the entrepreneurs see behind the curtains of how deals got done. When I started to approach the how to be a lawyer, I realized, look, there's a lot of different lawyer jobs that I haven't had. Things have changed since I've got out of law school. Things have changed from a diversity standpoint that the practice has become much more diverse, both on race and sex and gender identity and all those different factors. And I said, I wanted to build a rainbow of, we've got 28 guest attorneys of age, sex, everything, the cover of the book, I'm really proud of it. It's all walks of life, plus different professions. I don't know what it's like to go clerk for a judge. I don't know what it's like to go straight for a judge. I don't know what it's like

to go straight from law school and put out your own shingle. I mean, two of my students were like, screw this. We're not going the traditional route. We're going from law school to shingle. And you're sitting there going, can they do it? Is that even possible? And these two guys did. And now they're writing about it. And I really wanted to say, what is 90% of the outcomes out of law school? I got to find somebody who's going to talk about their path. And so, you know, the older I get, the more stupid I am. I'm more wise because I realize I know less than I thought all the time. And that life is much more nuanced than, you know, most everything we see in this world,

the black and white and yelling headlines. And so it was really important to me to assume I knew little and find other people who are experts in certain fields. When you think about putting that together, you mentioned venture deals and other books. And it sounds like over the years, you've gained this broader perspective that says, okay, beginner's mind, like I'm always in learning mode. But also it sounds like there's a broader consciousness about the fact that, okay, so I exist in a world which is not like me and I have a certain amount of access and privilege and status, which a lot of people don't have. So how do I actually speak to or be of service to a broader set of humanity. That seems to be woven into so much of the way that you step into

the world beyond the education of lawyers, whether it's the choices that you're making from a venture investment standpoint or supporting whatever goes on there, to also your commitment to criminal justice reform, which drops into your life, it sounds like a chunk of years back. And I've got the best friends any person could want. I love my life, but I still always carry that chip on my shoulder as an underdog, asking my mom, mom, do we have any more food? And the answer was, no, we don't have any more food. I've seen what it's like to be on the other side and I've gotten really lucky and I've worked hard, but I make no illusion that a lot of luck went into my success. And I owe so much to mentors and whatnot. When I started studying the criminal justice space and realizing, you know, there's two huge problems in the criminal justice space, right? There's the

sort of the entry into the criminal justice space, which isn't a fair game, right? If you got money, you've got less of a chance to ending in jail than if you don't. But then there's sort of this release, most people get out of jail, right? And we as society do nothing while you're in prison to get you prepared. We do nothing to help you once you're out. We basically set up a system that is rigged that you'll go back, which is why we have recidivism rates of 50% and more depending on what state. And when I started thinking about how unfair this was, I was like, well, I don't feel like I can fix the front end of this because that's political and it's laws and it's legislatures and it's police. And the people who work in that front

end, God bless them. Like, oh my God, you're doing incredible work. Me as sort of an entrepreneur and a venture capitalist, I want to hack stuff. Like I oh my God, you're doing incredible work. Me as sort of an entrepreneur and a venture capitalist, I want to hack stuff. Like I want to do stuff without asking permission. And I said, wait a minute, what can I do to fundamentally change people's experience as they're getting ready to leave prison and then leaving prison and having a support network? And so my wife and I co-founded an organization called Breakthrough in Colorado, which is in five different facilities that we teach people life skills, entrepreneurial skills, business skills, and then have a post release program. And we've been around for six, seven years now. We've got a 5% recidivism rate.

People aren't going back. And it's not just them, it's their families, it's their kids. If you've got a parent in jail, you're like 75% more likely to go to jail yourself, like trying to break these cycles and create upward economic mobility for these folks. And so I got into this late in life. It's only been the last eight, nine years of my life. But I mean, frankly, I've never had any passion that rivals music until I've had this in my life. This beats software engineer and company starting and venture. Like this is it. This feels like the lane I'm supposed to be in. And I feel like it's not only effective for me,

but my network, you get just as much out of it that you put into it. And it's been a really special ride and it's something I'm going to do till I'm dead. The Apple Watch Series 10 is here. It has the biggest display ever. Hmm. Charge in just 15 minutes. The Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone XS or later required. Charge time and actual results will vary. Mayday, mayday.

We've been compromised. The pilot's a hitman. I knew you were going to be fun. On January 24th. Tell me how to fly this thing. Mark Wahlberg. You know what the difference between me and you is? You're going to die.

Don't shoot him. We need him. Y'all need a pilot. Flight risk. So what happens eight or nine years ago that becomes the inciting incident? Because at that point, your law slash venture capital, you're in the world of venture capital for quite a long time at that point. You build a long reputation. It sounds like music is worming its way back in in a world of venture capital for quite a long time at that point, like you build a long reputation.

It sounds like music is, you know, like worming its way back in a lot of different ways, but like for you to be in that place comfortable in a lot of ways, and it sounds like enjoying a lot of what you do in a lot of ways and then say, okay, there's this whole thing over here and then to have something happen that is so profound and powerful that it becomes a devotion where you say, this is going to be central for the rest of my life. Was there something,

was there an experience, a moment that actually set it off? Yeah. I went to prison with a different program to check it out. We did this exercise called step to the line. I don't know if you've ever experienced this, but everybody wearing green jumpsuits is on one side of the line and all the volunteers on the other side. There's a person who's going to make declarative statements. And if the statement is true, you step to the line. So, you know, the first, there's a couple of icebreakers, you know, I've been in prison. Everybody laughs and you all step to the line because everybody's been in prison.

And then the discussion gets more serious. Like I've had a parent who's had addiction problems. I stepped the line, 90% of the people in jail stepped the line, a couple of volunteers do. And I've seen somebody try to kill themselves or really, really dark experiences. And what I realize is 90 plus percent of all of these terrible, horrific things that kids have had to grow up with, people in the green jumpsuits are stepping in line. And I'm also stepping to the line many times by myself. And I'm just crying. In fact, I'm emotionally even thinking about it right now. I'm crying because I'm having to relive these moments of my childhood, but I'm also crying because I have tremendous guilt and

maybe survivor's guilt or, oh my God, these people never had a chance, right? Like in shock that I'm there and in shock that I'm not wearing the green jumpsuit. And it was just, I mean, even right now, I mean, this was a lot of years ago. I struggle explaining to you the emotional, the intellectual feeling of this isn't fair. I got lucky. These people got a raw deal. Doesn't excuse them for their crimes, but these people got a raw deal growing up. If I'm not going to help them try to have a chance in life like I've had, even if it's going to be later in life, post-release. Shame on me if I'm not motivated to help. And that was the moment. I would imagine, I am familiar with that exercise and the organization that used to

lead a lot of those experiences. I would imagine a lot of people go through an experience like that, have a really emotional day and then step away and that's it. It sounds like part of what was triggering you was a sense of there but for God's grace go I. Because of your early life experience in no small part, there was a level of not sympathy, but empathy. And like that just said, I can't not in some way, shape or form do this. And that becomes a devotion to the level where like you keep going back and you start an organization with your wife to say like, what can we do? I'm fascinated by what you said though, about like the point of intervention, because I think this is something a lot of people struggle with. We see a cause or we see suffering, or we see something going on that we either see as wrong or we feel compelled to do something about it. But either the nature of the problem is so vast and complex, we feel powerless to be able to make a difference or we just cannot figure out where to step in, at what point and what way can we actually

be of service. And because of that, even though well-intended, we just do nothing. So it's interesting to me that you said, you basically spent time and said, I have all these same questions. Where and how is the way that I can actually do something and not feel like I'm one person who will never make a difference? Not that it was entirely about you, but just in terms of wanting to not just show up and give lip service to something, but actually support impact.

It sounds sappy. I do think one person can make a difference. I know I can. I mean, if I think about whether it was starting my startup, whether it was co-founding Founder Group, whether, I mean, we had some issues when we were at Founder Group. I mean, the IRS came after us and the SEC, and we hadn't done anything wrong, but without belaboring the point, I remember our outside lawyers going, look, you're never going to win this. Like, yeah, you're right. But they found a technicality and you're hosed and

sorry, there's nothing we can do about it. We're washing our hands. I'm like, no, we're going to freaking win this. If we're right and we haven't done anything wrong, losing is not an option. I remember PWC decided to retract an audit from us because their local office had done something wrong. And they said, if you sign this document saying everything was your fault, we'll reinstate the audit. And I was like, I talked to everybody like, well, you have to sign that document. And I remember my partner, Brad, we were out at dinner and he's like, dude, do not compromise your morals. Do not sign this document. You didn't do anything wrong. But now you got to figure out how to bring down the Denver office of PwC. Short story, they make it so I don't sleep a lot

and I get excited. I do believe that one person can make a difference. I literally don't think there's anything too big that would scare me. Like I just, I've never found that. I mean, it doesn't mean I don't lose a lot of sleep and I don't stress. Like I'm not saying it's easy,

but like give me a bigger problem, fine. I mean, I worked for the attorney general's office for a year here in Colorado, on huge, on huge, big projects in the criminal justice reform space. I don't know. I dig it. It's great. It's like that creative burst and it's everything is possible. And how do we bring resources and people to the table and how do we organize this and how do we find like-minded volunteers? And I mean, man, what's more exciting than that? And the end is somebody's life is going to be better, right? I mean, you know, I was a venture capitalist for 20 years and it's great

when companies go well, but like we're affecting, I mean, there's 120 people that are released from prison who went through our program, who are doing well and they've got great jobs and their kids are happy and their families are reunited. Who cares what I did as a tech guy, right? Like this is a generational changing for these people. Like I don't have kids, so I guess I don't have a legacy and I don't really care about legacies, but if you're going to use that word, like that's it. So you seem to be wired to believe in yourself in nearly every domain and in the potential for you to actually both accomplish things and make a difference. You also taught for over a decade and guaranteed a whole bunch of those young adults who you

were teaching weren't wired that way. And a whole bunch of people just out there in the world are not wired that way. Do you believe this is teachable? And if so, how? I do. I think it is teachable to some extent. I call it the entrepreneurial mindset. I think the word entrepreneur has been hijacked by the startup community that people say entrepreneur means I've started a startup. I think everybody can be the entrepreneur of their own life. An entrepreneurial mindset of I'm resilient,

I have control, I can make opportunities, I can control more than I believe. We touched on this earlier about not having the bias that I have to go into the law firm and be what they want me to be. You said you don't know what they want you to be. And by the way, we haven't even talked about the clients. At the end of the day, who cares what the firm wants? It's really about the clients, right? And so I really spend a lot of time trying to empower people that I work with to explore their life experiences of where they took control in some situation or some domain in their life and say, see, you do have it. Like you do have this gene that you were able to be an entrepreneur within your own life in this situation. Let's see if we can bring that out in more different situations in your own life. I mean, it's interesting, right? Because what you're talking about relates back to your earlier notion of flattening

hierarchies, but in a different context. It's like, okay, so let's look at different domains and see, because somewhere at some point during some moment that mattered, you figured it out or you showed up in a way that you don't think you're capable of now in this different domain. But it's interesting because it's almost like a methodology that you have. Let's find the other domain where you actually, you were as you wanted to be and you did what you wanted to do. And now let's figure out how to bridge the gap. Like if you believed and acted in that way,

in that place, in that moment in time, why not this? It's basically a skillset. You wonder why things like that aren't taught in sort of like core education. We're so obsessed with just domain expertise, but what about like critical thinking and problem solving. Yeah, I feel – I mean, if you look at most of the ills of the world right now, I think it's a failure of the education system. Part of it's failure of evolution, right? We don't evolve very quickly as humans. And, you know, we went from interpreting this much information as cave people to, you know, every day we have access to every piece of information in the world. So, you know, I'm not trying to be too harsh. This is hard. Like we, we evolve slowly. So I think one of the ways we should be evolving is, is highlighting things like critical thinking. I also think you, you've said the word a couple of times today, empathy. I think we need to teach empathy or at least teach why it's important and what the implications are of empath. And I think those two things, if we had more

empathy and more critical thinking, we'd be in a lot better shape. Yeah, I agree with that. So the work that you've been doing in criminal justice reform, I'm curious also to basically say you have dual passions at this point, music, criminal justice reform. Yeah. And I've combined them. Do those weave together? all major streaming platforms and whatnot. But I've got about two and a half million hits so far in my album that are released last year. Each one of the singles, which is on YouTube, highlighted a different charitable organization. Two more criminal justice reform organizations. I also did one for Ukraine because I was motivated to help some families there. But I have been able to weave those two things together and even deeper working with a few family foundations

that are very deep into criminal justice reform, being able to bring some of my musical connections into that to give it some star power, to give it some voice, to give it a megaphone. One of the people I'm working with is Aloe Black, who is a very, very important musician as well as social justice performer. He'll actually be down in my music studio in Palm Springs in a couple of weeks. We're going to record his next single. But everything he does has an impact either around criminal justice reform, immigration, or just free speech and standing together as humanity

and working through these problems. And so it's been really amazing. It's one thing to write a song. It's another thing to write a song. It's another thing to write a song with the obligation, responsibility, and burden that it's going to try to highlight an organization or highlight something and do good in the world. You take a few extra minutes on the lyrics and the melody and all that stuff. And it's like, wow, this isn't just your high school rock band throwing out a song and seeing what sticks. This actually might matter.

So it's been a wild ride. It's been a short ride. I've only been doing it for about 18 months. So ask me again in three or four years. But it's funny how that's overlapped as well. Yeah. I mean, it's interesting. We had a couple of years back, we had her and Zoe and they were working on Zoe Bookbinder

on this thing called the Prison Music Project, where Zoe had been going to New Folsom, working with incarcerated people and realized that they were stunning artists and writers and started taking their writing, their songwriting out. And then they organized performers on the outside and then some formerly incarcerated people to actually create, to actually record an album based on their writing and then release it under Righteous Bay Records. And it was incredible. And it's interesting, right? Because things like that, things like what you're doing, it also circles back to this notion of valuing both the humanity and the contribution and the creativity and the wisdom and the intelligence of people who have lived very different lives than you, are in a very different place, are incarcerated, but also saying, yes, and they're human beings with value and worthy of dignity and being in

partnership with that and with them in a way that is of service, not just to them, but also to others. Yeah, I couldn't agree with you more strongly. There may be people listening to this who have doubts or biases because they've been affected by somebody who's in the criminal justice system. And I respect that. If we look at it, even just from a cold hearted standpoint, if we help these people succeed upon their exit from jail, they're by definition not doing other crimes, committing other crimes, which leads them back to prison. There's a victim of those crimes. That victim could be you or I or someone we love or a business we care about. Even just from an economic cold-hearted standpoint, we don't want anybody in

jail. We technically want a world where nobody's a victim. That's Pollyannish. That's not going to happen. But if we can look at a marginalized population and we can help them, to me, it's ethically and morally the right thing to do because you're right. There's a ton of talent behind bars. But even if you're not totally sold in on that concept, let's, from a public safety standpoint, reduce the amount of victims by helping the system perform better. If we start to zoom the lens out a little bit,'t make a lot of distinction between the way that you live your life or the values, the relationships that you have in life. And this thing called work, no matter how that shows up in your life, whether it was a professional musician in the early days as a consultant, as a lawyer, as a venture capitalist, as a musician and composer and label at this point now, or in criminal justice reform, that's over here and life is over here.

It seems like for you, it's all one big smorgasbord. I never understood the concept of work-life balance. In fact, ironically, I've always thought, look, there's a certain amount of hours in the day I have. There's a certain amount of hours in my life. I've got to figure out how to allocate them in a way that I'm passionate and I care about. It's a little easier to do that as you get older and more successful. It's harder to do when you're younger, but it doesn't mean you shouldn't strive to be deliberate about how you allocate time and setting boundaries. And it's not about work-life. It's about life, which is life. Some things do you get paid for some things you don't, but you know, hopefully the things you're getting paid for, you like enough that you

want to put some effort toward that. I think ironically was a very amazing decision maker professionally and a very terrible decision maker personally personally through the first 40-odd years of my life. I had incredible luck, everything sort of non-relationship and incredible bad luck. And I put that in air quotes for those of you listening in sort of my personal life until I met a gentleman who basically deconstructed my decision-making process and realized I had completely separate decision-making processes for personal decisions versus professional decisions. And perhaps I could learn from that. And that was sort of the last of the integration for me as sort of life is just life. And I think being a drummer, being a musician that's getting paid, it's still a job. People see it as glamorous

and it can be. It's also Groundhog Day because every day is kind of exactly the same when you're on tour. It's literally Groundhog Day, but it's also a pretty fun job. And I've been fortunate that I've had fun jobs, at least for me, all lawyer jokes aside or startup CEOs aside, blah, blah, blah. And so I try to minimize time spending on the phone with Comcast and I try to maximize my time doing all the other things that I care about. We started our conversation talking about how you were drawn to music as when you were three, it became your central devotion, your identity, your really early profession. Then it was taken away for a lot of times and slowly, slowly, slowly has been weaving its way back in. It's been integrating into your professional life, into your volunteer, your devotions, your philanthropy. and central pursuit these days. You have your own studio in Palm Springs right now. You're

back in playing form as a multi-instrumentalist, singer, songwriter, composer, producer, and you released your first ever album last year. I think it was July of last year, right? So this is you in your 50s, thinking back to when you're in your teens, thinking that back then you would probably be like, by the time you were in your fifties, oh, you'd probably have a long music career with tons of albums behind you. That all gets cut short. It vanishes for 30 years. And then in your fifties, you come back and for the very first time release an album that ties you back to that deep love affair that you had since you were as young as you can remember. What's that like? Hearing you say it is unbelievable. Feels like

I'm listening to somebody else's story, not mine. I'd been on some band albums and played some tracks in here, but this album called Taking Sides is all me. I play all the tracks, but a few, I wrote all the tracks, produced them all. I just don't know. I don't know where it comes from. I'm lucky. I work hard at it, but music, creativity, there's so much luck. I mean, I can't force myself to be creative. I can try to set myself up in mind spots and in situations where creativity may flow, but I just feel unbelievably fortunate. I feel unbelievably fortunate for the people who are supporting the music. I feel unbelievably fortunate for working with artists right now that I have no business working with. Business partner, Matt Sorum, who was in Guns N' Roses,

Velvet Revolvers, the co-owner of the studio down here in Palm Springs. I'm not going to lie. I get a huge tickle every time some famous rock star, friend of his walks through and records. And I'm like, oh my God. And I feel like I'm eight again. I try to keep my cool and pretend like I'm cool, but in the inside I'm eight. And I built a recording studio in Boulder where I spend, you know, seven months a year, which for those who are listening, there's two guitars behind Jonathan and there's two guitars behind me. And anybody in Boulder wants to come to the studio, please come hang out. It's a great hang space. I don't know, man.

I don't know what I did to deserve this. I don't feel like I don't deserve it. I feel like I'm a pretty good guy, but I certainly don't know what I did to deserve it. Do you feel like from the early days to now, the good, the bad, the high, low, the complex, the easy, the implosions and the celebrations, that it's all been jazz? I have never thought about it that way, but yes, it's all been one large improvisation, which I think my brain got wired pre-10 years old to improvise and react in the moment as a drummer. And I was playing with people when I was nine. So there was that. And yeah, now that you mentioned it, I think this has been one

big long jam that hopefully doesn't end anytime soon. Feels like a good place to come full circle as well. In this container of good life project, if I offer up the phrase to live a good life, what comes up? I think to live a good life is about maximizing everybody's own potential in whatever areas they're passionate about. The ability to dive in, do important things, and just be the best that you can in whatever matters to you. To me, that's a good life. And for me, there's specifics around giving back in marginalized populations, but I don't judge. That could be different for

everybody. So I think keep a continual learning mindset, stay on top of your mental health, maximize your potential, and just try to be nice to people. That's a good life. Thank you. Hey, before you leave, if you love this episode, safe bet you'll also love the conversation that we had with Adam Grant on rethinking beliefs Thank you. favorite listening app. And if you found this conversation interesting or inspiring or valuable, and chances are you did since you're still listening here, would you do me a personal favor, a seven second favor and share it maybe on social or by text or by email, even just with one person, just copy the link from the app you're using and tell those, you know, those you love, those you want to help navigate this thing called life a little better so we can all do it better together with more ease and more joy. Tell them to listen. Then even

invite them to talk about what you've both discovered because when podcasts become conversations and conversations become action, that's how we all come alive together. Until next time, I'm Jonathan Fields, signing off for Good Life Project. Mayday, mayday. We've been compromised. We'll be right back. Flight risk. the Apple Watch Series X. Available for the first time in glossy jet black aluminum. Compared to previous generations, iPhone Xs are later required. Charge time and actual results will vary.