From Teacher to Startup Operator to Venture Capitalist - Owen Willis (Opal Ventures)

I had an absolute blast speaking with Owen Willis of Opal Ventures. I am thankful that he chose to share his story, knowledge and experience with me.

We talk about:

🔵 Gender
🔵 His childhood
🔵 Solo vs team work
🔵 Profitability in healthcare
🔵 Future of training in healthcare
🔵 How to hire, onboard and scale a team
🔵 Success, failures and market tailwinds
🔵 Introspection, philosophy and reflection
🔵 Is early stage investing a game of picking or making winners?
🔵 And more!

Transcript

Owen: [00:00:00] Uh, I do something that I describe as kind of a deep dive interview. It's an hour and a half long, and I am going through line by line of their resume. Of like, what they did, who they worked with, what that experience was like, what went well, what failed, and what I find is that the best candidates, kind of the A level candidates, are not afraid to really dig in and talk about the things that went wrong.

Rishad: Thanks so much for joining me today, Owen. To get started, let's talk about your childhood. There are things we learn in our childhood that help us in life, and there are things we have to unlearn from our childhood to be successful. Talk to me about your childhood and talk to me through the lens of learning and unlearning behaviors, skills, knowledge, and talent.

Owen: Yeah, that's, uh, that's a really [00:01:00] great question. So, um, you know, I grew up, uh, I grew up in Chicago, suburb outside of Chicago called Evanston. Um, my dad was a grad student. Um, he, uh, would kind of go on to be an archaeologist. Um, my mom was, uh, she had actually stopped going to school, um, when she had me and my brother.

Owen: Um, but on the side, uh, was a folk singer. Um, so she, um, was very, very musically gifted. And, um, You know, I would say kind of up until the age of 10 or so, I had a fairly standard childhood. I mean, I think the, um, the thing that, uh, I think like so many, you know, kids in, in, in the suburbs growing up, going to public school, you know, you're always told you're exceptional, you're gifted.

Owen: Um, and, uh, you know, things just kind of come easy, right. [00:02:00] And I would say, uh, up until about sixth grade, like. You know, everything, everything came fairly easily to me. Um, and you know, that wasn't true for, for my brother. My brother, um, struggled a bit more in school and I would see him kind of struggle and kind of not understand why it was easy for me and hard for him.

Owen: Um, but you know, really kind of the pivotal moment in, in my childhood was my parents getting divorced and. Uh, both, you know, kind of them getting divorced and then actually my mom coming out of the closet. And, um, so this is, you know, in the 90s in Chicago, fairly liberal suburb. Um, and, you know, candidly, it was not okay, uh, for my mom to be gay.

Owen: Um, and I think the, uh, the thing that, that, that I learned was just about, you know, not taking things for granted. I think there's a lot of [00:03:00] learning and unlearning I did around, um, around friendships, right. You know, uh, friends whose parents, um, wouldn't let them play over at my house after, after my mom came out.

Owen: Um, I think there was a lot, uh, for me to kind of learn and unlearn about kind of stability, right? And kind of like, you know, your parents being kind of these, these perfect adults and then all of a sudden not being that, um, and so, I mean, I think, you know, candidly. I grew up pretty quickly after that I had to kind of become a little bit more of an adult after that and for me, like, education and learning was a way for me to kind of escape right and and kind of build my own thing and kind of have ownership over something.

Owen: And so, yeah, I mean, I think that was like a big pivotal part of my childhood. I was, you know, always interested in any kind of, uh, in history that that became a big obsession for me. Okay. [00:04:00] Um, I thought I was really interested in, uh, math and the sciences, uh, until I took chemistry and realized that I was never going to be a doctor.

Owen: Um, it just, like, didn't click in my brain the way, the way that so many other things did. Um, and... I think, I think more than anything else, um, it gave me a, a really strong sense of resiliency, right? Of, of, you know, kind of building and rebuilding, building my own communities, um, and, and understanding the value and importance of, of all of that.

Owen: And, and hopefully kind of think maybe developing a little bit of sense of humor, um, with that as well. Um, but yeah, I mean, I think as a kid, like. You know, every kid has their rebellions and kind of their, you know, their rebellious things like, um, you know, for me, my rebellion with kind of two hippie parents was.

Owen: You know, um, applying and going to college right away. Um, it was being a boy scout and, and eventually becoming an Eagle scout. [00:05:00] It was, um, you know, playing lacrosse, right. Things that like were a chance for me to kind of discover my own person. And I think that ended up being the resilience, the. Community building and understanding the value of those relationships and those bonds that you build, um, and that, uh, curiosity and self discovery, I think those were the big things I took out of my childhood.

Rishad: Thank you for sharing that. To set the record, I almost failed OrgoChem in undergrad and biology. And

Owen: I... I feel, I feel like those, those are, those are, they make them, like, just so much harder than they need to be. Um, One of the things, too, that, like, I did learn out of this was, um, you know, I, I, I think, you know, because my, my dad's from not, not from the us he, he's, he is from the uk, which is, you know, about as close to the US as you can get without being from the us.

Owen: Um, but you know, growing up in the Midwest, uh, you know, he definitely [00:06:00] felt like a little bit of an outsider. Um, having kinda my parent, my mom come out of the closet, like made me a little bit of, of an outsider. Um, and, and I, I think like being an outsider lets you be an observer. Right, in a way that I think, um, is really, really hard to do if you are just kind of fully ingrained and fully involved and everything going on around you, um, at the time, candidly, I hated it.

Owen: Right. It was super isolating and lonely. Um, but like, it's something that I am very, very grateful for. When I think about, like, my ability to spot opportunities and think about, kind of, how things work, I'm able to do it with more of an observer's lens than, um, I think a lot of people are, and that's something I think can be credited to, you know, my parents and a little bit of the way I grew up as well.

Owen: I recently

Rishad: posed a question on my LinkedIn, which I will ask you, [00:07:00] it's not a question we discussed before. The question I posed was, would a genderless, raceless society have more equality? The answers were very interesting, and most of the people said no, it would not have more equality. But the people who said it would, half of them were women.

Rishad: Mm hmm. And the people who said no, I wouldn't. Most of them were men. Yeah. I would just pose that question to you. Would a genderless and I won't say raceless. Let's just focus on gender for now. Would a gender society have more equality?

Owen: I mean, I think I would argue yes. Um, but like, there's a huge caveat.

Owen: Right. So I think that in terms of the way we think about, you know, structures and, uh, Uh, the way we think about equality today. I mean, I think, you know, if we, [00:08:00] I think it's pretty telling that the women that you've talked to and ask this question of would argue that there would be more quality, right? Um, there, there are many things about, uh, culture and society that, that are frankly stacked against women.

Owen: Um, there's a lot about our healthcare system that is, is, Uh, deeply unfair to women. Uh, this is something that I, I, I talk to folks about all the time in terms of thinking about opportunities and healthcare and health tech. Um, and, uh, but, you know, that being said, I think we would just find another way to, for, for there to be hierarchy.

Owen: Right. I think just kind of as, as a, uh, um, you know, you see this in, in kind of any group, right. That groups have all sorts of different ways of organizing themselves and creating hierarchy. Um, I think we just find another way to do it.

Rishad: That, that makes sense. I agree with that to an extent. [00:09:00] I also fall in the camp that we would have more equality, the fewer tribes and labels we have.

Rishad: A

Owen: hundred. Yeah. A hundred percent. I'd agree with that. I mean, to be fair though, like, you know, At a certain point, you know, maybe that hierarchy would be, would end up being people have facial hair versus those who don't. Right? And, and you, you would be up here and I would be down here. Um, because I, I can't grow a beard without looking like a creep.

Owen: So, um, yeah,

Rishad: yeah, exactly, I, I think there's like.

Owen: Humanity like has a strong, strong, it feels like kind of an innate desire to organize, right? You see this across every different type of group out there, you know, there, there are almost no groups that have absolutely no hierarchy or structure, it would just look different. Um, that being said, like, you know, if we're thinking about this as a everyone magically becomes genderless, um, [00:10:00] for the people who were maybe formerly women, things would be better, um, in terms of day to day quality of life and experiences.

Rishad: I would love to go deeper on this, but for the sake of time, let's, let's talk about other topics as well. Yeah, yeah. I'll just say one thing in vitro gestation. The concept of that is fascinating to me, and I think it is a must to move towards more equality. And I'll stop there. Why, why did you become a teacher, Owen?

Owen: Yeah. Um, so, uh, when I was in college, uh, well, when I was in high school, actually, uh, I did a program, um, where we worked with peer students, um, who had autism. And a big part of, uh, a big part of that work was using theater games and workshops to teach social skills. Right. And it was, it was kind of two part one, you know, running through scenarios and kind of helping people figure [00:11:00] out how to work through them and talk through them on the one hand, and then on the other hand, you are building these relationships with peers that you could say hi to in the hallway, right?

Owen: Or that, you know, you could kind of like pat on the back, back in class and, you know, check in and see how they're doing. Um, and that was super impactful for me. I think there's, um, You know, not everyone accesses society. The structure is what we've built to date equally, right? And not everyone can for a number of different reasons.

Owen: Um, and when I graduated from college, um, and I was thinking about what I wanted to do next, uh, You know, Teach for America became this really, really interesting option where, you know, I could go spend a couple years teaching, spending time with students, um, doing something altruistic, really giving back, um, and then from there, figure out what I wanted to do with my life, right?

Owen: I was, you [00:12:00] know, 21 years old. I was a finance major, right? I thought I was going to go into investment banking. Um, there weren't a ton of investment banking jobs in the year that I graduated. Um, and so my initial thought was like, okay, I can go do something really, really good and positive. And then kind of get on with my career.

Owen: So that was kind of my 21 year old brains, uh, thought process there. Um, when I, I started teaching, I was teaching in Washington, D. C. My first year I was teaching kindergarten special education. Um, I was going to school at night as I was teaching, so I was getting my master's degree in education. At night and teaching during the day.

Owen: Um, and, you know, one of the things that, you know, kind of stepping into that is you don't really have a ton of training, right? You get a month of training over the summer. They have this kind of like teacher America boot camp, but like, as a special ed teacher, I just like really had a hard time kind of like getting [00:13:00] up to speed and adjusting to the role.

Owen: And so what would end up happening is, you know, we'd be teaching during the day. And then at night we'd have these classes and we'd be like, okay, like here are the 50 questions we have, like, you know, like, how do we think about this? How do you address this? How do you approach this? And, um, it became just this incredibly strong community of, of, you know, educators and now, um, kind of many, many years on friends, people kind of all going through that same challenging, difficult experience together, um, and, uh, you know, getting through it as, as a group.

Owen: Um, you know, teaching is far and away the hardest thing I've ever done in my career. Um, it is the most difficult job that I have ever had, both on a micro kind of day to day sense and on a macro, like, you know, sustainability sense. Um, one thing I think people don't realize about teaching is that, uh, you know, only a small [00:14:00] percentage of your time, especially if you're teaching special ed, is spent on instruction.

Owen: Um, there's like so much you have to do around instruction before you're even able to kind of get in front of students and make it successful, right? You're creating the space within a classroom that's safe for students to learn. You want, you need to create a feeling of psychological and physical safety for them.

Owen: You need to set these boundaries for them that they are learning within. You need to make it them feel okay with failure and, um, you know, really focus on. Uh, this idea of productive struggle and and making making that productive struggle be something that's fun and encouraged and part of the learning experience.

Owen: Um, and, uh, you have to obviously plan the lessons as a special ed teacher. You also have to do all of this paperwork, right? Because what you are providing the child is legally mandated. Through an agreement between the [00:15:00] school, uh, the teacher, the student and the parent. Um, and so you have to spend a lot of time thinking about that.

Owen: And so what I found was, you know, the things that I was really good at were kind of creating those spaces that were safe for people, right? And building trust with my students and giving them kind of the encouragement to try new things and fail and grow. The thing that I really struggled with was the actual kind of like planning a lesson and like, um, you know, like making sure that it, it checked these four boxes and that sort of thing.

Owen: And so I think for me, like as I got to the end of my third year of teaching, I was thinking like, what are the things I really like about this? I really liked the coaching. I really liked You know, building trust with students and getting them to believe in themselves. I really liked, um, [00:16:00] being able to celebrate their wins and failures with them.

Owen: Um, and so, as I've thought about my career and as I've kind of grown in my career, that's a piece that I always want to keep as part of my job, whatever it is that I'm doing. It's something that I've brought to, you know, startup coaching and advising. It's something I've brought to managing teams. Um, and it's something that I've, I've, I've brought to the table as an investor in terms of building deep relationships with founders.

Owen: Let's

Rishad: talk about managing teams. Do you think humility can be taught or is it something we have to arrive on our own? I

Owen: think it'd be, I think it can be, I think humility can be taught. So, uh, I think a lot of humility though, um, comes from expanding your worldview. I think a lot. It's it's not something that [00:17:00] like I as a manager could necessarily teach somebody.

Owen: It's something that you learn through your experiences in the world. Um, I think there's and there's different types of humility, right? Um, I think if you're a founder of a company, um, you have to have a certain amount of hubris around like you being the person to solve a problem. Um, you also have to have a layer of humility.

Owen: Insofar as you should know and, and, and understand that you are not going to know everything about building a company, right? And that there are going to be people who can step in and do things better than you, if you're able to kind of give, give up the reins and do that at different points in the company building.

Owen: Um, I think, you know, fundamentally, like, a lot of my own personal [00:18:00] humility that I've developed in my career has come from rejection. Right? So, um, it is, it is both the, the chip on my shoulder that is, is my motivator. Um, it is also my understanding that I am not going to be perfect at everything. Uh, there are things that other people are going to know and do way better than me.

Owen: And the big one of the biggest strengths I can bring to the table is understanding what my limits are, where my knowledge ends and where I need to be asking for help and I think that, um, hopefully this is something that's kind of changing in culture and work culture, um, but this idea of kind of like knowing the extent of your knowledge and the need to ask for help, I hope is something that's becoming more prominent and prevalent.

Owen: I think previously it was seen as a sign of weakness. Um, but, [00:19:00] you know, at the end of the day, you are not, you are going to hit a wall if you are not able to ask for help. And that, that's, you know, that wall is going to look very different for different people of different skill sets and backgrounds and networks and things like that.

Owen: But if you don't know how to ask for help, um, there is a ceiling to how

Rishad: much you can achieve. I agree with that. Let's talk about hiring and let's talk about structure versus intuition when hiring. If we borrow Danny Kahneman's framework, hiring is a process which requires structure and you can apply intuition after a structured process.

Rishad: I'm growing my team right now and I am terrible at hiring. I want to rely on intuition. I want to give people lots of roles, give them big titles. And what happens is when they fail, it's very difficult to take away titles from people. [00:20:00] It's easier, um, to withhold titles initially, which is not inherently what I want to do.

Rishad: Talk to me about hiring process and give me advice on, on, on how to hire good people. And what are some questions I should ask? To evaluate specifically for, is this person committed to what I'm doing or not? Because I believe early on where I am in my health tech investors journey, commitment is what I need right now.

Rishad: I don't need rock stars. I don't need super quality candidates in terms of industry experts. I need people who are committed to the mission.

Owen: Yeah. So I think there are, um, a couple of things and what you're describing is, is both hiring and onboarding, right? So I'll stick first to kind of like the hiring side.

Owen: Um, I think, you know, the number, there are like two things that I've learned in hiring. So, uh, [00:21:00] and this is from my time at Osmosis, where we grew the team from, 20 to, um, just over 150 people when I left, um, in, in just a couple of years. And then, uh, when I was at On Deck, um, I think I was employee number 36, we grew to more than 300, um, while I was there.

Owen: And so I would say, you know, on the, on the hiring side of things, you know, first and foremost. A lot of the work happens even before the hiring starts around thinking about and scoping the roles, right? And, um, when I am designing and scoping a role, I'm very, very clear about what the role is and then what the role isn't.

Owen: I think, I think we, everyone spends their time on kind of just what the role is. But there are just, like, certain things that, like, somebody will not be doing in this role, um, or certain types of, of, of candidates or certain qualities that you just, like, don't want in this role. [00:22:00] And I think the more that you understand that, you are going to be able to do a better job of filtering for that early on, uh, as you're looking at candidates, but also, um, it really helps you with expectation setting.

Owen: For the people that you're wanting to bring on. Um, I think so much of why candidates fail early, um, you know, other than maybe the person being the wrong fit for the role is that there are misaligned expectations from the start about what the person is doing or should be doing or what the role can turn into.

Owen: A lot of that, you know, comes with things like title inflation, right? And this idea like, oh, I'm like, you know, VP of product. I'm going to be VP of product forever, whether we, or like, I am like in line to be chief product officer, even though we have a team of 10 right now. And we expect this to be a team of, you know, 200 or 300 in a couple of years.

Owen: Right. Things change, uh, you know, roles [00:23:00] change, um, people's ability to grow into those roles changes. And, um, I think you need to do, spend time setting that expectation really, really early on with, with folks who are joining. Um, and I think part of that is you, you can make it clear as well that like. You know, that includes your role, too, right?

Owen: Like, your role is going to evolve and change over time. You're going to bring in people to do certain parts of your role better than you ever can, um, and that's just, like, behavior that you have to model, um, for, for your employees. So, that's kind of the pre hiring. It's, it's, you know, making sure that you have a good understanding of what it is that you're bringing on, and then, like, what this role is not going to do.

Owen: Um, I think the, the second piece is around kind of the interviewing and kind of hiring process. Um, you obviously want to spend a lot of time on top of funnel, uh, the stronger, obviously it sounds so like [00:24:00] basic, but like the stronger you're at the top of funnel is the more likely you are to bring out a rock star.

Owen: Um, and so, you know, I spend a lot of time, you know, even when I was in very, very senior roles, very actively doing kind of proactive outreach for folks that I think could be a good fit. Um, you know, even so, even if I'm sending out, like, you know, 50 messages and two of them converted to interviews, those are two people that I've, like, gone out into the world and saw, oh, actually, this person seems pretty well aligned to what I'm wanting to do.

Owen: And it helps me just also get a better sense of like, who are the types of people that I wanna hire and how do I want to kind of benchmark this role? Um, and so I think that is, that is something that's, that's incredibly helpful. Um, on the actual interview process, uh, man, I, uh, I would say that like, I'm a pretty annoying [00:25:00] interviewer.

Owen: Um, I am, uh, really, really nitpicky on my interviews. Um, I, uh, with every candidate that I'm hiring for kind of a mid level role or higher, uh, I do something that I, I describe as kind of a deep dive interview. It's an hour and a half long, and I am going through line by line of their resume, of like what they did, who they worked with, what that experience was like, what went well, what failed, and what I find is that the best candidates, kind of the A level candidates, Are not afraid to really dig in and talk about the things that went wrong, um, right, and the learning opportunities and how they responded to feedback, how they responded to failure.

Owen: I think all of that stuff is really, really interesting, um, and I think the candidates that are a little bit more insecure. Um, we'll try to [00:26:00] either sugarcoat it or kind of brush some of those things off. And that for me is a pretty strong signal about resilience in, in, in kind of their, their ability to work.

Owen: Um, it also gives me my list of references. So, um, as I'm going through, I'm writing down names of people and like, out of, out of those conversations, I'll pick two or three people on that list and ask for them as references. Um, and I find that to be, uh, I think jarring, a little jarring for folks. But again, it gives me just a really good sense of kind of who these people are, um, and, uh, you know, their experience, their skill set, who likes working with them, who doesn't like working with them, um, and yeah, I mean, I think on the other side of things, you know, that asking for that level of openness requires candidness.

Owen: So, you know, on those calls with people, I am very open about my own career failures, right? And I, and I use. [00:27:00] My own career mistakes to model the behavior that I want to see from them on those calls. So, again, it's really, it becomes much more of a conversation. Uh, I'm sure it is a very stressful call to be on the receiving end of, but for me, it gives me a really good sense of kind of who this person is.

Owen: What makes them tick? What is their motivator? Um, and by the end of it, I, I know, like, I'm either really excited about this person or I'm not. And at the end of the day, when you're hiring, it has to be a hell yes or it's a no. And so that is my own way of kind of getting to that answer.

Rishad: This is very helpful.

Rishad: And I think a good frame for me to shift my mindset is treat my hires like I evaluate founders. I get very nutty to the founders and give details about their product. Yeah, I think the gold is in the details. It's getting nuanced, getting granular, getting complex.

Owen: And understanding motivation, [00:28:00] right? I think, I think that is a big part too, right?

Owen: Like understanding kind of what makes them tick, how they respond to feedback, how they respond under pressure. Like all those things are really, really important at an early stage company as you're scaling, whether it's a startup or. You know, a a a fund or a media company. Or any. Or anything. Right. Um, I would also add in, I mean, I think there's, uh, um, so the, the, the last thing I'll add in here is, is just kind of that reiteration around trusting your gut.

Owen: Um, I would say, uh, you know, of all I, you know, everyone makes bad hires, right? Um, of all the bad hires I've made, In my career, um, I've had a gut feeling that there's something off, right? And, you know, for whatever reason, um, almost, it's almost always credentials, uh, and credentialing. I, I, I've ignored it and I end up with a person who [00:29:00] might be great in another role.

Owen: But it's not right for this role, right? Either. And oftentimes it's, um, they either just like, don't have the right initiative and kind of self motivation and self drive. Um, or, uh, they can't ask for help, right? Those are kind of the 2 things that I always find, uh, as, as being kind of big issues. And a lot of that comes from the fact that, um, for most of my career.

Owen: Uh, as a consultant at Osmosis and on deck and now, um, with what I'm building, all of my work is remote, right? And so, you know, if I'm operating remotely, I need someone who has a ton of autonomy, uh, who can kind of operate with agency, but who also knows how to raise their hand and say, Hey, I fucked this up.

Owen: Um, or, oh, and you screwed something up, right? We need to kind of talk about it and work through it.

Rishad: That gives me a lot to think about and [00:30:00] gives me a lot of actionable advice. So thanks for that. Oh,

Owen: yeah, of course, of course.

Rishad: I was going to say, I am not a team player. I am a solo person. I like working by myself.

Rishad: I like working alone. I'm happy to work on projects with teams, but I don't like being paired with someone or working in teams in a day to day process. Is there a role for someone like me in any corporation? The moment I say I'm not a team player, people, they don't like hearing that. Yeah,

Owen: well, so in the last two organizations that I was, uh, was a part of, um, and, and, and also, um, just kind of in, in the advice that I give founders that are slightly later stage, um, you know, I think, I think what you would find is that in corporate America today, there is this hierarchy of.

Owen: You know, individual contributor and then kind of that individual contributor because they're [00:31:00] good at that individual job that they're doing, then becoming a manager, right? And the things that make somebody a good individual contributor, uh, don't necessarily make them a good manager and oftentimes actively make them a bad manager, right?

Owen: Um, and so, but like right now, the only way to kind of advance in, um, in roles, I think at a lot of companies is, By going from being, uh, an IC to a manager, to a director, VP, et cetera. Um, when I think about startups. You know, those early hires that you bring on, oftentimes that expectation is that you are going to start again as somebody just doing everything, and then you're going to manage a team, and then you're going to become a VP, and then you're kind of going to grow in a very similar way.

Owen: Um, but like, some of the best people at a startup are like, you know, your 10x engineer. Right? Um, and if you have like a, if you have a [00:32:00] 10 X engineer, do you want them managing a team? Uh, do they want to be managing a team or do they want to continue to bring a tremendous amount of value as C? Um, and I would argue, and I've seen this with a number of companies that you're able to create a structure internally where you are still able to advance in your career as an IC.

Owen: Right. You're expanding the scope of your responsibility. You're expanding the type of work that you do, but you're never directly managing individuals. Um, and that is a parallel path to becoming a manager. Um, now, if you think about it, uh, you know, a lot of the reason why people make that jump to becoming a manager is because it's a promotion, they get a pay raise, et cetera.

Owen: Um, some of the best companies I've seen actually give managers a pay decrease when they go from being an IC to a manager. Thank you. Right. So the ceiling to be a manager is much higher, right? You can make a [00:33:00] lot more money over 10 years in your career at those companies. But to make that commitment to being a manager, you have to take a little bit of a step down from a compensation perspective.

Owen: Um, and honestly, I think that is how most organizations function, right? Like they're going to be people that I hire today who, you know, probably aren't going to be very good managers. Um, but are hopefully going to be really, really good at bringing a ton of value to startups, right? Um, and candidly and selfishly, I want to keep them in those roles, and I want to find a way to compensate them in those roles.

Owen: And so I do think we're starting to see a little bit more of that shift of kind of these, like, super individual contributors. Um, I would also say that, uh, the kind of increase in proliferation around. Um, uh, you know, solo entrepreneuring is is another path for that as well, where you are able to work adjacent [00:34:00] to teams.

Owen: You're probably bringing value to some extent to larger organizations. Maybe you have a small team that is working for you, but it's another path in order to be able to spend the majority of your time focused on the things that you are best at, uh, and the things that bring you the most joy in your work.

Owen: I'm happy to

Rishad: hear my lack of desire for constant collaboration is not a bug and possibly a feature in my programming.

Owen: Yeah, no, I would I would 100% argue that and like, I again I think it I think it's there is this kind of weird. Societal expectation that like, because you are a strong individual contributor around something, because you are an expert around something, that that suddenly means you're good at managing a team.

Owen: Um, I think it honestly devalues what it means to be a manager, right? And what it means to be a good manager. And like, I know I, you know, probably everyone listening to this and I'm sure you have had [00:35:00] terrible, terrible, terrible managers. And I think a lot of it comes from the fact that like, these are people that were kind of shoved into this role.

Owen: There's not a, they don't get a ton of training around what it means to be a good manager. Um, and it's not something that necessarily aligns with their skill set. And so if we were able to kind of separate that out a little bit, I think, I think generally people will be happier, uh, both kind of employees that are reporting into managers, but also individuals who are looking to contribute and bring value, but just not in that way at a company.

Rishad: You know, I wonder if the reason and I'd like you to challenge this as well. I'm not a good manager. I feel and I would, I would separate managing from leadership is because of a very strong bias towards action and chaos. I am not a planner. I don't plan. So if you ask me what my one year plan is, My answer is I don't know, and I don't want to know.

Rishad: I [00:36:00] don't have a desire to make five, ten year plans. Now, if I take on a project that lasts five years, that's different. I'll commit to it. But inherently, I plan in months at the most, not beyond that. Is that something you resonate with? Or is that something, um, that you think is a deficiency?

Owen: So he asked me to challenge you. I'll challenge you a little bit on this. Um, I think that's a little bit of a cop out. Uh, so I think a part of being a manager is the first step of what you described, which is. There is this thing that you know is important in terms of working with and supporting teams, but you know, it's something that you're not necessarily.

Owen: It's not your strength, right? That's step one. Step two of that is, you know, if you are having to manage, right? If you're building a company is building a team [00:37:00] around you that makes up for that, right? Your strength is not planning, right? Um, or kind of that, that, that, you know, long term strategic planning, bring in somebody for whom that is a strength.

Owen: Right. Or like kind of day to day organization is a strength and have that person be kind of a part of that team and part of a part of the process. Right. You know, I, I think the, there are all things, there are things like nobody's a perfect manager. Nobody's a perfect leader. Nobody's a perfect individual contributor.

Owen: Um, the ones that are most successful are doing that first step that you're describing, which is identifying those deficiencies and. You know, to some extent working on them, but really making sure that they're surrounding themselves with people who are going to enable them to succeed and enable the team to succeed, despite that.

Owen: Um, and so that's what I would challenge you to do and challenge you to think about is like, you know, are there people that you can bring on that enable you to not have to worry [00:38:00] about that in the same way? And you can focus on on the things that that you do best. Um, One of the things that I think is, is, you know, really important is that there are, there are always things that we need to work on and improve, but like, at the end of the day.

Owen: You know you or me like, you know, we might not be the best at x y or z thing Um, you could hire to make up for that and you can double down on the things that you are absolutely the best at Um, and I think that's something that I see a lot of great leaders do um, and it takes a a lot of kind of personal honesty Around what your strengths and, and, and what your areas of, of, um, deficiency are.

Rishad: Let's talk about investing. Do you think early stage investing is a game of picking winners or making them?

Rishad: I think

Owen: you, that's a, that's a [00:39:00] great question. So early stage investing is a game of picking the founders who are most. Likely to be successful with the information that you have and then doing everything that you can to stack the deck in their face. Right? So, uh, you know, pre investment, it's obviously making sure that you are understanding the person you're understanding the motivation you're understanding.

Owen: Where they fit within the ecosystem and the problem that they're solving, um, you're making sure that they, uh, know the space better than you do, right? And they are surrounding themselves with the right people to build, right? And at that point, you're putting in, uh, you're putting in a check. Um, I think at the, like, at the earliest stages.

Owen: [00:40:00] You're not going to know everything, right? The, you know, the business model might still be in the process of being defined the exact go to market strategy might change the team composition is certainly going to change over time, but you are going in with confidence that there is a major problem to solve in that space.

Owen: And this person has a really, really good chance of solving it, um, given everything that you know, uh, post investment, um, it is your job to de risk that investment as much as possible, right? It's making sure that they're getting the introductions to the right people that are going to help unlock pieces of everything about health care, little pieces of knowledge around how decisions are made or how things are purchased.

Owen: Or introductions to the right person who is going to help them get that first contract or help them set up a clinic or kind of go through FDA approval, um, [00:41:00] without making a major mistake that's going to take the company, right? You're trying to get rid of as many of the obvious points of failure as possible early on.

Owen: Um, and then making sure that they're not doing anything. That is going to be catastrophic enough to sink the company in two or three years. Um, and I think really at an early stage investing that that's all you can do. Um, a big part of that, uh, and we're seeing this a lot now in, in kind of the healthcare health tech space is just helping them understand what's around the corner.

Owen: And what the expectations are down the road, right? So if you're raising, if you're a pre seed founder, what do you really need to have in place? What are the milestones that you're working towards in order to raise a seed round, right? Like being really, really clear about and helping them think through.

Owen: What are the things that made they need to be focusing on and building [00:42:00] in those early stages to be as capital efficient as possible when they're building on the other side of that coin? You also need to be, uh, doing everything you can to make sure that they are able to stay capitalized, right? As a precede investor, you're, you know, one of your biggest risks is that you are the last person to put a check in.

Owen: Um, and so it's a lot of it is about making sure that you have a network that you can kind of reach out to that is going to be able to be aligned with that founder, um, that is going to be potentially interested in investing and simultaneously, you need to make sure that that founder is actively building that network on their own as well.

Owen: And so, um, yeah, I mean, it's a lot of. Thank you. Information just dropped all at once there. But what I would say is kind of fundamentally it's, it's, [00:43:00] it's about making a really strong decision and who you think has the best chance of succeeding in a space that you know exists in an opportunity that you know exists.

Owen: And then on the other end, how do you do everything you can to make sure that they are successful after the investment?

Rishad: A problem I foresee in my investments is identifying the laggards or the companies that are not going anywhere. Are requiring more and more of my time. There's some things I should look for.

Rishad: Should I look for a exponential burn rate and a stagnant run rate? What are the things I should look for to identify those laggers beforehand? And if I identify them, should I continue my investment or should I look at the secondary market to exit in some capacity? Yeah,

Owen: I think, I think it's hard. [00:44:00] It depends on the stage that you're investing in.

Owen: I think sometimes it's fairly hard to to kind of sell off the secondaries, uh, sell off to the secondaries. Um, and especially in in the earlier stages. Um, and so, you know, I've seen some investors take the approach that, you know, until they hear otherwise, all their investments. You know, kind of go to zero, right?

Owen: And so at the very least, they're just being the most conservative that could be. And then if something kind of comes back, uh, then that's that's a minor miracle. And that makes their numbers look even better, right? It's all about kind of setting those expectations with the LPs, um, or your significant other who might be might be your LP.

Owen: Um, so, uh, there's kind of that side of it. I would say, you know, as you're talking to founders, It's really, I find the most interesting kind of nuggets and insights [00:45:00] in the investor updates. Um, and kind of reading through those and kind of like looking at what is the net change month over month, right? Um, are they kind of focusing on, um, kind of that continued slow kind of building of the business?

Owen: And if that's the case, it might just be that things are moving slowly, right? And obviously you want to check in. Um, Does do their kind of investor updates feel a little schizophrenic, right? Like, are there Are kind of are they kind of pursuing all of these different initiatives trying all of these different things?

Owen: um Kind of seemingly switching their strategy kind of monthly that for me is is much more of a red flag, right? And um, That's where I would want to actually spend some time sitting down with the founder And getting an understanding of where they are, what's working, what's not working, how are they thinking about focus, how are they thinking about burn, [00:46:00] um, and, you know, I think the thing with startups is, you know, there are two versions of what is happening at a startup.

Owen: There's the version that is being shared with investors, which is like this really romanticized version. Of what's happening and what's working and what's not working and and kind of how I'm building a company. Um, what's happening on the inside is almost always chaos. Right, it's all it's almost always like, we are trying everything that we can.

Owen: We are scraping. Everything that we can to get to this next stage of building and. I think sometimes we forget that, um, by being slightly removed from from those conversations. And I found that when I'm able to engage with founders at that level and roll up my sleeves a little bit, you can kind of see pretty quickly, Oh, you know, this is just good startup [00:47:00] chaos.

Owen: Versus this is bad startup chaos and I should be worried. I'll ask you two

Rishad: questions and you can answer either one or both of them. We tend to think of our successes as internal and our failures as external when it's usually the other way around and tailwinds Drive a considerable amount of success, especially in the startup ecosystem Build growth study, but why now or market timing being the biggest predictor of success What are some tailwinds you're banking on in healthcare or what is the biggest opportunity in healthcare right now?

Rishad: Yeah, I mean, I

Owen: would say, uh, there are two things that I'm really excited about in health care right now. So, uh, number one, I'm really interested in what I would describe as kind of health care for the 65%. Right. So, you know, and that's a that's a rough number. Right. But like. There's probably about 65% of Americans have what we would describe as, [00:48:00] uh, subpar access to health care.

Owen: Um, and it's, it's a huge part of the population. Um, these are people with willingness to pay, um, often, um, but are just unable to access health care for a number of reasons, whether it has to do with kind of financial instruments or insurance or geographic access, um, uh, or, or kind of technology limitations, right?

Owen: I'm really interested in companies that are increasing access to care to serve those populations. Um, a really good example, uh, that, that I, I keep coming back to is, uh, the company that, um, and the business that good Rx built, right? The entire good Rx business. Is built around a population of patients that were written off by the health care system, right?

Owen: These are patients who couldn't afford medication for a number of reasons. [00:49:00] And, you know, their doctors assumed that, uh, they were not taking their medication because they didn't care. Right? Um, and GoodRx was actually able to prove out, actually, no, it's a matter of cost. And then were able to turn doctors into the number one drivers of adoption for their business.

Owen: Um, that is a publicly traded company. Uh, they... And they built that business off of a gigantic patient population that people just assumed wasn't worth anything. Right. And so I think there are a lot of other opportunities like that out there in health care. It requires, I think, some unique insight and understanding into what makes those populations tick and why they are not able to access care.

Owen: Um, it takes some unique insight into how you can kind of turn that and align incentives of that into a business. Um, but I think the opportunity is there. 100%. Um, [00:50:00] simultaneously. I am really interested in, uh, what I described as kind of the nuts and bolts of health care. It's how do we actually make sure that there are, that health care businesses are able to run better?

Owen: Um, you know, there are all sorts of opportunities out there that in other industries are already taken care of by software, um, that just aren't in health care. And the thing that I think is kind of a little bit of a moat, um, for people looking to build in those spaces, Is that these topics are and kind of products are going to be really complex, right?

Owen: They involve a lot of understanding of, uh, policy and regulation. They understand they require a lot of understanding of kind of the internal workings of the health care system. Um, and because they're complex and they're kind of boring, uh, people tend to shy away from them. Um, and so I think a lot of, about this idea as, uh, boring as a moat in [00:51:00] healthcare, um, where if you are able to build something in a space that is deeply, deeply complex, you're not going to have a ton of competitors because, you know, most people are not going to be willing to spend the time to learn how to actually solve that problem.

Owen: Um, and so those are the things that I'm, I'm kind of most interested in today. Um, the third, there's a third bucket of stuff, and I think it kind of touches on the first two. The lives of doctors are pretty shitty right now. Um, I feel like I'm preaching to the choir a little bit here. Um, but, uh, you know, what are things that we can do to make the job of being a doctor actually more sustainable?

Owen: Um, based on kind of what we know about what causes burnout, um, and what a lot of what causes burnout is, uh, a feeling of lack of agency, um, and lack of autonomy, um, and for clinicians specifically. It's, uh, the feeling that they are not able to spend enough time with their [00:52:00] patients or that the things that they're doing are not actually helping the patients.

Owen: And so, you know, thinking through what are the opportunities there where we can make the lives of doctors better really address. I think the elephant in the room around potential clinician turnover, um, that's going to be coming down the pipeline in, in the next, you know, five, five or so years. Um, and ideally, you know, any company that I'm personally investing in is going to be touching on all three of these things.

Rishad: Yeah, do not get me started on physician. Um, I will say three things. I will say we cannot continue relying on people to train for 12 to 15 years to become a physician. The opportunity cost is too much. We are not burnt out because of a lack of mindfulness, because of a lack of resilience, because of a lack of wellness, because of a lack of yoga, [00:53:00] because of a lack of meditation.

Owen: You're you're saying you're saying that like perks for doctors are not the solution You don't need a ping pong. You don't need a ping pong table in your break room. No,

Rishad: no and no more pizza You know what would help for me personally? What would help most with burnout is a house cleaning service and a laundry service provided by my employer So

Owen: I think I think that that is a that is a call for a startup right there.

Owen: Um So,

Rishad: uh, physical service, uh, will be a much harder sell to me as an investor than a software service, which might not offer much value. And I will call it common headspace on this, but it's much cheaper and the profit margins are much better. Yeah.

Owen: I, I, to that, to that point, um, like one, one thing to add in here, I, um, the majority of businesses in healthcare are not venture scale, just like flat out.

Owen: And, and like, I, [00:54:00] I think the. You know, when you think about what is the purpose of venture dollars, right? Um, it, you know, I think a lot of kind of healthcare businesses are just not going to fit the mold for that. And I, and I think the thing that I really want to reiterate is that that's not a bad thing.

Owen: Uh, that doesn't mean that they are worse businesses. They are just a different type of business that requires a different kind of capital. Um, and those can still become gigantic successful businesses. Like raising venture dollars is not the mark of success. It is the starting point in a sprint, uh, that you are, you are agreeing to be a part of.

Owen: And so, um, You know, that that is something for folks who are kind of building companies right now. I'm telling you spent a lot of time with founders is, you know, whether or not something that is being built is actually going to be venture scale. If that makes sense from a venture return standpoint. And if it doesn't like helping folks figure out what are the better pathways for building [00:55:00] that are going to candidly make their lives less miserable, um, you know, as, as they're actually building this company.

Rishad: Let's talk about the venture model in healthcare. Do you think there's room for a longer time frame that you want model where funds are returned say over 20 years instead of 10? And what are your thoughts on profitability in healthcare? We are profit driven creatures. It is important to have profit motives to drive innovation, to drive the best of us, to work in healthcare.

Rishad: Where should profit be driven in healthcare you think? Do you think it should be? In care delivery or in pharma or biotech, do you think of it differently? I like the Swiss healthcare model quite a bit, especially from a pay wider insurance perspective where healthcare is mandated, but it is private and [00:56:00] private corporations can deliver it.

Rishad: There is a base level of healthcare that everyone has access to and the government subsidizes it. And then you can sell more tiers of health care for the bells and whistles. Um,

Owen: yeah, those are those are great questions. Um, I think there's room for that model of that kind of like longer time horizon. Uh, but like, that's something that, you know, an investor has to convince their LPs.

Owen: Right. Like that, that's kind of the, that's the trick there is, is, you know, is an LP going to be patient for 20 years, um, uh, as part of a fund. And, and, and honestly, with a lot of funds, you're able to, um, you know, based on kind of the fund structure and, and, and the LPA, like, You can add, you know, 234 years onto the end of the fund, right?

Owen: You just have to get LP approval to do that. Um, so I, I think, I think that model is, is a possibility. I would also say, though, that the, the exits in health care are a little bit different, [00:57:00] right? And the exit opportunities are different. I think you have. Um, a higher likelihood of, you know, things like private equity acquisitions or kind of being part of a roll up.

Owen: Uh, there are a lot of strategic requires and health care a lot, um, compared to other spaces and they're fairly active. Um, and so part of it also, I think, is thinking about, like, fund model and fund structure. You know, maybe you're not going to hit as many home runs in health care as you would. With a kind of, you know, kind of consumer generalist fund, but you're definitely going to hit more doubles and triples.

Owen: Right. And, you know, if that's the case, is your fund designed to maximize returns for LPs based on the realities of health care and the realities of building companies in health care? I think that's something that you should be thinking about and focused on as, you know, as you put together a fund. In terms of the actual kind of model of healthcare, uh, [00:58:00] it's really funny how many conversations I have with healthcare investors, you know, and these are kind of private equity people, you know, um, uh, venture funds and, um, You know, kind of very, very successful founders in healthcare were kind of like out of the corner of their mouths.

Owen: They're like, man, Bernie Sanders might be onto something around, you know, honestly, like the answer to solving healthcare is probably blowing it all up and kind of going with something that's more akin to a single payer. Um, but like,

Rishad: I will say, I'll be fairly quick to say no to that. Yeah, I will not bring the answers that I think it's a, it's a fallacy in comparison because Because we're so close, we compare ourselves to each other quite a bit in terms of Canada's health care system.

Rishad: Our system is as fragmented, if not more. And the lack of interoperability here is, I would argue, more than the states. And it's a single payer system. [00:59:00] The pain of the system is decoupled from the delivery. And a single delivered system would be different. And that could be an answer.

Owen: Totally. And what I would say is, like, I think you're, you're, you know, kind of the Swiss model.

Owen: I think the French, um, and the Dutch have similar models as well. Um, but this idea of, you know, healthcare being a right, um, as a starting point to the conversation, um, there being a, a kind of mandated baseline level of care, and then being able to kind of purchase additional care over the top of that, it makes a ton of sense, right?

Owen: Um, in the U. S., you know, there's a reason why people come to the U. S. from all over the world for healthcare. We have some of the best health care. We have the best health care in the world for those who can afford it and who have access to it. Um, we also have a huge percentage of the population who just cannot access health care or for whom accessing health care is.

Owen: Stressful because they have no idea how much it costs. And so what I would say is like, you know, uh, [01:00:00] those are, those are kind of the two things we need to be thinking about is how do we make sure that we keep having the best care possible? But how do we also make sure that, you know, the 65% of Americans or so who have.

Owen: More limited access to care, you know, aren't worried about bankruptcy because they broke their arm, right? And and I think there's a way to thread the needle there. Um, I think the the system that you described, uh, in in switzerland makes sense, um, But like at the end of the day, you know healthcare in the u.

Owen: s. Really only works for a small percentage of people um, there's some things that you can do to like increase access to care and like, you know when I You know, when I talk to folks about this and kind of that those marginal increases, they might not seem like a big deal to us. But if, if, you know, a startup is able to go out and help someone get access to an OBGYN, um, which is some services they maybe haven't received [01:01:00] in, in three to four years.

Owen: Right. That can be potentially life changing for somebody. Right. And like, I think, like, that's just something that we need to keep in mind is like, because there are all of these opportunities out there in healthcare for folks who, um, really just aren't receiving care right now, you know, it might not feel like a gigantic change day to day for you or I, with some of these companies that are getting up and running.

Owen: But it is going to have a meaningful impact on people's ability to access health care. And for those individuals, it will be life changing. And I think that's something just important for us to consider as we look at founders. Um, you know, and then in terms of like, uh, the actual kind of like, you know, making money in healthcare and kind of that broad question.

Owen: I mean, um, the thing that is most important to me is, uh, you know, I want to be finding companies where [01:02:00] Um, you know, by doing good in the world, they are then doing well financially, right? By increasing access to care, they are, and helping patients get access to care, they are then able to make a lot of money, right?

Owen: And, and I think that is, you know, as an investor, like, Important to be thinking about, you know, what are what is the impact of your investment? How is it impacting? Um, you know the people that are being served by it and you know, it is not a replacement uh for financial success Um, but if it is a driver of financial success, then you are investing in in the right spaces I wanted to

Rishad: ask you a question about our educational institutions as more curiosity.

Rishad: The value of them has decreased quite a bit in the software engineering space. Their value has held, if not increased to [01:03:00] an extent in the physician training space and in the legal space to an extent, although I'm obviously not an expert in that. What do you think is the future of training, do you think we will move towards the certification in health care, which will allow us to provide the same level of care physicians can, but not having to spend 400, 000 on getting an MD?

Owen: Man, that is, that is a good question. Um, I have a couple of thoughts here. So number one, uh, a lot of the people That I see on Twitter, especially talking about how, you know, the education system is broken, right? And it doesn't work and it's failed, uh, our graduates are some of the most prestigious universities in the country, right?

Owen: Um, they benefited from the education system. Like, there's no question. Um, you know, it might not be because of exactly what they learned at those [01:04:00] universities, but those universities. Gave them opportunities in their careers, open doors for them because of the credentialing associated with it. I think credentialing is always going to be a thing, right?

Owen: Um, you know, we need to, like, as an employer, you know, you need to have, like, certain things that you can check a box on to say, I actually feel pretty confident that this person knows enough to do this job. Um, and when we're thinking about healthcare, uh, and, and people's lives and risks of lawsuits and malpractice and things like that, I think it's gonna, I think it makes it really, really hard to move away from that quickly.

Owen: Um, so, I mean, I think we're already seeing it a little bit in terms of the increased roles that nurse practitioners and VAs are playing in the healthcare system around care and delivery. Um, I think we see a lot in startups around, um, building businesses that are being really deliberate about having people operate at the [01:05:00] top of their licenses to drive margin.

Owen: Um, but I don't think that that is necessarily going to replace the role of doctors. Um, similarly, I don't know necessarily if, if, if AI or things like that are going to replace the role of doctors. Um, You know, the, the thing that at least on paper, the value that doctors bring is the relationship that they built with the patients, right?

Owen: And I think more and more and more, the value of the doctor, it has to do is going to have to do more with kind of relationship building bedside manner, um, and, and kind of treatment. Versus diagnoses. I think, I think at the end of the day, like, AI is probably going to take over a ton of that. The, the diagnoses work.

Owen: I think the doctor's job is going to be much more about people, um, and, and relationships with patients, um, and, you know, I, my, my question is, and, and, and, um, this is, I think a [01:06:00] fairly controversial statement, you know, is the, the current training for clinicians, the current selection process for clinicians in the U.

Owen: S. Selecting for people who are going to be good in that role. Um, and my argument is probably not right. We're selecting people who are unbelievably smart, right on wildly, wildly smart, incredibly hardworking, you know, to to prerequisites. Um, but who's, you know, strength is, is taking tests, right? And an ability to kind of perform well on assessments.

Owen: Um, I don't know, necessarily as the role of doctors evolves, if that is going to be the number one thing that we need to look for. in identifying who is going to make a good clinician. I think

Rishad: a quote from Vinod Khosla is appropriate here where he says the future doctors will be actors or counselors.

Rishad: And I agree with that statement. Yeah.

Owen: I mean, I, I would [01:07:00] say, um, anyone who's in kind of a professional services role, you know, you're, everyone's playing a little bit of a part, right? It's, it's a, it's a version of yourself, but it's. Your job is, is to make someone feel safe and welcome and get them help that they need, right?

Owen: Whether or not they know they need it or whether or not they want to receive it. And so I think that is kind of how the role of a doctor is going to evolve and it's how it's going to be kind of complemented by technology. Um, you know, I, I, I think the, uh, like thinking broadly about educational institutions.

Owen: I, I think the, um, I, I'm a very, very fortunate recipient of a liberal arts education. Uh, it's something that I, I hope that my children are able to get as well. Um, it, I took a lot of classes that I think people would probably consider to be kind of [01:08:00] like, not important. Um, but the thing that it, it did was it taught me how to love learning.

Owen: It taught me how to learn and it taught me how to be curious. Um, and, uh, You know, that I think is one of the most important and valuable skill sets that you can have, um, stepping out into your career. Um, and so, you know, I, I, I have a sneaking suspicion that liberal arts education, in person education, education with a live teacher versus AI, um, I think all of that is, is going to eventually become a little bit of a luxury good.

Owen: Um, and, uh, you know, I, I think that's. not great for society. Candidly, I think there's a lot of value in it in person learning. But my sense is that, you know, kind of the people with the most are [01:09:00] always going to make sure that their kids are learning in person. With a real live teacher right in

Rishad: front of them.

Rishad: I think if there's some flexibility in the structure of the curriculum, if each undergrad isn't four years, cause that doesn't make any sense to me and each master is in two years there. Mm-hmm. , there's a lot of room there for different paths. Um, totally. For people just to follow their passions. One of my favorite classes I took in undergrad was cartography or the study of maps.

Rishad: Um, yeah. And which, you know, it's, it's not useful for me

Owen: in medicine. Are you, are you, are you saying you don't use that data? You're not orienteering in, in, uh, in medicine.

Rishad: I use that as much as I use organic chemistry. I'll say that.

Owen: Fair, fair. Yeah. And like, I think from my end, I, you know, the two, um, the two classes in, in college, uh, there, there are three classes that I took that I, that I think were like most valuable for me.

Owen: Um, two of them are ones that I think are, [01:10:00] uh, would would generally be kind of. Seen as kind of fluffy, right? Um, one was, uh, just the, the, the intro to philosophy class. Um, so kind of started down that track and I done a ton of work. Um, I spent a lot of time learning, like, focus on classics in, in, in, in, in college.

Owen: And this was kind of a compliment to that. But a lot of it was about thinking about how to think, right? Like, how to be kind of a really critical thinker. Um, the second one was a, a history course that I took on. Um, Islam, uh, the religion of Islam in Africa. Um, and it was, it was taught by a, uh, a professor, um, who kind of grew up, um, in, in that environment and was kind of sharing, like, his experience about kind of, uh, the religion and that space.

Owen: And it was, uh, you know, learning a ton about, about this, this religion through, um, Um, through history, essentially, [01:11:00] of the African continent. And then, um, those were kind of the two, you know, that would maybe be seen as more fluffy. And then, like, my senior seminar, uh, for, for Econ, um, was on negotiation. And, like, that is, like, maybe the best, you know, most practical class I have taken in all of my schooling.

Owen: I use it every single day. And, like, um, It's something that, like, I think everyone would benefit from, right? Just, like, learning how to, learning how to negotiate, learning how to kind of think about, um, you know, how different parties value different things, um, learning how to kind of build consensus. Um, and, uh, yeah, it was just kind of like a random seminar that we did.

Owen: Right. And so I think to your point, like, you know, one of the things I really liked about a liberal arts education was I could just kind of take all of this. I could just kind of do whatever I wanted. Right. And kind of take all of those things and like, [01:12:00] end up kind of somewhere with an econ degree. But like, um, it allowed me to be curious.

Owen: And it allowed me to kind of explore my curiosity. Um, and it allowed me to fail at a lot of different things, um, in terms of learning about things that I thought I was going to know a ton about, or thought I was going to be really good at. And as it turned out, uh, was, was pretty bad.

Rishad: How did you learn to recognize your biases?

Rishad: How did you learn how to think? What were some takeaways from that class? Yeah.

Owen: So I think a lot of it was, um,

Owen: so it was, it was two things, right? Like number one, it was. Making it very, very clear that, like, a big part of our biases is, are kind of, like, driven and reinforced by what we consume, right? The content we consume. And I think the, [01:13:00] um, you know, a big lesson for me in that was being really deliberate about consuming content that I objectively disagree with.

Owen: Um, right. And so, you know, I, I think about that, you know, I'm very grateful for that in terms of how I think about, like, what I read on a daily or weekly basis, right? Um, or what kind of podcast I listen to, or, um, what I, uh, what I see on, what I see on Twitter, right? Like, Twitter's really good at just showing you the things that you really like.

Owen: And you have to actually work pretty hard to find the things that that you disagree with. Um, and so that pursuit of disagreement, um, even kind of within kind of the things that I believe, I, I, I have found to be really, really valuable at enabling me to kind of challenge my own assumptions. And, and how I think about things, um, and, you [01:14:00] know, honestly, it leads me like reading things that really fucking piss me off, right?

Owen: And like being, and having to be okay with that, right? Um, I think the other piece of it that was really, really helpful was just this understanding that there's no absolute truth, right? Um, you know, I, I, I think there, you know, and, and, and that, you know, there are different, that is a, I'm separating truth from faith.

Owen: I, I think, you know, there, there's, you know. Um, it is a faith and then there's kind of ideas of truth on the truth side, you know, nothing is 100% 1000% true or false. There's always going to be some shade of gray around it. It might be more great. It might be less gray kind of on that spectrum of, like, theory to scientific facts, essentially.

Owen: Right. But, like, that understanding of, like, nothing that there is, there is great area to [01:15:00] explore in every topic. I think was really, really interesting for me in thinking about, like, the things that I assume about the world, the things that I quote, unquote, know to be true versus not, um, and, and, and that was really helpful.

Owen: So, like, I think it's fundamentally again, like, what do you consume? What is the content that you consume and making sure that you are. Being really deliberate about expanding it beyond what is comfortable for you. Um, and then I think on the, on the other end, it's about being able to acknowledge that, you know, there are shades of gray in even the things that we believe kind of wholeheartedly.

Owen: Right. And so I think that was really helpful. The last point I will kind of add in there is when I was a kid, um, I grew up in a Unitarian church. So the Unitarian church, Unitarian Universalist church, um, is, is really driven around this idea of, um, [01:16:00] uh, you know, there being multiple paths, um, to a higher power, right?

Owen: And, and just, and, and kind of understanding your path, um, as, as part of like a broader collection of paths, um, to God or Um, whatever the higher power might be. And, um, a big part of that was, uh, you know, once a month we would actually go to a different house of worship and see how they worshiped. And, um, you know, so we, we got to go to a synagogue, we got to go to a mosque, we went to Hindu temples, we went to a Baha'i temple, we were in Evanston, fortunately, we got to have a big Baha'i temple, um, we went to, uh, Catholic masses, and, um, I think that, for me, was a really, really powerful way to kind of see, like, what are, you know, what are all of the things that these religions have in common, what are kind of the nuances in terms of how they think about things, Um, and then kind of like, what, what are the end goals, right?

Owen: And [01:17:00] kind of what, what are they kind of working towards? What are they thinking about? And, you know, in a lot of ways there, you know, there's a lot of similarities, right? And like, I think that was a really interesting entry point for me in terms of thinking about, um, uh, thinking about kind of what are the different paths to truth and, you know, what are the things that are kind of within our comfort zone and our understanding and what are, what are the things outside of it?

Owen: And to be really, really deliberate about pursuing those. So, I feel very grateful that I got to do that as a kid.

Rishad: That is a beautiful answer, Owen. Recognizing the shades of grey in our truth is incredibly important. It's easy to question beliefs and ideas we hold that are not important to us. It's much harder to question our identity, our gender, our race, our religion.

Rishad: But that is equally important. Thanks so much for this conversation. This has been amazing. I've only asked about half the questions I wanted to ask. [01:18:00] So I think a part two is inevitable, if that is

Owen: okay with you. Of course, man, I really appreciate you having me on. I really enjoyed this conversation and I'm definitely on board for a part two.