Ben is joined by Maia Bittner to discuss her personal life and career.  Delving in to how her anxiety has driven her so far and how she's working to recalibrate for what's next. 

Maia is an entrepreneur and investor.  She founded Pinch (which was acquired by Chime) and Rocksbox.  She is on the board of trustees for Olin College. 

Transcript -
Ben Edmunds:
Thanks for joining me today, Maia. Appreciate your time.

Maia Bittner:
Thanks so much for having me here.

Ben Edmunds:
Let's start from the beginning. Where did you grow up?

Maia Bittner:
I grew up in rural Washington State, so just south of the Canadian border and quite near the coast.

Ben Edmunds:
Nice. I've been up to Forks, and I've been down to, I guess like Vancouver. Right? Where were you in relation to those?

Maia Bittner:
Yeah. Well, I was outside of Bellingham. It's about 90 miles north of Seattle.

Ben Edmunds:
Yeah. Cool. Nice. Where are you now?

Maia Bittner:
Very close. At the moment, I'm actually spending COVID times in Skagit County, which is just south of Bellingham. It's a little bit closer to Seattle, and close to all my family.

Ben Edmunds:
Nice. I saw you were recently in New York. Do you still have an apartment there?

Maia Bittner:
Yes, I do still have an apartment there. Yes, I was in San Francisco for 10 years, and just moved to New York when the whole world came crashing down. Since I've been working from home all day, I came here just to shelter out the COVID time because there's a lot more space. I'm in this beautiful apartment. I spend all day, every day at home. Now, I don't know what the future looks like. It's hard to plan.

Ben Edmunds:
Understandable. You have your own place there or you're staying with family, or what's the situation?

Maia Bittner:
It's kind of a perfect situation, actually. My sister has an apartment that she normally rents out on Airbnb. I'm staying in that apartment, right? It's kind of a win-win scenario because fewer people are traveling on Airbnb, and I needed someplace that I can move in. It's all furnished and all decorated, and stuff like that. I just showed up with my suitcase.

Ben Edmunds:
Nice. That's a pretty great setup. What took you from San Fran to New York?

Maia Bittner:
I needed a change of scenery. I had always wanted to live in New York. There was always something keeping me in San Francisco, mostly running companies there. For the first time, I realized that I didn't need to be in San Francisco, and so I wanted to take the chance to live in New York, and I love so much about New York. I love cities. I'm a real city person. New York is the best city. It's this hyper functional city in comparison to San Francisco, and I love public transportation, and I love walking and I love coffee shops and restaurants, and things like that. Yeah, I just wanted to live there.

Ben Edmunds:
Nice. I lived in New York for three years, and moved away two years ago. Nothing compares to New York anymore. I'm in Boston now and I'm constantly comparing Boston to New York, and it's not nice to Boston.

Maia Bittner:
Totally, right? Boston, I lived in Cambridge. It's fine, right? It's just, like you're saying, you just can't compare it to New York.

Ben Edmunds:
Yeah. I miss it. Let's see, your family, you said is near there in Washington?

Maia Bittner:
Yeah. My whole family lives in Washington State. My dad is in Bellingham, my sister's out on Spanish Island, which is beautiful a island. My mom is east in the woods, and then my brother lives south in a suburb of Seattle. I'm sort of surrounded by everyone in my family right now. I've never lived here forever. They were like, "Maia's lives in California. We don't know why. We don't know what she's doing there." I was always the strange one that lives outside the state.

Ben Edmunds:
How did you end up in San Fran? Was it for school or for companies?

Maia Bittner:
The internet, right? I grew up even on the internet and enmeshed in internet startups. I love startups. I love new projects. I love trying ... I remember trying all the new browsers that existed, right, in the browser wars, and I was big on eBay, and I used [inaudible 00:03:56] never ending, and I was one of the first users of Flickr. I was really in that world. I actually ... I went to college in Boston, as many people do. After my freshman year, I had an internship in San Francisco, which makes sense. That's where all the things that I like were located. Then once I got there, I was like, this is amazing, This is exactly what I want to do with my life, and I didn't go back to school for a while after, I kind of I took some time off to stay out there.

Ben Edmunds:
Nice. It has a very specific energy there. That's the great thing about New York and San Fran, to me, is they have they're own vibe.

Maia Bittner:
Definitely.

Ben Edmunds:
College, where'd you go? How'd you like it? I believe you're still involved. Tell us a little bit about that.

Maia Bittner:
Yeah. I went to ... it's a very unique school, so called the Franklin W. Olin College of Engineering. It is only engineering. They only do engineering degrees. It's very small. There's only 75 students per year, so 300 students in the whole school, and it's very new. The first class graduated in 2006, so it's a whole bunch of crazy all at once. I liked it okay, but I also think it was the best possible school for me to go to, if that makes sense. I think that I am not a great fit with school. I've always struggled with school. I didn't want to go to college because I hated school. I didn't really believe in formal education. I thought I would learn more on my own, and I thought that it was also super expensive to go to school and not just the cost of going to school, but it's four years of lost earnings.

Maia Bittner:
You could be making money, and instead you're spending money, and so I wasn't going to go to school, but then I found Olin. At the time, they don't do this anymore, but they offered full tuition scholarships, so it was very affordable. Every accepted student got a full tuition scholarship. They thought that formalized education was broken as well. They were like, it doesn't make sense for the modern era. The world has changed and we're still teaching people the same way. Engineers are still thinking inside the box and coming up with the same solutions to the same problems. We want to innovate and do things differently. They have a different grading system. A lot of the coursework is different.

Maia Bittner:
There's no concept. There's no calculus class at Olin. Calculus is not taught separate from Physics. It's just one course, where physics is just applied calculus. Calculus is just an obstruction of physics, and they're just related to each other. Very cool school. It really looped me in and very recently, I actually joined the board. The reason I did that is, I'm very excited, so Olin, the impact it has had, honestly, has been so amazing. It doesn't really get credit for that, which is okay, but it has changed the way that engineering education is taught at MIT, at Caltech, at the University of Illinois at Urbana-Champaign, as well as in schools around the world, right? More schools are doing the Olin way of having people try things first, and then learning the theory behind it, rather than having to learn the theory first, before you ever build anything.

Maia Bittner:
More schools are being more flexible about emphasizing communication and teamwork, and other modern skills, rather than just memorizing equations and things like that. Olin had this big impact, I joined because I want to help shepherd in the next phase. How does Olin continue to innovate on education, specifically engineering education, but education more broadly as well? I think that we had our phase one and it was a big hit. We can't just lean on, "Students should be able to work as a part of a team and to be able to communicate forever." Everyone is now on board and that's done. Now we need to continue experimenting, and experimenting is going to involve some failures, it's going to involve some successes, but we need to have the stomach to do that. Then when we do find things that work really well, publicize those more broadly, so we have a bigger impact.

Ben Edmunds:
You're working to shepherd in the next phase for Olin. Is COVID changing that for them, or what's their plan?

Maia Bittner:
Yes, dramatically. COVID's having a big impact, but frankly ... We actually have a bunch of things happening at once, at the same time. Olin has had the same president that it started with, which is not so unusual, right? It's a new school, but we're basically doing our first presidential transition right now. Our next president starts tomorrow, July 1st. We're doing this whole new presidential shift, and she's been selected to lead us into our next phase. As well as the presidential shifts, and then we have COVID happening at the same time, and so there's a lot of things happening.

Maia Bittner:
The approach that we've tried to take is like, look, Olin was kind of built for this, right? It's supposed to be an adaptable, flexible, experiment-oriented curriculum that isn't rigid. What we've just had to do is try and take advantage of this opportunity, and say, "Okay, school, it's not going to look like it normally does, so let's lean into that. Can we use this as a time to innovate on what it means to do an online course?

Maia Bittner:
Or can we do hybrid online and offline courses? How do we preserve the teamwork aspect of Olin, it's still integral to the curriculum, in a world where it's not safe to spend an infinite amount of time with other people, or in close quarters with other people? How do we translate communication in a socially distanced world? Yes, COVID is having a big impact, and we're looking at, right? It's like the financial stability of a college? What is that going to look like, if you can't have two students in every dorm room, like we've had historically? How are we going to house them in a safe way? There's downsides, but we're also trying to view it not just as a problem, but also as an opportunity.

Ben Edmunds:
Very cool. Is Olin still doing the 100% scholarship, or is that changing?

Maia Bittner:
No. Now it's 50% scholarship.

Ben Edmunds:
Where's the funding for that from?

Maia Bittner:
Olin started with the liquidation of the Franklin W. Olin endowment. The Franklin W. Olin endowment, for years, was interested in improving engineering education, and donated large sums of money to Stanford, and I mean, all the famous engineering schools across the country, towards this end. What they found is that their donations weren't really changing, right? It wasn't really doing anything. They tried to refocus their strategy. They said, "People really aren't making better engineering education. We are going to have to do this our own. We're going to have to start our own school."

Maia Bittner:
They created the Franklin W. Olin College of Engineering, and started it with an endowment from the previous charitable endowment. When Olin first started, we had a $500 million endowment so we could run the school off of the interest in returns from the endowment, and use that to those that we didn't need to charge tuition. Then, you maybe familiar, in 2008, there was worldwide financial crisis, and the endowment suffered quite a bit. We've had to reduce the scholarship from 100% full tuition scholarship to 50% full tuition scholarship in order to ensure the financial sustainability of the college.

Ben Edmunds:
Cool. Even 50%, though, is pretty amazing, right?

Maia Bittner:
It was much more affordable than most private colleges. On top of that 50% scholarship, right, Olin meets all demonstrated financial need through other financial aid. Students are actually paying quite little to go to the school.

Ben Edmunds:
That's pretty cool. You went from someone that didn't feel comfortable with education, even yourself going, and now you're contributing to a college.

Maia Bittner:
Right, and now I'm on the board and working towards ... Well, and it feels more productive, right, to be like, okay, if education is broken, let's work to fix it, rather than just abandoning the whole enterprise.

Ben Edmunds:
Yeah. All right, so let's talk about working from home. We're working from home right now, what's your setup? What's your working productivity hacks? What's your day to day routine?

Maia Bittner:
Yeah, it's a good question. I've realized, when I was working in an office, I think this kind of got hidden in my schedule, but now that I work from home, it's become much more obvious to me, and I think my boyfriend has also really suffered from this. When I wake up in the morning, I'm very anxious. I'm anxious and I am on, and everyone in my family is like this. When we wake up, we don't sleep in, in the mornings, and it's impossible for us to fall back asleep. When we wake up, we are up. We are morning people. We hit the ground running and ready to go. I wake up, and I'm like, I'm in. Let's do it.

Ben Edmunds:
I have a hard time relating to this. I'm going to ask some dumb questions. What time do you get up?

Maia Bittner:
I usually get up at 6:30.

Ben Edmunds:
Wow. Do you have coffee or you're just awake?

Maia Bittner:
I have coffee. Well, I usually make coffee around 8:00, but I don't think caffeine affects me and I don't drink coffee to wake up. I drink it because I love the way it tastes.

Ben Edmunds:
Okay, interesting. All right, keep going.

Maia Bittner:
Yeah, I wake up, and I'm very stressed out, so, well, I do what I consider to be the hardest work, which is writing my to do list, and the way that I write my to do list is I write it so that ... I mean, I think of it so that anyone could do it, or that a robot could do it, or that you don't need to think at all in order to do it, if that makes sense. I'm trying to come up with an example, but it's not high level things. It's very low level, very tactical things, and I come up with my to do list first thing in the morning, and then I do all the stuff that I'm stressed out about, I do all that stuff first, so that it's not bothering me the rest of the day. I send all those emails or whatever. I get that done.

Maia Bittner:
Usually it's not big projects or things like that. Usually, it's sending emails or kicking things off, or pretty straightforward stuff. I do that first, and then the middle of my day is often, it's like a lot of video calls. It's a lot of, I want to reply to my Slack messages quickly, and it's filler time, I really think, and then at night is when I do my head down work. That's a lot of ... I like go through ... A lot of it is going through my to do list and checking things off that. I always think this is so interesting. I think the most valuable work that I do, or not necessarily the most valuable, but the stuff that people appreciate most and seems the rarest is the least intelligent or the least sophisticated work that I do. Honestly, I think the reason that it's so valuable and so rare is just other people aren't willing to do it.

Maia Bittner:
It's just boring and sucks to do, but I just heads down to it. An example of that is one of the things I did recently at Chime, is I identified the source. A lot of people are on unemployment these days, and so I created a definition of, here's how to know if an incoming ACH is unemployment or not. It's different for each of the [inaudible 00:15:40] different states. Everyone's like, "Wow, this is so interesting. This is so awesome." They're like, "Maia, you're so great. How did you do this?" The way I did it is, I went through each of the 50 states, and I said, for members who live in Alaska, what are the top sources of direct deposits for the past month?

Maia Bittner:
Then I looked at all of them. I was like, this one seems like it's unemployment. I wrote down the name, right? Then I said, okay, the next state in alphabetical order is Alabama. For members who live in Alabama, what are their top direct deposits? I looked at them all, and I was like, this one seems like unemployment, and I wrote that down. Right, and I just did that for 50 states. I mean, you could have an intern do this, probably, or anyone. Anybody could do this, but I think no one is willing to do this, because it takes forever and you hit the load button, then that thing spins, and you sit there. I mean, it took several hours to do.

Ben Edmunds:
Almost like it's a problem with being an engineer. I'd probably be more likely to write a program to figure that out with some type of artificial intelligence that takes two weeks, than I would be to just sit there for three, four hours. Right?

Maia Bittner:
Totally. Well, and I think everyone is ... Well, and people ask me this all the time. They're like, "Maia, how did you do that? Did you write a machine learning script?" I'm like, "No, that would have taken two weeks. I just sat down for four hours and cranked it out, and now, it's done." This is my approach to too many things. I think, yeah, it's funny. Right. I think a lot of people assume, or they're like, "Can we automate this?" I'm like, "I don't know. Maybe, but in the time that it would take to automate it, we can finish it."

Ben Edmunds:
Yeah, I like it. Brute force solutions, right?

Maia Bittner:
Yes. It's funny. I think, that is my go to, is working hard, and just brute forcing stuff. I think that has done a lot for me in my career, but at this point in my life, it's maybe I should be brute forcing fewer things. It's interesting. My boyfriend's been a really helpful sounding board for a lot of this stuff, because I'm always ... whenever something seems hard or annoying, or I don't want to do it, my immediate first reaction is, I will try harder. I will work harder, and I will get this out. Anytime I feel bad, anytime I feel anxious, anytime anything, I'm like, I will work harder. I can always depend on working harder and having that work out for me.

Maia Bittner:
My boyfriend keeps being like, he's like, "What if we didn't work hard?" Then sometimes I'm like, here's this horrible problem. He was like, "What if we didn't do it? Wouldn't that be fine?" I'm always like, oh my god, I have never considered that there are some problems not worth working on, where the impact we get from it, it's just not worth it. Maybe we just shouldn't do it. Or, that maybe there's a 80/20 rule. We should just do this the easy way, and that's good enough, even though it's not perfect. It's just all these ideas that I've never even thought of, because my whole life, my approach to stuff has been just brute force it, and get it done and get it out the door.

Ben Edmunds:
Interesting. There's a couple things I want to dig in there. Let's do the first one, right? You described the way you wake up and think about the day as anxiety and stress, instead of you're excited to tackle the challenges or whatever bullshit, somebody might say. Why do you feel it comes from a place of stress for you? How does that motivate you?

Maia Bittner:
Yeah. I guess the reason why I talk about anxiety and stress is I don't think it's a good thing, and I don't always think it's right. I don't know that it makes me happy. I also think about, I took ... what did I take? Some anti-anxiety drugs. What happened? I take this drug, and the thing that happened immediately is, my face got so much longer because these muscles in my jaws relaxed, and I was like, my god, I didn't even know that I just keep my jaw clenched 24/7.

Ben Edmunds:
Like you haven't seen your natural face in years?

Maia Bittner:
Yes. I didn't know that. I literally didn't even know. I was like, what is happening to my face right now? Now that's something I've tried to be really conscious of. Maybe I can relax my jaw. I think it also shows up in back pain. I think it mucks up a bunch of my life. Honestly, I think there is a lot of stuff that I'm really excited about. So much of the stuff that I do with FinTech and with startup investors, and founders, and stuff like that, I love it. There's nothing else I could imagine doing. I've talked a lot about this, too, on Twitter and things like that, where, if you are trying to fake it, you will never ... I'm listening to FinTech podcasts in all my downtime when I'm washing dishes, right?

Maia Bittner:
Because I love it. I love learning this stuff. It's really interesting. A lot of what I do is motivated because I like to do it, but I do think that a lot is driven by insecurity or proving myself, or things like that, right? Which I think is unhealthy. It's hard to critique it too much because I think so much of that insecurity has 'gotten me to where I am today', and has gotten a lot of things that people respect and admire about me, but I don't think it's healthy for my mental wellbeing. I don't know if it's worth it. I think it's probably clear that it's something I really struggle with and grapple with.

Ben Edmunds:
Interesting, I can relate a lot, especially how the anxiety leads to the brute forcing, because I tend to brute force problems as well. I thought for years that my superpower was that I would do the shit work no one else wanted to do, and I would work a 15-hour day, seven days a week and not think twice about it, right, because I was good at that. I just really love what I'm working on when I'm in the middle of it, something I'd rather do, right? Then as I get older, I'm in the 30s now, it's like, oh wow, I'm not a super well rounded person in a lot of ways. I'm just really into tech. In the past several years, I've tried to work on that. Right?

Maia Bittner:
Right. It's like, damn, maybe I don't have to work so hard. When I look at, people are really impressed. They're like, "You did this by this age and that by that age," and all these other things. For sure, I did that and it's very cool, and very interesting, but you have to recognize that it wasn't free, right? I didn't just have the life that my peers had, and also this on top of it. They have to do a whole bunch of cool stuff that I didn't do, right? It's everyone else is doing ... and I was like, I'm working. There's trade offs, right, and in some ways, I feel like now, I'm like, guys, I'm not working that hard anymore. Let's hang out and play board games, and things like that. But now my friends are married and having kids, and they're past that phase of their life as well. I feel like I kind of missed out in this cool part of my 20s. Well, it's a time of life. It's a phase of life, and work goes on forever.

Ben Edmunds:
Yeah, and it's hard to say, was it worth it? Yeah, probably because it gives us a lot more security now than you would have otherwise, but you can't get the time back. Right? Interesting. Let's talk about that a little bit, actually, work life balance. How are you doing that nowadays? Do you try to manage that? Do you just integrate the two? What do you do?

Maia Bittner:
Yeah. That's always been something ... I literally don't understand the question. Work life balance, yeah, implies that there's these contrasting forces? I often think, right, people say, "What would you do if money wasn't a factor?" Things like that, right? If money wasn't a factor, right, I would probably build products with my closest friends. That's what I like to do. I love building stuff. I love getting stuff out there. I think it's so cool watching other people use what you build, and software happens to be the tool set that I have to build things. That's what I would do, and that's what I did with Pinch. I co-founded Pinch with my best friend, Michael Ducker, and we were building things together. Then we sold Pinch to Chime, and now we work together at Chime building things. That's what I would do if money wasn't an issue.

Maia Bittner:
Then Chime also pays me. I'm like, this is amazing. I would be at Chime, even if they didn't pay me, and they give me a salary every two weeks. That's incredible. I really like that. Then I do a bunch of stuff on the side, or what does that mean, right? I'm advising companies and investing in companies, and I do conference talks and things like that. I really love that, too, right? Because it's funny, people will refer to that as work. I don't even know what the definition of work is. What's the definition of work? I sure as hell don't get paid to invest in companies. At least I haven't yet. I don't get paid to be an advisor, so I'm not doing it for money. I'm doing it for ... One, I think people would say that I get somewhat like professional accolades doing that, so maybe that counts as work.

Maia Bittner:
When I was in college, and everyone was not working, I feel like my life was so similar to what it is now, which is that, we were talking about cool ideas. We were talking about the impact we wanted to have on the world. We were building stuff. We were testing the products that our colleagues had built at the college, right? We were iterating and spit balling on ideas. We were white boarding. It's my same life now. The stakes feel higher and everybody's budget is bigger, but, well, I think the stakes feel higher for other people, they don't feel that much higher to me. It kind of all feels the same. It just happens that the numbers are all bigger, and now we're raising millions of dollars to go pursue opportunities instead of scraping together $100 to kick start a project.

Ben Edmunds:
Do you feel your risk tolerance has gotten higher, lower since, I guess, particularly since you'd been acquired by Chime, and now that you're in a day job situation?

Maia Bittner:
It is interesting. It is an interesting question. I feel like the day job situation, it basically, it makes my null hypothesis, or my base case much bigger. If I think about, say, starting a company, right? For a company that I start to pay me the same salary that Chime pays me, it feels like a really hard to reach bar. I could never imagine starting a company that's as successful [crosstalk 00:26:25] as they would need to be to pay me the same salary. Yeah. And so I do think about that, but I don't know if that is a big driver for my decision making, if that makes sense. We don't just live to make money. In fact, in some ways, over time, I feel like I'm a founder at heart. One, I feel like I'm not that great of an employee and I'm not extremely employable. Everyone always asks me, they're like "What do you do? Do you work in products or marketing, or engineering?" I'm like, "I don't understand the question."

Maia Bittner:
I'm not good at living inside of a specific box, I don't think I'm a great employee, I think I'm a mediocre, fine employee. I think I'm a founder at heart, and in some ways, working at Chime doesn't necessarily feel like a contrast to being a founder, it feels like it's giving me the space to catch my breath again, because it is very exhausting to work as a founder, but I just feel like this isn't rational. This isn't a logical pros and cons list, or a way of evaluating it, but just emotionally, I just feel like founding companies is what I have to do. It's what I love and what I'm here to do, and even, I like a lot of stuff about investing. A lot of people have pitched me on being a VC.

Maia Bittner:
Maybe I'll do that at some point, but it's hard to imagine doing that next. It just doesn't feel like that is my calling. It really feels starting companies is, I mean, that's what I really like to do, and not even ... And it's specifically starting companies, it's not even running companies or growing companies. I think hasn't really happened yet, but I think my dream would be to start a company, hire a great team, work towards product market fit, get it to a place where the product resonates and customers like it, and it's providing value, and the thing kind of works. Then honestly, pass it off to someone else to run it and grow it. I really like that first part. It's not like I have grandiose visions of running a billion dollar company necessarily. It's just that I really like the getting things up off the ground stage.

Ben Edmunds:
That's cool. I've always been kind of the opposite. I kind of hate the uncertainty of trying to figure out the product market fit, but I love the day to day of running a stressful startup type environment, right?

Maia Bittner:
Yeah. The running fast and scaling things. Yeah, and I think I do have a higher risk tolerance than most people do. Frankly, the conversation that's happening in my head is, okay, given that I was born this way, or built this way, or broken this way, or whatever, how can I use that for a force of good for the world, right? I have really high risk tolerance. Great. How do we leverage that to do good things? I think what I would like to do is experiment on ways of running companies that are better for employees and team members, and people, because since I have such a high risk tolerance, I'm happy to try things that might fail, but I can also try things that might work out. If it is something that works, then I can evangelize it more broadly outside my company, and hopefully improve the workplace for many more people than I could ever personally hire.

Ben Edmunds:
That's a good segue into, I saw you had done some work with Rocksbox to revamp the hiring process. I felt like there's a lot of issues with our hiring process in tech, especially for engineering.

Maia Bittner:
Yes.

Ben Edmunds:
Tell of your thoughts on that, and what you tried.

Maia Bittner:
Yes, so much. I think engineering hiring is crazy. I think it is crazy what we do. And it's even crazy like, everyone is desperate ... I mean, just one of the things that's crazy. Everyone is desperate for engineers. Everybody wants more engineers. Everyone's like, "We need more engineers. They're so expensive," like duh, it's like whatever.

Maia Bittner:
Okay, but the recruiting, it's brutally ... The candidate experience is so lopsided in favor of the company. Everything is on the company's schedule at a location most convenient for the company in that like it's so one sided. We put these people through these horrible, day long whiteboard interview questions or things like that and then we're like, "Oh, we'll let you know if we're going to give you a job offer or not." It's not a good sales process. I'm like, "God, no wonder you're having trouble hiring engineers.

Maia Bittner:
Who would want to go through that and you have to pay people so much money to basically be put through this awful gauntlet." I don't think that you necessarily ... it's like even not effective. What I did is very much ... I think in an early stage company, you really need to work well with someone, and that that is so much more important than any specific skill set, because it's like people can learn different skills and they can be flexible. You should be hiring someone that can learn new skills, because the world is going to change underneath you.

Maia Bittner:
I was just talking to this guy, Apple just did their WWDC conference or whatever and this guy, he's like, "Hey, the product that I've been working on for three years, Apple just announced that they're doing it. Shit, this is going to kill me."

Ben Edmunds:
Sherlocked.

Maia Bittner:
... The specific instance of bad luck, but this type of thing happens nonstop to startups. COVID as an example. It's like, you can't predict this stuff. It's going to happen. You're going to have to adapt on your feet, and maybe he thought he was building a hardware company, and he needs to build a software company or a community or something else. If he has this whole team of hardware people who can only do that, it's like, you need to totally change what your company looks like in order to react to the world today and in order to be successful. I really focus on hiring people who can learn new things and on their own. I look for resourcefulness.

Maia Bittner:
I look for being able to find experts and garner the resources that you need to be successful at any given new thing. With engineer hiring specifically, I don't look at resumes. What I do is, I have ... For the screening, I have them send me something that they've built. It can be in any form. It can be a zip style code. It can be a repository on GitHub. It can be a website or a [inaudible 00:32:34] or things like that. It can be in different forms. I have them send me something that they've built, I talk to them about that. If that's exciting, then I just invite them to come in and do a project usually like, usually about 10 hours of work over two or three days, and we just build something together.

Maia Bittner:
It's like, let's build something and usually something that ... I try to make it something that is not critical to our company's operations, but that if we build it and if it works I would love to have it. I just see like, do we like working with each other? It's a two way evaluation process. It's, do they like working with me and do I like working with them? Then I make the decision like, if we're both excited about the idea of working together, then we come up with what an employment contract would look like. Obviously, it's only work for super small scale.

Maia Bittner:
There's a ton of reasons why it doesn't expand beyond that. But yeah, I always found ... I think that's one of the reasons that I like being a founder is like, the two things that I really like doing is I like fundraising and I like hiring. They're good skills for an early stage founder, and I really feel like I'm very good at finding the diamond in the rough, or finding candidates that I don't know, like people are like, Maia, how do I find candidates as good as you do?" It's like, "Well, you do every single thing differently and you have to have so much respect for engineers," and I think, frankly, that a lot of businesses and a lot of companies don't really, and they can tell that comes through.

Maia Bittner:
If you don't respect engineers, they can tell. If you think like, "Oh, engineers, they shouldn't have a say on anything, they should just do what we tell them to do and just execute on what we tell them to do." You can hire people like that, but it's like they're not going to be that good and they're going to be quite expensive. If you like respect engineers as people who have good product ideas and good marketing ideas and are more competent full fledged people, one, I think you'll attract really amazing candidates, and I think as an early stage startup, you don't have to pay as much to afford these really great candidates, because you're giving them a workplace that they enjoy.

Ben Edmunds:
I'd love to see more companies experiment with us. The thing I've always hated is interviews are very synchronous, right? You're in a room with someone grilling you, and there's this fake pressure they put on that in no way mimics the real job. If there was that kind of pressure at a real job, I probably wouldn't want the job, right?

Maia Bittner:
Right.

Ben Edmunds:
If there's a lot of people in the room grilling you with programming questions while I'm trying to work during the day, I don't want that.

Maia Bittner:
Right. At Rocksbox, we didn't do it in quite the same way. But we would have like someone come in, and they would just sit down next with our lead engineer and build something together. We had a laptop that had our code base and it was like, "Hey, this is what it would be like to work here." It's like the two of us would be sitting next to each other building this feature together, and you can be like, "Oh, I don't know what this is or how do I find that?" You two can ask questions and have a dialogue, and I can look stuff up and you can look stuff up and we could have ideas and bounce it off each other.

Maia Bittner:
I really think in interviews, people tell you who they are too, and that's my number one piece of advice for founders new to hiring is like, if you're interviewing someone and you're like, they're great in every way and they have this great resume and they just did this one thing that I thought was a little bit odd, but I'm happy, we can excuse the one thing. It's like people on their best behavior in an interview, if they do one thing that's odd, they're going to do that thing. It's like, could you sit in the same room with them for 10 hours every day for the next several years while they're doing that thing because they're going to?

Ben Edmunds:
Great point. 

Ben Edmunds:
Let's change it up a little bit. How did you get started with investing? That seems like a very different skill set from engineering.

Maia Bittner:
Yeah, it is. I am not sure that, yeah, I'm very good at it. But, frankly, Sequoia invited me to be a Sequoia scout in 2016, about four years ago, and that is how I got started is through their generous invitation.

Ben Edmunds:
What does a scout do?

Maia Bittner:
Yes. I choose companies to invest in and Sequoia provides the funds. You can see how it would be much more accessible than it would be otherwise. Frankly, the real value that I have gotten out of the Sequoia program is actually not necessarily the investing piece. But is the process of having to say like, "Oh, can I invest in your company?" You're sort of crossing a line and you're formalizing the relationship. You're shifting it into a different place, and so it's only from being an investor with the Sequoia's help, that I've now also been able to be an advisor, because I have more practice now. It's not just casual coffee meetings and giving advice and things like that, but how to say like, "Hey, I've really loved working with you and I'd be interested in coming on as an advisor if you're interested in that too."

Maia Bittner:
I was very uncomfortable with that before and I didn't know what that would look like. But being able ... like having a practice of saying like, "This is really cool. I want to support you. Is there an opportunity for me to invest?" Doing that has also taught me to ask for advisor shares, which has been really, really valuable.

Ben Edmunds:
What stages are the companies you're investing in?

Maia Bittner:
My bread and butter is participating in seed rounds. I do some earlier. I've been the first check into a couple companies, and then pre-seed and then I occasionally will do an A round. But most often, I'm participating in seed rounds that have a lead investor.

Ben Edmunds:
Cool. How do you find the advising? That has always seemed like probably the sweetest gig in tech with pay versus work, but that might just be my naiveity.

Maia Bittner:
Really? I don't get paid to be an advisor, I get equity. I guess I could be like a consultant or something, but I haven't done that. It's interesting. It reminds me ... It's very similar to being on the board of my college, and it's very new for me and it's very hard for me, because for our earlier conversation, my approach is like, if there's a problem, I will just work hard and working hard will solve the problem, because just no one can understand how hard I will work. As an advisor, you're not working on the company. It's like, being in the board of trustees for my college is problems come up, and I'm almost not allowed to work on them. That is not the context in which the sort of relationship that we have.

Maia Bittner:
I can't just work hard. It's really interesting to be able to be a sounding board and to be able to support people. It reminds me a lot of managing employees frankly, because that sort of this balance of how to have people who are doing what I think is most useful and most productive and most valuable to the company, while also having them do what they find rewarding and fulfilling, and what they think is a good idea, and it's like, where is the overlap there? That's how advising is, is because there are some times when a problem will come up and the company is like, they have a plan and I would never do that plan. It's not really my place to stay I would never do that, because it's not my fucking company. It's their company.

Maia Bittner:
I often say that I'm like, "Look ..." I was on the phone last night with a friend who, oh, he didn't like ... He's a portfolio company and his employees present decks at meetings and he's like, "Can you send me the deck an hour in advance, so they I can review it before we did a meeting?" They were like, "No, I don't want to do that. I want to be able to provide the dialogue and lead you through this narrative process here." He's like, "Yeah, but it's my fucking company and you just have to do what I say." I was like, "Look ..." I was like, "I wouldn't do that. You can do that. That is the value of it being your company is you can lead your company in however you want. You can create whatever type of culture."

Maia Bittner:
If this is a culture where people don't give presentations the way they want to, they give presentations, the way the CEO wants to, that's fine, and there's a bunch of successful companies that have been built like that. I wouldn't personally do that, but it's not my company. It's his company. I told him that and he was like, "Okay." He was like, "Yeah." I'm like, "I appreciate the pushback here," and he's like, "I'll take that into consideration," whatever. I was like, "Yeah, you don't even have to if you don't want to," but that's the kind of funny balance with advising is, it's not my company. and further, I'm often reluctant to give people my thoughts, because I think that starting companies is so hard.

Maia Bittner:
It's like you have to bring your A game. Even if you're bringing your A game, it's still probably not going to work. The worst thing in the world would be to bring your B game, because then it's definitely not going to work. I really think people could only bring their A game if it's their idea and they're 100% bought in, and there's nothing else they would rather be doing and things like that. It's the only way they can bring their A game. Sometimes there's some ... I have really healthy relationships with some companies. There's some companies that I advise that they idolize me, and they're like, "Well, what would you do?" I'm like, "I'm not even going to tell you what I would do.

Maia Bittner:
Because it's not ... You are not my employee, and it's not valuable for you to take marching orders and just go run with that, because you're not going to bring your A game, and like you have to bring your A game, and this is your company to even have a chance of being successful. I can work with you to figure out what the best idea is and what would happen, but I'm not going to tell you what I would do so that you can take that as a to do list item, because that's definitely not going to work.

Ben Edmunds:
All right, so what is the favorite thing you've ever shipped?

Maia Bittner:
Ooh, my favorite thing I've ever shipped? My favorite thing I've ever shipped for sure hands down, Rocksbox cool feature. Actually, I didn't even really ... From an engineering perspective, I didn't write most of the code for this but my team did. What it is, so Rocksbox is a jewelry rental service. You get jewelry in the mail, you wear it around for a while, you send it back. Our customer base is very much on Instagram and jewelry really lends itself to Instagram. It's like it's a visual platform. That's where people are finding cool ideas and falling in love with products and things like that. Rocksbox has an incredible Instagram, with beautiful photos, beautiful jewelry, beautiful girls, the whole side, the whole brand, the whole lifestyle.

Maia Bittner:
All the time people would comment on our photos and they would be like, "I love this necklace. This is the coolest necklace I've ever seen." I was like, "This is where our customer is. This is where our engagement is and our Instagram profile is a huge asset, so let's just consider this an extension of the product. I built this feature that if you commented hashtag wishlist on one of our Instagram photos, you would get the piece of jewelry in that photo in your neck box. It's the same type of thing, I think if you ask ... There's a lot of engineers if you were like, "Oh, can we do this?" They would be like, "No." they're like, "It's too hard.

Maia Bittner:
We don't know what customers have with Instagram handles. We don't know what jewelry is in the photo. We have limitations on our inventory." Engineers can be very narrow minded. I mean and I gave you the whole respect engineers spiel but sometimes they're extremely short sighted when they consider the feasibility of a project. The way that we did this ... so the way that we did this is I was like, "We don't know if it's going to work. We don't know if it's going to have product market fit. We're just going to fucking launch it and figure it out." Because if you just launch it and no one uses it, then it doesn't matter that it doesn't work yet.

Maia Bittner:
If you launch it and people love it, then you have a really big incentive to make it work. When we first of all, I was like, "Just launch it," and I searched through all of our Instagram comments, and I found every time that somebody commented hashtag wishlist, and I looked it up in our customer user base, and I found the customer and I found the item of jewelry, and I built ... The only code that I built for this, the first piece of code that I wrote for this was, just the ability to reserve specific skews for customers if we didn't have. I built that and we did that and it was getting really popular.

Maia Bittner:
I passed it off to our social media manager and he was doing that and that got really popular. Then we hired a team of people in the Philippines to do this work, and build some tools around managing Instagram comments, and finding new comments and things like that. Then we built a tool for our social media team, so that whenever they posted photos, they'd upload photos through our admin site instead of directly on Instagram, they would just comment which skews were in the photos. Then we built a tool so that our customers could add their Instagram handles to their photos, and then we built a tool that automatically DMed people on Instagram, if we didn't have their handle in our database and we couldn't find them.

Maia Bittner:
Then we ... It was only as inspired by the enthusiasm and the adoption that we kept building out tools, until finally at the end of the whole day, like the whole fucking thing is automated and it works flawlessly and people are amazing. I've never seen another company that does something like this. That's a really integrated experienced. People instead they're like, "We have to own it on our platform and our end," whatever. I think this is the coolest feature that exists that you can just be scrolling through your Instagram profile, and you can comment and you get that jewelry in the mail coming up soon.

Maia Bittner:
If you're not a member yet, it sends you like a coupon and says sign up, and then you'll get it in the mail. Favorite feature, yeah, for sure.

Ben Edmunds:
I see a pattern here, where you do things manually and then automate later.

Maia Bittner:
Exactly, yeah. That's kind of the brute force plus the MVP plus the product market fit. It's certainly always like I just gave you a cool story where it worked out. It sure as hell does not always work out and it often doesn't. I did the same thing where people complain about shipping time at Rocksbox. I was like, "I personally I'm going to hand deliver people's boxes the same day they put their return box in the mail. So I did this in San Francisco, particularly the office buildings in downtown San Francisco, I got on an electric bicycle and biked around San Francisco delivering boxes to stores, right?"

Maia Bittner:
I was like, "You're complaining about shipping time, we are going to fix shipping time with brute force." So I did that. People hated it for a bunch of reasons. They had a whole process to get things in the mail with USPS. They do not have a process to accept courier shipments from me. It was too fast. It was all this stuff people hated it, and that's actually how I found that. I was really measuring the wrong KPI, and I think choosing correct KPIs is really important. People complained about shipping time. I made a dashboard, I was like, "Here's our average shipping time, and we need to get this number down as low as possible."

Maia Bittner:
It turns out that looking at average shipping time is not a good representation of the customer experience with their boxes, and with average shipping time what I was doing with the same day shipments in San Francisco is, I took people who had a three day average shipping time and I brought it down to one. Turns out people like having a three day shipping time, they just don't like having a 10 day shipping time. So really the behavior is more of a threshold experience. Instead, I measured ...

Ben Edmunds:
Okay ...

Maia Bittner:
Exactly. So the new KPI was the percentage of shipments that were delivered by four days and that was the real thing to optimize. It's really the long tail experience that mattered. We focused all on the long tail, on that 10 days, on the seven days. We would even if it got too long, we were like, "Your box is taking too long. We don't know why. We're just going to send you a new box. We're going to send you a second box, we're going to overnight it. It's just going to be there, don't worry about it. You'll have two boxes. Enjoy the jewelry, it took too long to get to you. We focused on those people, and that's when we really saw our NPS and our retention and all of our customer happiness metrics go up.

Ben Edmunds:
That's awesome. What are you struggling with right now? This could be personal, it could be work, both.

Maia Bittner:
Yeah, struggling with, I think it's kind of the same, like the same things I'm always struggling with. Part of it is, it's around boundaries and it's around working hard. I feel like I need to go through this transition, where I don't just address everything by working hard. I set boundaries and I say no to some things. It's happened to me on Twitter about this recently that, I think part of the reason that I have gotten here is I say yes to everything. I say yes to every single thing. I do all the things and I've always done all of the things. It's interesting, people are like, "Oh, you're a co-founder at Rocksbox when you're 24," and things like that. But I did things that they wouldn't have done.

Maia Bittner:
When I started, it was a job that all of my friends were like, "I'm too good for this job." They were like, "I'm a product manager at Google, I'm better than this." That eventually ended up being something that they were really interested. I'm like, "Well, it didn't start that way. I did something that you weren't willing to do in order to get there." I think now it's like, basically my whole life strategy which has gotten me everything is no longer the right strategy for the next phase of my life, and that's really a struggle. There's a great book on this.

Maia Bittner:
It's called What Got You Here Won't Get You There. It's basically like, it's more about, it's like the skills that make great insight. Individual contributors don't create great managers and leaders. I'm going through the same thing. I need to start saying no to some things, because I just don't have enough hours in a day, and I'm not being the person I want to be, since I say yes to everything and I don't have enough hours in the day to do everything, I am telling people, I will do things that I don't end up doing. That is the ... I feel like that's not the person I want to be.

Maia Bittner:
I hate that. I really have to change that. The real answer is like, I can't just say, "Oh, yeah, I can help. I can do that. I can do that," because I can't do everything. Saying no to things, I have some crutches that help with that. I think we scheduled this podcast with my assistant and she's so amazing. She settled everything with me. One of the things is that, when other people would ... If I'm like, "Oh, what about Thursday?" They're like, "Oh, it'd be really great if we could do before Thursday. Do you have any time on Tuesday?" I would kill myself to make it work on Tuesday. Doing stuff like, I'm doing phone calls on the bus, in between ... like just kill myself.

Maia Bittner:
But now my assistant she goes, "Unfortunately Maia's quite busy on Tuesday." We don't have to be ... like Wednesday the earliest. It's so funny, I would never advocate for myself in that way, but she does. She's almost teaching me how to set some of those boundaries and how to prioritize things.

Ben Edmunds:
What is your production function? The idea behind this is, what is unique about your, what drives you in the ways you're driven that have enabled you to accomplish what you have and be who you are?

Maia Bittner:
Yeah, I am not familiar with this phrase. But I do think a lot of it is insecurity or particularly being ... I'm pretty un-credentialed. I went to this college that no one has ever heard of, and then I worked at some startup no one's ever heard of and I founded Rocksbox which maybe some people have heard of, and then I founded Pinch which no one has ever heard of. Now, I work at Chime which historically no one's heard of. People are starting to hear about Chime because it's now quite big. But, I'm just an employee there.

Maia Bittner:
I think I feel un-credentialed and that I've always been, the front ideas is like, fuck the establishment and things like that, but I'm kind of insecure about being un-credentialed in that way. I think that that has been a big driver to prove myself that again, that is not that healthy, but here we are. I also think ... I don't know, I feel one of the things about me that has really helped is, I think I'm very smart and I'm very secure in that. But I think everyone else is really smart too and I'm very quick to, if someone says something that doesn't make sense to me, I'm like, "Oh, this must make sense.

Maia Bittner:
It must make sense to them. But I am just not understanding the way in which it makes sense." I'm very quick to take ownership of like, "I don't get this. I am not quick enough to get this." I think people say ... I honestly think it's like a form of respect for other people that a lot of people don't have. I think that's why it's like, people can tell that I respect them and that has brought a lot of good things in my life.

Ben Edmunds:
Awesome. Let's close out with a couple of fun things. Star Wars or Star Trek?

Maia Bittner:
Star Wars but only by happenstance, I don't know. I grew up watching it. I don't think I've ever seen Star Trek.

Ben Edmunds:
Yeah, I think I've seen one of the movies somewhere. Hobbies? What do you do for fun away from the keyboard?

Maia Bittner:
Yeah. I love yoga. I love meditating. I loved reading. I read a lot. I love walking. I know that sounds funny, but I love walking. I love walking around with coffee, I love walking around sometimes playing a podcast, but sometimes just cruising around, and I walk ... Well, historically when I was in cities I walked as like my primary form of transportation. Also my favorite way to spend a Saturday is like walking around, pick up coffee from the coffee shop, walk around the park, walk around the city, kind of do my thing.

Ben Edmunds:
I see that you climb. What kind of climbing do you do? Indoor, outdoor?

Maia Bittner:
Yeah, I do. Sport climbing is the type of climbing that I do. Sport climbing is when either inside or outside, there's bolts in the wall that you can clip quickdraws to and then you clip your rope in as you go up. It's a little bit ... It's like, I feel like it's the less respected form of climbing. Traditional climbing kind of has more respect, which is where there's no bolts in the wall, but you place your own protective anchors as you go up. I like sport climbing because I really love ... I have a very pure love of climbing. I love the act of climbing itself. I don't like all the shit around it. Most people I think like all the shit around. They like getting out into the woods.

Maia Bittner:
They like this, that whatever. I literally, I like the climbing part. I like the problem of how can I move my body in the most efficient, highest leverage way to solve this problem? It's very mental and very intellectual for me. Honestly the reason I like climbing, it's like outdoors over indoors, it's just less crowded, there are fewer people, I can focus more on the problem, stuff like that.

Ben Edmunds:
I know nothing about climbing. Give me an elevator pitch for why I should try it.

Maia Bittner:
Yeah. Like I said, it's very, and you even ... In bouldering, which is when you climb shorter things without rope, it's called bouldering problems, because it's very much about problem solving. What you do is ... so your goal is very clear, it's get to the top right? But there's more and less elegant ways that you could do that. You could brute force it, or you could use angle correctly. What I like about it is, you might try ... you might think ... You kind of look at it and you might think, "Okay, I think I can hang on to that part. What I'm going to try and do is I'm going to try and get my foot up to here, and then push hard on that foot in order to reach this with my left hand, and I'll be pull up on my left hand to do this," and you try that and it just doesn't work, right.

Maia Bittner:
You're like, "Okay, we have to do a totally new plan, totally new plan. Instead of putting my left foot over here, I'm actually going to push it down on my right hand, in order to move my torso up a little bit, so that I can reach this ledge here." You do it totally new approaches, and it's very ... I feel like it's very strategic. Honestly it reminds me of programming. I think a lot of software engineers rock climb, because it's very much the same way. Software engineering, you could solve it. There's more and less elegant ways to solve software engineering problems.

Maia Bittner:
You can always brute force it. Other people might look at it and be like, "Oh, this is a really clever way to do this." It's very fast or it's very concise, and it's the same way with climbing. There's really fast and really concise ways of solving problems, or there's really ugly and messy ways and it depends, it's like a combination of what you're working with, what you're trying to do, your skill level, your specific experiences, all that. It's very rude to give someone unsolicited advice in climbing culture. Instead what you do is, you ask people in advance.

Maia Bittner:
You might see them struggling, you ask them like, "Do you want to just figure this out on your own or do you want me to give you a hint on how to solve this?" Honestly, I wish we had the same thing in software engineering like, "Hey, it seems like you're really struggling to get this done, and it's kind of like failing this test. Do you want a hint or do you want to figure this out on your own?"

Ben Edmunds:
We definitely need that. Nice. All right. What games, video games, board games do you play?

Maia Bittner:
Love board games. I love card games. Love board games. I really like card games. Really like collaborative games, my favorite game hands down as Hanabi. I've played it like thousands of hours in my life. Hanabi is a collaborative game. You either all win together as a team or you all lose. Basically you hold your cards facing away from you. You don't know what card you have in your hand, you really depend on everyone else in your team in order to guide you and lead you to the right direction so you know what cards to play, because you don't even know what you're holding. But you can also kind of remember stuff, so I love Hanabi. I'm obsessed with Hanabi. I love that it's an exercise in how well can we work together as a team to achieve this shared goal, that's also really, really, really, really hard.

Ben Edmunds:
What books have you read or listened to recently that you'd recommend?

Maia Bittner:
Yeah, so ... Well, I love ... This is going to be, this is going to be a weird one. Just from finishing this book called Ada Blackjack that I loved. It's not ... this is not business or investing or neuroscience or any normal recommendations, but basically I was looking at ... Well, I was looking at National Geographic [inaudible 00:59:00] exploratory cruises and I was, "This looks amazing." There's this one that goes from Alaska to Norway, over the top of Russia and I was like, "It's incredible." I was looking at the path there and it stopped by ... there's an island called Wrangel Island that has the highest density of polar bear nurseries in the world. It's full of polar bears, this crazy Island north of Siberia.

Maia Bittner:
Then I got really interested in Wrangel Island, I was researching that. Then I found out about Ada Blackjack to she went on this expedition in the 1920s with four guys to Wrangel Island and they all die, and she survives by herself on the island. She was there for two years before she got rescued. It's an incredible book that it feels like fiction, but it happens to be nonfiction. It's like really, really interesting. One of the things that it just, it takes place 100 years ago and so many things felt similar to today, like the fake news thing. That was very prevalent 100 years ago, when it was hard to fact check things.

Maia Bittner:
Even the way they talk about ... They were explorers, and the way they talk about explorers reminds me of how we talk about founders today, and how ... It's like this interesting thing like, these guys were going to Wrangel Island, so they announced that they were going to Wrangel Island, and they were instant celebrities before they had even done anything, they hadn't done shit. They were just about to get on the boat to get there, and the press want to interview them and everything.

Maia Bittner:
It's the same thing today with founders, you cannot do anything but you can be a startup founder and people are interested, and they think it's cool, and they think it's high status. There's this weird societal interest in it, even if you haven't done anything. I think exploring was the same way. I think ... And it's funny because the explorers also talk about, they're unfit or unsuitable for any other occupation besides exploring things. It was just like always their drive is like what is the next expedition? What is the next place to explore?

Ben Edmunds:
Awesome. I'll have to check that out. That sounds really cool. I've also seen you mentioned Taleb's books in the past. I wanted to call that out because I believe his writing has probably influenced my day-to-day thinking more than just about anyone else. Anyone that hasn't read him... I love it. What are your thoughts on his writing?

Maia Bittner:
Yeah, obsessed with himself, maybe off the deep end a little bit, but I think ...

Ben Edmunds:
He writes like such an asshole. I kind of hate recommending it because it just ... His writing style or just his ego, I don't know.

Maia Bittner:
I feel like it reads poorly but I love it. I feel like I read Black Swan and I was like, "This is what I have been thinking my entire life." That people, I have a lot of criticisms around ... I also really like this book called The Mismeasure of Man, which talks about how we're always trying to measure how good people are, or how smart they are or how ... You just can't do it, and I'm just like ... Oh, every time I go to a doctor's office, they measure my blood pressure. It drives me nuts. It cannot be that important. I don't understand how this is about my blood pressure. I don't know. I think that I've thought forever that we have a tendency to hyper focus on the stuff that is easiest to measure, not the stuff that is most important.

Maia Bittner:
I feel like he really gets at that with Black Swan. I think it makes people feel fundamentally uncomfortable to be like, the stuff that is going to have the biggest impact, we can't predict. We can't control. Instead, we have to be adaptable and get more information and change on the go. But yeah, it's stuff that I've thought for a long time, so when I read his book, I was like, "Oh, my God, this is everything." I think being really conscious of ... You should optimize for the most important thing regardless of how easy it is to measure that. I think that's really, really important. You can have your whole thing. I think weight is a similar one. People use weight as a measure of health, but I think just because it's really easy to measure.

Ben Edmunds:
Yeah, totally agree. I think Skin in the Game is probably the one I find myself referencing the most often, both to myself as like how do you determine who to listen to? And then also to other people, and just about, how do you give good opinions, how do you give good feedback? You just can't do a good job of that unless you actually have skin in the game, so you need to ... If you want to have an opinion, you need to make sure you have skin in the game somehow, get involved.

Maia Bittner:
My friend sent that to me after I read Black Swan, he was like, "This is awesome. You're going to love it," but I haven't read it yet, so thank you for the recommendation because I need to read it.

Ben Edmunds:
Do it. All right. Thank you for your time Maia. This was just amazing conversation.

Maia Bittner:
This was so fun. It was great to jam with you.