Maia is an entrepreneur, investor, and start-up advisor. She co-founded two companies and now does Business Operations at Chime, who acquired her last company, Pinch. She graduated from the Olin College of Engineering and taught herself HTML so that she could spice up her eBay listings in high school. Here’s her story!
What is the current role or passion project that you find yourself working on?
I work at Chime, which is a neo-bank. We have a debit card with a checking account, savings account, no branches and no fees. Then on the side, I advise and invest in early stage startups. I’m focused on a couple of different things in that regard.
I really love the “zero-to-one” phase of a company, so my number one thing is helping people work towards product market fit. I particularly enjoy coming up with what is the cheapest and fastest way to hack some systems together and see if there is a spark of delight in someone’s target customer base.
I also have this scrappy approach of doing things cheap and fast. And I help startups apply it to hiring, to funding their company, and a bunch of different ways. It’s an overarching strategy that I have towards different projects in life.
To go back in time for a second, I got here by selling my last company, Pinch, to Chime. At Pinch, we were reporting rent payments to the credit bureaus so that people could build their credit score simply by paying their rent.
Could you give us an idea of how you got to where you are now?
eBay came out when I was in high school and it was really, really exciting. This was actually before Paypal, so the way eBay worked is you would sell something in an auction, and then someone would mail you a money order or cash in the mail and you’d wait until you got it. Then, after you got it, you would mail them the item. And I was absolutely enthralled because I realized that you could make money on the internet. And that’s what I wanted to do with my life. It was incredible. I started by selling stuff that I bought at garage sales or goodwill, and I really kind of developed a big business here and specialized in a couple of different things.
This is actually how I learned HTML, because I wanted to make my eBay listings look as good as possible. I also learned a lot about customer service, auction mentality, how to create listings that appeal to people and a bunch of cool stuff like that.
So that was my high school. I didn’t like school itself and I always kind of chafed at the structure of it. And I didn’t really want to go to college because I thought formalized education was broken. I thought it was very expensive, and I thought I could just learn more on my own. I wanted to try a couple of different things, and just teach myself as much as I could.
But, I was worried that if I didn’t go to college, that people would think that I wasn’t smart. And so I said, I’ll get into Harvard, Stanford, and MIT and then not go to college. But then everyone will know that I’m smart, but I won’t have to pay for college. And that was my plan.
I started getting these glossy college brochures in the mail, and I got them from other colleges and kind of ignored them all. Then I got one that looked really different. It was shipped in an electrostatic bag, like the ones computer parts are shipped in, and you take it out and it’s got duct tape on the cover and it had like coffee stains and stuff Sharpied out. It looked very different, design-wise, from all the glossy college brochures, and on the cover it said, “What’s the one thing cooler than getting into Harvard, Stanford and MIT?” And I thought, “Shit, how do these guys know my plan? What is the one thing cooler?” Then I open it up and it says, “Turning them all down to help build the Olin College of Engineering.”
And then it said, “We think formalized education is broken. So we decided to try and fix it and we created a school that doesn’t charge tuition. It doesn’t have departments. It doesn’t have tenure. We have this new form of grading,” and it was this whole thing. So I decided to go to Olin because it was free, and because I thought that these people are aligned with me. They also think education is broken. They’re working to make it better. It feels more productive to actually work on making it better than to just sort of abandon the whole system. So I went to Olin College.
After my first year at Olin, I got an internship at a startup in San Francisco, and I loved it so much. It was incredible and I decided this was exactly what I wanted to do with my life. I dropped out of Olin and became the director of marketing at this startup. So I was like 18 years old, and just a child, but it was amazing. I had a team of four people and this big budget, and I was in charge of all the signups for the website. Then I switched to being a product manager at a different company and – I’m really kind of a control freak. I started out marketing and I was like, it’d be so much easier to get people to sign up for the website if the website didn’t suck. So then I went to product management and I still didn’t have enough control so I went back to school and became a software engineer. So I finally graduated from Olin and then I came out to San Francisco.
When I moved to San Francisco I was in bad shape. I had been in a car accident and I was having a terrible time. I got this job that was kind of awful, as a software engineering consultant and I just didn’t know what to do with my life. So I applied to this grad school in Copenhagen and as soon as I got in, I quit my job and I said, “I’m going to grad school in Copenhagen.”
School doesn’t start the week after you get the acceptance letter, it starts like six months later. But I quit my job and they said, “Cool, send a postcard from Copenhagen! Bon voyage.” I quickly realized that I needed a new gig to fill my time for the next couple of months until I went to grad school. So I told every single person I met, “Hey, my name is Maia. I’m looking for a job.” And this one guy was in my kitchen one morning eating breakfast—he had come over the night before with my roommate—and I was like, “Hey, my name is Maia. I’m looking for a job.” He told me I had to meet his friend Meaghan who’s starting a company.
So I met Meaghan. We met for coffee for half an hour at a coffee shop, and then she hired me as the first employee of her new company, Rocksbox, which is a jewelry rental company. Then we loved working together, so I didn’t go to grad school. She invited me to join on as a co-founder and CTO of Rocksbox. I loved getting Rocksbox off the ground. It felt really amazing to build a product that people loved so much. As a CTO, which is a fancy title for being the only engineer, I built our website, which was pretty straight forward, but then I also built our internal admin site, which was much more complicated.
That’s when I really started to fall in love with operations. It was my experiences working with people’s credit cards and information at Rocksbox that got me really interested in people’s financial health. From there I thought, “Wow, there’s a huge problem with American financial stability and managing cash flow.” And this is something that’s hard for people to do, but much easier for computers to do. Then I thought maybe I should start a company that addresses this. So I started Pinch and that lead me to Chime!
What does growth mean to you?
Growth is about changing myself so that the impact I’m having on the world is what I want it to be. I think that’s the shortest definition, but I think underlying that definition, there are so many different pieces.
One piece is simply knowing what impact I’m having on the world, and I think people are often really blind to that. For me, it’s required a lot of dedicated work, self-discovery and being self critical about what’s happening. I also try to see things with objective eyes in order to figure out the impact I’m having on the world.
I think figuring out what impact you want to make on the world is a ton of work. It requires being deliberate and trying to imagine how I want the world to be different than it is today and how I want to get there. And then figuring out, given the differences in impact I want to have and the impact that I’m having, what the right path to closing that difference is. And then actually doing that. There’s so much underlying that short statement that builds up the pieces and turns it into quite a big project.
Do you have a self care routine that you’ve found to be particularly helpful or effective?
Yes, I have a couple. One of my indulgences—and this is kind of funny, because I talk about being self aware and I didn’t actually realize this until a guy I was dating pointed it out to me. But whenever I’m really stressed out, what I’m inclined to do is go on a really long walk.
So much of my life is about optimizing and about being super efficient and super fast. And so when I’m really stressed out, what I’ll do is look on Yelp for what’s the best cafe in town or the best whatever, and then I will walk there, even if it’s several miles away. It feels great to do something that isn’t efficient and optimized. It’s just walking to the other side of town, and that feels like a cool release for me. And then I get to go to a cool cafe and relax, which I like.
On top of that, the process of walking is helpful for me to work through stress. It’s almost like walking it off, you know? I don’t think about anything for 10 minutes as I just sort of walk and notice my surroundings, the birds, the trees and whatever. Then I can come back to the thing that’s stressing me out and work through it. Then I can stop thinking about it, again and just keep walking a little bit. It’s a really nice on and off experience.
Walking is an instinctual thing that I do when I’m stressed out, but another thing that’s not instinctual, at all, but is always super helpful is writing. So when I’m stressed out about an emotional problem, I’ll journal. Writing through my feelings and writing it down is enormously helpful for lifting that weight off my shoulders.
It works 100% of the time. But it’s never my instinct and I almost have to force myself to do it. Every time I’m like, “I don’t want to do this. It’s not going to help it all.” And every time, it does help, but it’s just not natural for me. So for emotional stress, journaling is helpful, but then even if I just have a ton to do, writing down all the things I have to do and getting it down on paper, also relieves that stress. If I have a really gnarly problem at work, I’ll sit and write out whatever it is, like a product spec or a new policy or whatever. It’s so effective and so helpful for me in terms of both problem-solving itself and then grappling with the stress that results from problems like this.
If you could say one thing to our readers, what would it be?
My number one thing is to encourage people to be really honest about what motivates them and what they’re trying to get out of an experience. Frankly, I think that for a lot of people, their motivation is to feel like a whole person who is valued in the world and who deserves to exist. It’s kind of weird and kind of heavy, but I think that for a lot of people that’s why they’re out there hustling and working so hard. And that’s fine, but I think doing that inner work to figure out why you’re working so hard is really helpful in order to make sure you’re accomplishing your goals and being strategic about where you’re putting your effort.
I think sometimes people start companies or do things because they want to be rich. Often times, they don’t say that because it’s not an approved thing; it’s seen as sort of shameful. But I think if that’s true, they should be honest with themselves and own that, because it will affect your decision making in a way that’s more likely to result in you being happy.
The second thing with being rich specifically, is I think oftentimes people think they want to be rich, and that’s not actually what they’re looking for. They’re actually looking for that acceptance that I was talking about, they’re looking for freedom, they’re looking for other things like status, or they want to be admired by their peers.
Being clear about the why behind your goals is really important, because I think as I’ve gone through my career, I made all these decisions where there’s usually not an obvious right answer. I’ve had to be really honest with myself and not ashamed about what my objectives are.
Focusing on that has been really helpful for me, so my number one generic piece of advice for people is to really be curious about what is driving them, and be honest and not ashamed. Because I think sometimes if you’re ashamed then you don’t actually get what you want and then nobody’s happy, you know?