For Maia Bittner, the daughter of “hippies,” her love for technology started with eBay. And it didn’t hurt it that she found out what that e-commerce site was when she was an 11-year-old living in “the middle of nowhere” Washington State.

She would buy video games from garage sales, then auction those same discs off on eBay for a profit.

“I was like, literally, strangers are sending me money in the mail,” she told Crunchbase News over the phone. She loved the concept of mail so much that she would’ve made “a career out of it.” Fast forward two decades and a move to the Bay area, Bittner resorted to founding her own company: Pinch.

Pinch helps apartment renters that pay their rent on time boost their credit score, and it was acquired by Chime in 2018. She’s currently still working with Chime and invests as a Sequoia Scout.

In this Proust Goes Tech, we learn about Bittner’s favorite neighborhood in San Francisco, the lunatic behind her favorite novel, and what she wishes she knew in her 20s.

The interview has been edited for brevity and clarity.



What would you otherwise be doing right now?

I would be a tour guide. I love giving walking tours of different neighborhoods in San Francisco or New York; I feel so alive. I think half my time my friends are indulging me, and the other half of the time they are actually interested.

I love Western Addition in San Francisco. It has a mixed energy with all this different industry. The neighborhood is known for sushi and jazz music, and I love the physicality of its history: the history is a little yucky and sometimes not sugar-coated.

Your main fault?

I’m not very good at working with other people at a peer level. I’m good at reporting to people above me and working with people below me. While collaborating on a peer level, I tend to discount my own opinions and feel insecure in what I think. It makes my partnerships not as strong, and I think it comes across in work, very obviously in romantic relationships, and in friendships. I think there’s this balance between preserving myself and what I want and not wanting to disappoint other people.

Your idea of misery?

When I can’t make progress on a problem to move forward. Any time when I don’t know the next step, I fall into despair.

What do you appreciate the most in your friends?

I know this is going to sound snotty, but there’s a lot of people really look up to me, and I’m not into that. I’m so human. It’s my friends who push that have been the most valuable to me.

I have one friend that always asks, “Can I ask you a provocative question?” And I’m always like, yes. And then it’s always an interesting question. And I’m like shit. Yes. Yes. Please send all provocative questions. Always.

Your chief characteristic?

Curiosity. I’m really endlessly, and so certainly, curious. I always kind of want to pick apart stuff and unravel it.



What’s a skill you wish you possessed?

I wish I was better at connecting with people. I feel like that is not a strong suit of mine. But Twitter has helped me with that, weirdly.

My Twitter is very vulnerable and in a pretty performative way. So there’s energy, and it’s entertaining. But then I’ll get coffee with someone I meet from Twitter, and they’ll kind of ask for me to tell them a funny joke. Or an off-the-cuff interesting metaphor. But I think really slowly. So I tell them, most of the time, I am quiet or reading or something.

The quality you most desire in a tweet?

I love Twitter because it feels like a non-stop new idea dopamine rush. Like, is this new? Is it plausible and interesting? I feel like there’s an infinite number of new ideas and new ways of seeing the world.

Your most impactful book?

“The Black Swan” by Nassim Nicholas Taleb. He’s a lunatic. He kind of barely pulled it together to write this book. It is about our propensity to try and predict.

What defines success?

Success, and for what I’m optimizing for at every turn, is the freedom and ability to work on things that I’m going to work on.

For, like, all of my 20s I basically didn’t think about impact as a form of success. I was, you know, proud of the work that I was doing in the way that I was going about it. I’m 31 now, and wish I thought about that sooner.

When is confidence lost?

I would say confidence is lost with inconsistency. Or it’s when confidence in leaders and organization goes back and forth a bunch and nothing makes sense. Sometimes, it’s better to know the path you’re on and stay on the path versus switching between different paths.

Which buzzword is exhausted?

I like buzzwords!

I think when somebody says they have an AI startup, what they’re trying to say is, “I’m creating something really valuable here; it is really important to us. And I want to be associated with this class of extremely data-driven startups who are investing in this infrastructure and focusing on it from day one.”

What virtues do others have that you don’t?

I’m a little gossipy; I wish I was more firm. I can’t imagine saying, “I can’t tell you that.” I’ll always answer questions. I would be the easiest person to interrogate in the world.

What impact do you want to leave behind?

I really like entrepreneurship and seeing people carve their own way into the world. I would love to encourage more people to do that.

What is one problem tech is failing to solve?

I think there’s a bunch of problems, and tech shouldn’t solve all of them. But I think one of the things it affects, but it’s kind of ignored, is that tech has an opportunity for a really big impact on culture.

But the cultural impact of tech people has been hoodies and ugly shoes, you know, and it could have been empowering employees of an organization or bringing inclusion.

But tech is not leveraging all that. It’s just like, oh, yeah, hoodies are cool. Like, that’s what’s done with its power.