New Podcast Release: Cyan Banister

In the latest episode of Lives Well Lived, the podcast I co-host with Kasia de Lazari-Radek, we speak with angel investor, technologist, and unconventional thinker Cyan Banister.

Cyan’s life defies the usual arc of success. Raised on a Navajo reservation and homeless as a teenager, she is now one of Silicon Valley’s most distinctive investors, with early bets on companies like SpaceX and Uber, and a commitment to backing people and ideas that change the world.

In this conversation, we explore how Cyan’s early experiences of isolation and poverty shaped her outlook, her views on education and self-directed learning, and how sleeping under her desk prepared her for a career in tech. She explains why she doesn’t believe in “impact investing” as a label, and why she invests based on long-term social transformation rather than short-term metrics.

We also discuss her unusual daily thought experiment, “everything is my fault,” and how radical accountability and love drive her philosophy for living well.

Below are some highlights from our conversation, edited for clarity. You can listen to the full episode on Apple Podcasts, Spotify, or your preferred platform.

On her extraordinary start in life

PETER SINGER: So, you grew up on a Navajo reservation, as I understand. Although you are white and you've spoken openly about your difficult early life, including periods of homelessness. Can you tell us something about that and about how those experiences shaped your sense of purpose and your understanding of what it means to live well?

CYAN BANISTER: Growing up on the Navajo reservation was an incredibly unique experience, and one I wouldn't trade for anything. I got to feel what it’s like to be isolated, to be other, to be alone. But I also got to discover myself through that process, what I really care about and what drives me.

I also got to see the beauty of a culture that a lot of people don't get to see. I experienced it and lived in it. On the reservation, we had one movie theatre that played the same movie for a month. We had one grocery store. We actually had an interesting amount of fast food, which is unfortunate for a variety of reasons, but most of the landscape was just vast desert and tumbleweeds, basically small animals and things like that.

You really have to use your imagination a lot. I think those early formative years really shaped what drives me, which is curiosity about all things. When you don’t have distractions like movies or TikTok, you can really ponder life's mysteries. Later in life, I experienced a period of homelessness as a teenager. I look at that as a blessing. It was a time in my life when I learned to become resourceful, when I learned what friendships are.

To this day, I always joke that you can't take the homeless out of a person. It’s very true. I see resourcefulness wherever I go. I see opportunity wherever I go. I think it's made me a better investor. It's given me more empathy for other people and a better understanding of how others might live in the world.

KASIA DE LAZARI RADEK: But it seems to me that you are still a rare example. Not many people who graduate from only eight classes or were once homeless end up with a life like yours. What do you think are the special characteristics that allowed you to develop into such an amazing life?

CYAN BANISTER: That's a very good question. I've examined this a lot because I get asked it often. Statistically speaking, I shouldn't even be here. I'm an investor in startup companies, but when I was younger, I didn't think I would live past 30 years old.

I took one day at a time. The next day was all that mattered. It wasn’t until I had the foundations of a home, a roof, some kind of income, the ability to go to the grocery store and not have to count up everything to make sure I could pay for it, that I was able to start dreaming ahead. Once those basic needs were met, I could start planning for the future. That was something new for me: thinking about what I could do next week, next month. I don't think I really started thinking about the future until I was in my mid-twenties.

I think what got me here was being present. You have to realise what's in front of you, what you have, and what you can do with it. You have to apply that to your everyday life. You have no other choice. And you have to be optimistic. Even though I thought I wouldn’t live past 30, I didn’t take things too seriously. I didn’t let them weigh on me. I didn’t ruminate about the past, because the past didn’t matter. Every day was a new day.

And then there were really remarkable people who stepped in at just the right time. I can’t tell you how many people recognised that I had abilities I didn’t even see in myself and helped nurture them. When we look in the mirror, we often don’t truly see ourselves because we’re looking through the lens of our ego. So I really credit the world around me and the people who saw the things I couldn’t.

On education and self-directed learning

PETER SINGER: So can I ask you about those abilities that you had and that you didn't see in yourself? You studied up to eighth grade in school before leaving, right? How were you as a student? Were you keen to learn? Did you do well?

CYAN BANISTER: I technically dropped out at the beginning of the tenth grade. I say I have an eighth-grade education because I stopped paying attention after that point. I realised I was in daycare, experiencing childcare by the state. Everything I wanted to learn was outside of school, not in it.

I would ask questions that were too challenging for teachers, and they didn’t want to answer. So I started realising that if I wanted to learn anything, there were libraries, there were grownups around, there were businesses I could study. I could ask questions about how the world worked instead of relying on a school system that was really failing me and everybody else.

I didn’t enjoy school. Early in life, I definitely did. I had some remarkable teachers that really impacted me, I can name three. But once I got older, I felt we were just doing busy work. We were constantly memorising things without understanding why we were learning them or how they applied to the real world.

I would always ask people: How is this going to help me with my life? How is this going to improve the conditions that I’m in currently? No one had an answer. I would ask about geometry or anything else, and no one could give me a concrete answer.

So I decided to take my education into my own hands and pursue my passions and dreams. I’d go to the library and check out books, or just sit there and read them. I love to quiz people. I love to ask questions. I’d ask questions of anybody who looked remotely interested in answering.

I think I’m just very inquisitive and curious, and that was very helpful. If you can learn how to learn, that’s the most important gift you can give a child. Somehow I picked that up, or someone taught it to me early on, and that’s carried me through even today.

The book that changed her life and career

PETER SINGER: So, when you were reading the tech manuals, were you actually working for a firm in coding or computing?

CYAN BANISTER: Yes. My very first tech job was actually one of the first miracles in my life. I was working at an internet service provider, my friends coached me on how to get the job, doing dial-up tech support. While I was doing tech support, I would register domain names, which at the time were free.

I probably registered thousands of them. At some point, they started costing around $70. These mail bags of domain renewals were showing up at my work, and I couldn’t pay for them. I had to pick one or two.

One day my boss came over and threw a book in my lap. He said, “If you didn’t waste all your time registering domain names all day, you might actually make something of yourself if you read this book.” I thought he was crazy and just let it sit there, collecting dust.

Eventually, I opened it, tried some things, and figured out how to change my boss’s password on the Unix operating system we were using. I came in and handed it to him and said, “This book is amazing. Here’s your new password.”

He said, “That’s impossible.” I told him, “No, it’s really possible. Try logging in.”

Most people, when confronted with something like that from an employee, would fire them. But he said, “Grab your seat, sit next to me. You’re now my padawan. I’m taking you under my wing. You’re a junior system administrator.”

Once I unlocked that cheat code, I was insatiable. I read every manual I could get my hands on. That one book took me from an $8/hour job to $13/hour. O’Reilly books were my go-to. Tim O’Reilly published these amazing books about anything you could think of in the early internet world.

Eventually, I decided to go into security, to stop bad people from exploiting others. I started studying fraud, phishing, malware, spam. I landed a job at an email service provider, and eventually at IronPort Systems around 2003 or 2004.

I left in 2007. I was employee number 30-ish. Instead of raises in cash, I took equity, I loved the company and the leadership. We sold to Cisco for $830 million. That was my first financial windfall.

I asked everyone I knew: Should I buy real estate? Stocks? Gold? My friends said, “You’re young. You have a safety net. Take risks.” I’m not risk-averse because of my background. I take risks others wouldn’t, and it’s paid off. Great risk, great reward.

So I put all the money I made at IronPort into startups. My first investment? SpaceX. At the time, it looked really stupid; they were blowing up rockets on the launchpad. People ridiculed me. I said, “Set it and forget it.”

I learned a valuable lesson: Don’t watch your investments day to day. If it causes anxiety, you shouldn’t be in the game, unless you’re a day trader. I treated it like I threw that money away. It worked out, but not for a long time. Eventually, people saw it as a credible investment. That’s when I started doing angel investing.

On living with mortality in mind

PETER SINGER: I know you've spoken before about your awareness of mortality and how it's shaped your decisions. Can you tell us a bit more about that?

CYAN BANISTER: I always thought I would die young. As I mentioned, I never thought I'd live past 30. So I lived urgently. I tried to do everything I could each day, because I wasn’t sure I’d get another.

That sense of mortality gave me clarity. I think a lot of people live like they have unlimited time, and they end up putting things off, important conversations, risks worth taking, dreams worth chasing. I couldn’t afford that mindset.

Even now, with more stability in my life, I try to make choices that reflect the fact that I won’t live forever. I think a lot about legacy, not in the ego-driven sense, but in the sense of impact. Did I help someone? Did I make something better than I found it? Those are the questions I ask.

I also think being comfortable with mortality frees you. You're not paralysed by fear. You're not hoarding experiences or possessions. You're focused on what matters. And for me, that’s love, curiosity, kindness, and the ability to make things better in some small way.

On redefining philanthropy and social impact

PETER SINGER: Let’s talk now about the ethics behind your work. You’ve spoken about working with nonprofits, and also investing in companies with social benefit. How do you think about your role as a philanthropist or social investor?

CYAN BANISTER: I love social enterprises and would love to invest in more. However, I take a different view from many who use the term "impact investor." I think that phrase can sometimes be a marketing trick.

A lot of the investments I've made, at the time I made them, I believed they would make the world better. That might not be obvious on the surface. Take Postmates, for example. You could say, how is delivering a sandwich helping the world? Isn't it just putting more cars on the road?

But I met people whose lives it changed: single parents, people undergoing chemotherapy, college students, people who needed flexible work. It gave them options. It created new types of jobs and economic freedom.

I always try to think long-term. If I invest in something today, where will this technology end up in ten years? What will it make possible that we can't imagine now?

Of course, social enterprises like Newman's Own are different, and I’d love to find more founders who build that kind of mission into the core of what they’re doing. But for me, even marketplace platforms like Uber or Airbnb, controversial as they can be, can have positive impact when you think about access, autonomy, and underutilised assets.

It's interesting because you can look at it both ways, right?

Her personal philosophy: ‘Everything is my fault’

KASIA DE LAZARI-RADEK: You mentioned responsibility, and I found it really interesting that you're working on a kind of theory about being responsible for everything, saying "it's my fault." Could you explain what that means and how you practise it?

CYAN BANISTER: Every day when I wake up, I try to run a little thought experiment. One that I'm working on now is the idea that everything is my fault. It’s been incredibly helpful.

Now, when people hear that, they often jump in to say, “Oh no, it's not your fault,” or they try to absolve you. But that’s not what this is about. It’s not about blame. It’s about figuring out what role I played in getting to this moment.

Say I have a co-worker who’s behaving immaturely. Instead of just blaming them, I ask: why am I in business with them? What am I choosing to tolerate? Why am I still here, getting irritated?

Once I take responsibility, the irritation disappears. Then I can deal with the situation more clearly, and with love. That’s the goal: to get to love as fast as possible in every situation.

So I ask, how is this my fault? And I usually come up with ten or fifteen ways it is. That shifts everything. It stops me from externalising problems. I’m choosing to be here, choosing to be annoyed that’s on me. And once you see that, you can act from a place of love, not blame.