Stride Stories: Don't forget to change the world for the better

Stride: Randy, you grew up in New York and went to Yale to study history. Did people try to dissuade you from that study?

Randy: History is one of the most impractical majors out there, but no one did [laughs]. Yale can be an unhelpfully supportive place - people will encourage your passion no matter how impractical it is. I’m one of the lucky humanities majors that has skipped the job market meat grinder.

Stride: After school did you know what you wanted to do right away?

Randy: While in school, I decided the purpose of my life was to maximize the happiness of others. My ideal profession was to be a billionaire philanthropist, but I wasn’t sure I could make those billions on my own. The next best thing would be investing somebody else’s billions, and I thought I could do that at a large philanthropic foundation.

Stride: The concept of maximizing others’ happiness, or at least stating that as your life purpose, is pretty unique. Were there events that led you to that ethos?

Randy: It was always a part of me. When I was younger, I would get annoyed when people said they wanted to change the world and forgot to add “for the better,” which is the crucial part [laughs]. Maximizing happiness was fostered by my upbringing as a Quaker and its key principle of everyone being equal. The most emotional thing that prioritized altruism was losing my aunt – she was only 25, and she took her own life. Seeing my mom in the wake of that, sobbing nonstop at our kitchen table, made me realize how much our happiness is dependent on other people’s happiness. If one person is tragically unhappy that will hurt everyone.

Stride: I’m familiar with Quakerism, but haven’t studied it. Can you tell us how it affects your values.

Randy: Well, we consider oatmeal a sacrament [laughs]. Kidding. The way I think about the core of Quakerism is the idea that we each contain an inner light – whatever it is that’s divine in this world is contained within each and every human in equal measure. The root of Quakerism is that everybody ought to be tolerated and treated with equal respect. Pacifism is big, you shouldn’t kill anybody; also consensus, you’re not supposed to override a bunch of people, since we all have this inner light pointing us in the right direction. The way to reframe it outside of religion is a profound respect for the human conscience – it is the good that needs to be served above all else.

Stride: Fascinating. After graduating as a history major you went to a big consulting firm. How did that help you along your path?

Randy: Out of school I was a pretty sheltered, theoretical person. I needed a boot camp to expose me to all the real stuff in the world. Consulting threw me into situations in which I had no expertise, where I would have to figure it out or perish, and that’s the best way to learn. For someone like me with a fuzzy head coming out of undergrad, it was a perfect place to get those hard skills.

Stride: Then 2 years after you got your dream job at a large philanthropic foundation?

Randy: Yes. This was where I wanted to end up my whole college career. When I showed up, I thought, this is it, I’ve arrived [laughs]! The foundation is an amazing place doing an incredible amount of good for the world, but it’s like a large grandfather clock. It tolls very loudly, it has a lot of cogs that fit together intricately, and it runs all the time. I wanted to work someplace that was like a wristwatch, where my contributions would be of greater weight. There had to be a role where I could be one of the only people that could do it very well.

Stride: Ultimately that experience pushed you to the Stanford business school, to learn how you might better fit within an organization. How do your ideals differ from your classmates?

Randy: If I had to point to one area where I feel some difference it’s the relative importance of strangers. Most of us have an instinctive bond with our family and immediate friends and trust they are the most important people in the world… and I’m like that too. But, I don’t think those people are intrinsically more worthwhile than anyone else. When I force myself to consider the needs of 1,000 strangers in developing countries against the needs of one person I know here, I have to admit intellectually those thousand people are far more important.

Failure of moral imagination is the biggest issue facing our generation – we grew up in a time when none of us would have stolen a CD, but we all stole music from the internet. That felt different, but it was actually the same thing – just because something is physically removed from you doesn’t make it any less of a crime. It’s the same thing with helping people. We feel like we’re helping when someone is right in front of us; we don’t feel like we’re helping when we send cash to Subsaharan Africa. But we’re actually doing far more help with the latter. I’m not sure what I can do to help get us past the “Girl Scout Effect,” the feeling that you’ve done your charitable duty by giving $5 to the adorable little girl on your doorstep, when 20 adorable little girls could’ve used that $5 to buy a new roof for their house in Kenya. It’s helping 20 people in Africa the same amount you’d help one person here with the same amount of your resources. This is what I’m most concerned about in life.

Stride: Do you ultimately hope to start your own company that addresses these issues?

Randy: I’m agnostic to whether I create or join something. What I’m thinking about right now is how to create a better platform for charitable donations – finding a better way for people not to just give money, but to give money to the highest impact things. The movement around this idea is called “effective altruism,” and I’d love to make some kind of contribution.

Stride: Where would you improve on what’s been done by other companies?

Randy: The fundamental problem with the do-gooding sphere is it’s been immune to the digital and the capitalist revolutions. You don’t have people behaving like shareholders who give money to these companies – they just give the money away and don’t really care what happens to it. Because there’s no accountability to the people providing the capital, incentives aren’t aligned with improving the lives of people on the ground. The big question is, can you transform this entire landscape, so those who are giving feel like they’re investing money in helping people? Flip the switch in their heads from “does this make me feel good?” to “will this actually help people?”

Stride: Many of the people who go to the Stanford GSB have already done very well for themselves financially. How do your ideals of pursuing something altruistic fit in with your classmates?

Randy: That was something that drove me to come to Stanford. Maybe just by spouting these kind of ideas amid a bunch of people who are likely to become wealthy and conventionally successful, it may help steer some of their resources towards the right kind of reforms. I’ve been surprised since I got here though – most people have the same idea of a higher purpose to their actions, but everyone’s reasons are different. We can debate what the best outcomes are, but we know that everyone is following their own moral compass.

Stride: You’re 26, so this is the first time you’ve had to deal with buying health insurance?

Randy: Yes [laughs]. It was really night and day between the official state exchange website and Stride’s website. A few weeks before my employer plan ran out, I googled stuff, looked at the state’s site, and filled out a bunch of forms, only to get hopelessly ensnared by all the random information they threw at me. While on the phone with a customer rep for Covered California, I threw up my hands and stopped looking for a couple weeks. Then I stumbled on Stride, and in literally 10 minutes I had all the information I had been vainly trying to extract from the government sources. From that pure time savings component alone, Stride was a miracle. And then the fact that you gave me an actual rational for which plan I should choose based on my information – instead of dumping a ton of different plans on me that I had to sift through – makes Stride so obviously the best thing that will take over the market.

Stride: What health problem are you most concerned about for the general U.S. population?

Randy: So few kids know what their parents want to have happen in the end stages of their life, it’s a tragedy. The kids have to make all these medical decisions that are expensive to themselves and to the entire tax base – preserving one day of life for loved ones that might prefer to pass away naturally. If you can fix that, you have so many more resources to throw at the stuff that really makes people sick and unhappy.

Stride: As you’ve thought about maximizing the happiness of others as a main driver in your professional decisions, have you thought about the income tradeoff for that pursuit?

Randy: Yeah, it’s an ongoing debate for me. I think you should do whatever you can that will have the the greatest positive effect on the world. For some people that’s being in the soup kitchens, for others it’s becoming a billionaire capitalist and giving some of those billions to the soup kitchen. I think it’s really important to know why you’ve ended up on the side of the spectrum you’re on, not just passively falling into something and doing good as an afterthought. Be intentional with where you’re going and how you’re going to use that for the common welfare.