Raph Lee

Raphael Lee knows his way around Silicon Valley, having started his tech career as a software engineer at Adobe Systems shortly after graduating from Brown University with a computer science degree and then moved on to Airbnb where he was one of its first engineering hires. “I felt stifled being in a corporate environment,” he recalls. “I wanted to get into the startup world.” His other tech employers have included the Lob direct mail automation platform, and he has invested as an “angel” in such startups as Maad, a B2B e-commerce marketplace in Senegal.

But last summer, Lee stepped away from the tech world, joining the MSx program at Stanford GSB to add to his entrepreneurial toolbox. (That has meant taking a break from extracurricular activities like playing the bass guitar in a “sing-along” band called We Used to Praise God.) But he remains a true believer in the power of technology to improve people’s lives, recently taking his talents to relationship mentoring app Meeno as an executive advisor. “At heart,” he says, “I’m a techno-optimist.”

Early in your tech career, you worked for two high-profile startups — Airbnb and Lob. What was that like?

They were pretty similar in that they were both fast-growing startups, attracting really brilliant people. My fear coming out of Airbnb was that the lessons I learned there wouldn’t generalize to other places. You never know if the lessons that you’re learning are unique to the situation and the circumstances that you’re in or if you’re learning something that’s universal and can be brought to other places. And so I felt very gratified to be an engineering leader at Lob because all the things that I learned [at Airbnb] about building teams and hiring well and performance management and building this strong engineering culture really did translate pretty effectively.

How did you start being an angel investor, putting your own money into companies?

Initially, it happened because a bunch of my colleagues at Airbnb who had also left the company were beginning to form their own companies. I just wanted to buy a ticket to get on the bus and stay close to them. So that was the basis for my initial investments. And then, over time I learned a lot more about how to evaluate the potential of an investing opportunity — how to think about the team, how to think about the market, how to think about the products.

What do you look for in a company that you get involved with as an angel?

The things that I look for are largely about the potential size of the market, the founder’s hypothesis, if I believe it personally. The founder’s background — if they’re a good fit for the problem. The founder’s product fit is incredibly important. And you look for a track record of trying to do a lot of things really quickly with very few resources, which not everyone is capable of doing. I want to see evidence of scrappiness. The only real advantage that startups have over big companies is that they can execute quickly.

Is there a particular investment that stands out for you?

Maad, the company in Senegal, is very interesting for several reasons. One is that it was founded by someone [Jessica Long] who is both a close friend of mine and someone who I think is very talented. Another is its mission. In Senegal — I think this is true in many parts of the developing world — a lot of people consume household items and groceries from corner stores. What the company does is make those boutiques more efficient by cutting out most of the middlemen in the supply chain. So it’s an interesting way of harnessing market forces and by making those more efficient indirectly improving the lives of a lot of people.

What were you doing immediately before you came to Stanford?

I had co-founded U.S. Digital Response, which is a non-profit that worked with state and local governments on their COVID-19 response. My co-founders and I saw that COVID-19 would create a series of crises that were hard to anticipate but which we knew would be large in scale. Governments are not particularly well-equipped to respond to crises in a timely manner. Our thesis was that we have access to a large community of volunteers who are experienced professionals from the tech sector, and if we can work with state and local governments on implementing projects, we can potentially impact a lot of people. We ended up doing work in 37 states and territories, and we’ve impacted at least 14 million people.

You seem to be interested in projects or ventures that have some sort of social improvement aspect to them.

I think it’s the most important thing. Technology is so powerful and has so much potential to improve people’s lives that it kind of drives me crazy when I see companies that aren’t trying to create value that affects people’s lives positively. I really believe that if you have a good understanding of the kinds of problems that everyday people deal with, you can design experiences for them and deliver them through technical means to make their lives better. And you can do it at unprecedented scale when you use software. I’m definitely excited about that. I think it’s been the binding principle for the projects that I work on.

Why did you decide to take this mid-career step and go back into an academic setting?

I’ve been working mostly as a technology executive and what they tell you is that you learn all the business stuff on the job, maybe through osmosis. This has not been true in my experience. The more I worked at different startups and got more exposure to different companies, the more I realized that there is a big world outside of the technology-specific functions at these companies. And I felt that my understanding of what these companies could do for the world would be incomplete unless I understand the other parts.

There are other people in the [MSx] program who come from financial and consulting roles who felt like they didn’t need a refresher on those aspects of business. I ate it all up. It was all fun for me. The accounting class was fun for me. The finance class was fun. The operations class was fun for me. I’d never seen that stuff before. They really have, I think, given me a well-rounded understanding of what businesses, nonprofits, and governments do. My understanding of how these institutions moved in the world is now more informed.

What’s an example?

One is that I think people in pure software businesses have some blinders about the way that the cost structure of the company breaks down. Because when you’re delivering software, there isn’t a cost of goods sold per se for each piece of software that you sell. We mostly don’t have to worry about inventory management or need tons of capital to get started. So really spending time looking at financial statements has made me more appreciative of how the world works. It’s given me some insight into the way that the CEO thinks, which I really wish I’d known 10 years ago.

Are you interested in a CEO role?

I’m looking to move toward bigger roles for sure. I would love to start a company or join a startup in a particular role. Being able to think like a CEO will really help me in those roles, whether I’m the CEO or not.

You recently became an executive advisor for a relationship mentoring app called Meeno. What is that all about?

The idea behind Meeno is to help use technology specifically to cure loneliness. In 2023, the U.S. Surgeon General released a report showing that the majority of adults feel lonely. If you believe that social connection is a skill that can be developed, there should be ways to help people develop those skills. And so that’s what Meeno is trying to do.

How does this mentoring happen?

It happens through chat. It feels like you’re talking to somebody. Something I think is very important about Meeno is that it is an AI and it never pretends that it’s not an AI. I’m concerned that in one possible near future scenario, AI begins replacing human relationships. But at Meeno, we really want AI to help people apply and build relationships in the real world and to help people form those relationships instead of replacing them.

Meeno is kind of a symbol of the world that I want to be living in in five or 10 years. When AI has realized more of its potential, I hope a lot of that potential is used to bring people together in the real world instead of locking people into their own little boats. That’s what I want the world to look like.

Photos by Elena Zhukova