Rob Chesnut: Bringing Ethics and Values to Silicon Valley

Rob Chesnut: Bringing Ethics and Values to Silicon Valley

Rob Chesnut, Chief Ethics Officer of Airbnb. Photo by Asa Mathat.

“Lead by example.”

Rob Chesnut’s open-mindedness to the possibilities of the internet led him to be a part of some of the most influential companies of our times including eBay and Airbnb, among others. A graduate of Harvard Law School and the University of Virginia, he began his career as a federal prosecutor for the U.S. Justice Department. Unsatisfied with the negative nature of being a prosecutor, he left to go work for eBay in the late 90s. He cites AOL’s dial-up internet as a precursor for his early use of eBay. He knew there was a place for him in tech when he found out AOL had hired a person who had previously had a background in federal government. Seeing there were no jobs posted on the e-commerce company’s website, Rob sent his resume and cover letter to jobs@ebay.com. In his cover letter, he outlined their need for someone who could deal with fraud, the sale of illicit items on their platform, and regulations. The next day, he received a phone call (they had left a voicemail on his home phone) to come in for an interview. Almost immediately, he was on a flight to San Jose, California, to meet with the CEO at the time, Meg Whitman. He got the job. In two months he resigned from his role as a prosecutor and moved out West. His life was changed forever.

Today, he is the chief ethics officer of Airbnb (after serving a long run as Airbnb’s General Counsel). Rob laid the groundwork for more companies to have dedicated departments that thought about what is ethical and just. Now he has written a book titled Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution, out July 28, 2020, to help companies become more ethical and fair to their employees, customers, and the world at large. In our interview with Rob Chesnut, he gave us a look into his upbringing, his time at eBay, Airbnb’s culture of ethics, what intentional integrity means, and the issues that most concern him today.

Intentional integrity is a recognition that leaders need to talk about integrity and they need to talk about what it means in a specific way so that everyone in the company can get aligned around it.”

Where are you from and what was it like growing up there?

I grew up in Southeastern Virginia in the Tidewater area. My dad was in the Marines and retired in that area. It was, in a number of ways, a typical suburban neighborhood. I had a good childhood although my father left when I was fairly young. I was an only child raised mostly by my mother.

Who or what was your biggest inspiration growing up?

I was always inspired to make the world a better place, but I had no idea how to do it. I figured perhaps being a lawyer would give me the greatest number of options. There’s a picture of me in the high school yearbook with one of my classmates, each of us holding a briefcase. I guess people thought we both would end up being lawyers and we did. I was influenced by the legacy of John F. Kennedy. I was very moved by public service and sports, too.

Dr. J was my role model growing up. He played for the local professional team. Back then Norfolk had a professional basketball team—the Virginia Squires. He was fantastic. I remember meeting him as a kid and shooting baskets with him. He had some relatives that lived in the area. I was so impressed with him as a human being. He has gone on to be such a well-regarded figure even well after his playing days, but he had a certain way about him back then that I had always admired.

Did your parents give you any valuable advice growing up?

Yes, I’d like to think so. There is one thing worth mentioning in particular though. My parents held a belief that you may not be the smartest person in the room, but if you have a smile on your face and you work hard, good things will happen to you. From a young age, that was something that was always instilled in me and I kept that with me throughout my life.

Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution will be out July 28, 2020.

What was it like working for eBay?

I was a senior hire for them and they didn’t do much recruiting outside of Silicon Valley. I didn’t know what I was doing. The CEO at the time, Meg Whitman, was going over these numbers with me and I saw these lines going up into the right. It struck me that they had the best business model I had ever seen. Even though I didn’t understand much, I knew I wanted to be a part of it. I was so impressed by how the company could connect people from different parts of the world over a common interest and how trust was at the heart of it.

I remember the first time I was on eBay. Back then you couldn’t buy an item with a credit card. You could only send a check or money order. I was thinking: Wait, I’m going to put this money order in an envelope and send it to somebody I don’t know, just to get this item? What are the odds that this is going to work out? I trusted it would come and sure enough, it did. In a way, eBay restored my faith in mankind. To be able to make successful transactions over and over again on eBay and then to be a part of the company that was enabling it was pretty cool.

Do you feel like you have made it?

I don’t think you ever feel like you’ve made it. I recently turned 60. I always think of it more as a journey that doesn’t have a clear destination, but you kind of have an idea of the direction you want to go in. Every day is a new adventure. If your goal is to contribute in a positive way to the world, then the task is endless and in a sense, you never really get there. You evolve and learn to figure out new ways to do it.

“If I come into the meeting and everyone in the meeting looks like me or has the same background as me, then we’re heading towards the wrong path.”

Greatest achievement?

I guess I don’t reflect on that too much. I reflect on what my mom would be most proud of: me being open to the journey and not afraid to try new things.

You are now the chief ethics officer of Airbnb. How would you describe your role and why do you think this role is so important for companies?

It is a relatively new role in the business world. I spent the first five years of my corporate career at eBay as a lawyer and then Meg Whitman said to me, “We need to start a fraud department. We need to start something that will proactively detect fraud before it occurs and protect people from getting ripped off.” She knew I could figure it out and they gave me what I needed to get it done. We ended up creating the first trust and safety department in Silicon Valley. Now everyone has a trust and safety department—Facebook, Uber, Google, etc.

I think similarly when I got to Airbnb and I started as their general counsel, I noticed that the world was changing. Me Too became a movement. Leaders who were getting away with things for so long were getting called out for bad behavior publicly and it struck me that this is powerful stuff and a company needs to get ahead of this. In other words, how do you drive integrity into the culture of a company? This was new territory.

How did companies handle ethics in the past?

In the past, at least what I’ve seen, companies worked on something called compliance. Compliance might be a code of ethics. You may put a poster on the wall in the break room that’s got that tiny font that nobody reads or a sexual harassment video that people just click through. We asked: How do you get people to pay attention? How do you get people to see that this is the way we want to operate as a company?

That is when I became really invested in the issue. I knew then that I wanted to write a book about it and really focus on the issue. Airbnb is one of the first companies, not the very first, but one of the early companies to actually devote a senior level person full-time to thinking about integrity and ethics and drive it as the culture of the company.

Rob Chesnut speaking to UC Berkeley Master of Engineering students about the importance of intentional integrity in the workplace. Photo courtesy of Rob Chesnut.

You have a book coming out titled Intentional Integrity: How Smart Companies Can Lead an Ethical Revolution. Can you explain to us what intentional integrity means?

Intentional integrity is a recognition that leaders need to talk about integrity and they need to talk about what it means in a specific way so that everyone in the company can get aligned around it. In fact, it’s a powerful force in business but only if you make it a part of your culture by having a real human conversation about it.

I talk to all of the new hires at Airbnb. It can be anywhere from a dozen to a hundred people. I think folks are quite surprised that we have an open conversation in the group about things like alcohol and relationships in the office. The reaction has been overwhelmingly positive. We do reviews with blind surveys at the end of these classes. It is the number one ranked class at orientation. People walk up to me and say, “You have no idea what it is like to work at a place that genuinely cares about this and actually talks about it and makes it a part of their culture.”

In the old days they thought, “Oh, it is a dog eat dog world out there. Ethics will get in the way.” I think the way the world is evolving now is that ethics and integrity are superpowers for businesses these days. It’s something that actually resonates with employees, with customers, and the community at large. Companies that intentionally act to do the right thing will be rewarded and outperform companies that don’t.

That message is similar to Harvard professor Lynn Sharp Paine’s. In her book Value Shift, she makes the case for a more ethical perspective in business-decision making. Being ethical benefits your company in the long term.

The problem today is that so many companies are forced to do what is in the interest of today’s stock price or this quarter’s numbers. We talk about the long-term perspective at Airbnb. Brian Chesky, the CEO of Airbnb, calls it an “infinite time horizon.” I think that phrase comes from Simon Sinek and having that long-term perspective makes it easier to do the right thing.

I love what you said about the Harvard Business School professor. So often people don’t ask the right questions. Is it legal? Is it ethical? Instead, companies ask: Can we figure out how to budget? Can we find a way to skirt around the law? Nobody asks if it is the right thing to do. I think there are distinct questions, and both are important. Even if it is legal, how would it look? My mom would always say, “How would it look if it was on the front page of the paper? Always think about what you do.”

In today’s world, you have to assume it will end up on the front page cover. Back when I was growing up, a whistleblower was an anomaly. It was maybe one Edward Snowden. Today, everyone walking in your building is a potential whistleblower because the internet has given everyone a platform. One person has the power with one blog post to change the course of a brand or company. Look at what Susan Fowler’s blog post did for Uber. I think companies have to recognize, and this is a good thing, that anything they do is going to be written about online and therefore, be proud of it and if not, reconsider.

Photo courtesy of Rob Chesnut

What advice would you give to young people who would like to make their mark in the tech industry, but are not necessarily software engineers or computer programmers?

[Laughs] Learn to code. No, there are so many ways to bring value to the table. At Airbnb, we talk about diversity as another superpower and we talk about it in so many different ways—the color of your skin, your background, your religion, your political affiliation, your gender. I think what’s dangerous is when companies start to think that engineers are king or we’re just going to hire the best person that’s defined by “us.” When more backgrounds and perspectives are represented in the room, the better decisions you will be making. A room full of 10 engineers is not going to come up with the best idea in the room. A room full of 10 lawyers is not going to come up with the best decision or 10 white people or 10 women or 10 men, etc. If I come into the meeting and everyone in the meeting looks like me or has the same background as me, then we’re heading towards the wrong path. I love rooms that have people that think in different ways and when that happens, we are a lot less likely to miss something important.

How has Airbnb thought about diversity?

Airbnb was really torn up about three years ago when it came out that users were discriminated against based on the color of their skin. Black users were having trouble being accepted by hosts on Airbnb and the first reaction in the company—I had only been with the company for a few months—was surprise. There were genuine people in the Airbnb leadership who were shocked because that was not Airbnb as we saw it. Airbnb is headquartered in San Francisco and the environment in San Francisco is very open and accepting of people of all races, nationalities, and sexual preferences.

Why would we think Airbnb is immune to that when there is so much discrimination in the world? Maybe because Airbnb itself was not diverse. If we had more employees of color, it would have helped us to see it earlier. We learned we needed to be more diverse so that we could have a better understanding of what our customers have to go through every day. There has been more of a conscious focus in the last couple of years to understand this.

How do you relax when you are not working?

I love hanging out with my kids. My daughter is in college in New York studying to be an actress. Watching her perform gives me tremendous joy. Like me, my son loves basketball. He plays AAU basketball and he and I will spend time watching basketball on TV and playing basketball out in the yard together. He is only 13 and his feet are already bigger than mine and he is growing like crazy. Just getting out in the yard and hanging and playing one-on-one with my son is something I get a great deal of joy from. 

What’s up next?

My mom used to love to read. There was always a book on the coffee table right where my mom would sit on the sofa. My mom instilled in me at an early age a love for reading. I’m saddened that my mom is not around anymore to be able to see that her son actually wrote a book.

I am deeply concerned about climate change. I am deeply concerned about the world I am handing off to my kids.”

I’m still not over the fact that I’ve written even one book. I think when I see it at the bookstore, it will become a little bit more real. I haven’t given one second of thought to another book. We will see where this one goes. As I said, I love the idea of changing things up in life and I like the idea of changing it up again. At age 60, there is still a lot to give and a lot to do.

I am deeply concerned about climate change. I am deeply concerned about the world I am handing off to my kids. My mom always told me to leave the room better than you found it. My generation hasn’t done that when it comes to the Earth. I think we failed. I’m doing a lot more reading and thinking about climate change.  I think that is an issue that needs a lot of people thinking and contributing in many different ways.

Pre-order Rob Chesnut’s book here.