Something Ventured -- Silicon Valley Podcast

Rob Chesnut is an advisor to Airbnb, where he was previously Chief Ethics Officer and general counsel.  His recently released book is Intentional Integrity: How Smart Companies Can Lead An Ethical Revolution.

Rob started his career as a federal prosecutor, but decided he could do more good in the world by working for companies like eBay and Chegg.

Eventually joining Airbnb, he helped Brian Chesky navigate issues such as racial discrimination by Airbnb hosts.  He also helped Airbnb create a culture of “Intentional Integrity”.

In this episode we discuss Rob’s journey to and through Silicon Valley, and his experience creating ethical cultures those companies.  We also discuss what happened to Airbnb when the COVID crisis hit.

Hear what Brian Chesky said as Airbnb was faced with lawsuits over discrimination by its hosts

Rob Chesnut Episode Excerpts

On leaving the role of federal prosecutor to work for tech companies:

“After a while, it's a real negative. It has a negative aspect to it.  You're putting young people in jail for long periods of time, and you feel like you're not contributing in a positive, proactive way to society.”

 “On the Future of Travel”

“I don't think that the pandemic is going to push people to stay in their homes forever. I think that people are going to travel. But what I think we're going to see is that there's a maybe a different type of travel. One thing that there's a trend, I think, that may come out of the pandemic, which is really going to help Airbnb and that is ‘work anywhere’. So if you can work and do your job from literally anywhere that has Internet access, that suddenly frees you to go places and do things 52 weeks a year that you might otherwise have only been able to do three weeks a year.”


On Intentional Integrity

“I think that integrity is a word that people are often uncomfortable talking about because it gets to people's morals, their purpose, maybe even their religion. And so leaders are uncomfortable talking about it and what they do is outsource it to lawyers and it becomes compliance. There's a difference, though, between compliance and integrity. So the point of the title is we have to get over the discomfort, we have to have the conversation. And if we want integrity to be part of our company, we can't just assume that it's going to happen, that we're just going to hire good people and that it's going to happen. We have to make an intentional effort to weave it into our culture. And so the point of that title, is a call for getting through that discomfort and taking affirmative steps to make it part of what you do in business.”


Intentional Integrity


Rob Chesnut


Something Ventured


Direct download: 144_Rob_Chestnut_of_AirBnB.m4a
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