Q: In the book, you talk about the younger generation who value experiences over possessions: we want flexible transportation, but don’t want the hassles of car ownership, for example. How did you come to realize this?

CR: I guess self reflection, and taking a step back from life and looking at where I derive value and where my friends were deriving value, and realizing I wasn’t really motivated to be a VP of marketing at some big company — being what is quote unquote “successful.”

I think also the recession hit home for a lot of people. it’s like “Hi! Owning a house isn’t what you were told and marriage is not what we were told.” It was a period of disillusionment that led to the question, “What is important and where do I get value?”

Q: The American Dream used to mean owning a house, a car, a TV, a refrigerator. It was all about things you own. How would you define the American Dream for our generation?

CR: Freedom. Creativity. Purpose.

Q: You are an entrepreneur, though. What, for you, defines success if it’s not just money or status?

CR: I think a lot of the people I value the most, and get the most out of being around, are people that are building communities, that are bringing people together online and offline, you know, having a big impact in a different kind of way.

I think we’re in a different stage of the Internet now, where creating products and services is still really meaningful, but how you do that and the types of tribes you create around that, are just as important.

Q: Let’s talk sharing economy. We’re all naturally suspicious of anyone we don’t know: stranger danger. How does the sharing economy address this?

CR: I think it creates an interface and a consciousness around trust, that we haven’t had previously. You can peer into who someone is, what they do and who they are, who they say they are, and what other people say about them. You get this digital footprint that allows you to see enough information to decide “do I want to meet up with this person or not?”

It also enables you to trust your gut a little bit more. You use that information, those inputs, but occasionally take a leap on somebody where you’re like “Oh, I don’t know a ton about them, but I talked to them on the phone, and you know, I feel fine about this.” I’ve done that too.

Q: I like couch surfing. I’ve hosted and surfed — they were great experiences. That seems like pure sharing — there’s no money involved — can you talk your feelings on couchsurfing?

CR: Just to be clear, I’m a consultant for them right now, but I’ve done a ton of stuff for them before working for them. I worked on a documentary for free, for like 2 and half months of my life, and I couchsurfed a bunch. I’m not speaking for them at all…

I love couchsurfing. I think it’s one of the most amazing things on the Internet. I’d like to see it sort of come back to the original energy. I think it’s a platform for world peace.

Q: I’m surprised a lot of people my age have never even heard of it.

CR: Yeah, in the U.S. especially. There’s 10 million members. The idea of hospitality in the US is not the same as in Europe. Having a stranger that you just met on the street come stay in your home is not so crazy there.

Rustrum, Stempinksi and Liss sharing a moment.

Q: You and the two co-authors connected while filming a documentary about Couchsurfing, can you tell me about that?

CR: It’s called One Couch at a Time. It was six months of traveling on Couchsurfing and documenting that process and telling the story of couch surfing. It’s really hard to tell people what Couchsurfing is without showing them. You can’t show them if they’re not ready to have the experience.

I was of the mind that more people needed to know about Couchsurfing. That’s part of what led me to this whole sharing economy movement and caring so much about it: the entry points were Couchsurfing and co-working.

Q: Some of the sharing in the book is more transaction-based, like Uber or TaskRabbit. Some is more swapping or giving, like Couchsurfing or Freecycle. Do you have a preference, personally, between those two, or do you think both have their place?

CR: Things like couchsurfing, time-banking, freecycling, even using craigstlist in different ways, There’s something about giving and receiving without money that’s really really powerful. It reaches people on a different level. They go away feeling something different than when they exchange money.

Q: In the book you ask an interesting question: there’s been so much technological progress, but we don’t seem to be getting happier or more fulfilled. Can you talk about that?

CR: Broadly I think we’re not happy because we’re not focused on love. We’re focused on accumulation and belonging in really weird messed up ways.

So many things that we do that boil down to: wanting to be loved or wanting to belong, wanting to be powerful and strong enough to have other people like us, and wanting to work enough so we can live in the right neighborhood and have the right friends.

But you know, working 15 hours a day, and having two kids, and hiring a nanny, and both people never seeing each other or their kids is not a recipe for people being happy.

And then creating the economic prison of owning a big home that costs a million dollars and saying that you have to do that… you don’t!

Q: I’ve never heard of a home called an ‘economic prison’ before, but that’s interesting. It’s like how they call cigarettes ‘cancer sticks.’ It’s makes you see home ownership in a whole different light.

CR: I mean, if you have a million-dollar house, what’s your house payment? What does that mean that you have to do? That’s a 30-year commitment for many people. Thirty years you have to do this. If you decide to do something that makes less money, you lose your basic piece of security.

Q: The book is half manifesto, half how-to guide. In terms of the manifesto: ‘this is how things could be,” what were some of your influences? What got you off the normal track and thinking about some of this pretty radical stuff?

CR: I was never on the normal track. I grew up vegetarian in southern Oregon. My parents owned a health food store before health food was cool… I could go on and on.

I started building websites in 1997 and started making more than my parents by the time I was 18 or 19. I grew up with the Internet, which I think was a big influence for me. I grew up with the ideas of participation, the collective, involvement.

Q: Are you influenced by the hippies at all, the 60s? The Diggers would collect old clothes and have free stores. Stuff like that. Do you think you have some hippie in you?

CR: Tons. I call myself a digi-hippie. I think i’m an interesting intersection between wanting to use business and new technologies to bring back humanity, you know? Our collective humanity and what it means to be human and loving and kind and open and generous.