In the Room from Day One: Ron Klain on Legal’s Role in Driving Innovation at Airbnb

Klain:

The story of Airbnb predates my time at the company. A little more than fifteen years ago, our founders — Brian Chesky, Joe Gebbia, and Nathan Blecharczyk — were living in San Francisco. They had an apartment they couldn’t really afford. Brian and Joe were industrial designers, and they knew there was a big industrial design conference coming to San Francisco and the hotels were sold out. So they got some air mattresses, blew them up, had their friend Nate build a website, and called it AirBed & Breakfast. They invited people in town for the conference to stay in their apartment. Three of them did. The first few years were very, very slow — but obviously it’s taken off. We’re now the largest global hospitality provider in the world.

Klain:

A little over a year ago, our co-founder and CEO Brian Chesky asked: Why do people still choose hotels over Airbnb? One reason is hotels have services — you can get room service, a massage in your room, all kinds of amenities, and a front desk that connects you to tours. He thought we needed to add that to our offering.

I’m fortunate that at Airbnb the general counsel serves on the executive committee. From the very first time Brian had this new idea to offer Experiences, I was in the room. We built into the roadmap the need for global legal review of Services and Experiences — first to determine which offerings required licenses or government permits. We operate in hundreds of jurisdictions around the world, each with different laws and permitting systems.

We decided in May 2024 to launch on May 13, 2025. After that decision, the legal team got to work. Virtually every member of our legal team, regardless of specialty, set aside time to help with these reviews and to work with local counsel. If we were going to offer a certain kind of tour in Florence, Italy, what license did that tour provider need? If we were going to provide massages in Paris, what license did the therapist need? We engaged in a massive global legal review, developed a point of view on those questions, and then worked with our operations team to build a process around providers and their licensing.

I also oversee the function that sets the rules for Airbnb — our Community Policy team reports to me. We wrote the policies these new services required: cancellation rules, refund frameworks, whether a guest could request a massage therapist of a particular gender, and so on. We were ready on launch day, and we’ve now launched in hundreds of geographies. It’s going very well — people are using the Services and taking the Experiences, including some truly one-of-a-kind offerings.

Klain:

We started with a low risk tolerance for this new product. Our brand reputation matters, and our core business is heavily regulated around the world. We didn’t want to create a host of regulatory problems around a new business.

It’s complicated around the world: In some places the relevant rules are national; elsewhere they’re regional or municipal. In the US, some rules are state law, others local. It’s a lot of law and a lot of complexity. I have an incredibly talented legal team at Airbnb, and working with outside counsel we got it done. It wasn’t easy — but our legal work supported the business and we launched on time.

Klain:

We’re a very creative company. Many leaders come from Apple, and our CEO is one of the very few tech CEOs who’s a designer by training. We have a strong artistic sensibility, so we let product lead. Legal provides advice like: If we design the experience this way, it triggers this kind of license; if we design it that way, it triggers another.

Klain:

We’re a legal team that knows how to give advice and draw clear red lines, but we always try to find solutions and work hand-in-hand with the business. One thing that struck me at Airbnb is how many people love their lawyers — not because we just give advice, but because we’re partners in building. This is especially true of our lawyers around the world, who are often co-located with business teams and deeply invested in growth. About half our business is in the US, half is elsewhere, and we’re growing quickly in Asia and Latin America. Our legal team works very closely with country business leaders to facilitate that growth, mindful that rules, laws, and cultures differ around the world.

Klain:

Absolutely. I have a Trust legal team that partners with the Trust operations team. Our guests must feel safe, and our hosts must feel safe — while we comply with global privacy laws. I spend a lot of time on GDPR and other privacy rules, and on how we screen hosts and guests consistent with those laws — particularly in Europe, which is a very important market for us.

We also need sensitivity to local laws and norms. We’re growing in the Middle East — including Dubai and Saudi Arabia — where rules and norms are different. We’re also growing in Southeast Asia, Japan, and Korea. Having great local lawyers and regional leaders is critical. I spend substantial time traveling to visit those teams.

Klain:

We operate in the real world. Unlike some tech platforms, our users interact offline — in physical environments. Some experiences involve activities with inherent risk, like surfing. Great things can happen when you surf; bad things can happen, too. We write rules and policies that acknowledge those risks and do as much as we can as a platform to protect our guests. You’re not surfing in the metaverse; you’re surfing in actual waters with tides and riptides.

I also spend a lot of time with operations monitoring weather around the world. We don’t want guests traveling into dangerous storms. We have policies that allow hosts and guests to cancel in the event of severe weather, so people aren’t coerced into traveling because they’ve prepaid. It’s a big world; bad things do happen. We try to be very responsive when they do.

Klain:

It was an iterative conversation with the business about which services had risk we could responsibly manage. For example, massages involve physical touch in a very personal setting. We looked closely at providers, vetting, and reviews, and put strong controls in place. It’s about taking offerings one at a time and applying judgment.

Klain:

Trust and safety are core to what we offer. We have an extensive review system so guests can see what others say about hosts and experiences. We have robust enforcement to remove hosts or guests with trust or safety problems. Where permitted by law — including in the US and India — we conduct criminal background checks on hosts and guests before check-in. We also work closely with law enforcement around the world, consistent with privacy laws.

Klain:

We were fortunate — and I think wise — that legal was in the room from day one. We weren’t seen as an obstacle; we were seen as facilitators of a complicated new product launch. Trust between business and legal is essential. Our business leaders know we’re here to make the business more successful; our lawyers know the business will take our advice. That cooperative, iterative relationship makes us more innovative and more effective. No one asks, “Why are the lawyers here?” They know why — and they appreciate that we aim for sound, innovative solutions.

Klain:

The most important thing is: Move quickly. The instinct in big organizations is to seek more information, schedule another meeting, decide next week. That’s a mistake in a crisis. Stakeholders need to see you act. If a hurricane hits Puerto Rico tomorrow, hosts and guests don’t want to hear next week that reservations are canceled — they want to know now.

You often must decide on incomplete information. We lawyers like completeness, but sometimes the most prudent thing is to decide with the best information available at the time. Comfort with that comes from experience — there’s no substitute. We have a lot of super-smart, super-talented young people here, and they make vital contributions. But sometimes you need someone who has seen the movie ten times and knows how it ends. Not all decisions will be right, but to not decide is to decide.

Klain:

I’ve been lucky to have a diverse career — public sector, private sector, in-house, big law, startups, and now a big company. If there’s a throughline, it’s a belief in team building and assembling talented, diverse teams. That leads to the best outcomes. I really love my job at Airbnb; it’s one of my favorite jobs I’ve ever had.

Klain:

I’ve always been interested in travel and how it brings people together. The mission resonated. The outgoing general counsel, Rich Baer, had been a client of mine years before when he was GC of Qwest, so I knew him well. He urged me to put my hat in the ring. Then I spent a day in San Francisco with Brian Chesky and was incredibly impressed by his leadership and vision. Brian’s been at it over 15 years and has more passion for the future than the past. Some founders get nostalgic; Brian believes he has the best team he’s ever had and the company is doing the most interesting work it’s ever done. The leadership, the team, and the mission drew me in — and I’m grateful they did.

Klain:

First, build relationships with key stakeholders before the hard moment. I spend a lot of time with our CEO and senior team so they know where I’m coming from. When it’s time to deliver tough advice, I do it directly and candidly — and privately. I don’t tell a leader in front of their team, “You’re wrong.” I’ll take them aside and explain why we need to change direction so they can recalibrate on their own terms. I’m lucky: our leadership accepts legal advice and appreciates our role, so the tough conversations haven’t been that tough.

Klain:

I was both fortunate and unfortunate to get very senior roles early — before I was fully ready. I became Chief of Staff to Vice President Gore in the 1990s, and in 1999 we had a big internal fight and I got pushed out. It was a bitter pill. As I left, I realized I hadn’t been very nice to my colleagues; I’d been too harsh as a manager and pushed problems down. I vowed that if I got another leadership role, I’d be different. Credit should flow down and blame should flow up, not the other way. You need accountability and rigor, but you can’t be too harsh. The goal is to build the team up, not tear it apart.

Klain:

Keep a long-run perspective. There will be a tomorrow, and you want to be proud of how you conducted yourself today. Losing your cool never helps. I’m a little famous for sending ALL-CAPS emails — not something to be proud of — and I try to cut down on those. A leader’s job is to absorb stress, not pass it downward. I’m not always successful, but I’ve gotten better over time.

Klain:

Early on I worked for Warren Christopher, both in government and at O’Melveny. His character and leadership style were critical influences. I’ve had many others help me along the way. But my most important advice to young professionals is: more important than mentors is your peer network. Your peers know about opportunities at your stage. When I hire, I’m less interested in a mentor’s letter than in what peers say — people who worked with you at your level and know how you collaborate.

Klain:

What I would say is it’s important to have a diverse set of experiences, because in the end, yes, as general counsel we manage the legal department. But in the end, you’re the person in the room with the board or the CEO when they turn to you and they ask legal advice. They don’t want to hear, “I’ll call someone and get back to you.” They want to hear your legal advice. So you need to have a diverse personal law practice and a diverse set of experiences so you can offer that advice.

If you want to be a general counsel, expand your knowledge, expand your skills. If you are just the best litigator in the world, you are not a general counsel. If you’re just the best corporate lawyer, you’re not a good general counsel. Focus on the “general” in general counsel. Make sure you have the ability to advise generally and broadly.