Taking Matters Into Your Own Hands: How Belinda Johnson Ended Up As COO of Airbnb
A fifth year associate quits her law firm job to go in-house and ends up gaining massively valuable skills that one of the world's hottest startups needed 15 years later
In 1996, Belinda Johnson was at a career crossroads. She was five years out of law school and working at Littler, a well-known Texas Biglaw firm. From the outside, her career was going well. But Johnson felt like something was … off.
After law school, I put on my power suit and worked at a series of law firms. By the time I was at my third in six years, it dawned on me that a traditional law job wasn’t for me. Source
The problem wasn’t necessarily the subject matter. Her problem was with law firm work generally. They offered “narrow specialization, monotonous cases, and mountains of endlessly proliferating paper documents that could not be taken out of the office.” Johnson wanted something more dynamic and interesting. As she recounts:
I was living in Dallas, and everyone was talking about this entrepreneur Mark Cuban, who was starting a streaming-content company that would later become Broadcast.com. We happened to work out at the same gym, so when I saw him there, I summoned my courage, went up to him, and said, “I would love to understand what you guys are doing and how I might help.” I was 29. It was a pretty bold move! Source
The startup didn’t need an in-house lawyer yet but they were looking for good people. Johnson was fascinated by the company because it was involved with this new thing called The Internet. She didn’t know exactly what she’d be doing at this startup, but she knew she wanted in.
“I fell in love with technology,” Johnson later said. “And I really liked the mentality of startups who have everything difficult, sometimes chaotic, but never boring.” When she told her friends and family that she was leaving Biglaw to join this startup called AudioNet (later renamed Broadcast.com) they all thought she had lost her mind.Why would she spend so many years to earn a law degree, get a high-paying job at a great firm, to walk away from it all? The lawyers at her firm were even more perplexed:
Colleagues from the law firm where I quit for this project asked: “Are you sure?” They thought I was crazy, because in fact the Internet then seemed to everyone just another crazy idea without a solid foundation. Source
Of course, none of that stopped Johnson. In 1996, she took the leap and joined the startup. Three years later, it was acquired for billions of dollars by Yahoo. But that’s not where the story ends.
Because being an early employee at a startup that gets a huge exit, was not how Johnson made her mark. To fully appreciate her legacy, we’ll need to discuss what happened after that acquisition, and how it helped her find Airbnb.
Before I move on, I want to be clear. This article isn’t a laundry list of Johnson’s accomplishments leading Airbnb between 2011 and 2020. You can read about that anywhere else. Here, I want to focus two things that often gets brushed over in other biographies and profiles:
First, I’ll focus on how long it actually took for her to become successful. And what she was doing during that time. Success didn’t come overnight. I mean, even though Johnson’s first startup got acquired for a ton of money—it presumably didn’t generate enough wealth for her to stop working.It wasn’t a lottery ticket. Which brings me to the next point.
Second, it didn’t happen by pure luck because she took matters into her own hands. There’s some belief among many lawyers that going off the beaten path means that you’re just trying to collect a lottery ticket. Usually phrases and words like “survivorship bias” or “non-representative” are thrown around. Truth is, success often takes longer than we think, because to find it, you need the right opportunity and the right skills. And then you need to go get it.
Johnson built up valuable skills after the acquisition, and proactively found an opportunity that was a perfect fit for her unique combination of temperament, personality, and experience. It took decades for her to convert all that value into a C-level position at Airbnb. But once she did, she had a huge impact and incidentally, quickly earned a massive amount of wealth, through its IPO.
So for those of you looking for an instruction manual on how to get rich quick, I’m sorry.
This ain’t it.
If you look at the biographies of successful lawyers, like really read into them, you’ll this pattern everywhere.In case you missed it the first time: Success takes a really f***ing long time. Even though Johnson got incredibly lucky as an early employee at Broadcast.com, a startup that went public within two years and acquired the year after that for $5.7 billion(!). I’m speculating here, but I don’t think she got a windfall from that job.
What the acquisition did for Johnson though, was give her the ability to develop rare, valuable skills at Yahoo. Or, as Cal Newport called it, career capital.Remember, this was between 1999 and 2011, when Yahoo was considered one of the most valuable tech companies. They were doing really interesting things, and Johnson got a front row seat to all of it. Here are a few of the things she worked on during that time:
Overseeing legal strategy for Yahoo products which notably included litigation defending Yahoo from a major copyright infringement suit from Sony BMG;
Dealing with a major international PR crisis and learning about the power of an apology, even if it might hurt the company’s legal position;and
Working on regulatory clearance for a search agreement / partnership with Microsoft.
You can get a ton of experience in just a few years working in-house. Johnson spent twelve f***ing years at that job. By the time she walked out of there, she had unparalleled experience leading litigation strategy, handling high profile crisis situations, and getting regulatory clearance for technology companies.
Now it was only a question of who needed that skillset.
In 2011, the founders of Airbnb took stock of what they had accomplished, and what was coming next.Their three year old startup, which was less than two years out of famed Silicon Valley accelerator Y-Combinator, was absolutely crushing it and about to hit an inflection point. They founders knew they were about to hit hypergrowth but there were a few challenges looming ahead.
The nature of Airbnb’s offering—short term room rentals—meant that it ran afoul of laws designed to regulate traditional hotels or housing. For example, just that year, New York City enacted a law that “prohibits most rentals of less than 30 days unless the owner or tenant is present or no money changes hands.” Source How would you be able to run a short term housing marketplace in New York City when that activity was outlawed?
“Early on, I had an instinct we should fight cities,” Airbnb CEO Brian Chesky said.
So Airbnb needed someone who could help them fight back against the regulations. Through litigation, maybe? Or an aggressive lobbying effort. Perhaps they should leverage the media. How would they do this? Was there anyone out there with this skillset who might be able to help?
Right around this time, Belinda Johnson was restless at her Yahoo job. By now she was 44 years old and two decades out of law school. The Deputy GC job was great while she raised her two daughters, but by 2011, she stopped growing and felt an “already familiar emptiness” that “was gradually growing.” It was time to move on. So once again, Johnson did something that would horrify most lawyers:
She quit her job without anything lined up.
The goal was to spend more time with her husband and children. Which she did, for about four months.During that time, she came to a realization. She needed to go back to a startup:
I realized what I want from the next chapter of my professional life. I was looking for the energy of a startup and the possibility of closer communication with the consumer. Source
Johnson had recently come across an article about this new startup, Airbnb. It wasn’t one of the typical fawning articles about some hyped startup. Instead, the article covered an unfortunate incident where a guest robbed their host. And the way the Airbnb responded to that situation made her realize how special it was:
I immediately saw the mistakes that the company's management made . . . then CEO Brian Chesky surprised me: he took responsibility, apologized, quickly initiated the necessary changes and fixed everything. Public admission of mistakes was not a trend in corporate culture back then.Few people understood that consumer confidence in a company could not be restored if they did not go directly to him, did not say what the problem was and how it was planned to solve it. I got excited about working with people who realized that acknowledging flaws does more for the company's image than hushing up.” Source
Johnson decided that she wanted to join Airbnb.However, there was just one small problem: When she looked them up, there were no job openings for someone like her. So just like she did years ago, Johnson decided to take matters into her own hands. But this time, she didn’t need to rely on a chance encounter at the gym to meet the founders. Instead Johnson relied on her existing network and found a mutual contact:
It wasn’t easy. She finally tracked down investor Ron Conway, who made the introduction.
I feel like it’s necessary to point out how this very act—going out of her way to try to get a job that’s not posted anywhere, where the founders weren’t even looking for someone—was an extraordinary step. I know this because I’ve done it before.
A few years ago, as I was nearing the end of my third year at Logikcull, my first legal tech startup, I knew I needed to leave to take things to the next level. At the time I was a successful sales rep with minimal management experience, but my ultimate goal was to become a VP of Sales. I knew that I could get there faster if I went elsewhere, so I started looking for my next role.
Instead of doing what most people do, like applying to available job postings, I decided to reach out to startup founders directly. I focused on legal tech companies that had just raised money (they would likely need help scaling their sales teams, and would have budget to hire.) That’s how I came across a contracts tech startup that had just raised a round of funding and was looking for sales reps. The CEO saw my skillset and background and realized that in addition to selling, I could also lead the team. As its head of sales.
Let me put that differently: He hired me for a job that didn’t exist before I talked to him.
Now let’s place it all in context. At the time I was an inexperienced account executive with just three years of sales experience. Belinda Johnson, on the other hand, had twenty years of legal experience. Someone at that stage of their career probably didn’t need to be proactive to find a good job. Her peers were probably waiting for calls from companies or recruiters. For someone of her stature and experience to hustle her way into getting in front of Airbnb’s founders was, well, unique.
By putting herself in front of the Airbnb founders, Johnson was able to “box” out other candidates. Not that Airbnb was looking for anyone at that time. From what I’ve read, they didn’t allocate any budget to hire a general counsel. So Johnson offered to work for them, as a consultant, free of charge. Which is yet another extraordinary move. How many experienced lawyers in her situation would offer free services to a startup that had just raised $112 million?
There was method behind her madness, though. I’m speculating here, but if the Airbnb founders really wanted to find a general counsel, and had the budget to make the hire, they would’ve have gone with someone else. Johnson had regulatory experience but she had no experience dealing with hotel laws or local regulators. She’d never really been a general counsel herself (her 3 years at Broadcast.com was likely spent as a hybrid GC/business, at a smaller org involving more routine work). So despite her lengthy record of accomplishments, it might not have been enough to get chosen to lead Airbnb’s legal team.
You could imagine what a doubter might have said about Johnson. She has zero experience with hotel or housing regulations. Let’s wait until we can find a real heavyweight with more experience. Like a gray-haired partner from this big firm. I can totally picture an investor or board member saying that and offering to make an introduction. Besides, one of them might say, this Belinda Johnson lady doesn’t even look like a GC.
But you know what? Going with a traditional candidate would have been a huge mistake. Because the job Airbnb needed done was really, really complicated and sort of weird:
[The job] feels more like navigating policy and sculpting a new regulatory framework; very little of the industry deals with established laws, says Vivek Krishnamurthy, clinical professor at Harvard’s Cyberlaw Clinic. Johnson learned to look by analogy at other industries, she tells me, and to think about self-regulation. Source
Would an established hotel or housing lawyer know how to look at other industries by analogy? And sculpt a new regulatory framework? Probably not. Johnson, on the other hand, worked on exactly these types of high level issues at Yahoo. Remember those twelve years long f***ing years as deputy general counsel we talked about earlier? Dealing with PR crises and getting regulatory approval for an unprecedented partnership with Microsoft? This was the moment all that suddenly became really valuable:
“We were the first to start thinking about new laws, clearing a place for the Internet among traditional media, creating a legal framework” [said Johnson] who joined Yahoo specifically to formalize the new rules from a legal point of view. ‘In those days, before Google, Yahoo was the most visible company in the emerging market, and it was incredibly exciting to be involved in its rapid development.’ Source
When you read all of the profiles of Johnson about her time at Airbnb, you’ll find a common theme among people who talk about her. She’s “very easy to work with.” She’s highly strategic when it comes to the the law or regulations. “She never says no.”Which is rarer than you think! The combination of her personality and professional experiences were perfectly matched what Airbnb needed.
More than that, it was the perfect place for Belinda Johnson. In 2011, she was hired to serve as a General Counsel full-time, and spent the next few years growing and scaling with the company. Her role evolved to something more strategic, and more than just handling legal or regulatory matters. In 2016, Johnson was promoted to Chief Business Affairs and Legal Officer, and then to Chief Operating Officer two years after that. In 2020, Johnson stepped down from her position, but continues to serve on the Airbnb Board of Directors.
When you look at Johnson’s story it’s tempting to believe that I’m making a big deal out of a few lucky breaks. Maybe she just stumbled into success. It’s possible, I guess. But I think that when you really dig into the details of her journey, it’s becomes more clear that she made a few big, calculated bets that paid off. She didn’t just fall into opportunities. And she definitely didn’t listen to conventional advice.
Instead, Johnson drew her own conclusions about where the world was headed and where she might be valued. And then acted upon them. I think that’s the real lesson here. Whether you’re unhappy at your job and or bored and looking for something different. The takeaway is this: You need to make a calculated bet, too.
Because in the end, to find meaningful work, you really do have to put matters into your own hands.
Thanks for reading! I hope you enjoyed reading this as much as I enjoyed writing it. Let me know what you think by leaving a comment or emailing me directly. And if you want to see more of lawyer stories in your inbox, smash that subscribe button!
From an article published years later, about when she made the move: “At some point, Belinda was so desperate that she suggested that her husband give up everything and go on a voyage around the world on a cargo ship. She even approached this rather insane idea thoroughly: she typed brochures, laid a route, calculated a budget and held a presentation. But the wind of distant wanderings could not blow away her husband, who was very pleased with his legal practice in Dallas.” I’m speculating here, but I’d bet Johnson didn’t chart out a very specific career plan but instead, faced challenges and was forced to improvise. Reminds me of what happened to me right after I got fired from my law firm job.
I’m not sure if there’s any way to find out but as mentioned in another footnote, her name was not mentioned in the S-1, and there might have been a more senior lawyer with a non-legal title at the company during its acquisition.
This involves a ton of speculation but given where Airbnb’s share price is, and assuming Johnson kept most of her shares over the years (a pretty big assumption) she’s worth at least half a billion dollars today.
I’ll be sharing the story about Joe Tsai in a future Substack. He was more “lucky” than Johnson in the sense that he got into Alibaba as a co-founder, which is why he’s worth a cool $10 billion today. But for Tsai, he still had to work 6 whole years in the industry (on top of the 3 years he spent at Sullivan & Cromwell) before finding Alibaba. I’ve shared a bit about his story in this Twitter thread.
Her name isn’t mentioned anywhere in Broadcast.com’s S-1 filing. There also appears to be some VP of Operations (who had a legal background and General Counsel experience) whose name did appear in the S-1. And even he didn’t get a ton of equity. Source
Here’s a quick description of how useful career capital is from Newport himself: “The conclusion is that if you want to do something truly useful with your professional life, don’t start by figuring out your “mission.” Instead, identify some potentially useful-looking skills, then push yourself to the cutting edge with a single-minded intensity. It’s only then, once you’ve mastered the foundational abilities, that you’ll be able to find that spot in the adjacent possible where the meaningful mission lurks, waiting for its champion.” Source. I highly recommend his book So Good They Can’t Ignore You, which had a huge impact on how I viewed career planning during my transition to legal tech sales.
Johnson was an employment litigator early on in her career, but the Sony BMG case was a very different kind of case, and was incredibly high profile. The litigation lasted for six whole years (2001-2007, right in the middle of Johnson’s 12-year tenure at Yahoo) and involved novel issues, like whether Yahoo’s “Launchcast” product was an interactive or non-interactive music service. As the in-house lawyer responsible for leading Yahoo’s defense, Johnson likely received a bird’s eye view of litigation tactics and strategy, which likely helped her develop the judgment necessary as Airbnb’s Chief Legal Officer when they decided to pursue proactive litigation against San Francisco. Source
From a 2016 profile in Marie Claire: “In 2005, Yahoo China turned over user data to the government, which led to the jailing of a Chinese journalist named Shi Tao. The company was criticized by everyone from Chinese bloggers to The New York Times—and executives had to testify in front of Congress. ‘You get into these crisis situations, and you get a lot of advice coming from outside crisis firms, PR offices, law firms, everything. You might have a set of lawyers who say, 'You can't go out and say you're sorry, because that's an admission' or 'You can't have a conversation with the other side,’’ Johnson says. "At the end of the day, you have to do what you think is right and be human. Even if it's an opposing party, treat them with respect." She believes that if her team at Yahoo had just reached out to Tao's family right at the start, it would have saved everyone a lot of time, money, and pain.
In 2009, Yahoo agreed to license its search engine technology to Microsoft. The deal had to be approved by U.S. and E.U. regulators (ie. Department of Justice & European Commission). It took a year but it went through because it was viewed as a counterweight to Google’s search engine dominance. Source
Some irrelevant trivia: My sister and brother-in-law were both in the same class at RISD as Joe Gebbia and Brian Chesky. I still remember hearing Chesky’s graduation speech in person. Which, as I recall, was the funniest one I’d ever heard in my life. Maybe that’s why I decided to run for commencement speaker when I graduated from law school six years later: I wanted to give a funny speech too.
If you haven’t heard of Y-Combinator, it is the most successful startup accelerator in the world. Some of the world’s most successful companies have emerged from their programs, like Stripe, Dropbox, Coinbase, and yes, the world’s number one contract lifecycle company, Ironclad (where I work today).
Once on board, Johnson encouraged the Airbnb founders to take a more strategic approach. Why not collaborate with the cities who wanted to work with Airbnb first? They could always fight later. “She reminded me there’s a time for that, but you’re in these cities and you have to collaborate with them. It really changed my point of view,” says Chesky. Johnson was always thinking a few steps ahead.
There’s something to be said about not rushing off into your next role. Time off, whether it’s coming off a successful 12-year run like Johnson, or coming off a failed entrepreneurship venture like me, seems critical when looking for the right opportunity.
I’m not convinced it is today either. Over the past six years working with lots of different startups, I’ve found that not all act with integrity. The good news is, the bad apples do get exposed eventually. Because your customers will talk to each other. That’s one of the things I love about the rise of the community function for tech startups. There’s huge marketing value to it, sure. But more importantly it requires vendors to do right by their customers, again and again over time. Having a thriving community is a strong signal of quality to potential buyers. See e.g. Ironclad Community
There were probably other reasons too. Johnson likely recognized that Airbnb was the type of company that would need heavy legal firepower in the years to come. Related article from Bloomberg Law about this trend. And it wouldn’t be just be the blocking and tackling work that most experienced lawyers could handle. They needed someone who could see the whole field: strategy, litigation, regulatory agencies, and how all of those things interacted with one another. They needed someone like her.
There’s another cold outreach story from my law school days that I’m going to save for another day. It’s about how I was able to beat out hundreds of applicants and land a federal clerkship despite having weaker credentials than most. Getting that clerkship job was one of the hardest things I’ve ever done, especially since I had to also tell my judge that I had just failed the bar exam.
This wasn’t the only reason I left. One of the biggest reasons was to leave e-discovery for the contracts space. I’ll explain why in a future post.
I’ll write more about this someday, but being the head of sales was an eye-opening experience. It gave me a true appreciation for what sales leaders do.
Cold outreach to find opportunities is valuable and works precisely because very few people do it. For example, I wrote about Tom Goldstein, who cold called lawyers to represent their clients for free, in the hopes that their case would be reviewed by the Supreme Court. That is how he ended up building a Supreme Court practice (despite having a “weak” resume for that type of law) and led to the creation of SCOTUSblog.
From a 2016 Wired article: “Johnson won Chesky over early on because, he says, her default answer to any question is “yes.” It cannot be overstated how unusual this is, given both that she is a lawyer, and that she is working in an industry for which the rules have mostly not yet been written.”