A conversation with Nick Grandy, Airbnb’s first employee.

Employee #1 is a series of interviews focused on sharing the often untold stories of early employees at tech companies.

Nick Grandy was the first employee at Airbnb. He is currently building Outschool, which helps parents find and book learning activities for their kids.

Discussed: Closing Down Your Startup, Finding a Startup to Join, Meeting the Founders, Interviewing at Airbnb, Growing From Four to 500, Leaving Airbnb, and Hiring Your First Employee.

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Craig : Could you just start by explaining how you ended up at Airbnb?

Nick : Yeah, for sure. I had come out to Silicon Valley with the intention of getting into the startup world though, to be honest, at the time I didn’t know anything about Silicon Valley or startups. I just knew I wanted to explore that world.

I moved out to San Francisco at the same time I joined YC in the winter of 2008. I was working on this company, Wundrbar, with a friend of mine and had a fantastic experience in YC and learned a ton and met a lot of people.

I think actually my high-level plan was “Okay, I’m going to go do this startup, I’m going to do YC, I’m going to figure it out, this is going to be awesome and that’s Plan A. And if that doesn’t work out, well, Plan B is that hopefully I’ll join some other cool company and get into a startup that way.”

Plan A didn’t work out. We shut down the company after about a year and that’s when I started looking around for other startups to join. I think I had the appetite at that point to join an early-stage company so I still had a pretty high risk tolerance but I also wanted to work on something where I felt more assured that my efforts would be put to good use and that there were actually customers and users.

I was meeting with various early-stage companies and ran into the Airbnb guys at a YC event, actually. I met Brian [Chesky] at one and then at a separate event met Nate [Blecharczyk], and the conversation continued from there.

Craig : Were you interviewing with other companies?

Nick : Yeah, I was interviewing elsewhere. Another company I interviewed with was a brain-training game company. I actually worked in a neuroscience lab previously and had an interest in that realm as well. They offered me a job but I passed. I wasn’t fully convinced.

At the same time I was talking to some other people about starting a new company where I would be CTO. But again, I think it was too early, too risky, and I didn’t want to spin wheels for another year trying to get something going. Whereas with the Airbnb guys, they were super early and small but they had a product, a V1, that was up and running. And the product was working. I used it as part of my application process and was like “Yes, this is super cool, this works, I can totally envision this growing and taking over the world and I want to help do that.”

Craig : In terms of interviewing, what was that like?

Nick : I met them socially then swung by the office one day for a pretty casual chat, sort of like “get to know you.” We went to the roof and chatted and had an introductory conversation. Then there was a take-home coding test. Which was basically building a web app. They wanted an answer to, “Can you be productive immediately?”

And then there was an in-person interview with each of the founders. Lastly there was what at the time was termed “the beer test” though now it has more appropriate names.

Craig : Was there anything in particular about the founders that made you want to join Airbnb or was it the product entirely?

Nick : I think it was both. I knew that I’d be working with those three guys very closely. I had to be impressed by them and excited about the prospect of working with them and I was. I was at a point where I was looking for both a product and a vision that I was excited about in addition to the people.

Craig : In terms of the early days, how long was it before there was another employee?

Nick : It actually wasn’t long. They had been looking to hire a first engineer for a long time and the product was starting to take off in such a way that it was then like, “Okay, we need to scale.”

At the time that I joined, there were some sales contractors who were there and pretty soon after, we brought on support contractors. I think actually the second full-time hire came on like a month after I did and then probably the next full-time hires came on maybe like a month or two after that. And then it just picked up steam.

Craig : When it was just four of you, what was that environment like?

Nick : It was the four of us around a giant desk–like four desks pushed together in the middle of a living room.

I think that they, as the founders, they remained more concerned with the corporate questions. I was brought on as an engineer specifically so I had a pretty specific domain. But for things like product questions – “How do we fix this problem?” or, “How do we do this?” – I think those questions were fairly collaborative.

At the time we had weekly product meetings where we talked about the work in progress, challenges, priorities, and how we were going to invest them. It was a fairly collaborative environment.

Craig : You were there for several years, how did the environment change over the course of your time there?

Nick : It definitely evolved. I think that as the company grew, more separation was created. Initially The founders would independently talk about the high-level priorities and then Nate and I would talk about engineering priorities–what we’re going to build, how we’re going to sequence it, and the allocation of work. As the company grew, early employees, myself included, had larger responsibilities in terms of onboarding new people, setting product direction, and defining the direction of the company. I was basically an individual contributor engineer in my first year, an engineering manager / product manager in my second, and a general manager in my third.

Craig : How did your opinion of the company change as you came into this role where you were managing other people?

Nick : The company definitely scaled very quickly. I was there for three years and when I left it was about 500 employees globally. In the last year that I was there, we basically opened like 10 international offices and hired a ton of people because it was just this incredibly rapid growth.

I preferred the small company vibe and was less interested in being a senior manager at a larger company. My favorite stages at Airbnb were when we were around 10, 15 people plus or minus, where there was some focus and specificity of roles but the whole team was also really intimate and you knew exactly what was going on. There was a very fun feel to working at the company. It had this sort of Wild West feel then.

Craig : I’ve noticed that desire among a few first employees. They seem to like that stage where it’s kind of in-between. Do you know what I mean?

Nick : Yeah, totally. I was going to say that by comparison I also worked at Clever. I was there immediately before Outschool. I joined when they were about 20 people and left when they were around 80 people. I started to have the same feelings in relation to the size of the company. That said, Clever is an awesome place and I actually would have stayed except that the time was right to start Outschool with Amir [Nathoo] and Mikhail [Seregine].

Craig : So what was the trigger for you to leave Airbnb?

Nick : There wasn’t one trigger in particular. I was and remain super excited about the company but it was basically the organization growth. Scaling from four to 500 people in three years is super chaotic, and I was less excited about being part of a large company.

Craig : You picked a winner in joining Airbnb. You could have tried to do that again. What made you feel that you wanted to start your own thing?

Nick : That’s a bug that I had prior to being in Airbnb. I had gone through YC. I wanted to start my own thing. Where that came from, I’m not really sure.

I think it’s just different strokes for different folks. Some people would be really thrilled to pick a winner and join a hot startup early on, then grow and become a senior executive at that company. For whatever reason, that wasn’t the vision that was exciting to me. The vision was to create something from the ground up.

Being at Airbnb also created a really tough baseline. Airbnb’s such an awesome business. It’s a really great business model, it’s really fun and it’s exciting and romantic. There are so few businesses like that. It’s particularly difficult when comparing it to other businesses that I’ve looked at and considered joining or starting.

Craig : I assume you learned a lot at Airbnb. How are you translating that now into Outschool?

Nick : There are a lot of parallels in the two-sided peer-to-peer market. I think pretty much every day there’s some parallel or learning I think back to or recall for Outschool.

In terms of product, marketplace dynamics, and organizational growth, learnings are applied every day. Actually, working at Clever was also a fantastic experience because it showed me that it’s possible to have a high-growth company with a totally different culture and different approach. That was a great learning experience and one I’m glad I did before starting a new company again.

Craig : Have you hired someone yet as a first employee?

Nick : Actually we’re in the process of that right now.

Craig : So what are you doing? How’s it going?

Nick : There’s all of that tension around how much you optimize for every hire. And I think Airbnb sort of optimized very carefully and it was really painstaking in the early days of hiring me and then also hiring subsequent employees. We were really careful vetting and then on the other hand you have the advice to, “hire fast, fire fast.” I think actually my approach is going to be a little closer to that.

Craig : Are you narrowing in on a person?

Nick : We have two roles: a customer success manager and an engineer. We’re in the interview process for both of those and we’ve had a pretty good response. We’re interviewing people in person so hopefully we’ll have a hire in a matter of weeks, hopefully not months.¹

Craig : What are you looking for in a first hire?

Nick : The thing that we’re screening for in the first hire are someone who’s comfortable with a dynamic environment and comfortable with change. They need to recognize that week-by-week there might be differences in the company. You just have to be comfortable with that or it’s not going to work.

We also want somebody who wants to help build a company from the ground up. Not just someone who’s just looking for a job, somebody who’s really excited about the idea of helping to build an organization.

Those are sort of critical for any role, independent of the particular skill sets. And then also things like being an independent thinker and being able to solve problems on their own, because we can’t oversee everything.

At this point we’re essentially looking for partners as opposed to people who are simply hired to do a 9-5 task and then go home.

Craig : What about somebody who’s looking at companies and thinking about being a first employee? What should someone know if they’re going to do that?

Nick : That’s a good question. I think a lot of that’s pretty context-dependent by where the company is at. I joined Airbnb at a time when we were just starting this very aggressive growth curve and the whole organization scaled very quickly. That’s different than if I had joined early on and for a year we struggled to find product/market fit and didn’t hire anybody else.

Those are very different things and imply different relationships. I think for a lot of YC companies there is a pretty big distinction between the founder role and an employee role where the founders are thinking about corporate-level things and a different set of problems than any particular employee will who is brought in to solve a particular problem for the company.

Craig : Is there anything someone should know about setting or managing their expectations when joining a company as a first employee?

Nick : Generally, it’s a super risky thing to do. The sweet spot generally comes later where there’s more clarity that a company is on a great path and has a great growth curve. For very early employees often that’s not clear, let alone how long the company will be around or what things are going to look like in six months or a year.

I think that anyone looking for an early role needs to be comfortable with that high level of risk and needs to be particularly excited about the benefits of being super early, such as being able to touch all parts of the company and see all the parts clearly. There’s also the team intimacy, the Wild West feel, the lack of process, and then the immediacy of doing anything that comes along when your team is then only four people or ten people large.

Craig : Thinking back on Airbnb, how do you feel about your time there?

Nick : I feel incredibly fortunate that I got connected with the company at the time. It was a fantastic experience in growth and I’m itching to have that experience again.

1 Since speaking with us Outschool has hired their first employee. ↩