Uber turns five this week. For many users it’s hard to imagine a time when taxis or dial-a-number car services were the only way to be driven around. If Uber isn’t quite grown up yet, it certainly has grown. It is now in 311 cities in 58 countries, and it employs more than 3,000 people worldwide. To celebrate its anniversary the company is running a series of promotions in its home town and first market, San Francisco. Travis Kalanick, the company’s chief executive, also plans to give a speech to Uber’s employees, drivers, and various dignitaries. He’ll focus on the challenges that cities face (including safer roads, congestion, and economic opportunity) and how he thinks Uber can help. As well, Uber’s San Francisco employees plan to fan out across San Francisco over the weekend, volunteering on a handful of public-works projects.

In celebration of its anniversary, Uber recently made five of its earliest employees available for interviews to talk about how they came to Uber and what some of their first tasks were. Their stories have some common themes, including the serendipity of joining something that didn’t look like much at first, scrapping to get something new going, and using Twitter to job hunt and stay abreast of critical developments. Their comments follow.

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Ryan Graves and Austin Geidt in an undated photo from the company’s early days.Courtesy: Uber

Ryan Graves was working for GE in 2009, and he decided he needed a change.

I said, “I cannot be the GE guy.” I wanted to get into the startup world. I started following on Twitter a lot of guys in New York and angel investors around the country, figuring that angel investors know what’s coming next.

I wanted to know what was coming next in terms of starting something. I met the Foursquare guys when there were four or five them. They weren’t offering any kind of internships or business roles at the time, but I went out to Chicago and essentially started working for Foursquare. I did that for about three months. Then I saw a Tweet from Travis through some random angel investor who I was following who didn’t know him from Adam. He talked about big equity, big people involved. And I thought that sounded interesting.

So I tweeted at him and I shot him a couple of paragraphs about who I was. We spoke that night ’till one in the morning. It was a two-hour conversation. I woke up my wife in the middle of the night and said, “Hey, what do you think about moving to San Francisco?” We were in Chicago at the time. To her credit, she said, “If you think it’s a good idea, I’m up for it.”




Graves moved to San Francisco in February 2010. There was a lot of work to do at the new company, including improving on the work of one of Uber’s co-founders, Garrett Camp.

Garrett had a prototype that didn’t work very well, so one of the first things we did was go out and get a firm to rebuild it before we pushed it to the App Store. They were called Mob.ly and were later acquired by Groupon. Then we designed the site for UberCab.com. We also worked on things like the sign-up flow and integrated credit card payment systems. All of the basics of commerce needed to be built out. We had one guy who was a driver that we would meet with at coffee shops, asking him questions so we could get an idea if the real world would accept this idea.

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Uber CEO Travis Kalanick in an undated photo from the company’s early days.Courtesy: Uber

Conrad Whelan had been working in technology his native Calgary. He’d known Garrett Camp, a fellow Canadian, for years. An eye-opening trip and a phone call changed everything.

I did a crazy road trip across Europe, across Spain and Portugal in January of 2010 and realized: There’s a whole world out there. I’ve got to get my stuff together and get out of Calgary. I wasn’t actually really intending doing another startup at that point. I was actually planning on taking some time off, but I just happened to give Garrett a call to see how he’s doing. When he found out I was sort of free and ready to move, he basically told me I was hired and to move to San Francisco and help him get Uber Cab started.

Whelan was Uber’s first engineer.

When I joined the company, you couldn’t actually sign up for the product. It was just a way to order the car. So I built the sign-up flows that would take a credit card and make user accounts. So as soon as we did that, we could officially launch, which was June 1st, 2010, two months after I started.

I think the next thing I did, which I really enjoyed, was optimize the dispatch algorithms to take into account drivers that might miss a dispatch. That lasted like three years, or something like that, which is pretty cool.

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Uber CEO Travis Kalanick in an undated photo from the company’s early days.Courtesy: Uber

Ryan McKillen was Uber’s second engineer. He learned about the company from Graves, a fellow alumnus of Miami University of Ohio whom he’d gotten to know in San Francisco. The company was using a small amount of office space from another startup called Zozi.

Somehow we ended up in a tiny conference room in their office, this glassed-in little conference room. The table was about as big as the room. On the morning of my first day I remember crossing the threshold of the door and noticing this stack of books on the table. All these computer science books, programming, databases, all this stuff. They’re pristine—the bindings on the books had never been broken. And there’s this one tattered book on the table that looks like it’s gotten all kinds of love, a lot of use. And so, first thing I say is, “Hey, Conrad, why is there a Spanish-to-English dictionary on the table?” And he looks back up at me and goes, “Well, Ryan, because the code is written in Spanish. Welcome to Uber.”

Austin Geidt started at Uber as an intern. Eventually she’d do so many jobs that she’d be the expert on Uber’s “playbook” for opening new markets.

I was out of school. I was looking for jobs. It was a bad economy. I was following a few random tech people on Twitter, and I think it was from Jason Calacanis, but I saw some tweets about Uber, and it looked interesting. I heard they were looking for an intern, and so I reached out to Ryan Graves, who was CEO at the time, and basically was like, “You’ve got to give me a shot.”

This was in August of 2010. And he called me pretty immediately. He said, “Answer a few questions for me.” I put together a little deck of some sort. I’d love to see today what it looks like. And then, pretty immediately, he was like, “Why don’t you come on in?” And then I met with them.

They were sharing Zozi’s office. They had very little space at the time. I met them. I don’t remember what we talked about but it was very casual. I liked that. I remember that I came very overdressed and they were just, like, these nerdy guys.

I remember thinking, “These guys are really cool, they’re really passionate about what they’re doing. Their products are really interesting.” And so I pleaded [to Graves] and he gave me a shot. I wasn’t super-qualified at the time, to be completely honest. It was a struggle for the first couple of months. I didn’t do super well, but they kind of hung on to me while I was green until I got the hang of it.



I was an intern, so the job wasn’t very defined. I remember handing out flyers at the Moscone Center that no one wanted. I remember cold-calling drivers off of Yelp. Then our first support ticket came in. I was like, “I got this.” And we experimented with phone support early, which just went to my phone. If I didn’t pick up, it went to Graves’s phone, and then to Travis down the line. But then I would get calls at 3 a.m. saying, “I can’t get a car.” So we shut that down. But in the beginning, it was just kind of making up value where I could find it.

I was so green out of school that I thought I didn’t know how to write a proper email. Then I quickly learned: “Oh, everyone’s kind of making this up.” In a start‑up, no one knows what they’re doing. As soon as I got confident on that, I was pretty much off to a running start.

When we started getting support, I was like, “All right, I’m going to do all the support.” I took on the community-management side of blogging and whatnot. And then our driver operations guy left the company. They said, “Austin, can you take this along with what you’re doing?” And I said, “Sure.” And so then I was managing relations with partners.

Remember, we were just limos at the time, right? And so I remember onboarding someone. I happened to walk him out and see that he was in, like, a pink [Chrysler] Caravan, and I was like, “Oh, we should probably do vehicle checks going forward.”

I took notes on everything that I was doing as I was launching a city. It kind of became a very sloppy version of our first playbook. And then each city I would go to thereafter, I would try and refine it, make it more efficient, just streamline this process. Then they said, “Okay, why don’t you hire a couple of launchers?” I ultimately hired about 50. My attitude was, “Ask for forgiveness.” I managed the expansion.

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Uber CEO Travis Kalanick and GM Rachel Holt in an undated photo from the company’s early days.Courtesy: Uber

Rachel Holt moved to Washington, D.C., to be with her boyfriend, who is now her husband. She answered a job listing to start Uber’s operations in the nation’s capital.

I got to D.C. on November 8th, 2011. We did our first ride on November 18th, 2011. So in 10 days, we sort of got everything fully spun off. In the beginning it was just me and another launcher team that started about two weeks after me. I think it was a little bit of the blind leading the blind.

D.C. was the first market that we ever had any regulatory challenges. Ironically, when I went to D.C. I said I wanted to do nothing remotely political. Our official launch was December 15th, 2011.

I remember it was January 11th, 2012—less than a month after we launched. I actually had just come back from San Francisco. D.C. was really on fire. It was doing so well from a business perspective. In San Francisco I had met with Travis and with Bill Gurley, who was in the office at the time. I was so excited to share all this early success we had had. We were really working—really, really working hard. The team was working their tails off.

I got back to D.C. and this tweet comes up saying that the taxi commissioner declares Uber D.C. illegal. Suddenly we were scrambling to figure out what to do. And of course, because it was D.C., everyone is interested in this regulatory story. So the Washington Post was writing about it and blogs in D.C. were writing about it. And then there is a taxi commissioner, not citing any rules, saying, you know, “This is illegal.” And that really sparked two incredibly crazy days. I got a call saying, “The taxi commissioner has requested a ride. What do we do?” And I was like, “Let him take the ride. We’re not doing anything wrong.” And he had called the press before he took this ride, and ended the ride at the Mayflower Hotel, which of course is where all fun things go down in D.C. And he had the press there, and he impounded the driver’s car and gave him $2,000 worth of tickets.

I spent the rest of the day calling every partner that we had, saying, “This is what happened. We’re 100% behind you. If anything like this happens again, we’re going to reimburse you for any tickets and any citations. We’re behind you.” We called every driver personally. We had more drivers on the road that evening than we had ever had before.

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