Infiltrating any startup

The next Google, Microsoft, and Facebook are among us. They’re run by founders who refuse to sell their companies and have staggering revenue and growth. In Startups Open Sourced, I asked cofounder of Brian Chesky a few questions about

Infiltrating any startup

by Jared Tame on May 10, 2011

The next Google, Microsoft, and Facebook are among us. They’re run by founders who refuse to sell their companies and have staggering revenue and growth. In Startups Open Sourced, I asked cofounder of Brian Chesky a few questions about this:

If you got an offer from Google or any major tech company tomorrow to get acquired would you accept it?

Even if it was ridiculously good?
Even if it was ridiculously good, I’d say “no.” I think we can build a company like Google. When I said “like Google” I mean I think we can build a company that—success for us is people forgetting what the world was like before Airbnb. I don’t think it would exist as a business unit inside a large conglomerate or as a subsidiary. I think for us to truly accomplish what we want—which is to connect millions of people and give them access to all these experiences and spaces around the world—I think we need to remain an independent company. I’m pretty forthcoming and open with people about how big I think we can become. I think we can become at least as big as eBay, and maybe even bigger. What I like to say is “if eBay can become a billion dollar company by monetizing stuff in their house, how big could a company be if they monetize the house?” We’re in a multi-billion dollar market. How big could a company be if they became a marketplace for unique experiences and spaces? With our growth trajectory, I couldn’t imagine a reason to sell. We didn’t start Airbnb to make money; we started it to do something significant for the world. I think all of us on the board and the team feel that way.

And Airbnb aren’t the only ones who are operating their own money-printing treasuries in their server rooms. There are other companies that have blasted past Ramen profitability. Wufoo was at that point before they got acquired for $35 million, and Weebly is in that same class of startups right now. Even though Dropbox isn’t in the book I imagine they’re at that point. Other companies are just waiting to flip the revenue switch: Grooveshark and foursquare have massive crowds engaged on their applications, but they haven’t started to focus on revenue yet. If I had to guess, pulling company names straight from the book: Justin.TV, WePay, Little App Factory, AppSumo, Hipmunk, Indinero and eventually Greplin–as long as they refuse to be acquired by Google and Facebook–will all be in that same class of startups.

Getting into these companies will translate very well as an early employee. You know you’d be well off as an early employee at Facebook or Google. It’s probably already obvious to smart students because I’m getting e-mails about it. Getting into one of these startups has become the single question I’m asked most over e-mail when people read Startups Open Sourced. They want to know how they can stand out. I’ll probably point future questions about this topic to this post. For some reason, I doubt that most people will take this approach because it requires a bit of hustle to pull off. If everyone does it, it wouldn’t be as effective, but I don’t think many students will walk away from reading this and actually do this.

Get it out of your head. Resumes suck. Stop sending them.

I talked to a friend a month ago with a liberal arts background who came to tears at dinner because she told me she couldn’t find a job. I asked her what she was doing, and she said “I’m sending my resume to everyone, but nobody responds.” I told her that’s exactly what everyone else is doing, so why would they pick hers out of the entire deck? Unless there’s something remarkable on her resume, she’s just another sheet of paper full of stuff. There’s no way for a recruiter to even know which piece of paper would be better than the others. You could look at stuff like GPA, but that’s a speculative measure at best.

The bar for joining a startup is higher. Startup founders know they live and die based on the type of people they hire. Want to know what they uniformly all look for first?

Startup School 2009. Why didn’t they put #10 first?

The ‘cultural fit’

When a startup is looking for an employee, they always say they’re looking for ‘cultural fit.’ I don’t think a single cofounder I spoke with would hire someone who is pretentious, no matter how smart they are. I know a few friends that are like this–I would never start a company with them because they’re almost intolerable; I can’t imagine spending 18 hours out of the day with them, but I’m okay grabbing drinks with them from time to time. In other words, the response from founders usually goes: “I’ll never hire someone who is an asshole, it doesn’t matter how smart they claim to be.” So it’s important that you’ve got the right attitude. Don’t go looking for a job thinking they owe you anything. Don’t assume that because you have a college degree that you’re entitled to any special treatment. The best attitude you can have is that you’re there to learn and help the startup be aggressively productive. That’s the type of personality a startup wants to see.

The hack: use it once, do it right

You are a fresh graduate. You have big aspirations, you’re a perfect cultural fit, you’ve decided not to send your resume, now you just need the startup founders to recognize you. So this is going to be your hack; your way of entry into the startup.

Choose one and only one company. You’re going to join this company. The reason you don’t want to do this to multiple companies at once is because it may not look genuine. Imagine if you were asking multiple girls (or guys) if they wanted to date you at once, and they all knew you were running around saying the exact same thing. Doesn’t look very good on you does it? You should really be excited about joining this startup. Having the idea that you’ll just blast out resumes is more of a passive approach–you sort of accept whatever you get, and that’s a poor attitude. If something excites you, go after it 100% and decide that you’re going to do it, don’t just take whatever gets handed to you by chance. If you have an offer from any company at this stage, that’s even better because it’s leverage and social proof. You can say “this other company wants to hire me, but I really want to work with you instead.” Shopping around for offers from multiple startups is not something I’ll cover in this, but it’s possible. That usually only works if you’re really good and the startups are knocking your door down to hire you.

Research the company. Find out who runs the startup. What are the full names of all the founders? What are they like? What excites them? What is their favorite sports team or programming language? Go watch all of their interviews on YouTube. If they’re in my book, read the entire interview and figure out what they’re looking for when they’re hiring. Figure out what keeps them up at night and what things challenge them. Almost every founder has something that stresses them out and keeps them up at night. Get a complete understanding of their company’s culture.

Get a domain. Something like “” is fine. It doesn’t matter if you’re technical or not–if you completed all the mundane assignments that come with 4 years of an undergraduate degree, you can figure out how to sign up for a domain and get a simple page working. It’s even better if you can demonstrate that you do this on your own, because it’s that much more impressive. If you’re a liberal arts major, you’re at an even greater advantage because it shows you’re not intimidated even by technical challenges. If you’re a computer science student, you should probably spend more time contributing to open source projects on or asking the founders if they will let you help write some code for free (this is how @jspeis approached me and started working on–knowing we’re a good fit, I’d probably start a company with him today). Technical students can still use this hack though.

Call the founders out. If you want to get the founders’ attention, call them out by name. Say “Hey Dennis and Naveen, I’m Dave and I think I’m perfect for foursquare because I use your app every single day. I am the mayor at Subway and Starbucks in my city. I can’t code, but I can get stuff done, no matter how challenging it is. Send me one of your to-do lists this week and I’ll have it done in 72 hours. If you don’t hire me, then you got some free work, which is great. If you do hire me, you’ll know you made the right choice.” Then include a paragraph about yourself: your hobbies, your skills, the 5 web sites you visit most often, where you grew up, where you want to live, why you’re interested in the startup you’re applying for. Put your phone number and e-mail address on there; make it easy for them to pick up the phone and call you or send an e-mail. Include links to all your social sites: Facebook, Twitter, Posterous, etc.

Get the site in front of the founders. Do whatever you need to do in order to get this site in front of the founders. Put it on Twitter and include the founders’ Twitter usernames, then get all of your friends to retweet it. Submit the story to Hacker News, generally the community is supportive of these types of things and wants to help you out if they’ve seen you’ve put in the effort. If you have a compelling story to share, people are going to help you get it out there because they want to see you succeed. If you contact me and ask for an intro, I usually don’t make cold intros because I don’t know you and bad introductions generally reflect poorly on the person giving the introduction. However, if it seems like you put in a lot of hard work, and despite everything you tried you couldn’t get the site in front of the founders, I’ll pass the link along and make sure they find out about it (at least if they’re in my book; if they’re a little bit more difficult to get access to then send me an e-mail and we’ll figure that out, just make sure you’ve tried everything else first).

Respond quickly. If the startup reaches out to you whether it’s on Twitter or e-mail, respond quickly. They might interview you, in which case you should be prepared for that by interviewing with other companies that you don’t actually want a job from. That helps you learn how to respond to certain types of questions without the added pressure of wanting the job. They might ask you to try a project so they can see how much self-motivation you have. If you give up on that project, they’ll know not to hire you because you too easily give up. If you do well, obviously they’ll want to hire you because they know there’s more where that came from.

Founders chime in, more tips

Here’s what founder Tom-Preston Werner says:

Don’t just send in your resume, that’s useless. A couple of times we have put out requisitions for jobs; the people that are most impressive to me, that I don’t know, are the people that have web blogs and write. That, to me, is extremely important. I need to know how a person thinks and I need to know that they can write well because that is indicative of having good communication skills and having thoughts they think are important enough to share with other people. Really put forth the effort; craft your response to the individual company, don’t just blast a bunch of resumes out to a bunch of places, that’s useless.

So what else should you be doing even before you reach out to founders?

Write a blog. Even if you don’t get a job with a startup you want, you may not realize that writing a blog is very important. This is one of those strange things that’s criticized, at least that’s my own impression. People think “why are you writing a blog? You should be working!” It’s the exact same problem where people say you should not be reading news or blogs because your time would be better spent working. I think that’s pretty naive; working is very important and you need to be productive, but to expect that it’s going to be done 100% of the time day in and day out as if you’re a robot seems like the shortest path to burnout.

Blog with a purpose. Don’t blog because you want to just blast out random stuff at people and hope to get attention, that’d be the wrong approach to take. Write a blog that is genuine about stuff you’re really interested in and thinking about every day. I write my own blog because I find problems that show up a lot, and I know I can go back there whenever I see a problem and I forget the solution to it. I hear from people saying “hey thanks, nobody else wrote about how to easily setup SSL certificates in Heroku and GoDaddy, thanks for doing this.” It turns out that it helps both myself and others who have similar problems. The reason Wufoo got into Y Combinator was because of their blog, Particle Tree. The reason they had users from day 1 was also because of ParticleTree. Make it fun, do it with some friends, be experimental.

To elaborate on the usefulness of blogging and writing, from cofounder Kevin Hale:

We had been writing a blog called Particletree for about a year and a half before we even heard about Y Combinator and, basically, we wrote about any interesting new thing or technique we came up with, or anything we discovered about how to write web applications. We wrote experiments and case studies that ultimately showed we knew how to create stuff that people were interested in. I think at the time we had 10,000 RSS readers on that blog.

One of the big things that Jason Fried talked about was: they created this blog first and they generated an audience and once they got that audience, then they released an app and were able to release it to this trusted users that they had established relationships with so it wasn’t starting from scratch. So we said “alright, we’ll start a blog and we’ll just write about everything that we learn about how to create software; then when we finally build this thing we’ll hopefully have an audience” and so that’s why we did Particletree. It was after South by Southwest and about a year and a half after getting into Y Combinator and building it, we were able to announce Wufoo to the 20,000 blog subscribers that we had cultivated.

Nowadays, Y Combinator people go in with finished products or things that have already launched or have user bases. At the time we didn’t even have a prototype, right? We hadn’t written a single line of code at that point. All we had was the fact that we had done Particletree and we had had all these ideas; it showed that we were technically capable; we definitely had a design sense; and that we knew how to work well together.

Q: If you didn’t have this blog would Y Combinator still have talked to you?

Probably not. The reason Paul picked us out there as one of the final interviews, he said, was because he had been an avid reader of Particletree, for a while. If we came with no prototype and we had never done Particletree, there would be nothing to prove that we would have been able to do it. cofounder Adam Goldstein says:

We were about to decide, when we got an application from this girl who said, “I’m a big nerd for flights. I live near Sacramento and I can hear the planes overhead and I can often tell you which flight number it is, just based on what time of day the plane is leaving because I know the schedules.” So, while that’s impressive, Sacramento doesn’t have that many flights so, if you put your mind to it, anyone could have done that. But, it’s cool that that’s something someone thought was worth doing, so it stood out as dedication to this field. We figured somebody who knew a lot about it might bring an interesting perspective.

To illustrate the second, one of the ways that we found our main contract designer, was, he put up a blog post where he talked about what he did and didn’t like about Hipmunk’s interface and what he would do to improve it; he basically put up a sketch of how he would have made Hipmunk himself if he’d started it from scratch. So, he already knew about us and thought that we were going in the right direction, but recognized that there were things he could contribute and improve upon; that was really appealing to us.

The takeaway shouldn’t be that Hipmunk is going to hire people who say that they love Hipmunk, because that’s not what I’m saying. Hipmunk really likes it when people say that there are certain things that they like about it but certain things they don’t and then offer us constructive suggestions or improvements on how to make it better.

People who do that, and there have been a couple, tend to be great hires. They’re self-motivated and have interesting product ideas and we are always happy to have people like that around.

If you’re a designer, redesign the startup’s home page. This is almost too obvious to mention, but I think it’s also easy to forget. If you’re a designer, your first reflex is to just blast your portfolio to everyone and see if they like it. In the design world–at least amongst really skilled designers–I think doing spec work is frowned upon. Designers should get paid for the work they do, sure. But there are times when you can throw rules out the window, like when you think you’re about to land a job with the next Google or Facebook. It’s sometimes worth taking the time to do some spec work and see if the startup likes it. At the very least, if you’re good at design and you do one of these, those tend to get lots of attention on sites like Hacker News because the community seems to enjoy those types of things. I distinctly remember Dustin Curtis’ redesign of American Airlines. I’m sure another company will come calling if that happens as a fallback.

For a great example, see how Loren Burton used to get the founders of Airbnb to contact him.


Jared Tame.

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