In college, I studied spent a lot of time studying warfighting strategies in the context of international security and politics. My pet topic was insurgent strategies––the strategies of the weak and poorly resourced. Amazing how many of those lessons transfer to technology startups in the broader Silicon Valley…

I had coffee this morning with an aspiring entrepreneur. He was young, still in college and interning at a pre-IPO “startup” in San Francisco. Toward the end of the meeting, he asked me a question that I think a lot of proto-entrepreneurs ask themselves (I know I did!):

It seems like every startup you read about on TechCrunch was started by ex-Googlers or Stanford kids. That’s not me. I don’t have that kind of pedigree. Should I try to work at Google and get that pedigree before I start a company? Will investors fund me if I didn’t go to Stanford or work at Google?

Translation: How the hell can I make in Silicon Valley if I’m not already in “the club”?

Many, many entrepreneurs––myself included––have struggled with this question. If you struggle with this quandary, here’s my advice…

Most people are outsiders. And even the people who are insiders now, by and large, were outsiders once, trying like fuck to break in––just like you are now. This is very normal.

Force the world to pay attention to you. There’s a few options for how to do this:

#1 Build something people want.

If you can do this, it is the most preferable option. If you build the next Facebook, people will throw money at you, period. Peter Thiel invested in Facebook because Facebook was awesome, not because Mark Zuckerberg had gone to Harvard. This is a case of “traction trumps everything.”

The reality of most startups, however, is that very often you need to outside resources (i.e. venture capital) to get to the point where you’ve built something that lots of people want (i.e. there’s a big market for your product). Nonetheless, you typically need to build something that at least a few people want to get funded.

#2 Make a name for yourself on Hacker News.

Get yourself on the front page of Hacker News! The top eyeballs in Silicon Valley visit the site daily. It is THE locus of the global startup community.

Your best bet here is to take a sacred cow and skewer it. Be a contrarian and mean it! Nothing pleases the entrepreneur soul like seeing a scrappy little David take on Goliath. The important thing here is to be thoughtful and intelligent, not simply provocative for the sake of being provocative. The key here is to earn the respect and attention of your readers. This was a large part of my strategy, but the guy who really nailed this is GroupMe’s VP of BD, Steve Cheney.

#3 Get Press.

Do something so outrageous that TechCrunch has to notice you. Back in Summer 2010, when SpeakerText’s finances were on, ehh, shaky ground and it was questionable whether we’d raise any money at all, there was plan C: “Startup Tent.”

The idea was simple: Pitch a tent on the Stanford campus, tweet like crazy & check in on Foursquare, livestream a video feed, and pray that Michael Arrington showed up before the cops. “Oh, those scrappy entrepreneurs!” would be the headline…and then angel investment would follow…? This was the #StartupTent strategy.

AirBnB used this strategy early on with their Obama O’s & McCain Crunch cereal box campaign. Landed them on CNN, then YC.


At the end of the day, breaking in is just the first step. Financial success is ultimately what matter:

Each time you crest the rise in front of you, it just makes it clear the size of the even larger hill that looms beyond it. It goes on for a long time. I pissed blood for years keeping Netflix alive while we figured that shit out – as did every other successful entrepreneur in the valley.

Ultimately, your reputation in the tech community is going to hinge on your ability to deliver this company to success. That’s the real – and only – responsibility of a CEO. Marketing yourselves well in the valley is just one of the many many things you have to get right to make that success happen.
Marc Randolph, February 28, 2011 (in an email to me)