An Outsider’s Guide to Visiting Silicon Valley

Despite the fact that this blog — and my recent book — are about startup nuances outside of Silicon Valley, the truth is that I really love the place.  It really is true that the Bay Area is a very special place for a startup entrepreneur to be.  I’ve had the chance to visit several times and encourage any entrepreneur to do the same.

Of course, it’s not all “rainbows and unicorns” over there.  I’m not sure what I was really expecting, but I found Silicon Valley to be mostly a “normal” place.  The cities that make up what people refer to as “Silicon Valley” are mostly sprawling suburbs with the same chain coffee places and restaurants that you’re probably used to seeing wherever you’re from (there are, of course, awesome independent ones, too).  The famed “Sand Hill Road” is really nothing more than a long string of office parks.  The actual buildings that house some of the world’s most famed venture capital firms are mostly “boring.”  It would be very easy to drive by and not notice them at all if you didn’t know what you were looking for.

Nevertheless, visiting this startup mecca is a must.  The historical significance of Palo Alto, Mountain View, Menlo Park, and even “The City” known as San Francisco are, alone, one reason to go.  Of course, I’d contend that the real reason would be to get to personally know awesome entrepreneurs that are working hard to see their dreams come to life… and build some real relationships in the process.

If you’re going to go, though, I have a few tips to share based on my own personal experiences:

1.  Don’t stay in a hotel.

If you truly want to get the full “Silicon Valley startup entrepreneur” experience, there’s no way you can stay at a lifeless, run-of-the-mill hotel.  That’s not how entrepreneurs live.  Often times, they’re living with other entrepreneurs in live-work setups.  That’s why I love using AirBnB when I travel.  In Atherton, there’s even a place called the Blackbox Startup Mansion that will allow you to live squarely in the center of Silicon Valley for as little as $70/night.  At Blackbox, there’s often at least a dozen other startup folks (usually from all over the world) visiting the Valley that are temporarily living and working there at any given time.  Despite the “mansion” in the name and pool and hot tub outside, this place is more akin to Erlich Bachman’s “incubator” than an actual mansion.  Be prepared to get assigned a bunk bed and share your frat-house-like room with other residents.  But hey, what startup entrepreneurs actually live in a mansion anyway?

Protip:  If you do some digging, you may be able to find specific angel investors that have their place up on AirBnB.  In my last stay, I was able to spend less than $150 to rent a room at a founder/investor’s condo within walking distance of University Avenue in Palo Alto.  Not only did I have an awesome place to stay, but made a great connection out of it as well.

2.  Set up a handful of coffee meetings with interesting founders, but keep your schedule mostly flexible.

Don’t make the mistake of booking yourself solid throughout your entire visit.  Part of the thing that makes Silicon Valley so special is the serendipity that it offers which other places simply can’t replicate.  One founder will tell you of another who’s going to be meeting him right after you, and invites you to stay.  That founder mentions how his VC is grabbing drinks with him later.  Are you game to join?  If you book yourself solid, you miss out on the chance encounters like these to build real relationships.  Instead, use tools like LinkedIn to find out what interesting startup people you may unknowingly be connected to, and ask your friends for introductions.  Set a few of these meetings, and leave a lot of time for serendipity to fill the rest of your schedule.

3.  Increase the odds of serendipity by putting yourself in places where entrepreneurs hang out.

If you like coffee, you’re in luck.  Because some of tech’s best startup entrepreneurs and investors do their work in public.  If you make the trek up to San Francisco, you can set up shop at The Creamery or Philz — two of the city’s most frequented java joints.  Work among them, and who knows — maybe you’ll end up finding out about where you should spend the rest of your day.

If you need some direction, though, you could check out what events are happening around you.  You can usually get a good pulse of what’s going on from Meetup and Startup Digest.  Check out some of these events and engage with the people that are there.  If you’re not the social type, suck it up.  This isn’t the time to be standoff-ish.  This is the time to take in what your surroundings are offering you and learn from the experience.

In the end, you should do what you can to get to Silicon Valley at some point to experience it.  If anything, it will give you some great perspective.  You may fall in love with it.  Or, you may find out that the grass isn’t always greener.  More likely, I think you’ll appreciate it for what it is — and appreciate your own startup community as well.  And heck, you may even build some relationships there as a result.

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