So Fifteen Entrepreneurs Walk into a Cave...

So, I’m standing chest deep in freezing water wearing a bright orange mining helmet, some water shoes with holes in the toes and a rented wet suit that was already wet when I winced and shimmied into it about ten minutes earlier. (Ew.) I’m hundreds of feet below the earth in an ancient Mayan death cave that’s just been discovered two years ago. Apparently a local who thought a creepy jungle 40 minutes from civilization would be a good venue for weddings and Sweet 16 parties bought the property a few years ago. One day he saw an Iguana, which is apparently equivalent to Kobe beef in Mayan culture. Like some Mayan Alice in Wonderland, he chased the Iguana into a hole and kept digging while the hole got deeper and deeper. He found this enormous cave. How enormous? No one knows. They haven’t even explored all of it yet. In fact the Discovery Channel is coming next week to help. A white thread tells you when you’ve entered unchartered territory. That, and some skulls.  After all, they don’t call this a death cave for nothing.

I’ve already been told not to hurt the spindly crab spiders who also share the death cave, and I nodded, even though I know I’m smashing that guy into a rock if he comes near me. I’m trying to avoid jagged rocks and growing stalagmites on the floor of the cave and looking up to see a huge vaulted cave ceiling with thousands of sharp pointy stalactites over which is our van or a forest or something. Maybe even that MIA iguana. Being from San Francisco, I immediately start thinking about earthquakes and these thousands of spears coming crashing down on all of us.

Just then, the guide tells us in broken English that we’re about to turn off our helmet lights and sit in total blackness for a while. And I freak out, mostly because I can’t understand what he’s saying I just hear “total darkness” on top of the uncomfortable situation I’m already experiencing. “I’M NOT COMFORTABLE WITH THIS!” I shriek. Yeah, all those people who keep writing about how fearless and ballsy I am? A cave full of entrepreneurs now know the truth. Especially Tony Hsieh of Zappos, whose hand I squeezed so hard, a few fingers could be broken.

Did I mention I’d actually signed up for a lazy afternoon of snorkeling?

At the end of the bizarre cave journey, I was glad that I went, even though I was a little terrified of what it would hold on the front end. Similarly, that’s my feeling at the end of a four-day entrepreneur summit in Cancun that brought me to this death cave.

Typically the destination, beachy conferences that I go to are pretty Valley-centric. They give me a great opportunity to meet people whose names I’ve heard over and over but somehow never crossed paths with, but more importantly, they give me several days away from the madness to spend quality time with some of my favorite sources in the industry. Conversations like those are the reason I do what I do for a living. Also, I usually get at least half a dozen story ideas.

But on this trip, I was largely the outsider. The bulk of attendees were from the East Coast or LA—there were only about a dozen folks and most of them from Facebook. Four days later, and I’ve met a lot of amazing people who I plan on writing about in the future (near term here; longer term, who knows?) and people I just like and want to stay in touch with. I’d name my favorites, but that probably wouldn’t be nice now would it?

There are some funny differences. For one thing, there was a lot of hand wringing about how few women were at the event, but there was a way higher percentage than a typical Valley conference. And they were all absurdly hot. That’s partially because a lot of East Coast web companies are more media centric, and also because the summit had a wide view of entrepreneurship including authors like me, and social entrepreneurs designing ways to give the world, say, clean drinking water not just a new social network.

Another difference? Web people who don't own their own names' domains (ala sarahlacy.com), and it never occurred to them to buy them. That’s pretty much step one for anyone in the Valley scene—if nothing else, it’s a defensive measure.  What few entrepreneurs that I know who are having babies bought their kids domain names the first week they were born, if not before. I don’t just own sarahlacy.com, I own sarahlacysucks.com, ihatesarahlacy.com, ilovesarahlacy.com, sarahlacy.tv, and several others. We immediately bought oliviahine.com when Olivia was hired, too.

Such discrepancies seem dumb, but it’s the sum of little cultural nuances like these that wind up creating huge differences between a company founded in the Valley or New York or even London or Tel Aviv. Increasingly, this concept—these nuances and what rises out of them—is captivating me, now that I’ve spent a decade focused just on the Valley and no longer have the blinders that come with a regular beat reporter job. This is especially pronounced in my thinking as 2008 comes to a close: an insane year where my life seemed to change every few months. I met literally thousands of entrepreneurs this year in London, Tel Aviv, and 15 cities in the U.S., thanks to my User Generated Book Tour. Next year, I’ll be hitting Munich in January, Israel again in the spring, potentially a few posts in Africa, and my first trip to India. I’d love to know any must meet entrepreneurs, angels, investors, human routers in any of these places, either in the comments or at sarah at sarahlacy dot com. Don’t make me sick a crab spider on you.