Tattoos and YCombinator Demo Day

It was June of 2003. I sat in a little ink shop on Rivington Street called Porcupine Tattoo. Emma was tracing the design I had given her--some wrap around barbed wire--onto my arm with a pen. She had flower sleeves of spectacular color.  Seven Nation Army was playing.

I never really thought much of tattoos. My dad has two on his arms and, after 50 plus years, they've faded quite a bit, blurring at the edges. He doesn't like showing them and seems to regret getting them.

I knew I wanted mine, though. I had waited since the previous Halloween when I found myself turned by some temporary tattoos sported as part of a goth costume. After deciding the spiderweb on my neck probably would have been a bit much, I gave myself until after the CFA exam in June to make a final decision. If I still wanted one after the eight months, I was going for it.

So there I was.

A couple of teenage girls came in as the first drops of ink went into my arm. They started flipping through some books and examining designs up on the wall. It wasn't more than about twenty minutes before one of the girls stands up and says "Ok, that one!"

It was probably one of the dumbest moves I've ever seen anyone make. If you're going to mark yourself permanently, you ought to spend more than a day or two deciding on what you're going to get--let alone 20 minutes.  I was stunned.  Emma picked her head up and flashed me an equally perplexed look.

Similarly, picking seed investors for your first startup in and around the craziness of an accelerator demo day can be just as scarring over the long term. In fact, you'd probably be better off both deciding on a tat on demo day. At least if you and some Silicon Valley VC get inked up in one of the breakout rooms, you can get it removed more quickly than you can get out of an investment relationship. (Trivia question: What active startup investor has the most tats?)

If you don't put in enough time to think about the investors you take or the investments you make, you're bound to regret what you picked.  You'll wish you had spent a little more time to find something that matches you or that you hadn't done this at all.  I'm not talking fifteen weeks--but at least share a meal together first.

I'm saying this because I went to my first YCombinator Demo Day last Tuesday.  YCombinator is an amazing program for the best of the best--catapulting them forward with a ton of buzz, very little dilution and the attention of the most experienced investors.

The problem is that the program simply attracts only "the best"--a group of entrepreneurs who, at first, self select and believe they fit this criteria and then displays whatever patters Paul Graham and his team believe to be indicative of success.  Somewhere within this portfolio, you're going to find some seriously huge successes and "the best of the best" will emerge--but you really never know which ones, just like any other venture portfolio.  The problem is, if you don't turn out to be in that group,  it's not clear to me the program helps more than it harms.

Most promising entrepreneurs that show well off the bat still need a lot of hands on help and guidance.  They need to walk before they can run.  They need attention.  You're not going to get a lot of attention when your angel round looks like a trophy room full of big names that have only committed small amounts--and it's tough to follow up with this week's press that you are the next big thing if your product isn't ready.  Just ask Cuil, Color, Highlight, etc., etc....

When your program's obvious main goal is funding, as soon and at as good of a price as possible, you're going to have situations like this:  An entrepreneur walked up to me while I was having a conversation Christina from USV.  He introduced himself and the name of his company, noted that he was helping his YC friend learn how to talk to investors, and just went off into his pitch.

When he finished, I turned to his friend and said, "Want me to critique his pitch?"  He said, "Sure!" and I explained to the first guy--whose name and company I don't even remember--how he should figure out who he's talking to first, what they're interested in, and if they're an asshole.  You don't want to waste your time pitching to assholes and you certainly don't want them involved in your company forever.  Get to know your investors first and make sure they're a good fit for you just as much as trying to get them to think that you're a good fit for them.  How active are they?  How much do they want to help shape vision?  Can they help you fill the holes you need to fill?

This is why I probably won't go to another YC Demo Day--on the off chance I get invited back.  It's just not how I want to get to know teams, nor is it how I want them to get to know me.  I like what Chris Sacca tweeted about it:

"I admire how easy fundraising is for founders today. But I've never made money nor friends on deals where I had to commit in 24 hrs." 

I spent a ton of time trying to get to know entrepreneurs early--even before their ideas are fully formed or before they have their decks.  That's where I think I'm going to have the best outcomes and where I'll be able to be the most useful investor--where everyone knows why they're in, what they're there for, and we can all thoughtfully get on the same page about the vision we're trying to move toward. 

Otherwise you might wind up with this: