This post is based on something one of my mentors told me about success and taking small risks. A lot of it is said really well in this video. Highly suggested viewing.

Like I mentioned a bit ago, I was a participant in Stanford’s EBootcamp program for a 4 day stretch. It was an amazing weekend with some great speakers, really smart student entrepreneurs, and overall just an exciting event to be a part of. For the first morning session on Friday, they had booked Vinod Khosla of Khosla Ventures to give a keynote and answer some questions from a moderator and the students who were at the event. It was a really cool opportunity to get in touch with him. Khosla is a brilliant guy and is well respected in the Valley – he’s definitely a good guy to know. Two days before the event was to occur, I found his email address and shot him a 3 sentence email about who I was, what I’m doing, and what I wanted. His assistant replied and said he’d be happy to meet up before or after the event for a few minutes.

After he was done talking, he was (predictably) swarmed by eager students who wanted 2 seconds of his time to get his thoughts on what they were doing or to try and connect with him on a meaningful level and get his contact information for later. Unfortunately, he had to get somewhere and couldn’t stick around afterwards. I approached him as he was leaving, introduced myself and mentioned that his assistant had set up a meeting for us. We walked to his car for a while and I got about 20 minutes of his time, as well as the offer to keep in touch and valuable feedback about a few things I’m thinking of. Doing something differently (emailing before instead of a post-talk cold approach) allowed me to stand apart from the rest of the group.

This doesn’t always work out. I also approached one of the speakers, Konstantin Guerecke (CMO of LinkedIn) and asked if I could get 20 minutes of his time in a few weeks to help out with a side project I’m working on. He flat out rejected me. That’s all part of the game – unless you’re willing to go through a few rejections of that type, you won’t get to experience massive success (not that I have, but it’s a simple risk-reward equation).

What matters in the end with all this stuff is the mindset you use to approach it, not the actual outcomes. Who knows, maybe the next email I sent Vinod he will ignore and we will never interact again. It’s quite possible, as it was a short interaction and he’s a busy guy. What matters is building these types of situations into your life. If you are constantly unafraid of approaching someone, of talking about a massive idea you have, or of doing things that others generally shy away from, at some point you will stand out. By definition, you can’t expect to stand out by following the crowd. Doing things like emailing people you are interested in, working on a side project, or trying to teach yourself a valuable new skill will eventually culminate in a remarkable life – or so I hope. All I know is that i don’t believe you can do the same thing as everyone else and expect disproportionate results. As Seth Godin said, don’t get picked. Choose yourself. And when you have applied this mentality to several years of your life/career, people will take note of your success and ignore the trail of false starts, failure and trials of confidence that marked the way.