Preparedness is many things.  It can be putting yourself in a new situations, going new places, and meeting new people.  It could be having expert knowledge in a domain.  Maybe it is something as simple as staying in contact with old friends.  Preparedness is the state of being constantly ready for luck to arise.

Luck is a necessary ingredient though.  However, you can “make your own luck.”  Often, the most prepared people are the ones who seem to get the luckiest.  By putting yourself in new situations and meeting new people, you open yourself up for new interactions and new possibilities.  You create more channels for “luck” to get to you.

These are the ingredients of opportunity.  It comes from a spark of luck and being prepared enough to take advantage of it.

On Sunday night, I flew out to San Francisco for a meeting with Dave McClure of 500Startups notoriety.  How did this “opportunity” come about?  A little preparedness and a lot of luck.

Lately, I have become more and more interested in private and angel investing.  I have spent the last several months reading everything I can about the tech start-up scene both from the entrepreneur’s perspective and the investor’s perspective.  Call this “preparing.”  A month or so ago, I stumbled upon a contest hosted by InternMatch to actually spend 2 weeks shadowing Dave McClure.  Call this “luck.”

Luck, meet preparedness.  Together, I shall call you “opportunity.”

After submitting a “traditional” resume + cover letter application (I think my cover letter was actually anything but “traditional”), I was selected as on of 16 semi-finalists from a total of 300 applicants.  From there, we were tasked with using social media to create a second application that explained why we wanted to shadow Dave (see my application here, and Dave’s extremely verbose follow-up comment here).  During this second round, I took the initiative to start an e-mail list with the other competitors.  I figure that even if I don’t get any further, these could be some great contacts.  Call this “preparedness.”  Fortunately, from this round, I was selected as one of 6 finalists who would get to interview with Dave.

I was given the opportunity to either interview in person with Dave, or Skype.  Fact: I live in Boston.  Fact:  The interview would be in Mountain View.  Fact: There is a considerable distance between those two places.  However, if we’ve learned anything so far, it is that we have to prepare so that we can accept luck.  So of course I am going to fly out from an in-person interview.  What good does staying in my house do me?  Who knows who I could meet just walking around the 500Startups offices?

So I arrived in Mountain View, CA with about two hours to spare and shoot out an e-mail to the contestants asking if anyone is in town early and would like to grab a bite to eat (call this “preparedness”).  While nobody responded, the extremely intelligent and passionate Jennifer Turliuk, another one of the final 6, was sitting at the same restaurant as me and came over and introduced herself.  We spent some time getting to know each other before heading over to a bagel shop next to the 500Startups offices where we met Andrew Maguire from InternMatch.

Andrew took us around the 500Startups offices, introducing us to partners, mentors, and other startups.  The energy was electric, as a whole new batch of startups were starting their first days.  Jennifer was off, having come prepared with a startup pitch.  She pitched and showed her slides to anyone who would listen.  The presentation was polished and the idea simple and powerful.  I’d be very, very surprised if a great opportunity didn’t come out of this for her, even if she didn’t get the shadow internship.  I’ll be watching for her to be in the next 500Startups class.  Preparedness (the pitch + slides) + Luck (being at 500Startups) = Opportunity.  She knows the formula.

Finally, it was time to meet and speak with Dave.  Dave is poisonously passionate and energetic.  You can feel it from the first second you walk in the offices.  Sitting with him 1-on-1, it is almost overwhelming (in a great way).  He is also incredibly forward thinking.  My “interview” was anything but a traditional interview.  After one or two questions about myself, the conversation spiralled off into all topics about investing, finally settling on a discussion on human capital investing and whether a fully open, capitalistic market, where everything is securitized, would actually promote greater good and happiness for the world.  I certainly wasn’t expecting the conversation to go there, but I couldn’t have been happier about it.  I love talking all things investing.

I don’t necessarily know if I was really what Dave was expecting for a potential shadow; most competitors are current or future tech entrepreneurs hoping to learn business lessons from Dave (and potentially even get into 500Startups).  I, on the other hand, am more interested in learning how to run an incubator fund like 500Startups, angel investing lessons, and how to manage a portfolio of private investments.

As my interview ended, Dave introduced me to Paul Singh, one of the newest partners at 500Startups, and told us we should talk.  Paul is working on some very cool stuff to help the fund scientifically measure its performance and ways in which they can improve their portfolio performance.  As someone who makes their living managing portfolio risk using quantitative methods, I am incredibly interested in what they were doing, especially since I don’t have a tremendous amount of experience with managing private investments.  Dave thought that there could be some interesting brainstorming that could come out of the discussion.  I don’t know if Paul necessarily got a lot from me, but I certainly learned a tremendous amount from him!

Even if I don’t win the competition, getting to talk to Dave was phenomenal.  The opportunity to pick Paul’s mind for half-an-hour was icing on the cake — an opportunity that I only ever got because of my preparedness and a lot of luck.

I can’t thank the team from InternMatch enough.  Without them, this opportunity never would have been possible.  They have put a lot of time and effort into this competition and have been incredibly accessible throughout the whole thing.  I sincerely wish them the best of luck in the endeavors and I hope they crack the internship code.

TL; DR: Preparedness + Luck = Opportunity