Although I do not suppose that either of us knows anything really beautiful and good, I am better off than he is, for he knows nothing, and thinks that he knows; I neither know nor think that I know.

Socrates

My father was a very successful CEO in his day, and while he will never shy away from telling me about how smart he is, in serious father-son teaching moments, he has always enforced the importance surrounding yourself with people smart in areas you are not.  Being smart doesn’t mean knowing everything, it means recognizing that you may not know.

The corollary to this lesson is that people on your team / advisory board / outside council should think differently than you.  If you have two people who think the same way, you have a redundant person.

This weekend, I had the pleasure of sitting down with a close friend of mine to talk about a start-up idea he has.  He has already gone out and gotten feedback on the idea from tons of different people, from potential clients to potential investors, who are now saying, “okay, build us a MVP [minimum viable product] and let’s schedule another meeting.” His problem is that he does not have the technical skills required to build the product himself, so he is faced with either finding a technical co-founder or hiring someone to build the product.  For the latter he has estimated a cost of about $10,000.  Besides this enormous upfront cost, the issue with out-sourcing your tech from the get-go means you have less chances to iterate, so he pretty much has the nail the MVP on the first go-round to make that sort of cash worth spending.

While my friend is incredibly, incredibly intelligent and business savvy, because he was so far deep in his own product, he couldn’t see any possibilities in between having nothing and having the full-fledged product.

To give a bit of detail, his product is very heavily based around generating reports for three specific target markets.  The underlying engine for the reporting system is identical (so the three markets are no extra work), but how the data is reported is different.

What I recommended doing was identify the metrics he wanted in the different reports, read “The Visual Display of Quantitative Information,” and work with a graphic designer to mock-up three different paper reports.  Estimated cost?  Maybe $1000?

From there, he can approach his target markets with an example product and get feedback — long before the website itself has even gotten close to the development stage.  He can even start asking people how much they would pay for the reports and how often they would want them delivered.  You never know what you will find in the field.  He may end up finding out that one of the markets he is targeting would actually prefer to have the reports physically mailed, rather than e-mailed, because of their age demographic.

While for me this was a pretty natural next step, because my friend was so deeply involved in his own product, he couldn’t see it.

I’m not saying I am particularly smart (or the advice I gave particularly good), but simply using this as an example of the benefits of being humble and asking for help or advice.  The smartest people know that they do not know and that is why they are successful.

I received the news last night while I was in the middle of putting together some furniture with my girlfriend.  I think she expected me to be more upset than I was (or am).  In fact, I think I surprised her with how little it seemed to affect my mood.

What she potentially perceived as a lack of caring wasn’t that at all.  In fact, I was extremely excited about the opportunity to learn from Dave and his team and  am very disappointed that I wasn’t selected, especially after the time and effort I put into the competition.

But I also believe that there is no point in wallowing in self-pity.  Letting the news affect my mood doesn’t bring anything positive to my life.  Rather, it is better for me to reflect on a lesson my father always tried to teach me: when one door closes, often another one opens.

If you are too busy focusing on the closed door, you won’t see the one that opened.

For example, while I may not have been selected to shadow Dave, I had the opportunity to meet him and several members of his team.  Recently, Dave Dave tweeted about a post I wrote.  From this tweet, the post got picked up on Barry Ritholtz’s The Big Picture, which gave my blog more visibility in a day than it normally does in 6 months.  From that, I got several new Twitter followers and a couple direct e-mails about start-ups.

Those are all open doors.  Open doors that would never have been there if I had never made it onto Dave’s radar.  So while I am very disappointed that I will not have the opportunity to shadow Dave, I know that the whole experience opened a whole lot of doors.

tl;dr: Don’t focus on the doors that close in your life or you will never see the ones that have opened.

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

As I was thinking of you, it occurred to me that I wanted to tell you: It is much harder to run with a full bucket than an empty one……

Wait, what?

Yep.  And it was in a fitness magazine, too.  And it wasn’t even an article about his life philosophy.  It was an article about his workout routine.

I don’t think he even realized he was giving such great life advice.  But he was.  And it is simple.

McConaughey has already invoked his motivation mantra, the one phrase that gets his butt out the door for both work and a workout: “Tie your shoes,” he says. “It’s that simple. You tie your shoes, man, you know you’re gonna do it.”

And he is right.  Unbelievably right.  In everything we do, we all have a tipping point — the point where we finally stop procrastinating and just get down to work.  The sooner we can recognize what that point is, the sooner we can be more productive.  So find your tipping point.  Whether it is opening the word document, excel sheet, IDE, legal document, putting your hand on the doorknob, putting your foot out the door, or just tying your shoes — find your tipping point.