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I’m in a zen mood today, and I’m thinking about the most important lessons that I’ve learned in my career so far.  Most lessons that matter sound like common sense, but in practice are profoundly complicated.  Although I have a ton more to learn, I bet this lesson will never fall out of my top 3.

The Most Important Lesson I’ve Learned Is: Big Rocks First.

I first heard this concept from my wife when she was in B-school at Stanford, but it turns out it’s one of those parables that’s widely repeated.

The gist is the following.  Let’s say you have a bucket and a bunch of rocks.  Some rocks are large, some are little pebbles, and a large number are tiny - like grains of sand.

The most efficient way to fill the bucket is to put in the big rocks first, which leaves room for the smaller rocks, which in turn leaves room for the sand.  But if you go the other way around, you may run out of space before you ever get to the big rocks.

The life lesson is to focus on the things that matter first.  Other things fall into place around those priorities.  It sounds obvious, but it’s not in practice.  We all get into a groove and sometimes do things out of habit without stopping to think why. Sometimes, we also just respond to things that happen to be pressing at the time, even if they aren’t the things that matter. Some people have called it the “tyranny of the urgent”.

The saddest example is when the small rocks displace things that really matter - like family, children, friendships, personal integrity, and faith. It’s amazing how easy it is for me to come home and be so distracted with what I’ve been working on all day that I’m not really present at home.  My family gets my “B” game in those situations, but they deserve much more.

Big rocks first.

This is a continuation from my previous post about fast followers.

Several times a week, I hear a pitch from for a company that is fairly similar to existing players in the market.  When I ask the entrepreneur how they expect to win vs. the various competitors, I’ll often hear something like:

“Well, they don’t have feature x, y, and z which has been built into our product from the beginning.”

These same folks usually include some sort of Harvey Ball chart to show how differentiated they are from their competitors.

My advice: if you need a Harvey Ball chart to show how you are different, you aren’t different enough.

In my view, winning as a startup doesn’t have that much to do with individual features.  Features do drive success, but great teams and great product development processes drive features.

I saw a talk a while ago by Mike Maples.  In it, he encourages entrepreneurs to “be different, not better”.  I completely agree.

Being different means being WORSE than competitors in some dimensions.  It’s a very intentional decision to forgo some areas of potential strength and choose the 1 or 2 dimensions that no one else is thinking about and absolutely destroy the competition in those areas.

Some examples?  Tumblr, Zappos, Milo, Polyvore, etc.

Be different.

All this talk recently about Groupon clones got me thinking about fast followers.

In competitive markets, fast followers pile on very very quickly.  Every one of them says to themselves “the market is wide open, we can be the number 2”.  There are 2 problems with this.

1. Most fast followers are not fast enough.  By the time they notice that a leader is taking off, do the market research to validate the opportunity, and start to execute, it’s too late.

2. Most fast followers think features will help them differentiate.  This will be a subject of another post.  But features won’t separate you from a bazillion other followers. It’s also a mistake to think that the leader will stand still.

But the bigger point is this.  Most fast followers are actually leaders in disguise.  They are usually the same entrepreneurs who have a knack for anticipating where markets are going and executing with crazy speed and passion.  What these folks find though is that they aren’t always right, so they have to pivot quickly.  That’s usually how fast followers are born.  They are usually entrepreneurs who already knew there was an opportunity in a sector, and were pursuing something that wasn’t quite right until they saw a leader emerge.  Then they iterated and became #2. For examples, consider Living Social vs. Groupon or Booyah vs. FourSquare or RueLaLa vs. Gilt vs. vente-privee.  Both knew about the success of the leaders earlier because they were already operating in and around the space.  And both pivoted quickly and had the means to quickly create some separation from all the other followers.

There has been some chatter on Twitter about the value of pitching to VC associates. Thought I’d lob in my 2 cents on the shuttle to NYC. Full disclosure - I am a senior associate at Spark Capital.

1. Roles have blurred between associates, principals, EIR’s, and VP’s. Regardless of title, different roles have different levels of influence within a partnership. Over the years, I think we’ve seen some title inflation at some firms. It comes down to whether a person can lead an investment. In some firms, senior associates can do this in certain cases (I am able to lead seed investments at Spark). Charlie O’Donnel is an EIR at First Round (and a pretty young guy), but just led their most recent investment in Backupify. But in many cases, associates can’t lead investments, and even principles or young partners will get unusually high scrutiny through the deal process.

2. High quality intros to GP’s > talking to associates > low quality intros. I generally agree with Keith Rabois that you want to get to a decision-maker. It’s common sense, even if it hurts. If I were an entrepreur, I’d try to talk to GP’s I know personally or can get a high quality intro into. But the emphasis is on high quality. A low quality intro is sometimes not much better than a cold call. Also, if you don’t have a quality connection to a firm, getting an associate excited about your company works. An associate pushing for a deal is almost as good as a high quality intro. If not, that VC firm is wasting it’s $ paying that associate. There are many examples of great companies that met their VC’s through associates.

3. Careers are long and Venture is a young person’s game. In many cases, the associates of today are the GP’s or corp Dev execs of tomorrow. It doesn’t hurt to meet them early in their career as you never know where things will go. There are many good GP’s and angel Investors that were former associates: David Cowen and Alex Ferrara at Bessemer, many of the Battery GP’s, Alex Finkelstein at Spark, Chris Dixon, Jeff Fagnan, Larry Cheng, etc (sorry for the east coast bias, but this is off the top of my head). I wouldn’t burn a lot of time with fruitless meetings, but I’d certainly be respectful and get to know the guys I like. Some of these folks will be decision-makers soon enough.

So, those are my thoughts on whether to talk to Associates. Here are two tips if you are talking to them.

1. Be mindful of associates at transition points. Usually, these guys have been associates for at least 1 year, more likely 2. They are either rising stars that will be tested by leading a few investments or guys just trying to survive. If they are the former, they can be great assets. These associates will hussle harder than other VC’s to prove themselves and usually have champions within the VC firm who will give them a lot of support. The latter are dangerous because you might spend a lot of cycles with them and get nowhere. Even worse, they may advocate for a decision, get you funded, but leave the firm in 6 months. Be mindful of the risk of becoming an orphan and make sure you establish a strong relationship with the partner on the deal early.

2. Favor associates with clear domain expertise or a strong thesis. This can be based on their operating experience, blog, or just clear evidence that they know what they are talking about. Meeting these associates can at least be helpful, and typically have a higher liklihood of culminating in serious consideration by partners. It also helps you figure out which firms “get it” in your sector or do not. Typically, I’d be more wary of associates that are clearly chasing momentum. These meetings are less likely to be valuable and could also mean that you are part of competitive due diligence for another deal.

Sorry for typos, this was written on my iPhone.

The Lean Startup movement isn’t terribly new, but the level of hype is reaching pretty significant levels. The contrarian in me is always a little wary when anything gets overly hyped.  To be clear, I really really like the concepts of the lean startup and customer development.  I’d recommend any entrepreneur who isn’t familiar with this to at least watch some of Eric Ries’ talks about it and try to internalize Steve Blank’s book.  However, I find that when lots of people start pontificating on topics like this, some parts of the message get lost or the framework gets portrayed incorrectly as some holy grail. Below are a few half-baked thoughts on what I think The Lean Startup is NOT (btw, I’m lumping the customer development methodology and Lean Startup Methodology together).

1. The Lean Startups Is NOT One-Size-Fits-All

I get a little worried when I see too many diagrams of work flows emerging around a particular methodology. I think discussing best practices is generally a good thing, but too much emphasis on the process sometimes fools folks into thinking that it’s a magic formula.  I think the principles of Customer Development and the Lean Startup that are the most important things, and the process is more of a guide. Common sense and independent thought should prevail over workflows and formulas.

2. The Lean Startup is NOT Static

The reason that #1 is important is because the Lean Startup isn’t a static thing. Steve Blank and Eric Ries both often discuss how their thinking is evolving as they think about how their principles apply to different types of businesses and get feedback from folks who practice these principles. Industries and technologies shift as well, and some of the tried and true principles of the Lean Startup will eventually change or major limitations will become well understood.

3. The Lean Startup Is Not a Substitute for Vision

This is my most important point.  Emphasis on creating Minimum Viable Products and finding Product Market Fit I think can be pursued at the expense of thinking hard about a company’s vision.  It’s true that some big companies can/have emerged from iterating and pivoting into new markets (Groupon is my favorite example).  But I think some really big and hairy opportunities can only be addressed if one really does the work to understand the problems and players and have a strong point of view of what could be possible.  I think from there, you can utilize Lean Startup Principles to connect the dots, and the dots may lead somewhere very different (thus, vision evolves as well).  But I think both are required to build industry transforming companies.

For example, I’ve talked a lot about what I see as a huge opportunity in the education publishing industry. I am 100% convinced that we are going to see a massive company emerge in this sector in the next few years.  And it will be a company that completely changes the way students learn and how content is consumed.  But it’s a complicated industry with lots of disparate players (an oligopoly of publishers, Professors, different kinds of educational institutions, Students, device makers, etc) and not one where you can do serious damage without some heavy lifting and crazy vision and conviction.

I’m interested to hear other peoples thoughts on this!  Also, I want to give a quick shoutout to David Vivero and David Cancel, who prompted these thoughts from some recent conversations.

Today is Ash Wed.  It’s not a very well known religious day, but it’s one I personally find particularly meaningful.

For those of you who are curious, here is a primer on Ash Wed. In a nutshell, it marks the beginning of Lent, which is the 46 day period in anticipation of Easter.

What I love about this day is its emphasis on humility. I think with the busy pace of life, it’s unfortunately easy for me to get caught up in my own self importance without even noticing it.  So I really appreciate hearing the words that usually accompany the application of the ashes: “”Remember O man that you are dust, and to dust you shall return”

The interesting thing I didn’t know until a few years ago is that the ashes used on Ash Wed are from the palms from the previous year’s Palm Sunday.

I once heard a minister explain the reason for this.  Palm Sunday was the day that Jesus of Nazareth was said to have entered Jerusalem amidst the cheers and adoration of the crowd.

The irony is that only a few days later, that same crowd would later make up the angry mob that called for his death. According to this minister, the use of the palms for the ashes symbolizes the frailty of human faith and goodness.  It’s a reminder for me to be humble, because I can remember many times when I was self-righteous about something, only to later realize that I was guilty of a far worse offense.

I know my readers come from many different religious backgrounds, so this post may not be that interesting to a lot of you.  But I like the thought of a day dedicated to humility.  I was talking to David Cancel last week and he lamented the sense to entitlement he encounters from people from time to time.  He said that he is a big believer in “servant leadership”, that you should just think about how to solve problems for people, or make life easier for your customers or those you work with. I thought that was a pretty darn good thing to focus on on Ash Wed this year.