24 8 / 2012

What I’ve Learned During My Summer in YC

I had grand plans to keep a journal of my YC experience so I could look reflect back on it after demo day. I was overly ambitious so as a consolation prize, I’m writing this post as a bookend to the first and only post I wrote three long months ago.

Back in May, I was running a web development firm that was growing and a ton of fun. We were following the 37signals model - building products for clients and using that cashflow to fund the development of our own products. Two pretty great things came out of that, DeckPub and I Heart Etsy. I was happy, I was constantly learning, and I was living in NYC, one of the greatest cities in the world.

Then I got the call. My friend and former colleague, Samuel, got accepted into YCombinator as a solo founder for NewsBlur and wanted me to come on board as a co-founder. I was initially hesitant because of my business, my existing commitments in NYC, and leaving behind my friends and family. After some soul searching and talking things over with my wife, it seemed like I would be crazy not to do this. The very next day I called him and told him I was in.

I reasoned that even in the worst case scenario - if the startup failed or I wasn’t the right fit - I would come out better based on the experience, the amazing people I would meet, and the lessons I would learn. It turns out I was right. This summer was the hardest and most mentally and physically exhausting summer of my life, but it was worth it. Here are some lessons that I learned, lessons that I thought I knew but never really understood  until now.

1. Your co-founders are your most important decision and assets

You will see your co-founders more than you see your friends, family, significant other, or children, make sure you choose wisely.

YC encourages you to get an apartment and work with your co-founders for the duration of the program. Let’s put that into perspective: you take people who have probably never lived together and put them in a small space where they work 12+ hour days, rinse and repeat. 

During the first few weeks, I thought this was an insane arrangement. Then it occurred to me that perhaps this was the goal. Doing a startup is difficult and there are a lot of schleps along the way. This living and working situation puts intense strains on the founders and makes everyone ask the hard questions early. Sometimes things don’t work out but when they do, everyone is now battle tested and ready to take on whatever challenges may come.

2. Persistence is a prerequisite

With the exception of Instagram, there are very few meteoric rises to the top. The startups and founders that find themselves at the top deserve it. It can take years of work and sacrifice to build something that people will love. If your heart is not in it, you will get discouraged and fail. If you take a look at any startup, there are tons of inflection points where the founders could have given up. If you cannot push through and persevere, you are setting yourself up for pain followed by no reward.

3. Motivation

For those that want to do a startup because they think it will be glamourous and a quick road to riches and success - the odds are stacked against you. You’ll be much happier if that is a secondary priority. Build something you love and something that you will want to use. You will be building, selling, pitching, thinking about, dreaming about whatever you are building - you better love it.

4. Revenue

This can kind of be contradictory to #3 but this has become even more important lately. You can build the world’s best ________ but if you cannot monetize it, things will be difficult. Unless you can bootstrap, you will need the aid of investors.  It’s much easier to talk with investors about your overall vision if that vision includes a path to monetization.

5. Users

Besides your team, users are your most valuable asset. Alexis Ohanian’s book, "Make Something People Love", puts it together pretty concisely. Respect your users, love your users, and wow your users. Do everything you can for your users and it will spark growth.  Beyond being the right thing to do, it contributes something fundamental to the ethos of the company - it makes everyone stronger, happier, and prouder to be part of the startup.

6. Cooperation

YC doesn’t fund jerks. There is this air of cooperation between companies, even if they are in overlapping spaces. The internet is a big place and you need friends. It will always be the case that cooperation is a net position for both startups involved.

That’s it. These might be fortune cookie sized bits of wisdom but IMHO all deeply important when you are thinking about your next (or first) startup.

18 8 / 2012

"T minus three days to Demo Day."

11 7 / 2012

Week 5

This is week 5 of 11.  Time flies.

15 5 / 2012

Wild Wild West

In June, I leave my little island called Manhattan and head toward California in search of new adventures, new opportunities and hopefully some stories that someone will be interested in reading.  The decision to uproot your life is always a hard one.  I reasoned that I was doing well in NYC, cofounded a nice little company and have great friends and family.  What would possess me to leave it all behind and live on the other side of the country away from my wife?  In a word, exercise.

No, I’m not going to California to hike the mountains and do yoga fulltime - although I could probably enjoy that for two weeks and then want to move on - I’m going to California to exercise my brain.  I think it’s true that when you stop using something it atrophies.  I’m not saying I don’t use my brain, but what I am saying is that I’ve fallen into a “comfortable routine” where I spend my days at work, my nights with my loved ones, and then my evenings reading code and culture.  It seemed as if my trajectory was already prescribed.

When you realize that this is happening, you can either get taken along for the ride or you can make your own way.  I’m lucky to have a loving and understanding wife and a good support system.  I’m going my own way.  This little tumblr is my attempt at capturing some of the goodness for future consumption or reflection.

15 5 / 2012

"Cooking is the source of truth."