The Most Important Things I Learned Last Year

As 2011 comes to a close, I can say that it has been a pretty exciting year overall. I switched jobs, going from a cushy job at a large company to the best job in the world (as founder of my own startup). I found a great cofounder, who eventually convinced me to move from San Francisco to New York. We built several cool products, and learned a lot about iterating towards product market fit.

So, I was ready to write an essay about all the things I learned this year, but I realized that I wrote that essay on my birthday. And I could have come up with a top 10 list, but that seemed kind of lame. In the interest of being brief, I distilled what I learned this year down to one sentence.

Follow your gut and move forward

So, that's the TLDR, so I'm pretty much finished. But I've never been known for being terse, and if you've read this far, I guess that I will ramble on for a bit longer.

Follow Your Gut
You may have heard that you have more neurons in your digestive system than in your brain (aka the Enteric Nervous System). What does this have to do with entrepreneurship? Well, it's easy. An entrepreneur is only as good as his gut intuitions. Sure, there is a lot of logic and problem solving involved with building a successful company, but if your intuitions can't guide you in the right direction, you will never figure out how to succeed. The most successful entrepreneurs I know have a mysterious ability to know which direction is going to be the right one (even before they have made a move). Of course they take missteps, but more often than not they can skip a whole bunch of things that aren't going to work. That's why Paul Graham is so good at what he does - he has a great intuitive sense for what will and won't work (and he freely shares that with the green entrepreneurs he invests in). Sure he's wrong sometimes, but so are we all. But I'm sure you know what I'm talking about - when you get the "right" idea, you get a good feeling inside.

Conversely, when you know deep down that something is wrong, you have to be able to quickly turn your back on it. As an entrepreneur, you are constantly being presented with opportunities of various types, and if you want to succeed, you need to take only the best ones. Weeding out the ones that aren't right can waste a ton of time, so it's useful to have a spider sense that can do it automatically (hint: you probably already have it). If an opportunity appears to be too good to be true, it probably is. If you have to vacillate too much over something, whether it's a candidate you are interviewing or a business partnership, it's probably going to be more trouble than it's worth. 

This past year, I quit my job to cofound a startup. As I was investigating startup opportunities, a pretty large number of options worked their way onto the table. Some of them felt right, while others didn't. There was at least one that I may regret not taking, but something in my gut told me to join Sam (even though other offers were more attractive on the surface). From pretty much the first moment, we got along remarkably well, and every time there seemed to be an insurmountable roadblock, things somehow worked themselves out.

There was also one time this past year where I ignored a bad vibe I got about someone, and it cost me a significant amount of time and money. Your gut won't always lead you in exactly the right direction, but it is particularly good at steering you away from trouble. When you get that bad feeling that makes you a tiny bit sick at the bottom of your stomach, it is time to start running.

Move Forward
I recently started reading "Not Everyone Gets a Trophy," which is a book on how to deal with members of Gen Y. One of the things the author says about Gen Yers is (and I quote):

They want to hit the ground running on day 1. They want to identify problems no one else has identified, solve problems no one else has solved, make existing things better, invent new things. They want to make an impact.

This sounds to me like pretty much every tech startup founder I know - I guess it's no coincidence that there are so many Gen Yers among the current batch of startup founders. If you want to make an impact, it is important to make sure that you are always moving forward, both personally and in your career. Set goals and milestones, both long and short-term, and then make sure that you hit them. Keep yourself honest, even (especially?) when it's painful. In addition to having a good intuition, all successful entrepreneurs are also operators. They figure out how make stuff happen, even when it isn't supposed to work out. That's one of the things that constantly amazes me about working with Sam - he is so darned persistent.

If the first thing you try doesn't work, throw ten more things at the wall until something sticks. Sometimes (usually) your first approach is the wrong one, so you are going to have to move fast if you want to find the right thing before the music ends (your money runs out or you get demotivated). We built at least three different products in the past year - we started out building a marketplace for speakers, and ended the year on a completely different note (which we will soon announce). In the interest of moving forward - we decided to finish out 2011 by shutting down our old service. This was kind of emotional since it was what we started out with, but startup founders don't have the luxury of being nostalgic. In the end, we realized that it was taking up time that we could be using to move our new product forward, so we canned it.

If you are a creative person, you will have about ten projects that you want to work on. Unfortunately, you will only be able to succeed at ONE. This is probably the biggest mistake that wannabe entrepreneurs make - they try to do multiple things at once and fail at all of them. Actually, you are even going to have to ignore aspects of your primary project because you will be so short staffed, but at the end of the day, all that matters is that you focused on the right areas and succeeded at those things. From what I understand, the books were a mess when Zecter was acquired, and they had to pay accountants a lot of money to get everything in order. However, the founders of the company focused on building great technology, which was the only thing that really mattered at that point, and the rest they could hire someone else to fix. The only thing you (usually) can't fix is forgetting to file your 83B election, so be sure to do that.

A Pitch For Your Personal Life
So here's something else to remember. While you are moving forward with your company, be sure to spend some time moving forward with other aspects of your life. It is easy to get wrapped up in work and not pay enough attention to yourself. Spend time with friends and family, and build your social circle. If you aren't an extrovert and don't have a strong social circle, those connections will wither if you don't pay special attention to keeping them strong. Otherwise, you will be alone and miserable when you aren't working, and no one wants to be like that. I know some people say that startup founders should spend all of their time working, but I think it's crucial to find a balance that allows you to be happy. If you are miserable, then your productivity will suffer, and your startup will have pretty much no chance of succeeding. I only say this because I personally have spent years working on startups while neglecting my personal life. At some point over the past year, I had a big realization that I wasn't happy, and that I cared as much about leading a fulfilling existence as I did about building a startup. I needed to figure out how to move forward with multiple aspects of my life - business was only one of them. I won't beat this to death because I have talked about it recently in other blog posts, but it definitely bears repeating.