Thoughts on being an “entrepreneur” 

I was recently asked — “what has it been like doing the whole entrepreneur thing?” I hadn’t thought of it too much, but at that moment I realized a couple of things.

First is that I’m now in this category of people we call “entrepreneurs.” I found this amusing, because I never considered myself one. What to others seems to be a conscious choice of working on a startup (or following an ‘entrepreneurial path’), is to me just a natural progression of making something interesting with a couple friends. When we started, we had no grand plans of conquering the world or trying to become the next hottest thing. We had a problem and an idea of how to solve it.

The second thing is that I could probably write an entire book answering this question. The experience so far has been exciting, and I’m learning an incredible amount; both about product management, development cycles, user testing, etc. and about myself — how to manage my psychology in uncertainty and how to reason through problems and recommendations with competing opinions.

While I’m sure I’ll reflect on more in the future, here are some lessons that come to mind.

Try not to set out to ‘work on a startup’
This is the most obvious, yet the most important to me. In my view, a startup is simply the resulting organization and solution of having a problem you want to work on. In fact it’s better to consider the whole thing a project until you and enough people (users/customers) confirm it’s a worthwhile problem. On the other hand, if you set out to create a startup, you’ll inadvertently end up creating problems — which is probably why you see so many trivial apps, or ones which do the same thing that currently exists, just slightly differently. Instead wait until you see a problem, or better yet, feel one. I think some of the greatest products out there are borne out of frustrations.

Focus on building what you really want
The caveat here of course is that other people need to want it too. In the early stages of your startup, everything seems to be flexible — and to outsiders, that includes why you exist in the first place—so a lot of people will give you input on what they think you should be doing. We’ve been told to move our idea towards everything from “enterprise collaboration” to “public social commentary” to a “research management tool.” The truth is that many of these recommendations seem like quite reasonable and even good ideas, but you don’t work on a startup to be reasonable or build what other people want you to.

An overnight success usually takes a couple of years (at least)
We’ve been working on our app for about a year now, which seems like a long time in the startup world, but it takes time to get things right. Part of our belief in ‘overnight success’ is probably attributable to media coverage— we pay attention to apps when they have momentum and hit the mainstream, but often don’t realize how long it takes them to get there. You’ve heard a lot about AirBnB recently, but those guys have been grinding since 2008. Same with Uber. It even took Snapchat 16-18 months before they started getting a lot of press. Good things take time, including startups.

The people you work with will determine the outcome of company
This has been repeated by nearly every entrepreneur and VC, but I can’t stress enough how important it is to have good co-founders. I’m working on Point with two incredibly talented friends who are awesome to be around and work with. If we couldn’t grab a beer after work or hang on the weekends, I’m not sure we could have made it as far as we have.

Move slow, fix things
The startup mantra is to “move fast and break things” or keep an attitude of “fuck it, ship it.” Sure, it makes sense sometimes, but there’s a benefit to moving slowly, taking time to understand your users, what they like and say about your product, and tweaking the product and messaging to play to that.

Always revisit where you’re going and what you’re doing
Every few weeks I sit down and write out what we’re working on and why. When you see your thoughts articulated on paper, it becomes easier to look at them objectively. I’m sure this goes beyond startup planning, so whenever you feel like you have have a lot going on, are confused, or feel anxious, take a minute to write it down and things suddenly become a lot more clear.

Seek criticism
No one wants to hear bad things about themselves, but only hearing positive feedback will put you in a state of complacency. Get more people to challenge your thoughts and product decisions. These people are few and far between, but they’re perhaps some of the most helpful in the formative years of your startup.

It’s hard but relatively speaking, it’s easy
I have friends who are investment bankers. They often work 12+ hours a day, 6, sometimes 7 days a week. They do work that 95% of the time they don’t like. That’s hard. We start work at 10-11am, stop sometime in the evening (though we’re sort of always working/thinking about our app), work on an awesome product we love using with people we like being around. What’s “hard” about that? Yeah you can read about startups getting millions of users and hitting insane engagement and growth numbers. All of that can be “hard,” but only if you allow it to consume you. If you stay present, focus on how to improve your product and how to get a few more users, you’ll one day reach all the stuff that seems ‘hard’ now. The only hard thing is that everything about a startup is opposite to how most people work. You’re not told what to do, you don’t have a boss, and there’s no right answer — so stated differently, it’s more contrarian than hard.

You’re better off out of the bubble
During the past year we’ve been living in the suburbs of Philly. None of us are tech-junkies or frequent tech blogs. In fact most of our interests lie outside of the tech space, which I think this has been a benefit to us. I find that people who are extremely plugged into the startup space typically do a few things: they build products for other startup people, and they get carried away with trends. Thinking on your own, without the influence of too many competing voices is good for your sanity and your product.