How To Cross The Street

There’s something I notice about people who cross the street. Most people look at the crossing sign. If there’s an orange hand they stay on the sidewalk. When it turns white they start walking. 

But sometimes you notice someone who has gotten halfway across the street just as everyone else is leaving the sidewalk. He strides confidently ahead of the pack, not fearful of wayward cars or motorcycles.

He’s ahead of the pack because he pays attention to the right things. He wasn’t watching the sign that told him when it was safe to cross. He was watching the traffic light and the cars. As soon as it turned red and the cars starting slowing down he knew he could start walking.

And that is business success in a nutshell.

SOPA: The Meek Shall Inherit The Earth

Doing Away With Dogmatism

The world is full of crazy people.

The Pope bans the use of contraception to preserve the sanctity of life, and ends being indirectly responsible for thousands of deaths through the spread of AIDS. Ron Paul seems like a pretty reasonable guy, but have you heard his foreign policy? And don’t even get me started on Octomom – the woman who ended up with octuplets after a disastrous fertility treatment and a decision not to abort. Continue Reading

What I Read Over Break

The Design of Everyday Things by Don Norman – link

Death In Venice by Thomas Mann – link

Meditations by Marcus Aurelius – link

I read Meditations and the Enchiridion after reading Letters from a Stoic last semester. I think the Stoic philosophy is absolutely fascinating and I think about my life in a completely different way than I did before. Although I think Letters from a Stoic is the best of the three, Meditations was still really valuable (although a little repetitive).

The Enchiridion by Epictetus – link

My Man Jeeves by PG Wodehouse – link

Hilarious stories about bumbling Englishman Bertie Wooster and his butler Jeeves (the inspiration for the Ask Jeeves search engine – remember that?) I think it’s a really good example of tight, funny, and witty writing although the style is a bit anachronistic and takes some getting used to.

The Rights of Man by Thomas Paine (still in the middle of it) – link

I starting reading this as a counter point to Reflections on the Revolution in France by Edmund Burke, the father of conservatism, and I can’t decide which I like better. Reflections is amazing because Burke basically predicted Napoleon’s rise in France after their revolution, and his writing style is awesome. However, I think Paine makes a lot of valid points. I’m reserving full judment until after I’ve finished it.

What did you read recently?

How To Tell Someone You Won’t Sign Their NDA

“Will you sign my NDA?” is one of those awkard questions I get fairly often. Over time I’ve used a few different responses for why I won’t sign. Here are three of my favorites. Continue Reading

Why We Do Startups

The following is an excerpt of the company manifesto I wrote for my current startup Airtime for Email.

There’s an old joke that goes something like this: 

An old fish swims up to a young fish and says, “Boy, the water sure is nice today!” 

“Yea!” says the young fish, “wait…what the hell is water?” 

The point of this story is that “the most important realities are often the ones that are hardest to see and talk about.” To put it bluntly, the point of the story is that most of the stuff that we take for granted as fact, or that we are automatically certain of in our lives, is very often completely and utterly wrong. [1] Let’s call these things that we are automatically certain of our “default settings.” 

Default settings are all around us. Why do we go into work at 9 AM instead of 8 AM? Why do sales people work on commission? Why do we have an 8-hour work day? 

The fact is that very often there are no good answers for why these default settings exist, they just do. And not only does that create a great deal of waste in a business environment, it also leads people to certain misconceptions about what is and isn’t possible that are simply false. 

Given the existence of our default settings, one of the most important questions in our lives then is: Why do we do the things that we do? 

We do the things that we do to be happy. So then how do we become happy? And how does this relate to startups?

In our heads we all have a vision of the person that we want to be. We have certain ideas and principles for how we want to act and how we want to be remembered. However, what we do every day makes up the person that we actually are. So what do we do every day? 

We go to work. 

Thus, the kind of people we are is, in large part, a reflection of the work we do. 

I would like to posit that happiness lies in matching the vision in our heads of the person that we want to be, with the person we actually are. In short, happiness is becoming the person you envision in your head. And if the person we are, is a result of what we do every day, and if what we do every day is our work, then our happiness is tied directly to our work. 

Let’s look, for a second, at our lives as a struggle to match the person we are, a collection of actions, with the person we want to be, a collection of principles. If we look at things this way then it becomes clear that the only way to live up to our collection of principles is to make our work a reflection of those principles. And so if the work that we do every day can be a mirror image of the ideas that we hold most strongly, then we will be happy.   

This brings us to startups. 

Since a startup is the work that we do, it is tied explicitly to our happiness. So the way for us to be happy is to make our startup a reflection of ourselves, and the principles we hold most strongly.

Doing so provides us with a motivation to go to work every day that is not only non-monetary, it provides us a way to be happy every single day of our lives. Because if every day at our startup gives us a chance to live up to our principles, and living up to our principles means being happy, then we will be happy every day.

And that’s the reason we do startups.

If you’ve read this far you should probably follow me on Twitter.

[1] Joke and partial analysis borrowed from a David Foster Wallace commencement address

How To Become A Competent Web Designer in 2012

After I submitted my 10-hour hack Mixmatic to HN on Tuesday I got a couple of emails and tweets asking me about the design and how to become better at doing good design work quickly. The short answer to that question is: that just like everything worth doing it’s really, really hard. But if you really want to become a competent designer from scratch in 2012 here are a few of the things that I’ve learned along the way.

Ignore the tools

At least one person on the Hacker News thread about Mixmatic asked me what tools I used to do the design. I told him that I used Photoshop to mock everything up and then SASS and HTML (what else) to actually create the site. But the tools you use don’t matter. The only thing that matters is who is using them (you). I know people who never touch image editing software during the whole process and create pretty nice looking sites. Like this. I personally have to design every pixel in Photoshop before I start doing CSS. But to each his own. 

If you’re just starting out and you don’t know what to use, try to find a designer you respect and ask them what they use. Then you can just ask them for help and tips while you’re learning whatever system or combination programs they like best.

Do it a lot

If you want to get jacked you have to lift weights. lf you want to run fast you have to do sprints. The same goes for design. There’s no magic bullet for it. Except maybe Themeforest. But the point remains: if you want to get better at web design you have to do it a lot.

Create a portfolio of sites you like and copy them relentlessly

The easiest way to get started immediately (assuming you have some competence with basic image manipulation and CSS) is to start noticing designs you like. Every time you see a new website examine the design and see if it appeals to you. Go back through the list of startups you like, or software you’ve bought over the past year and look at their websites. Once you’ve built this portfolio up it becomes a lot easier to do design quickly. All you have to do is take whatever your product idea is, and find site designs that are similar to the feeling you want your product to convey. Then take the principles from those designs, put your own spin on them and use them!

For example, the Mixmatic design leans heavily on the Instagram homepage. The DomainPolish design leans heavily on the old 37Signals Basecamp design.

Copying only gets you so far

Copying designs gets you about 80% of the way to being a good designer. The difference between a competent designer and a good designer is in the small details that are almost impossible to pick up by copying. They require technical knowledge. 

Acquisition of that knowledge is difficult to do but not impossible. Take a design class if you can (even if it’s not web design). Read books. Read blog posts. This one in particular blew my mind and changed the way I approach web design even though it’s about Renaissance book design. Once you’ve gotten to the point where you’re turning on the grid in Photoshop to lay out your pages, or you can wax poetic about the Van der Graaf canon you’re on your way there.

I hope you found this helpful. As always feel free to reach out if you want to talk – I’d love to!

If you read this far you should probably follow me on Twitter.

My 10 Hour Project

Just to prove to myself that I can still do it here’s a project I did today in 10 hours from first commit to last (with holiday shopping and dinner in between). It’s called Mixmatic and it’s a fun way to make mixtapes for your friends with Spotify. 

Basically I didn’t like how Spotify sharing worked, and wanted a more personal experience kind of like when I used to make mixtapes and CDs for my friends in middle school and high school.

Mixmatic makes it really easy to do that. Just give me a Spotify playlist URL, a message, and a friend’s email address and it will deliver them your playlist with style.

Feedback and bug reports are much appreciated!

“Damn” is a dirty word

I would like today to discuss an extremely grave and pressing matter that has weighed heavily upon my spirit over the last few years. Chief among the many problems facing America today ahead of such urgent problems as mercury in fish, urban overcrowding, and shark attacks is the vapid and profane use of the vulgar word “damn.” In the forthcoming piece I will posit the reasons why I feel it should be banned in regular conversation, and suggest a better alternative. Continue Reading

The Most Common Type of Startup Idea That Probably Won’t Succeed

Over the past few weeks a few friends at school and I have started doing technical consulting for MBAs who have a startup idea but have limited programming knowledge. Basically we run down the technical problems inherent to their ideas, talk to them about finding a technical cofounder and answer other questions they have. The program is called Rent A CTO and over the course of the two meetings I’ve had so far, I’ve had the pleasure of meeting two amazingly smart, talented and humble MBAs that don’t fit the stereotype that startup engineering culture has created to describe the prototypical busines student.

That being said, a common pattern has emerged over the course of these meetings. It’s also one that I’ve noticed over the past year in talking to as many people as I can about startups, and I think it’s a useful one to consider. Both of these entrepreneurs were trying to create what I call the “all-inclusive web app”, i.e. one that beats its competitors by bringing together their disparate features into one mega-app that does everything in the problem space. Essentially it’s the “Kayak-for-x” business model.

Those ideas are great and necessary. But the problem is that they’re unbelievably difficult to execute on. 

The first problem is that they’re almost impossible to whittle down to the MVP. I’m a big believer in creating things fast that solve the problem with the smallest number of features, releasing and then expanding. Case in point is my project DomainPolish or the story of How I Made $350 in Two Days With Three Pages and Some Payment Code. The biggest strength of the all-inclusive web app is that it takes ALL the features in the problem space and combines them. Because of this, eliminating ANY features essentially reduces the product to one if its competitors. This is anti-thetical to the MVP mindset.

The second problem is that because you have to include every feature under the sun for differentiation the feature spec becomes huge. This means that while you’re creating a huge app that you’re sure there’s a market for it takes a long, long time. Any project that takes more than a month to complete has an exponentially lower chance of actually reaching the market in my experience. You end up adding feature on feature on feature for months and months, and then finally just giving up for lack of funds, lack of time, lack of interest or a combination of the three.

And finally, the third problem is designing an interface to support all of these features you’re adding. Unless you’re a UX/UI master, who are incredibly hard to come by despite the protestations in the bios of many an aspiring start-junkie, creating a sleek, simple, and easy to use interface to manage all of these features is next to impossible.

So in considering which ideas to start pursuing, ask yourself: “Is this an all-inclusive app?” If it is, you may want to reconsider trying to build it. It’s not impossible, it’s just really really hard.

If you’ve read this far you should probably follow me on Twitter.