When I saw that tweet this weekend it dredged up a bunch of thoughts and experiences that I’ve been wanting to put down on paper for a very long time. Why not now?

Over the past 6 years I’ve worked with 8 different startups in different capacities and pitched or met with countless others. I’ve been a founder; I’ve worked for equity; I’ve been a consultant getting paid cold-hard-cash; I’ve built prototypes, full products, and everything in between. I know there are a lot of more experienced developers out there, but even so, I think I have some things to share, and lessons I’ve learned from the good, bad and ugly of being a developer in a startup.

Startups aren’t for everyone

Every company is different, and from what I’ve experienced so far, the mindset and attitude of the bay area is different in a lot of ways from the NY tech scene. At the same rate, though, there are a lot of common things between most startups. In general the environment and process is much different from a large established company, especially in the early days. This means if you need rock solid stability of schedule, work cycle, direction, space, pretty much anything, startup life might not be for you. There is one constant in being involved with a startup and that is change. If you’re just a developer along for the ride, or a co-founder, change should be something you take in stride. A lot of this has to do with trust. Do you trust the people guiding this ship? Obviously this applies to any job, but is amplified when your livelihood is directly tied to the people you work with.

Don’t invest in an idea you don’t believe in

This should go without saying, but you’d be surprised when people don’t really understand what taking equity or options really mean. When you take equity as a developer (especially as a non-founder) what you’re actually doing is investing in the company in exchange for your skills/work. This isn’t something to be taken lightly – even if it’s a tiny piece. Take yourself out of the position of making the exchange for work. Assuming you had the money and opportunity too, would you give this company you’re money in exchange for equity. This goes beyond trust into the realm of belief. Do you believe that the startup you are investing in will actually be successful and provide a return on your investment? If you don’t believe that or have any doubts then as a developer you’re probably not going to work hard to achieve that goal.

This isn’t just about actualization, it’s about making good investments. Whatever you charge for your time, putting stake in something you don’t think is going to be successful is basically taking whatever money you would have made for that time and flushing it.

Get paid

If you’re a developer working for a startup theres no reason you shouldn’t be getting paid, even if you’re developer numero uno. Perhaps this means taking a slight pay cut from what you would be making at an established company in exchange for some ownership, but the general rule is you should be making more then enough to cover your life costs and at least enough that you’re not bitter towards those paying you.

I’ve done pure equity in the past and have pretty much completely sworn off of it. Unless you’re a co-founder, it’s going to be a very rare case to be committed enough to go the long haul without getting paid. And even if you are a co-founder, you should have enough savings to pay yourself, or think about raising some capital so you can.

If you’re approached by a startup to build their prototype or work on their app and all they have is an idea, they should pay you for your services. If this is the founders ‘side-project’ and/or they haven’t raised or put in any capital, thats a definite sign that you should get paid. Think about it – if they’re not willing to invest the capital to pay you, why should you invest?

Retainers Rule

Going along with the rule that change is one of the biggest aspects of being part of a startup, if you’re working as a freelance developer you need to structure your contract so it accounts for this. If the startup is small or just starting, working on a project basis is a bad idea as a rule. If you’re working to a fixed scope like “Working prototype of myawesomestartup.com”, even if the details are very well defined, what happens when the entire goal of the startup changes? Do you scrap your work? Do you ask for a ‘change-order’? Do you have to just suck it up and forget about getting paid for the extra time you put in? If you don’t assume this scenario from the start, it’s often awkward and painful to try to negotiate this post-change.

At the end of my last round of freelancing, almost all the projects I was working on were set up on some sort of retainer. This was great for me, because I had a definite amount of work and dollars coming in every month. It was great for the startup because they didn’t have to worry about getting charged extra or haggling over money every time they changed their minds.

I pitched every new job and potential client like this, and in the end it worked out great. If the client thought this was a bad idea or was so sure that they had everything ready from the start, I made sure to put in a clause or section that defined exactly what would happen and how much it would cost when they did want something different. (it always happened).

Get the position and job you want

This all comes down to the final point, that as a skilled developer the ball is really in your court. The key is to not abuse that advantage, but definitely make use of it to get the job that you want. The reason I hadn’t settled down into a full time job was really because it took this long to find exactly what I wanted. Paperless Post finally met my criteria:

• Great people
• Clear direction and strong motivation
• A real business plan with actual revenue
• Willingness to pay and reward good work
• Dedication to Open source

It really shouldn’t be so rare to find this, but it really is from my experience. Your requirements might be different, but if you’re ready to take the plunge of investing a lot of time in a product or team it should always be doing the best to meet these goals. As a quick aside, Paperless Post is currently hiring in both NY and SF feel free to mention this post.

Working for and with startups has been uniquely rewarding for me, not just because I’m ballin’ but because I’ve learned more in the past couple of years then I ever could have hoped otherwise.

After freelancing (or hustlin’ – as I called it) for the past year and more, I’m finally settling down. As of last week, I’m now the CTO of Paperless Post. Though I truly loved working with a number of the clients I helped out over the past year, Paperless Post made me an offer I couldn’t refuse – not just monetarily. The team they’ve assembled is not only extremely talented, but is a pleasure to work with and constantly challenging each other to do great work. It would take nothing less to get me to commit to a project full time. That’s not all, though. For my friends and followers in the open source community, you’ll be happy to know that at PP we’re already using a number of my projects including Sammy.js. I actually worked to get into my contract that my responsibilities as a member of the community and a maintainer of these and new projects is part of my job. This means that I should actually get some dedicated time to work on Sammy and hopefully extract some of the cool ideas that we’re working on and get to share them with the community.

Paperless Post isn’t what you’d think of as a typical web startup. Sure, theres funding, competitors, crazy deploys, late night coding. However, they’ve actual made a business and the world outside of silicon alley has already noticed Its not a twitter mashup or a buzz word filled rails app with some missing vowels in the name. Our goal is not to constantly push the envelope, its to do a couple things really well and with style. I can’t tell you how excited I am to be helping to shape the future of this product.

The past couple of weeks has been a serious roller coaster of emotions but somehow thanks to my wife and friends I’ve landed on my feet and I’m better for it. Thanks especially to my former clients for being so supportive during this crazy transition.

What I haven’t been doing is blogging and that’s a problem. Looking into my archives, the times when I was blogging the most was when I felt most productive and clear headed. With that said this is going to happen more often.

On to the news: As of the end of this year I will no longer be working full-time with Intersect. The decision has little to do with the company and more to do with my desire to pursue a bunch of different projects and ideas I have brewing. Intersect has been extremely supportive and understanding and I’m really going to miss working with them everyday. They are some of the most talented and creative people I know.

With that said – What’s the plan?

Day to day is up in the air – but here are the things I’ll be focused on in the coming months.

1. Giving back to the community. This is probably the most important for me. I’m working on setting specific goals- but the important part is committing to and creating open source projects. Also writing a lot more here and on mailing lists. I’ve fallen in love with the idea of open-source and github really makes it so easy – it’s hard not to contribute.

2. Partnering with people to facilatate ideas. My dream is to not just work for hire and find client/developer relationsships but find people and ideas that I can help bring to life on the web beyond just building applications. I’ve found that my real skills lie beyond coding and are more in tune with solving challenging problems in creative ways.

To that extent if you are anyone you know is interested in teaming up on an idea or project – feel free to contact me (aaron at this domain). I’ve also put up a portfolio of some of my recent work if you want to see what kind of projects I’ve worked on recently.

3. Learning. Over the past 6 months with the help of Steve Shapero and mrb I’ve been filling in the gaps of knowledge I have in computer science. In a lot of cases, I had learned the concepts in practice but now got the terminology and theory behind them.

Now, I’m diving into new realms, like Cocoa and iPhone development. I’m also making an effort to push my knowledge of Ruby by diving into different frameworks and libraries – merb, sinatra, etc.

Next steps?

Read, write, do.

Using some simple software I wrote with mrb – columnlog – you can now follow my every internet movement in a single place.

The past couple of months have been hectic. They’ve been different. They’ve been a roller coaster of code, sweat, and new beginnings. I will continue to write in vague, general statements until someone stops me.

Lets start with the biggest news, I’m no longer working full-time for RadioTail. Greg has also started something new. There’s a lot to say about this – so details later.

So if I’m not heads down on RadioTail – what have I been doing? What I want to do! Specifically – code Ruby and Rails full-time. I’ve become the lone developer amongst a crew of amazing designers and thinkers at Intersect, Inc. Working with these folks has led me to produce some really awesome projects and code to back them. I’ve got to say that doing almost nothing but Ruby has been a joy. I’m constantly discovering new ways of doing things, and constantly re-factoring my own process to make it as streamlined and agile as possible. Again – more on this later. I’ve come along way from being just a side-line admirer of what the cool kids were doing.

One of the best things about working with Intersect, besides working with some of the coolest and smartest people in this fair city, is that they have been really open to me taking on whatever I want outside of the day. Whether thats working on my own ventures, or being a Rails Ninja for Hire. _I’m trying to say – hire me to develop your Rails dream project – email me at aaron at this domain._

So right now, I have a bunch of idea, a decent amount of energy, and I’m reveling in the awesome time of NYC in the summer. Its muggy, but there’s so many awesome things to do. Now that I’ve cleared my throat, maybe I can talk more about said awesomeness.

“We did all kinds of dumb, stupid things. But our unofficial slogan was, “F—up fast.” Make mistakes rapidly, learn from them, and move past them.”

I love this mentality. One of the most beautiful parts of building web apps is the ability to constantly update and fix and change. To constantly release.

I’ve seen a lot of great ideas crumble up and die, unreleased apps of genius that will never see the light of day. What better way to learn “what works” then by letting your users tell you. I love the Flickr interface, and you can tell its a constantly shifting landscape. Its fun to find new things to do every time you visit. It’s better to make mistakes and learn to shift and jive then retain an expectation that your app will ever be perfect.

I do think, before I eat my words, that a distinction has to be made between making mistakes and making buggy untested crap. Test, prod, poke, finesse and fix your code. Don’t release something that doesn’t work, but don’t wait to release something until the 100000 features you have planned are built. Don’t be afraid to do something stupid, the fact is – we all do something stupid sometimes. Assume somewhere near the worst, and get over it.

A little more than a year ago, Greg and I had made our first marketing push for RadioTail. The first Portable Media Expo was approaching and though our software was not fully implemented we had a working and tested technology for inserting audio spots into MP3’s. Instead of trying to wrap up a buggy Beta to demo, we tried something completely different.

I don’t remember who’s idea it was exactly, but after a bunch of brainstorming (and giggling) we came up with SELL OUT BIG TIME. The idea was by being as sarcastic as possible we would try to dispel the myth of taking on advertising being equivalent to selling out.

In one week of 20 hours a day, I churned out selloutbigtime.com (no longer active). Users could upload an MP3 and choose to insert one or more of the mock ads I produced into the file. You could then share the link or put it up on our Hall of Shame. We got a good amount of traffic and some great press.

The most fun of the whole project was creating the fake spots. Greg and I wrote them up in a Writeboard and I enlisted my friends to help me record them. Voices include, Jeff Bartlett (of The Saturday Saints), Derek Sandhaus, Catherine Mathes, and Myself. I did all the music (which is all original) . All in all I produced and recorded 11 spots in a single 24 hours span. I don’t think I’ll go through that kind of madness again, but it was a hellish blast.

Here for posterity and your amusement – Download the Sell Out Big Time ads as a Zip archive

As a freshman in College I took an intro sculpture class called ‘3D Design’. It was fun but plagued with the indifference of students who had to take it to fulfill a requirement. One of the projects was to design a bridge out of only centimeter thick cardboard and hot glue. It was to support a brick between the walls of a hallway. The designs the class produced ranged from successful ladder/tube structures to unsuccessful cardboard as string nets. My bridge was an arch supported by a web of trusses and triangular supports. Not only did it hold one brick – but it was able to hold three more before even showing any sign of stress.

Not extra credit anymore

Some might say I have a problem over-designing. I try to think things through to the point where I’ve created openings for every possibility I can think of and abstractions for every layer. When working on a school project ‘over-design’ can be a virtue – a source of extra credit. I’ve found that in the real world, over-design can be a real problem.

Over-design in retail

A new restaurant just opened up across from the office. I saw them working on it and building though the summer. The sign on the door proudly letting us know that a ‘Grill and Creamery’ was coming soon. I’m a little worried they wont last though the winter. I’ll be honest I haven’t looked at their costs or revenues, but just general observations have led me to believe that this a dire case of over-design. Walking inside it looks like they had custom fixtures and counters made, not to mention all the little details. Yeah, its nice – but taken in context this all seems like a mistake. First, consider the neighborhood. They’re on the wrong side of Manhattan bridge to really get the families, and the lunch crowd these days is a lot less yuppie and a lot more blue collar. Also, perhaps because of waiting for all this custom work, they opened their doors in October, hardly the time to open an ice cream store. When you place an order you have to confirm the details of your order on a touch screen by the register.

All of these are symptoms of solving problems that don’t exist. Its one thing to preemptively close open loops and sew a patch before the whole gets to big. Its an entirely different to spend time, money, and energy eliminating ‘potential’ problems.

Agile over-achieving

In coding and the web, over-design can be a feature. The fact that you’ve designed for every possible user interaction is zealous though sometimes worthwhile. There is still a line, though, where too much thought and debate over ‘potential possibilities’ can halt a project. Agile development is not under-designing – it’s riding this line. Determine the problem and work towards a solution, solving for possibilities and exceptions on the way. You’ll never be able to catch every possible issue in the initial design. There are always surprises. However, if you or your team is fast enough, you can close gaps as they arise, and sell that ice cream in the summer.

Photo Credit: http://www.flickr.com/photos/stoner/117939136/

At least, that’s how RadioTail was depicted in a spread in October’s issue of FastCompany. I’m not complaining, I mean we’re the only one in the spread with the awesome agileness of a snake. We’re not as cool looking as Scrivs, and the 9Rules guys, but really its just cool to be mentioned in the same league, let alone sitting at the same table, as The Deck and Federated Media.

Silently, like a ninja roaming the plains of the Serengeti, we launched a newly redesigned RadioTail.com.

It’s been about a year since we launched RadioTail the company, and a little less than that since we launched the first iteration of the website. We chose to redesign for a slew of reasons – most importantly, we have a much better idea of the goals of our company.

When a startup . . . starts up, as a founder and entrepreneur you think you have it all figured out. You think – “This is your business plan, this is your customer/client/user, this is your ultimate goal”. Then pretty quickly, things change. Your plan is redirected, Your goals shift, your users aren’t who you thought they’d be. A static representation of who you are as a company (aka your public web site) can become very outdated very soon.

The intention of this redesign was to showcase what RadioTail can do for you. Be you Podcaster, Media Co., or Advertiser, we created direct “call-to-action” to find out more information about our service.

The main aspect of the redesign was highlighting the most important textual elements of the site with darker, larger text. A scan of the site will give you the gist, without having to read every word. I also wanted to clean up the layout, get rid of the rounded corners (_thats sooooo 2005!_), and give the entire site more whitespace and contrast.

The only major hurdle in the design was dealing with Internet Explorer (as usual). Primarily, I wanted (NEEDED) to use 24-bit PNG’s for the Logo, so I could get that really nice drop-shadow without having to worry about matting garbage. Of course, IE doesn’t know what alpha transparency is. Luckily there are some good fixes out there.

Overall, I’m very satisfied with how it came out. Hopefully, this design will stick a little longer – but whose to say that a business shouldn’t redesign it’s site every year?

The design and website are all me, and the registration system is even hand built. The registration system was all done with agility – which was the most fun part of the whole process. I’m happy with the site as a whole, though I wish I was a better Flash animator – perhaps if I had more time/practice . . .

This is now the second full site that I’ve built with Rails and deployed into a production environment. Getting the first one up and running was a lot harder, considering I had to do all the fast-cgi/apache set up myself. My Rails skills are growing quickly at this point. I knew all I needed was to learn syntax and get some more real experience – I learn by doing. With the pickaxe at my side I can attack any Ruby mountain. Im always coming back to a quote in the font by Ben Giddings:

“In C, I’m always having to work around the limitations of the language; In Ruby, Im always discovering a neater, cleaner, more efficient way of doing things.”

Not only do I have an urge to share my thoughts and opinions but blogging might actually help my business. Considering my startup, RadioTail, exists at least partially within the bounds of the blogosphere – blogging should be an excellent way for me to expose myself and some of the workings of my business to the world. I agree with Scott completely and think that blogging is one of the best ways to (1) publicize and (2) instill trust not only in potential partners but also clients and the internet at large.

In a way its pretty humorous that an act that seems entirely narcissistic and exists only in cyberspace can make you seem more human.