Much has been said about the classic “Hacker + Hustler” dynamic, but I think a lot of the discussion misses the subtly of what both bring to the table and some of the other critical archetypes that need to be filled in a successful startup like the Designer and the Operator. I don’t think people need to be pigeonholed into a given role – everyone will find they resonate to varying degrees with each role – but if a team lacks competence in a critical type, they’ll likely need to fill it quickly to succeed. Here’s my take on the core personalities needed for success:

The Hacker

Look, if you’re building a technology business, you are going to need a technologist. And here I mean someone who loves learning and building technology. You can learn how to code. It’s actually going to be pretty important that you do have some grasp of coding regardless of your particular role at a company, so you should probably learn to code this year. Napster was Shawn Fanning’s first Windows program – he was teaching himself how to code on his uncle’s couch so the early betas had lots of atrocious bugs. The company didn’t need a longstanding Windows expert to put the tech together, it needed someone who was willing to put in the elbow grease to figure out how to do it. In other words if you’re looking for a technical cofounder consider becoming one. It’s just too hard to find random technical people who don’t know you, are highly competent, and are happy to work for no pay and very little equity on your idea. (surprise!)

The worst interview question I was ever asked was at a tech job fair in college; a recruiter enquired if I was the sort of person who loved to be locked in a dark closet for days on end with pizza shoved under a door. Seriously. For non-technologists, the important thing to recognize about the Hacker role is that when deployed well they are not just a code monkey who can take specifications and implement them like some kind of digital bricklayer. They can shape the product to do things that didn’t even occur to you to ask for because you didn’t realize they were possible. This is why it is critically important for your Hacker(s) to understand what the end user is actually trying to do. Otherwise you will get a very elegant but useless system.

A great example of this is PBworks’ CTO, Brian Kirchoff who two years ago dropped in drag-and-drop file uploading with inline image support into our editor one afternoon because he thought it would be cool. Nobody would have considered asking for this because the assumption would have been that it was not possible in a web browser but Brian knew it was not only possible but a Great Idea. So he did it. Brian’s a great Hacker.

The Hustler

If the Hacker role is misunderstood by business folks, the Hustler role is not merely misunderstood by engineers but loathed and derided as slimy, sleazy, lying, ignorant, petty, foolish, and to be avoided at all costs. It’s really astonishing.

What a Hustler brings to the table is a story. And this is critical because stories are how humans understand things. A story explains to a customer how the product is useful, to recruits why the company is awesome to work for, to employees what the company is trying to achieve, and to investors what the company stands for. If you are not able to tell a compelling and memorable story about your business you’ll find yourself mystified as to why the “idiot masses” are having trouble understanding your amazing technical invention or throw up all over it (as happened to me when I launched my first service).

The Hustler also brings a network to the table. Many Hackers understand Networking as “that sleazy thing that sleazy people do to pretend to connect with each other”, which was basically how I saw it post-college, too, until I realized I had built a real network by focusing on helping the people around me (e.g. by starting a nerd non-profit colo, suing bad guys, helping start hacker parties, and building a hackerspace). Helpfulness is actually the best currency; nobody cares about someone who just throws their business cards around, but if you pay into the karma bank by investing in the community around you, the community will take care of you. That is True Networking.

The Designer

If you are going to produce something that humans are going to have to look at and use, then you are going to need someone who can design a high quality experience. There are three important parts of providing good design – in larger companies these will often get broken out into separate roles but in a startup you often have to make do with these being mashed into one person:

1. The User Experience Designer (UX)

   To successfully spread via word of mouth, your product must get a user to the point where they say “Ah ha! I get why this is useful!” with as little effort or time as possible. Pay careful attention to cognitive load – the new terms or ways of thinking you ask a user to understand before they can reach that Ah Ha Moment. Your UX person will think through the paths that people follow in using the product (the “flow”) and what information to show where. Output is on whiteboards, pen and paper, and wireframes.

2. The Graphic Designer

   The product should also be attractive and un-intimidating, helping you focus on the task at hand and making clear through the use of font, color, and texture what information is most critical and what is secondary, and what the controls are distinct from content. The outputs of a graphic designer tend to be Photoshop mocks – “fake screenshots” if you will. Sometimes these folks work with “slicers” to be able to output static HTML and CSS.

3. The Interaction Designer

   Modern websites and mobile applications  are much more than brochureware or even statically rendered database outputs; they are richly interactive experiences. So while previously you’d hand the “sliced” HTML+CSS to a backend coder to wire up to the real database inputs, modern applications require substantial amounts of frontend coding, elegantly walking the user through large sets of highly dimensional data in an effortless fashion, handling corner cases and errors in a clear and empathetic way. Autocomplete boxes, pickers, and drag behaviors add up to more than can be fully spec’ed by a graphic designer, so the interaction designer must be able to take the spirit of a graphic design and realize it with highly efficient Javascript. You could also call this role a UI Hacker.

The Operator

Like protons in a nucleus, the creative forces of the hacker, hustler, and designer (often at odds with each other) will by want to explosively fly apart. It is the role of the operator to provide a binding force by “keeping the trains running on time”, ensuring the right paperwork is filled out, people get paid on time, the books are properly balanced, and the business operates in an orderly fashion. This person has exquisite attention to detail. Early on at PBworks we had an excellent operator; one day we got a new TV to display service metrics – she hunched over the display to count the stuck pixels. An ideal operator acts in part as project manager, making sure agreed-on meetings happen on time, getting project estimates and progress updates from people and holding them accountable. A pattern I’ve often seen is for this person to start off as an office manager and then take more and more responsibility for the running of the business (accounting, HR, interface to legal, etc) that they effectively become the COO/CFO/President. For sexist reasons I don’t fully understand, this role is usually played by a woman, and I’ve heard it more than once referred to as the “Mama Bear” role, perhaps as a tip of the hat to Den Mothers. It’s one of the least talked about and least public roles in a startup, but it’s every bit as critical as the others, e.g. Sheryl Sandberg at Facebook.

Conclusion

Take a good look at your founding team. If you’re missing competence in one of the roles above, you should see if you can bring on some help – or at least advice – to fill in the gaps, or see if you can grow yourself to better fill the role until such a time as you can hire someone to take care of it.

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Here’s a bold bet for the century: manufacturing will return to the U.S.

The 20th century was largely about realizing the vision of the Industrial Revolution: a world of plenty, where goods could be cheaply manufactured and efficiently distributed to consumers. We’re entering an era where those problems are largely solved thanks to the magic of Capitalism and global trade – the world is not lacking for Stuff. Even the poorest in the US don’t lack for T-shirts or underpants. We don’t need cheaper goods.

So the 21st century consumer isn’t just looking for Stuff, they’re looking to express themselves. Consequently we’ve seen an evolution of Brands from “Our Stuff Is Good,” implying you shouldn’t buy the possibly-shoddy stuff sold by other vendors, to “You Should Identify With Our Values.” People don’t buy Nike because they think non-Nike shoes are bad shoes – Nike marketing doesn’t even try to touch that – people buy Nike because they want to be and be seen as the sort of go-getters who Just Do It. Modern brands are about expression more than quality.

But expressing yourself as a brand’s identity is an abstraction – how much do you really understand me just because I am wearing Nike shoes? When the brands have small constituencies, identification is more meaningful, but without broad recognition, identification is much more challenging. Namely, it’s cool that you wear True Religion jeans, but until they become well-known I don’t know what that means — and by the time True Religion jeans become popular, it by definition means less to associate yourselves with them. This is part of the reason why we see “hipsters” always seeking to identify with a brand before it’s popular and move on once a brand “sells out” or becomes mainstream. While many people just dismiss hipsters, it’s legitimate that they’re looking to express themselves and their “brand churn” demonstrates that brand expression is inherently ineffective because it’s a generic intermediate, a poor proxy for values. Which is to say that no brand can actually represent you.

Consequently, the natural conclusion is that your only brand is yourself and your direct expressions. Online platforms like Twitter, Facebook, LinkedIn, and WordPress allow the individual to push their unique thoughts and tastes to a wider audience, but they still don’t cover the world outside of the computer. As people hunger to legitimately express themselves in person, they will want goods they identify with and that uniquely and directly express their values, without intermediaries. An increase in the sophistication of just-in-time custom manufacturing and the need for rapid turnaround and shipping will mean that “synthesis factories” in the US will be able to turn out large quantities of custom goods for consumers. Waiting for things to ship from China will just take too long, and lower labor costs will be obviated by automated machinery. Combined with readily available crowdsourced pools of designers who can help individuals create an maintain a personal aesthetic, by the end of the 21st century, most Americans’ clothes will be bespoke and manufactured here.

The same goes for custom skins for electronics, photographs, and other touches that help personalize a body or space. While bulk manufacture of electronics and other long-turnaround goods will remain overseas for some time, much of what is produced – like flash memory or displays – will be commoditized, much like importing raw materials. The actual synthesis and creation of value to pair a product with a consumer and put it in their hands will be done near the consumer.

Many thanks to @agentfin for a #brainbreakfast where we fleshed out some of these ideas.

A funny thing happens to technical founders: as the company you built takes off and a proper Engineering Team develops, you find yourself doing less and less code. You need to spend your time managing the business, recruiting new talent, setting direction for the product, prioritizing tasks, and the like.

As the percentage of time you’re spending coding drifts from to 50%, you’re surprised to note that you’re now only a quarter as effective; the context switches just kill you and the team is evolving new best practices and tools and building out the system’s complexity fast enough that it takes at least ~20% of full-time just to keep up.

Consequently, you hit the point where, even though it’s your company, your team gently asks you to stop checking code into production. There’s just no way you can make helpful contributions when only 5% of your time is spent coding – you’re using last year’s syntax, you forgot to create unit tests, you didn’t hook into the new functional test framework appropriately, and you totally horked the new Javascript minifier. You lose your commit privileges.

This has happened to nearly every technical founder I know – the only recourse I’ve seen is when, at some point, they give up managerial control and go hole up in a dark corner again to come back up to speed for a few months.

So I’ve found myself delighted to be back coding again, figuring out the state of the art for 2012, wrapping my head around jQuery, GitHub, node.js, SASS, Compass, HTML5 Boilerplate, MongoDB, and all these other things the cool kids have been playing with for the last five years while I was busy doing businessy things.

Got some pointers on what technologies I should be playing with?

Alan outlines the three rules of software testing:

• Rule 0: Write Tests.
• Rule 1: Test at the highest level that makes sense.
• Rule 2: Tests should be fast.

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