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:
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.
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.
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:
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.
The Graphic DesignerThe 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.
The Interaction Designer
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.
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.