We asked Darryl Gray, BNZ design consigliere, and founder of Hive, a nifty tool for scheduling projects and people, to interview Webstock speaker and all round awesome dude, Jason Cohen.

Darryl: Your Webstock talk (‘A Geek Sifts Through The Bullshit’) encourages a commonsense approach for startups, rather than following a set doctrine. How and when should entrepreneurs follow the advice of internet darlings such as 37Signals?

Jason: The thing to remember is these doctrines aren’t rules, they’re better named as “styles.” There’s no rules in business any more than there’s rules in art. It’s useful and healthy to explore various styles, figuring out which resonate with you, as you develop your own.

Rather than asking “When should I follow 37signals,” the question should be: “How do I know which of the various bits and bobs (as you say in NZ) from the 37signals blog applies to me?” If you can answer that, you can filter any advice anywhere, and that’s an invaluable life skill. That’s what the talk is about.

Darryl: You coined the notion of the Startup Death Clock (readers: calculate your own death at http://startupdeathclock.com). Tell us about the idea behind it and people’s reaction to it.

Jason: Sweet! I always wanted to coin something, but it’s something you can’t claim to have done yourself, just like you can’t give yourself a cool nickname. (Now I just need a cool nickname.)

The idea came from fear and worry of course. It’s something every founder faces; sometimes great “ideas” are merely articulating what everyone already knows tacitly but isn’t mindful of. It’s the simplest spreadsheet you’ll ever make (unless you use Excel for groceries like my wife does, but then she’s a chef and efficient at such things), and yet it’s a punch in the face. Or a kick in the ass — that sets the momentum better.

I think people loved it because it’s a combination of simplicity (easy to understand, implement) and truth. That’s always popular. The best bloggers already know this… It’s just easier said than done, for all of us.

Darryl: You’ve had all manner of roles in your startups (“salesman, designer, marketer, accountant, and changer of the pellets in the urinals”). Do you think that kind of experience is important for all entrepreneurs?

Jason: Yes, if you’re not the janitor you’ll never understand whether HTML5 is revolutionary or just another goddam thing.

Seriously, it depends on what you make by “experience.” If you mean “You need this experience first in order to be successful,” then absolutely not. I didn’t; most successful entrepreneurs I know didn’t either.

If you mean “You need to be eager for new experiences and willing to jump in on topics you’re uncomfortable and unknowledgable about, rather than saying ‘it’s HIS job’ or blathering on about how you’re ‘wearing so many hats’,” then yes. Get in there. The days of “I’m just a coder” or “I’m just a designer” are over. Not if you’re an entrepreneur.

Darryl: A theme of your blog is encouraging small businesses to ask hard questions of themselves, and give honest answers. Are most startups you meet in denial? (Bonus question: If so, how can they change?)

Jason: Of course, because most people are. Your idea is your baby. It’s tied up in your ego as well as your finances. It’s fine to do lip-service to the idea of being introspective and listing to potential customers, but in my experience few people actually ask the tough questions or change their mind. Human nature.

I’m not sure if you can fundamentally change who you are, but you can consider this: If you’re backing off rooting out the truth, you’re just making it less likely that you’ll succeed aren’t you? And final success — at whatever your venture morphs into — is the thing that will fulfill you, impress others, pump your ego, and whatever else you’re doing this for.

Seek truth and ultimate success, not validation of immediate ideas and notions. Don’t think of it as being wrong, it’s finding something even smarter.

Darryl: Tell us why you encourage small companies to “stop acting like a faceless, humorless, generic, robotic company!”

Jason: Because that’s who we enjoy doing business with, and because it’s one of the few things a small company can do that a large company cannot, and therefore an automatic competitive advantage that’s silly to discard.

Darryl: As you’re about to discover, New Zealand is a long, long way from … well, anywhere. What advantages do Kiwi entrepreneurs (or anyone outside Silicon Valley, for that matter) have when launching a web startup?

Jason: Silly-con Valley is where almost all companies go to die. You just hear about the raging successes because those make good press, but that’s not the usual story. So anyone striving to create a company that actually makes money for making a product people actually want is already, in my book, ahead of northern California.

Advantages in NZ in particular? It won’t be in connectedness, fast turn-around for tech support (for America/Europe), or access to vast capital or lots of employees. So it’s any company that thrives on the opposite: A product that doesn’t need tech support or big investment. A company which isn’t trying to be Facebook, but rather just trying to make a nice living for 1-3 people.

Example: The best on-line training class in CSS3 and SASS, sold for $99. It’s training in itself so you don’t need “tech support,” it’s needed by a million people, it’s useful world-wide, no one cares where the author is located. There’s a hundred other examples.

Darryl: What’s the single most important piece of advice for a fledgling web entrepreneur?

Jason: Success = Tenacity + Luck. Most startups die because the founder loses interest.

Darryl: Your latest company, WP Engine (wpengine.com), provides a fast, secure, and scalable platform for WordPress content. How did the company come about, and what interests you most about this area?

Jason: I needed it myself, then I interviewed 50 people and found that, with a pitch developed as I went along, 30 of them were willing to pay $50/mo if I built it. 20 of those actually did buy after we launched, by the way.

It was easy to recruit people to work for WPEngine, which is another good sign. If you can’t convince people to join in for little to no salary, how do you expect to convince customers or investors?

What interests me personally is the art of optimization. See, after all the writing and marketing and business philosophy crap, I’m still just a geek, and I’ve always liked optimization — making things faster, more scalable, more robust. WordPress needs it, and millions of people want WordPress to be optimized, so in this case personal passion matches (well enough) with market need.

Thanks Jason and Darryl!