(this post is prompted by 3 things. One, a friend of mine just dramatically shifted strategy on his 2-person startup… for the better. Two, Jobster is dealing with these challenges– and dealing with them reasonably well. Three, I just read some related thoughts on Andy Sack’s blog.)

My advice is this: If you’re going to scrutinize your startup idea, do it early and do it often.

Starting up a company is (as I’ve said before), pretty much laying down a bet on a hypothesis. As many startups learn, their hypothesis might be just plain wrong. Or perhaps their hypothesis isn’t nearly right enough to to justify the time, effort and/or funding that has gone into it.

So it’s time to punt on your idea and go with another one. This is one (if not the only) true advantage that a startup has over larger and better-funded competitors– the flexibility to change strategy and tactics at the drop of a hat.

The thing about shifting your idea in a new direction (whether it’s a big shift or a small one) is that it gets exponentially more difficult to do as your idea and company ages. Here are a few reasons that shifting is hard in a mature company:

-Codebase. Codebases have momentum, and they don’t often go away (or go in a different direction) without a fight. It’s oftentimes a lot easier to build something new than it is to shift a codebase in a new direction, but development teams are often loathe to give away their hard-won coding victories.

-People. People get passionate about ideas. The more people you have and longer you’ve pursued a given idea, the more likely you are to have someone importantly vehemently opposing going in a different direction. In short, any shift generally results in SOMEONE having their feelings hurt.

-Customers/Audience. Just because your product isn’t as world-changing as you need/want it to be doesn’t mean that you don’t have loyal and happy customers. If you’re going to shift direction, what do you do with your customers? How are they going to feel when your focus is (at least partially) shifted in a new direction?

-Investors. Investors and other shareholders know darn well that shifting strategy is ALWAYS expensive, even if it’s a relatively small shift. The more you’ve sunk effort, time, and cash into an idea, the more people will tend advocate for a “stay the course” attitude (even though it’s sunk costs).

-Cruft. Cruft is all the crap that your company accumulates that makes it go slower. It’s a database server that acts up from time to time. It’s a middle manager that schedules lots of meetings that never seem to lead anywhere. It’s slapdash code that a developer whips out and promises himself that he’ll fix down the road. It’s old hardware and old Windows installs that start misbehaving. Every day that passes, a little more cruft gets introduced that gums up the works.

All of these reasons get a heckuva lot more painful as a company gets bigger and older.

At Jobster, we’ve recently shifted our strategy in some new (and amazingly cool) direcions. Our attention is split between a few initiatives (which, in itself, is a challenge). While I think we’re moving forward at a brisk pace, I can’t help but ask myself “What if we started moving in this direction 2 years ago?” I’ve only been with the company for 10 months, but I tend to feel that the only thing keeping us from finding our muse earlier was a dogmatic attachment to the correctness of own ideas. We should have been more critical. We should have asked more questions.

We’re not alone in this.

Andy Sack, one of my favorite bloggers and CEO of Judy’s Book, has recently been blogging about his experience shifting his company from an online user-generated-review site to a local affiliate/shopping site (here’s his first post, here’s a longer and more interesting followup). Andy’s company is also about 3 years old and he seems to be experiencing similar challenges (and a few of the same frustrations) that come out of shifting late-in-the-game.

I’m sure Andy is wondering the same thing with the same 20/20 hindsight that I am.

“What if we’d shifted our strategy in this direction in our first week? Our first month? Heck, our first YEAR?”