Jot Thought

In case you haven’t seen these yet, compare the following two videos from StartupSchool ‘08: the first by Greg McAdoo at Sequoia and another by David Heinemeier Hansson of 37 Signals and Rails fame.

We found them both particularly interesting because we are currently wrestling with the decision of whether to try to go raise money for our company or continue bootstrapping it. We have two products in the market: Paybackable, which provides very simple online expense reporting and has a bunch of users and Bootstrap, which is in private alpha. We are close to releasing a major upgrade to Paybackable that will add support for company accounts and employees. The release will also introduce paid plans, much like 37Signals’ products. So we’re about to learn first-hand how difficult it will be to try the approach in David’s video.

For Bootstrap, it’s a much grander vision and frankly, we don’t know if we can afford to do it justice in a reasonable amount of time by funding it ourselves. Hence the interest in raising money. We’re gathering as much advice as possible and will begin getting feedback on our pitch very shortly. But it seems clear that once we head down this path, it’s go big and exit or bust.

So we’re at an interesting crossroad. Do we shoot for the stars? Or do we try to become a “lifestyle” company - to use a popular term in the private investing space. Right now, all we know is that there are some pretty important problems that we can solve for small business owners like ourselves. We’ll see what the future holds.