Cass: What was the biggest mistake you made in the early development of PBworks?

David: Probably that we tried to jump from being a consumer company to an enterprise one without pulling down the resources (financing, team) that we needed. By the time it became clear that we needed to really scale up - hiring an enterprise sales force, getting people on the ground in cities like New York, we weren’t really in a position to get access to that kind of capital.

Cass: How did you recover from it?

David: It’s not been easy - we basically have needed to bootstrap an enterprise organization, which is really not how you want to do things. There’s just a lot of infrastructure (both in terms of people and software) that is needed to start and run a successful enterprise operation and we needed to get that running with not only no budget but while keeping our consumer base of some four million people happy. After three years, we’re finally starting to scale up our deals and mature our pipeline to the point where we can more regularly line up big deals, but it’s been a pretty brutally challenging process. If we had pulled down a big wad more money and staffed up appropriately at the beginning to tackle the enterprise market, we’d be much further ahead.

Cass: What advice would you have for early-stage founders to avoid this in their own companies?

David: Two things: one is that once you’ve launched, you really shouldn’t try and switch from being a consumer company to an enterprise company, or vice-versa. The two have very different requirements in terms of team, DNA, capital, and focus. The other is that you need to remember to do a rewrite of your product - not constantly, actually probably just once, once you have your product-market fit and it’s turned into an execution plan. But if you organically evolve a codebase as you violently change business models, you’re going to have a lot of cruft that will be very difficult to maintain and won’t be architected for the right uses.