On 1 October we did something spectacular and totally unheard of (at least in terms of our own history) at WooThemes: we launched a complete overhaul & redesign of WooThemes.com in only 2.5 months. We re-did absolutely everything: redesigned every single page, stripped out our backend, replaced with a new system and migrated all of our old data across.
And oh my [insert expletives here], has it been the most painful experience since... We've had to fix so many bugs that were out in the public domain and our support channels have been over-run. It's really been bad.
Ask me whether I will do that again and I will say "Yes!" with the kind of gusto and confidence that belies the challenges we've faced since 1 October. That "Yes!" is entrenched in my opinion that you need to feel the pain, because that pain becomes the incentive to put a band-aid on it and stop the bleeding.
The fact is that this has been a major improvement for us as a team. The previous time we embarked on such an adventure, it took us 18 months to get to the point where we could publicly launch this thing. 18 to 2.5 months means a 720% improvement. :)
During the project, the decision to set a fixed launch date / deadline (for 1 October) and now in hindsight, I'm reminded by Reid Hoffman's famous quote:
"If you are not embarrassed by the first version of your product, you’ve launched too late."
I'm also reminded by Matt Mullenweg's experience (from "1.0 is the Loneliest Number" of how that "one more thing"-mentality totally derailed WordPress' progress in 2006, which felt like exactly the problem we had when we previously overhauled our website.
It's not been pretty and it's not been great for our customers (which IMO is the only downside to this). But it's been one massive learning curve and - as a team - we've never been so agile in iterating, fixing things and making everything better.
I'm so enamoured with the positives from this experience, that my mind wants to make me believe that there is no other way to go about this: launch early, be embarrassed, feel the pain and then put a Band-Aid on it. Simple.
On the other hand, this post might just be the result of the endorphines I'm feeling from an obviously painful 3 weeks...