Couldn’t you still do both though, by possibly having 2 companies under 1 umbrella:
- Basecamp.com (a product company for small businesses and the like)
- Basecamp.com/enterprises (a service company branch for large corporations and the like)
The two wouldn’t have to be connected except by the name and the top executive board. The first could keep the product intact from enterprise requests and keep serving it based on same-for-all model to small businesses, while the second could act as a service compartment with the whole set of managers and craftsmen specialized to customize the Basecamp’s enterprise version(s) to specific enterprise needs. If the enterprise compartment would fail by losing the enterprise customers, you’d actually just lose the compartment, keeping the original product company intact.
The income would grow, more people would know about Basecamp (e.g. think about people in enterprises that’d leave it to start new businesses which would circle them back to Basecamp again) and you could use the added resources, knowledge and experience to improve both.