It's possible to do both. At Twilio we started as a self-service, developer-focused company. Today we have many large enterprise customers (and spend a lot of effort to court those kinds of customers), but we still have a huge number of small developers, and one-person hobby shops can and do still easily set themselves up to use our platform. We have added some enterprise-only features, which I sometimes have mixed feelings about, but everything that's traditionally been available to non-enterprises is still available to anyone with a credit card.

I completely agree with you on (at least in terms of Twilio's experience):

> would Optimizely be doing much better if they hadn't pivoted into enterprise hell? Or would they be a much smaller company?

We were definitely going to hit a ceiling if we didn't add enterprise features and work on getting all the various certifications that large companies will require to even start talking to you, and build a sales force that knew how to sell to larger companies. If we hadn't done all that, we'd be a much smaller company today, and likely a competitor would have done it instead and eaten our lunch.