201–203 of 203 posts
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If the OP is telling the truth, there is no way he lost money on the stock he bought. The early shares are all up.
Not necessarily. There is liquidation preference for the preferred shares.
Another proof point that once the founder-CEO is replaced by a professional CEO, it's game over more often than not. This happened in 2017 at Optimizely.
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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 f…
> It's possible to do both. I think the more interesting question is: can you always do both? I agree in a general sense, as there are a lot of excellent examples in the wild at this point (of companies consciously maintaining their developer base), such as Cloudflare, Fastly, Stripe, DigitalOcean, Twilio, GitHub and so on. It may be a case where it's much easier for some types of services than for others.