As spullara mentions, owning a smaller portion of a more valuable company is obviously preferable than owning a lot of a less valuable company.

I am all for bootstrapping and people choosing their model, but lately there has been quite a bit of vitriol for these advanced growth stage companies (no longer startups) who are largely VC owned. My opinion is always - Ok, these founders/ early employees knew what they were doing at some level. They were the boots on the ground who - in this case - said, if we want to grow to the point we can IPO, need to raise $85.5M to get to that point.

Playing arm-chair quarterback isn't really fair when we don't have great insights.

The fact that Zendesk isn't profitable is related to the ownership. Growing as fast as you can often involves spending more money than you make. VCs can trade you that money for equity. The old saying goes that 100% of a small company isn't worth as much as 10% of a huge company.

The seems the money spent, more than anything

But: Enterprise is hard, bootsrap even more-so.

I don't know why I continue to be amazed at how pathetic the analysis of things like IPOs and venture investing is here on HN.

OK, I'll bite...what sort of model would you propose?