Turns out VC's don't give companies millions of dollars for nothing :)

True, but you can hardly call a company you only own 11% of - your company. It's someone else's.

But then again depends what and why your doing it. If that 11% is worth enough to you (and the company is otherwise healthy), then you might not even care.

Depends on the market though.

For example if your market requires large capital investment, e.g. insurance, banking, you could expect to part with a good proportion of your equity at every raise.

If you're a non-capital-intensive business and you still ended up with 10% at IPO I really wouldn't beat yourself up too much... You still did what very few people in the world have managed.

Yep. It totally depends. At the end of the day, if the company exits for $1B, whether I've got $110M or $470M is big in some sense, but immaterial in other senses. And how that money is raised is subject to so many factors that interact with where the business is and where the external market is. The way I look at it, the big differences in ownership stake are 51% vs. 30% vs. 3% versus 0.3% versus 0.03%. Do what you gotta do to be successful in the first place, don't worry about percentages of percentages.

If you are 3 founders, the initial value is already 33%...

Yes if you sold 90% of your company its not your company anymore

It perplexes me why such obvious realities are hard to grasp amongst budding entrepreneurs

Where does that misplaced pride come from?

Form the asset, sell the asset. Don't get married to it!