Earlier quoted context omitted.
Lets say your company is valued at $100 and all stock is claimed for current employees. Now you want to raise money by selling 50% of your company to investors. So you create $100 more and now they own 50% (at $200 valuation). This means the investors either over-paid (2x what they were worth!), or you were strongly under-valuing the stocks that existed before. If you dilute , they get 50% at $50, and the existing st…
Let's imagine that there are two employees who each own half the company, so each has $50 of stock in the $100 company. You wish to raise money. You can sell 50% of each persons stake, or all of one person's stake, or something else. Without dilution, it would be a founders job to convince the other employees that giving up some of their shares was necessary (assuming the employee equity pool was the only source, but…
Now your CEO has to horse trade with every investor in the round, and also every existing investor and every employee. Everyone who agrees to the scheme effectively gets diluted, but anyone who refused to go along effectively gets a "free" anti-dilution adjustment. So the incentives are all wonky.