Because you're exchanging stock worth $193 million for an equivalent amount of dollars, there's technically no profit or loss involved in the transaction. In the same manner, when paying stock as a compensation, you secure services valued at $193 million for an amount of shares worth the same: the transaction is entirely equal. So you don't make or lose any money by paying in stock.

Of course, the trick is that the value of the CEO's work for one year can be whatever he says. If your claim is that they could have gotten more value out of the stock had they sold it in the IPO, I think you are absolutely correct in that regard.

I know you're just being funny, but the idea is that Spez's shares and resulting influence over a publicly traded Reddit will incentivize investors to buy stock, raising the value of the stock for all shareholders. The problem with this idea is that Spez is an idiot who is actively sabotaging Reddit's long term viability.

Before they went public, who was foolish enough to invest in a company that has never turned a profit?

You'd be surprised. The basic strategy of losing money hand over fist for years to grow yourself to as large a user base as possible, before finally aggressively monetizing that user base, is well established in silicon valley. Investors would not even raise an eyebrow at the loss numbers posted by Reddit because of how exceedingly common that is.

And it has worked several times, making some people ridiculously wealthy. Good examples are Amazon, Facebook, and Uber. So usually companies on this level have raised hundreds of millions to sometimes billions of dollars in investment capital, allowing them to operate at these levels of losses for years at a time.

Reddit has a lot of users that spend a lot of time there, so it is advertising potential, and a lot of Brands pay for ads on Reddit. Investors hope they will eventually make enough ad revenue to turn a profit.

However Twitter was and is in the same boat, it is a big site with many users, but was never profitable.