I think your math here using different assumptions than he would.

"This was largely paid for by the tickets bought by the audiences at both shows."

Otherwise he would have been able to simply pocket 170,000 dollars worth of tickets, as if he had done a regular show.

So to him, that's a net loss of 170k, you don't get to add it back in at the beginning.

So, 550 - 170 - 30 = 350k

You've also got to assume that his time is worth something, he could probably be working on something else instead of arranging his own marketing blitz... Also have to assume he pays for his own travel expenses etc.

I can see that being an expensive proposition if he, for example, has to fly cross country, miss out on potential shows, etc. If he misses out on 2 shows, that's a couple hundred thousand right there (apparently).

The point being, if he had done this through a media conglomerate, he probably could have had time for other stuff that would have made him money.

Bandwidth costs money too. > 100,000 GB isn't particularly cheap.

"I only heard of Louis C.K. from watching one of his stand-up shows on TV on an airline, so even if he didn't get payed directly, there's still publicity value in them."

Same, except it was YouTube. There's even publicity value for him in piracy. If he can afford to sell this thing for $5 and make a profit, he only needs something like 1/15th of people to become fans, buy a ticket and see him live.

I was more concerned that he paid $35K for a paypal-powered commerce site that sends plaintext passwords by email.

Yeah, because if someone got ahold of that password...they could login and download that $5 video!

In this case, I think this is actually superior, because a lot of the purchasers are going to buy and download this, and never login again. Why have them type in the same password they use for their email and banking, and have to worry about keeping it safe indefinitely?

4 reasons the plaintext password is OK in this situation:

1) They generate the password for you, how else are they supposed to get it to you?

2) Just because they email it to you in plaintext does not mean they are storing it in plaintext (they could easily send the email at the time the password is generated)

3) You won't reuse this password on other sites because you didn't choose it. The primary reason why it's bad to store passwords without proper hashing is that a leaked password database means hackers can tap into everybody's email/bank accounts which are using the same password.

4) All the password gets you is access to download a video (no other personal info available). Not a huge risk.

The correct way to handle this is to email an authenticated link that prompts password setting on the store.

That's A way. For a virtually costless good, this is just as fine a way that has a much smaller chance of capturing a password anyone gives a shit about

Look, my point is that for $35K, a newly-built commerce site should follow basic best practices. It isn't exactly hard to implement, esp. if you're worth $35K. It isn't about someone stealing my account info – it's about evaluating what he got for $35K.

I disagree that's a best practice for all cases.

For a commerce site that you will not use or necessarily maintain for years, a system where you don't ever get passwords that other people give you can certainly serve better than one where you do, as the logins are only useful for the content.

This could be more useful to him as his security matters less, as he has less valuable things stored in his site. It may also work better to lower support costs (as many people are pretty bad about keeping track of passwords), and this approach means they can just look at their email to start.

I agree for many cases (say, HN), that it is a good practice, but it's not gold in all cases.