Looks like my old best friend is about to sell his website for an obscene amount

[TVC15]

of $$$.

What's the best way to approach leeching off of him?

[radioheadrule83]

How many figures we talking? Nature of the site? I wouldn't say which site, just incase people try and head you off at the pass

I wouldn't know where to begin. Be nice I guess. Or blackmail him.

[TVC15]

8 figures, which is obscene enough for me.  It's a music site, but I don't want to give any details outside of that because any further descriptor would make it easy to locate.

[Greatness Gone]

Offer him sexual favors for it. I dunno.

[radioheadrule83]

8 figures... he could pay your mortgage and make it back in no time. Jeebus.
I'd personally be happy with $10,000 or less for starters. He could give you that and not trigger gift tax (I think)
Say the recessions gonna hit you bad or something. Ol buddy ol pal.

[TVC15]

Blackmail is a no go.  He's a pretty vanilla person as far as deviancy goes.  He's the person I honed my ability of manipulation on, but I haven't tried that on him in years, and I'm not sure if it would even work in person.  I can always just ask him to fund me for a year so I can exclusively write without having to work.

I think I can have a bulletproof strategy by Monday morning.

[pilonv1]

tell him for 10k you will let him stick it in your pooper

[TVC15]

tell him for 10k you will let him stick it in your pooper

10k isn't so much to me anymore.  I deserve more.

Also, during high school, I was one of his only friends.  Similar to Sweet Dee in It's Always Sunny, my friend spent a lot of time in a terrible, horrible, back brace, and later on, some sort of other post-surgery, larger brace to prevent his upper body from moving much.  He had sever scoliosis and had surgery.  He probably would have committed suicide without me.

He's also the friend that pissed me off and lead to my terrible, horrible car accident, and I *know* he still feels guilty about that.  I have some leverage here.

[max_cool]

well, at minimum try to contact him with no pretenses. What university did he graduate from (assuming he did) ask him if he wants to watch the game next week with you. Mention that it's the last week that you will have the HDTV since you have to return to Aarons (or your regional furniture/electronics rental store) due to not being able to make payments. If he doesn't like sports and happens to like video games approach with the same strategy, if not games, then movies. He will have to like sports, games, or movies.

[TVC15]

well, at minimum try to contact him with no pretenses. What university did he graduate from (assuming he did) ask him if he wants to watch the game next week with you. Mention that it's the last week that you will have the HDTV since you have to return to Aarons (or your regional furniture/electronics rental store) due to not being able to make payments. If he doesn't like sports and happens to like video games approach with the same strategy, if not games, then movies. He will have to like sports, games, or movies.

He lives in NYC, I live in Seattle.  We still talk regularly via phone and IM, but it's like, if you're not friends in person, you really aren't real-life friends, so much.  You know?  It's been 4 years since I've physically hung out with the dude.

[Fresh Prince]

I'd do this: Call him up and say you'll be in New York on a business trip and you'd like to meet up with him on whatever night. Once you meet him, tease him about being an internet millionaire and try to get him to order the most expensive drinks there (which he should oblige) as much as often. Then get him drunk. Then remind him of all things you have done for him while acting drunk. Then one of two improbable things could happen 1) In his loosened drunken state his checkbook comes out and there's your money or 2) He feels bad the next day and contacts you to give you money.   

[muckhole]

Quick question: Does he already know that you're aware that he's selling it?

[GilloD]

well, at minimum try to contact him with no pretenses. What university did he graduate from (assuming he did) ask him if he wants to watch the game next week with you. Mention that it's the last week that you will have the HDTV since you have to return to Aarons (or your regional furniture/electronics rental store) due to not being able to make payments. If he doesn't like sports and happens to like video games approach with the same strategy, if not games, then movies. He will have to like sports, games, or movies.

He lives in NYC, I live in Seattle.  We still talk regularly via phone and IM, but it's like, if you're not friends in person, you really aren't real-life friends, so much.  You know?  It's been 4 years since I've physically hung out with the dude.

I'm in NYC. For 5% of total take, I'll be your liason and/or mugger.

[Powerslave]

I'd do this: Call him up and say you'll be in New York on a business trip and you'd like to meet up with him on whatever night. Once you meet him, tease him about being an internet millionaire and try to get him to order the most expensive drinks there (which he should oblige) as much as often. Then get him drunk. Then remind him of all things you have done for him while acting drunk. Then one of two improbable things could happen 1) In his loosened drunken state his checkbook comes out and there's your money or 2) He feels bad the next day and contacts you to give you money.  

[Eric P]

i can't really think of what music website exists which would be worth 10 million dollars +

[muckhole]

This is why i'm so glad nobody knows about my inheritance.

DING! DING! DING! DING!

[Madrun Badrun]

This is why i'm so glad nobody knows about my inheritance.

Buddy!  Have I ever told you how much money we are going to make together after you pay for my schooling?

[Powerslave]

This is why i'm so glad nobody knows about my inheritance.

Why do you think you're one of my favorite posters?

[Mr. Gundam]

i can't really think of what music website exists which would be worth 10 million dollars +

I wouldn't be surprised if Pitchfork was worth that.

[TVC15]

i can't really think of what music website exists which would be worth 10 million dollars +

This is why I'm somewhat ehh on the whole thing.  He wouldn't bullshit me, though, and due to the nature of his professional career, I don't think he's likely to be scammed.

[recursivelyenumerable]

too late!  don't feel bad though, you still have a chance with me.  at my current rate of income growth I'll have an 8-figure annual income in ~16 years; also intend to squander it in an orgy of disastrous investments, you could probably get some of that.

[TVC15]

too late!  don't feel bad though, you still have a chance with me.  at my current rate of income growth I'll have an 8-figure annual income in ~16 years; also intend to squander it in an orgy of disastrous investments, you could probably get some of that.

You can start funding me now.  Just buy me like a year's stay in the Chelsea Hotel, and give me like 100 grand on top of that.

[recursivelyenumerable]

i was being facetious.  my salary recently went from something very low to 2X something very low, hence "at the current rate of growth" (speaking geometrically).  I still don't have $100k (or $10k) to throw around.