I just did some research on dealing with wealth yesterday, and here is what I found:
Books talking about a sudden influx of wealth: Living Richly: Seizing the Potential of Inherited Wealth Navigating the Dark Side of Wealth, A life Guide for Inheritors I picked those books up because they seem to deal with personal issues surrounding wealth. Bitcoins aren't exactly inheritance, but the case is similar I guess.
I also asked on /investing
on the issue. Aside from some useless advice like "live just like you did before" people recommended the following books: - The Intelligent Investor - Benjamin Graham - The Snowball- Alice Schroeder - F Wall Street- Ponzio One more book, that taught me about stock investing in the past: - One up on wallstreet (or something like it)
As for "useless" advice I got: - "live just like you did before" - from people not knowing how badly, or how well I lived in the past. besides - what's the point of earning money if they don't change your lifestyle at all? - "sell it all, now!" - from the people who didn't & wouldn't buy in the first place - "keep it all, forever!" - from the same kind of people who invested in Pirate's funds and are afraid of btc failing if people start to cash in - "buy a house, pay off debt" - again - from people who don't know me/you. sometimes it's a good idea, sometimes you can get a better roi by not buying a house - "buy litecoins now" - there is no practical use for litecoins aside from speculation
As for the useful advice I received was to prepare my investment plan. I.e. how much % I plan to keep in ultra-safe investment vehicles, how much I can loan out to family, how much I can put into risky vehicles like Namecoin ;) Another useful advice was to keep a financial log. Each change I make in my portfolio I note down. It helps to clarify thoughts, eliminates a bit of emotional side, and allows you to learn from your successes & mistakes.
The two above points I'm using for a year now, so I can actually trace back why I bought bitcoins a year ago and ask myself whether it still holds true.
Finally, as for keeping BTC safe. I personally bought Asus EEE, installed a clean copy of Ubuntu, and turned off wifi. I kept my wallet there, and do not attach the netbook to the net. I have a copy of the wallet & my mpoe private key on an sd drive as a backup with me at all times. The sd card fits nicely into the jeans condom slot :) Everything is encrypted with a passphrase. Obviously.
I also have an MtGox account, with two-factor authentication (yubikey, and google authenticator on both my & my gf's phone), and a blockchain.info account, with two factor. Plus I've added a two factor authentication to my gmail account.
In case anything happens to me, there is a testimony written down, which contains all my passwords. I also trained my girlfriend in everything.
As for the cash taken out of bitcoins, my tax advisor is now learning what Bitcoins are, and figuring out how to tax it. It was a fun conversation.
Oh, and me, personally, I regret a bit already I shared with too many of my friends that I had so much btc. They're now calling me and asking whether I still have them :) I'm comfortable with just them knowing, but I wouldn't want the fame to go much further. If someone asks, I tell them that I sold most of my btc back when they were worth less. Which is almost true, anyway.
I also try to keep in mind, that the only "real" money that I have is the one I converted back to dollars, and sent to my bank account. Which "0" until I figure out how to tax this.
Finally - people are afraid of btc millionaires cashing out. I think they/us will to some extend, but due to the tax reasons, they/us will be pressured to spend it within the btc economy. That's good news for the btc price :)
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