I took out some money from my IRA and invested it with a stock investor. Can I count any losses from that investment against the taxes due on the income withdrawal from my IRA? For example, if I took out $200,000 and have a loss of$100,000, will I only pay taxes on the \$100,000 remaining? What documentation would I need. He is family, but not a business, he was just investing for us privately. Thanks for your help.