Supposing you require $20,000 for a heart operation?

Question

You own 1,000 shares of Google Inc., which you bought at IPO for $20/share; now worth $40/share. Should you sell HALF of those shares, considering that you are reaping the profit of your investment? Or should you sell ALL $20,000 of the stock you own in Ford Motor co, even though those shares may possibly be worth more in the future?

Which would you sell?

Answer 1

Accepting the prices in the example, you need to sell more Google because, after capital gains taxes are taken out, you won't have $20,000 any more. You don't mention your cost basis for Ford, but if it's a loss, you get a (small) tax advantage and thus do not have to sell $20,000 of stock to get that much benefit.

Generally, if you own company A and company B and the tax differences are trivial, then it doesn't matter which you sell because either could go up in the future. The stock doesn't know you own it, or what price you paid for it.