If I sell shares of stock in a company can I buy back my shares at a lower price (flip) and not have to pay capital gains? Can I flip my shares and postpone having to pay capital gains tax? I know alot of people who flip their shares, and are able to buy more shares back at lower prices. How are they able to do this when they have to pay a large % of capital gains tax on their profit. Can you flip stock without having to pay tax on the profit?