Sell stocks to reinvest in startup business tax consequences

[brandonlaundry]

What is the name of your state (only U.S. law)? Virginia
I'm planning on selling 15k of stock that I've owned for a long time in order to invest into a startup business but I'm concerned about the tax implications. Is there a way to offset capital gains taxes by investing in this new business? Basically I'm trading an investment for an investment. Thanks.

 

[davew128]

What is the name of your state (only U.S. law)? Virginia
I'm planning on selling 15k of stock that I've owned for a long time in order to invest into a startup business but I'm concerned about the tax implications. Is there a way to offset capital gains taxes by investing in this new business? Basically I'm trading an investment for an investment. Thanks.

Short answer, no. Long answer, no.

 

[FlyingRon]

There's no 1031 exchange for stocks/bonds. In fact, if you're asking now, you're probably already screwed. The long term gains treatment this year is terrible. The stocks for business wouldn't even be a like kind investment.

 

[tranquility]

While calling it an "investment" for an "investment" may be clever, they are hardly like-kind properties eligible for a tax-free exchange. Also, you have the problem that stock is specifically excluded.