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Well, as many on HN know, lots of startups fail. Investors write that off as a capital loss.

Maybe one day, long term capital gains tax will be on the same level as income tax, and then people will stop trying to use things like 83b elections.

But regardless of that, if you invest into your own startup by buying equity or lending it money, that is NOT currently a taxable event. And then that LLC’s losses are passed through to your Schedule C.

It may be strange to have you buying shares in your company if you already have 100% of shares. But if you do a Limited Partnership with a few people, then all of you could be competing to buy shares in it and dilute the others. Those are non-taxable events. And the members of the LLC are also its staff, who go watch movies and review them. Then the tax deductions are claimed on Schedule K instead, by each partner.

I am only talking about a bona fide business. You don’t have to go all-out for each business you start, working 40 hours a week for each one. You could even go to the movies and restaurants once a week and save 30% by turning it into an actual business. Can’t you?

Do travel bloggers deduct their travel expenses as necessary and ordinary?



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