Comment by 29athrowaway

A) Donating illiquid assets to your own non-profit helps a lot. I typically have acquired or bought or created something in prior years that can offset this year's income.

That one is up to a 20% tax deduction on this year's income without spending any of this year's money. and it rolls forward 5 years if its value is greater than those percentages of your income. so it adds up if you keep incorporating that into your strategy.

I like this more than donating generally appreciated assets

B) Traditional 401k contribution, with W-2 salary this is up to $22,500 this year in most circumstances. But, the next part is important too for double tax deduction:

C) Borrow $50,000 from the 401k (assumes the 401k already had more money in it from prior years and good investments) and donate that $50,000 cash to the above non-profit. Borrowing from a 401k requires you to pay it back across an interval over 5 years. So in future years you're doing that + 401k contributions. Or paying it off whenever you want. Or just accepting the tax and 10% penalty. On years where you have a ton more deduction you might only be paying the 10% penalty if you chose not to repay your 401k.

So now lets add this up from a $300,000 base salary.

The government was originally looking at a $300,000 AGI to tax you on, but now you reduce this by

A) $60,000 B) $22,500 C) $50,000

so now they are only looking at a $167,500 AGI to tax you on, while you still have $167,500 + A) $60,000, so $227,500 cash. But you want to keep reducing that AGI from here.

Stop here if you're plan is to put cash in a bank account and never take any risk. This is probably already way too much for anybody addicted to conservative generic personal finance forums.

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D) I typically have some expenses for a side project or something intended to be profitable. The great thing about this is that it involves you buying things you already wanted to buy. if you're in tech that's consumer electronics, software licenses, good CPAs, lawyers, domains, subscriptions.

I'm being conservative when I say $30,000, but lets say you actually did an ad spend, the sky is the limit.

Your various side project pursuits just have to make revenue in 5 years to prove that its not a hobby. make an LLC for all of your various interests and get around to it making some money eventually.

For sake of this, you spent $30,000 of your own money (but realistically, all the banks offered you credit cards with high limits and you can float this balance for years too, and interest on business purchases can also be deducted, if you're not allergic to the mere concept of holding debt)

AGI: $137,500

E) did you get a mortgage yet? lots of deductions there on a highly leveraged asset. too many variables for this, but just the interest is deductible not the principle payments. you can play around with a lot here, such as paying interest up front to generate more tax deductions.

on a $2,000,000 property with a 30 year mortgage, let's assume another $30,000 in interest paid annually.

AGI: $107,500

F) was the mortgage on an investment property? investment property is also depreciably on its current assessed value divided by 27.5 (residential) or 39 (commercial). so, on a $2,000,000 property that's another $72,700 tax deduction every year.

AGI: $34,800

in conclusion with a "salary" or AGI of $34,808, according to SmartAsset.com for someone living in San Francisco, they would be on the hook for about $8,000 in taxes. This is effectively a 2.6% tax rate and you’ve already bought most of the consumptive goods you wanted to buy anyway and have plenty of cash left over for savings and investments.

not advice. I could go far more aggressive than that.