[bogomipz]

>"My annual return on the stock market is always well above 10% YoY"

That would make you one of world's most elite money managers. I'm sorry but that sounds to good to be true. Bernie Madoff was getting his clients 10% year over year and that turned out to be too good to be true as well.

Could you share some details on this investment strategy you have?

[lettergram]

First, I hold all my investments for a year then dump them (occasionally, I'll rebalance before a year). I've been doing this for 5 years, averaging 35% returns. I said 10% a year, because I'm assuming one down year I will "lose" significantly.

I always do this in March, after my tax return, because that's my "play money". All the money I made from the prior years investments + tax return I usually dump into other investments that hold up over time i.e. gold, real estate, etc. or invest in my business.

Here's this years, which has been unusually good:

http://imgur.com/a/j8YWR

I pick the high movers using a method I'm not going to describe at the moment. However, I am making a website which will help others invest as I do. It'll be a paid service, but I'm not going to charge outrageously. You can follow on my blog, I plan to release it sometime in late spring:

http://austingwalters.com/

Feel free to follow me, and I'll send out an update when I'm ready to release the stuff.

[bogomipz]

You mentioned earlier:

>"I use part of my student loan payments to shield against higher taxes. AKA I can write off the interest payments on my tax return."

and then:

>"All the money I made from the prior years investments + tax return I usually dump into other investments that hold up over time i.e. gold, real estate"

I am sorry but that kind of sounds like you are gaming the system. I don't think the intention of the student loan tax deduction was to allow people to buy gold and real estate but rather to help people to make ends meet. You don't actually need that deduction it sounds like.

[toomuchtodo]

> I am sorry but that kind of sounds like you are gaming the system.

Story time.

A side hustle I'm working on is creating a site that matches investors with solar projects. Due to how solar tax incentives are structured, if I can properly estimate your tax liability, I can create a partnership vehicle where instead of your tax liability going to the US federal government, its all invested in solar generation projects.

You still have to pay taxes, but because of a legislative and tax code hack, you can fund renewable energy deployment instead of federal tax receipts.

This is gaming the system, but I'd rather my money go to clean energy and not bombing innocent brown people and another carrier group. Economics 101 is incentives matter. If you set a system up, be prepared for people to poke at it to find its weaknesses.

EDIT: @bogomipz

Regarding your comment:

"So that Federal Government was OK when it came to you getting a student loan for an education but it's somehow not OK when it comes to paying your fair share to fund it? I don't like paying taxes as much as the next guy but I do it and I understand why I need to."

I'm a high school dropout, and the services I care about (Social Security and Medicare) are funded out of my payroll taxes, which I'm fine with (I've paid $73k into Social Security, and $21k into Medicare, not including the exact matches my employers have paid in). I pay for the things that should be paid for (social services), and avoid paying for things that are unjust (the us military).

[bogomipz]

>"if I can properly estimate your tax liability, I can create a partnership vehicle where instead of your tax liability going to the US federal government,"

So that Federal Government was OK when it came to you getting a student loan for an education but it's somehow not OK when it comes to paying your fair share to fund it?

I don't like paying taxes as much as the next guy but I do it and I understand why I need to.

[lettergram]

You are on hacker news, I'm pretty sure hacking the system is part of what this site is about