Can I take a loan from my business tax-free like getting a loan from a stock broker?

But what about those stories of rich people never paying back those broker loans? I heard they just keep rolling them over until they die and then there's some loophole with the estate tax? Does that actually work?

The "buy, borrow, die" strategy you're referring to does exist, but it's more complicated than it sounds. Wealthy individuals can borrow against securities indefinitely in theory, but these are still legitimate loans with interest that must be paid. The strategy works because borrowing itself isn't a taxable event, and if held until death, assets can receive a "step-up" in basis that eliminates capital gains taxes. This doesn't work the same way with business loans to yourself because the IRS specifically looks for this type of avoidance technique. The tax code has specific provisions to prevent business owners from disguising distributions as loans. They'll look at factors like whether there's a history of similar transactions, if there's a written agreement, if interest is being charged, and if there's a realistic expectation of repayment.

Does it work for all business types? I have an S-Corp and have been trying to figure out the right way to occasionally borrow from my business without creating tax issues.

I'm skeptical about tax services that claim to have magical solutions. How exactly does this differ from just paying a regular CPA to structure things properly? Why would I trust some AI over an actual accountant who knows the tax code?

It absolutely works with S-Corps - that's actually where it really shines because S-Corp owners face specific challenges when taking distributions versus salary. The platform has specialized guidance for different entity types including S-Corps, C-Corps, and LLCs. Regarding your skepticism, I completely understand - I felt the same way initially. The difference is that taxr.ai doesn't replace your CPA; it complements their work. You're getting AI-powered analysis of tax regulations that can spot potential issues your CPA might miss, plus document templates that are specifically tailored to your situation. Many users actually bring the recommendations to their CPAs who appreciate the thoroughness. It's more like having a specialized tax researcher working alongside your accountant.

Wait, how does this actually work? Does it just keep calling the IRS for you or something? I've been trying to get through for weeks about a similar issue.

This sounds like total BS. Nobody can get through to the IRS faster than normal. They have one phone system - how could some random service possibly bypass that? I bet they're just taking your money and you're still waiting just as long.

It doesn't bypass the IRS phone system - it uses technology to continually dial and navigate the IRS phone tree automatically until it gets through to a human. Then it calls you and connects you directly to that agent. It's basically doing the frustrating part for you so you don't have to sit on hold or redial constantly. The service absolutely works. I was skeptical too, but when you consider how many hours of your time get wasted trying to reach the IRS, the service makes a lot of sense. I literally got connected in under 15 minutes when I'd been trying unsuccessfully for days. You still talk to the same IRS agents through the same system - it just handles the connection process for you.

What about for a single-member LLC? Are the rules any different since it's a disregarded entity for tax purposes? Could I take loans from my business more easily?

For a single-member LLC that's a disregarded entity, the situation is actually quite different. Since a disregarded entity is treated as the same taxpayer as you for federal tax purposes, technically you can't loan money to yourself - it would be like taking money from one pocket and putting it in another. The business funds are already considered your funds from a tax perspective, so there's no tax advantage to structuring withdrawals as loans. You're already being taxed on the business profits regardless of whether you withdraw the money or not (via Schedule C on your personal return). That said, for proper bookkeeping and to maintain the liability protection of your LLC, you should still document any personal withdrawals properly. If you're mixing business and personal funds without documentation, you risk piercing the corporate veil in legal situations.

Completely different. The billionaire strategy works because they're borrowing from a third party (bank or broker) using assets as collateral. They're not taking money directly from their companies without taxation. When Musk or Bezos get liquidity, they either: 1) Take loans from banks using their stock as collateral (legitimate third-party loans), 2) Sell shares and pay capital gains tax, or 3) Receive salaries/compensation that are taxed as income. The "loan" from your own business isn't actually a loan in the IRS's eyes unless it meets very specific criteria that most small business owners don't satisfy. Otherwise it's just income/distribution with extra steps.