You could own 5% of a tech startup that eventually sells for $1B

Yet, you could walk away with absolutely nothing from the sale

Here's why you should always ask these 5 questions about any equity you get granted in a startup: Question 1: How much is the liquidation preference on the company?

This is typically the total money raised & the minimum a company needs to sell for before you see ANY RETURN

If the company has raised over $1B, you'd make nothing on your equity if it sold for $1B

The best personal finance "hack" for anyone who works for themselves:

Setting up a Solo 401k

You could get a tax deduction of up to $70,000 while getting access to potentially the most powerful retirement account in America

Here's how it works: 1 - Invest in (almost) anything

Unlike a corporate 401k with very limited investment options, you control exactly how you invest your Solo 401k

You can invest in stocks, bonds, ETFs... or even startups, crypto or real estate

Super powerful

No one in America pays more in taxes than W-2 employees with a high salary

But, there are still lots of things you can do to pay less in taxes!

Here are my 10 favorite strategies for people with a high salary to pay less in taxes this year: 1 - Fully max out your 401k at work

Contribute the full $23,500 as an employee and get the full employer match

But your 401k plan technically has a limit of $70K! (Or $77,500 if over 50)

See if you can contribute the leftover amount as "mega backdoor Roth" to fully max out

The single best thing you can do to save money on taxes in America is starting a business

It could be a small side hustle or a massive venture-backed company

Here are 5+ tax benefits for business owners that have recently gotten even more generous with the new tax bill: 1 - Pay zero taxes when you sell your startup

If you hold shares in a qualifying C-Corporation (most tech startups would count) for 5 years, you can now pay no taxes on $15M when you sell your shares

No federal taxes & in 40+ states, no state taxes as well

$15M tax free!

The new tax bill created Trump accounts for all children under the age of 18

If you are a high earner, here's how you can arbitrage these accounts to make your kids tax-free multimillionaires: Trump accounts are special type of retirement account for your kids

They cannot get money out until the age of 18

Between age 18 and 59.5, while they can get money out, they have to also pay a 10% penalty on top of taxes unless it's for a qualified expense

So, why contribute?

70 million Americans will soon get access to an Invest America account

This "Trump account" is a brand new tax-advantaged account and most people are sleeping on just how powerful they can be

Here are 5 little known strategies to leverage it to its maximum potential: Strategy 1 - You can open these accounts for kids you already have

While the government is giving a free $1,000 to kids born between 2025-28, these accounts aren't just for them

All children under the age of 18 are eligible to have one... that's over 70M Americans!

I may have found a cool tax loophole with the new Trump accounts

High earners can potentially use this account type to set their children up with millions of dollars of tax-free money in retirement

Here's how this could work: Caveat: This is based on my interpretation of the law as it's written

Please cross-check me & be gentle in the comments. It also only makes sense for high earners with kids

I'm not a tax professional and this is not tax advice &for educational / informational purposes only

You could own 5% of a tech startup that eventually sells for $200M

Yet, you could walk away with absolutely nothing from the sale

Here's why you should always ask these 5 questions about any equity you get granted in a startup: Question 1: What is the total liquidation preference on the company?

This is typically the total money raised & the minimum a company needs to sell for before you see ANYTHING

If the company has raised over $200M, you'd make nothing on your equity if it sold for $200M

The new tax bill that just passed into law is the single most significant piece of legislation we have had in 8+ years

Here is everything you should know as a high-income professional or business owner:

Bookmark this thread as I'll be updating it over the weekend Background: I have run a startup for the last 3 years that helps business owners and high-income professionals be smart about taxes

So this is an area I know a thing or two about

This is also not a political post, and none of this is an endorsement for any specific policy

A crazy tax loophole for business owners in high tax states like New York & California:

You can pay a fully optional tax to your state from your business

And use this to bypass thousands of dollars in personal taxes every single year

Here's exactly how this works: The 2017 Trump Tax Cuts and Jobs Act (TCJA) was a slap in the face to taxpayers in high tax states

Previously, you could fully deduct your state taxes from your income for federal tax purposes

But, the TCJA limited ALL state & local tax deductions to $10K total!

You are probably leaving real money on the table by using a High Yield Savings Account (HYSA)

Yes, you earn 3%-4% on your cash but the entirety of that amount is taxed on both the federal and state level

Here's what you could do instead to optimize what you keep: A HYSA is a much better option than traditional bank accounts that pay almost no interest

Making 3%-4% on cash is a lot more than earning 0.01%

But, if you have high state or federal taxes, you could likely save a lot of money by using money market mutual funds instead

A Roth IRA was designed to be a tax break for the middle class

If you earn over $150K single or $236K married, you are not supposed to be able to contribute to one

However, here are FOUR separate (legal) loopholes that allow high income earners to make Roth contributions: 1 - Roth 401k

Even though the Roth IRA has income limits, a Roth 401k account does not!

Makes no sense, right?

You can contribute to a Roth 401k at work (no matter how much you earn) and move it to a Roth IRA when you switch jobs

Do you pay a lot of money in taxes?

If so, you are likely losing money by using a high-yield savings account instead of tax-advantaged money market funds

I just wrote an article on how to find the highest tax-equivalent yield on your cash (& how I earn 6%+): You can read the full article here:

I no longer require email addresses to read, so should be open to everyone

I'll also quickly share the process in this thread:sillymoney.com/p/how-to-get-t…

10 tips for anyone who wants to get better at money and personal finance

1. Always contribute enough to get your full employer 401k match.

It's the closest you will ever get to free money. 2. When traveling abroad, always decline the currency conversion offered by an ATM or credit card terminal.

3. Don't ever redeem credit card points on the bank website. Transfer them out to airlines and hotels to book directly.

If you have a business that is making as much in revenue and profit this year

And are clueless on what you should do to save money on taxes

I just published a detailed guide breaking down exactly what to do if you are lucky enough to find yourself in this situation: You can read the full guide here:

It requires an email address to read the entire thing, so I'll break down the playbook in a thread here 👇

But the full article has the most context and nuance, let's dive in:sillymoney.com/p/the-self-emp…

Most advice online about raising venture capital for your startup is written by other investors

Which is a bit of a farce since their incentives are completely different from yours

Here's my best advice founder-to-founder: 1 - Understand the math your investors are working towards

Most VC funds try to underwrite a scenario where they could return their fund on any given investment

If a $1B fund owns 20% of your company, they want to see you be worth at least $5B someday

Run the numbers!

People with a high salary pay the most in taxes in America

Most of the best tax saving strategies are saved for business owners

But not all of them!

Here are 10 things high W-2 earners can do to pay less in taxes this year: 1 - Set up a Non-Qualified Deferred Compensation (NQDC) Plan

An NQDC lets you defer a percentage of your salary until retirement when you are in a lower tax bracket

The entire pre-tax amount is then invested so it compounds to pay you out more later

Ask your employer!

There is a special retirement plan in America that most people don't know about

It's being used by wealthy doctors, lawyers & business owners to get up to a $300,000 tax deduction every single year

And it's fast growing in popularity

Here's how a cash balance plan works: Most people know about 401k plans

A 401k is awesome, but you can't contribute more than $23,500 as an employee

Even with employer matching, it's capped at $70K a year

That's a lot of money if you are making $150K, but nowhere near enough if you are earning mid 6-figures

The single most tax-advantaged account in America is also the most misunderstood:

The HSA or Health Savings Account

Despite the name, don't think of it as a savings account - it's actually an incredible tool for building wealth if you know how to use it correctly: An HSA is the only account in America that is TRIPLE tax-advantaged:

- Tax deduction for contributing
- Tax free growth & compounding
- You can also use dollars at any time for eligible healthcare expenses (all kinds of wellness expenses are now HSA deductible!)

One of the most insane loopholes in the US tax code:

If a household earns over $250K, they are not allowed to directly contribute to a Roth IRA anymore

But, they can still use their 401k to fund their Roth IRA with up to $140K every single year!

Here's a step-by-step guide: Roth IRA's are very powerful - you put in post-tax dollars but then never pay taxes again

They are so effective at saving money on taxes, the IRS limits high earners from contributing to one

Or at least that was the intent, until people found "the mega backdoor Roth" loophole

You could earn mid 6-figures as a digital nomad from America living in Latin America, Europe or Asia

And legally pay an effective tax rate of only ~10% to the US government

Here's how a friend of mine set up his business to optimize his taxes as a US citizen living abroad: 1 - Since his business has no US employees or offices, he set up a foreign business in the Cayman Islands which has no corporate taxes

He has a US C-Corp that wholly owns this operating company

This structure only nets out to a ~10.5% corporate tax rate to the US (vs 20%+)