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Traditional CPAs and advisors laugh off crypto gains. They call it luck. They do not understand the asset, so they assume anyone who succeeded in it gambled and got "lucky"
That is not what is happening, and these people need real help. They need someone who understands the asset class, the strategies that actually exist, how to take profits and realize losses efficiently, how to structure entities, how to track basis, and which lots to sell to minimize the burden
They need an advisor who does not talk down to them for investing in the space
If you are making serious money in crypto or holding over $100,000, most CPAs are not built to service you at a high level
In 1891, Andrew Carnegie wrote The ABC of Money, arguing for sound, hard money and warning against inflationary measures
The world's richest man over 100 years ago, understood the importance of sound money and the dangers of inflation
Reminder that between now and the end of the year are when you should be thinking about tax planning for this year, not in March-April next year right before you file
Many of the major tax strategies become unavailable after 12/31, so now is the time be taking action
10 ways to turn a dinner into a business deduction:
1) Have a board meeting and discuss small business and finance
2) Go with a client(s) and discuss how you can win more business/improve your services
3) Go with a vendor(s) and discuss negotiate better pricing/how to get more from them
4) Go with peer(s) in your industry and discuss strategies/what's working and not working
5) Traveling on business? Grab a bite to eat while your out
6) Have an employee event (even better, these meals can be 100% deductible)
7) Go with a mentor(s) and learn
8) Go with a mentee(s) and teach
9) If your spouse is in your business, hold a strategy meeting over a nice dinner
10) Run a new offering/promo by a friend
There are far more than 10 ways to write-off a meal. If you are creative about how there is an angle to make it ordinary and necessary for your business, you can incorporate it. Not only will you get a deduction, but you can get ideas, teach your loved ones and mentees something, learn from mentors and peers, or get more out of the relationship with a vendor or customer
Just remember, being creative doesn't mean making stuff up. Make sure there is an actual business purpose behind the meal and you document it to defend the position
Tax Strategy of the Day: HSAs
Why Consider It: One of the only accounts in the entire tax code with a true triple tax advantage. Deduction going in, tax free growth, and tax free withdrawals for medical expenses
How it Works: Contribute to the account and take a deduction the same year. The funds can then be invested and grow completely tax free. Most people don't realize you don't have to reimburse yourself the same year an expense happens. You can actually keep your receipts, let the account compound for years, then reimburse yourself whenever you want
Requirements: You need to be enrolled in a qualifying high deductible health plan to contribute
Biggest Mistake: Treating it like a checking account for copays instead of an investment account. Spending it down every year means missing the entire point of the strategy
Tax Strategy of the Day: Tax Deferred Retirement Accounts
Why Consider It: Set aside money for your future while getting a tax deduction today. Almost every business owner uses this strategy in some form
How it Works: Depending on your business structure and goals, options range from a SIMPLE IRA to a Safe Harbor 401k. Contributions reduce your taxable income now while building retirement savings that grow tax deferred until you take them out
Execution: Choosing the right plan depends on your income, whether you have employees, and how much you want to contribute. Deadlines matter, some plans need to be established well before year end to be usable for the current tax year
Biggest Risk: Waiting too long. Miss the setup deadline or contribution window and you lose the ability to use the strategy for that tax year entirely
Tax Strategy of the Day: The Side Hustle
Why Consider It: W-2 employees have a small menu of tax planning opportunities. But starting a legitimate side business opens the door to deductions employees never get access to
How it Works: Once you are running a real business, expenses you are already paying for start converting into deductions. Some examples include a portion of your phone and internet, the actual vehicle costs or mileage driving to clients, a home office, meals with someone you're doing business with, equipment or software used to run it, and so much more shift from fully personal to partial tax deductions
Requirements: The activity has to be a genuine business with a profit motive, not a hobby. Keep separate records, track expenses properly, and be able to show the expense actually serves the business
Biggest Risk: Treating true personal expenses as business ones without a real business behind them. That is the kind of thing that gets you burned in an audit
Here are 10 Ways to Avoid an IRS Audit
1) Respond to your Notices, don't stick your head in the sand
2) File you tax returns and extensions on time
3) File your payroll returns and timely remit your payroll withholdings
4) Issue your 1099s and treat employees like employees
5) Pay our taxes on time
6) Don't abuse the Dining and Travel deductions, make sure all expenses included are business related
7) Don't inflate your auto or home office deductions
8) Avoid Schedule C and Schedule E when possible (S-Corp and Partnership returns are less likely to be audited)
9) File an extension
10) Avoid using round numbers (especially on Sch C or E)
Tax Strategy of the Day: Oil & Gas Investing
Why Consider It: Depending on the structure of the fund, typically 60 to 90% of your investment is deductible against other income in year one, with the rest typically unlocking in year two
How it Works: Oil and gas investments qualify for intangible drilling costs, a unique benefit that lets investors deduct the costs of setting up the rig in the year they're incurred
Requirements: Interest positions typically start at 50k to 100k. Find a fund through an advisor, understand the fee structure, confirm the year one deduction available, and forecast what future cash flow will actually look like
Biggest Risk: You get the deduction, but the cash flow ends up worse than what was originally projected
7 Ways to Turn Your Trip into a Tax Deduction:
1) Have a Board Meeting
2) Go to a Conference or Workshop
3) Meet with a Client(s)
4) Meet with a Vendor(s)
5) Network with Affiliates
6) Scout your Competitors
7) Check/work on your Rental Properties
What Can You Write Off?
-Airfare
-Hotels
-AirBNB
-Uber
-Taxis
-Turo
-Ferries
-Tolls
-Valet
-Private Jets
-Buses
*Meals are also 50% deductible, but are separate from the travel deduction itself
What counts as "Business Travel"
-The day you travel to the location
-The day(s) you are conducting business, which is:
*A special meeting/event/action that requires your physical presence to execute or
*4 hours of work
-The day you return home
Tax Strategy of the Day: Short-Term Rentals
Why Consider It: Rental losses are usually passive, meaning they can only offset other passive income, not your W-2 or business income. This is one of the few ways around that.
How it Works: Pair a property with a cost segregation study, an engineering report that breaks the property into its components that qualify for accelerated depreciation instead of depreciating it over 27.5 years. That accelerates depreciation and often creates a large year one loss.
Requirements: average guest stay needs to be 7 days or less, you need to materially participate, generally with 500 plus hours a year (other tests can qualify), and property must be in service before year end
Risk: overpaying or buying a bad property just for the deduction, or falling short on material participation and losing the benefit entirely
5 reasons why every small business should have a board of directors:
1) Write-offs: The travel, meals, lodging, merchandise, and other expenses related to the meeting become deductions
2) Asset Protection: Company minutes and annual meetings are critical to keeping your entity compliant
3) Audit Protect: Tax elections/positions and accountable plans should be adopted by the board each year
4) Strategic Expertise: Your board doesn't need to be all family members. Invite mentors, other business owners, or experts who can provide additional insights to help your business grow. If you have to pay them, that's deductible, too
5) Accountability: Depending on the frequencies of your meetings (should be at least annual), discuss 1 , 5 , and 10 year plans, and review how you are trending, what went right/wrong, and make adjustments accordingly
Keys to making them productive and valuable:
-Make them official
-Have an agenda
-Set aside enough time to cover everything
Every taxpayer should ask this key question when evaluating a deduction strategy:
Is this a good investment on its own, or am I only doing it for the tax benefit?
The tax code rewards good decisions. It does not fix bad ones. Buying a property you wouldn't otherwise want, a piece of equipment you don't need, or a business you're not prepared to run, just because it comes with a deduction is how people turn a tax strategy into a financial mistake
Good tax planning means making good decisions. Tax deductions should be a factor, but never the sole reason to make an investment
Daily Reminder:
When $BTC is trading at 200k per coin in 3 years, you won't care if you were buying at 60k, 70k, 80k, or even 100k
You'll be happy you were buying and wish you bought more
Block out the noise and keep stacking
Average returns are not actual returns. That gap is exactly what most retirement portfolios get wrong
Say you are retired and heavily allocated in a fund like $VGT because its average return beats $VOO or $SCHD over time, and then a major drawdown hits. In retirement you do not have the luxury of waiting it out. You need income, so you are forced to sell shares in a down year, and that selling erodes the exact compounding that built the portfolio in the first place
Now say you had diversified into $SCHD or $VOO instead. Different risk profile, smaller drawdowns in almost every case. With $SCHD specifically, the dividend payouts alone may be large enough to live on, depending on portfolio size, without selling a single share. That protects the compounding instead of interrupting it
This is sequence of returns risk, and it is one of the biggest factors an average annual return number hides Two portfolios can carry the exact same average return over 20 years and produce wildly different outcomes depending on when the losses actually land
Have you ever wondered if it was possible to buy Bitcoin and hold it in cold storage inside a 401(k)?
Done right, this lets your $BTC grow inside your retirement account completely tax deferred, or tax free if you go the Roth route, while you still hold the actual keys instead of trusting a custodian with it
Let me break down how I set myself up to do exactly that 👇
Just like that, you have funded a 401(k), taken control of the funds, and invested in an asset you actually understand
That is the power of self-directed investing. If you are also pursuing the Mega Backdoor Roth, there is one more step, either converting the after-tax contributions to Roth or rolling everything into a Roth IRA
