Choosing Entity Structure for QSBS Benefits
One of my favorite things is when a client's accountant asks me to put together a model to compare being a partnership/SCorp v C Corp to see if they should reorganize to go after QSBS. What would you say you do here exactly? https://t.co/0EIOzkjHBD
Investors Pay Lower Taxes Than Wage Earners
The tax code loves investors. If you work a W-2 job, the max federal tax rate you can pay is 37%. But qualified dividends or long term capital gains are taxed at up to 23.8%. Real estate investors also enjoy tax arbitrage...
Expert Advises UHNW Clients on Advanced Tax Avoidance
I'm speaking at Spear’s 500 Live on 6 May - "bringing together the most senior and influential figures in private wealth, luxury and law" for "ultra-high-net-worth clients". Naturally I'll be talking about how they can avoid tax more successfully. https://t.co/sJTXik9aml https://t.co/Ha7mg0Sm2m
Track Home Improvements to Maximize Tax-Free Gain
Weird and important tax things to know about selling your house: - Keep a record of any capital improvements you make to your house. This increases your basis and reduces taxes when you do sell your house - If you make money...
Vanguard's NY Municipal Fund Offers Triple Tax-Free Returns
About a year ago, Vanguard launched a municipal bond fund for New York residents ticker $MUNY that is triple tax free for New York residents with a low expense ratio. Seems pretty good.
HSAs’ Triple Tax Benefit Can Be Outweighed by HDHP Costs
Why Health Savings Accounts (HSAs) Aren’t Always Worth The ‘Triple Tax Savings’ Advantage: https://t.co/6zrY3GAuEd HSAs require individuals to be covered by a High Deductible Health Plan (HDHP), which has tradeoffs compared to traditional health insurance plans. While HDHPs are often expected to...
Turn Your Home Into a Tax-Deductible Business Asset
The Augusta Rule lets you rent your home to your business up to 14 times a year at the going market rate. That payment moves from your business bank account to your personal account and the business writes it off...
Simplify Your Taxes: Avoid Complex Investments to Cut Costs
"Simplify. If you have sticker shock when you pay to have your #taxes prepared, it may be because you have made your tax life unnecessarily complicated. Heavy trading in stocks or commodities makes your return prep more expensive. Cryptocurrency transactions and...
Senior Deduction Falls Short of Tax‑free Social Security Promise
The senior deduction goes a long way toward fulfilling Trump’s campaign promise of no tax on #SocialSecurity, but not all the way for higher-income seniors. Tom O’Saben, an EA and director of government relations at @NATPTAX says that if he sees...
High Earners Cut Taxes with Short‑Term Rental Strategy
If you made six figures at your W2 last year and still felt personally victimized by your tax bill… Just know you’re just playing a game no one taught you how to win. One of the only ways W2 high...
Learn How the Ultra‑Rich Preserve Wealth Across Generations
How the Wealthy Mitigate taxes and pass on Generational Wealth. If you are wealthy or plan to be wealthy, you must be at the 10X Wealth Conference. I am bringing the best family office people, tax and estate...
Explaining Dual Consolidated Losses in Cross‑Border Tax
Today, I wrote an email explaining dual consolidated losses in the cross-border context. I feel like @adonnelly50 is the only person who would appreciate this tweet.
Convert Home to Rental, Leverage Deductions and 1031 Exchanges
Converting a home to a rental property fundamentally changes how expenses are treated, how gains are taxed, and how future sales can be structured to maximize tax efficiency. Advisors who understand these rules can help clients navigate the timing of...
Strategic Tax Planning Saves Over $260K Annually
If I did no tax planning or strategy, I'd give up $260K+/year to federal, state, and self-employment taxes. Here's every move I have mapped out for 2026 and why:
CA Wealth Tax May Target Founders' Voting Power
The California wealth tax could be levied on founders' voting interests in their companies, which often far exceed their economic stakes. The initiative's drafters say that won't happen. Here's why it might: https://t.co/i71izDeHPS
Travel Location Determines Players' Tax Liability
Accountants create a duty-day schedule by having players precisely track their travel. If a player spends an off day at home versus a road city, or rehabs an injury in Florida instead of the club’s home stadium or goes on...
LSDI Fees Often Outweigh Tax-Loss Harvest Savings
"For a typical investor, the fees paid to a leveraged long/short direct indexing (LSDI) tax-loss harvesting manager eat up most of the tax savings. In our base case, the investor pays more than half as much in fees as the...
Choose a Wyoming Holding Company, Not a Trading Corp
Most attorneys will set you up with a trading corporation when what you actually need is a holding company. The difference matters for long-term capital gains. DWP builds Wyoming holding companies with NAICS code 551112 or 551114, operating agreement provisions...
Cut Self‑Employment Tax: Use Dividends Over Salary
An investment-only LLC is a disregarded entity until you start pulling income out of it. Once you do, the IRS expects a reasonable W-2 salary, typically $50,000 to $70,000 a year if you are managing your own investments. That salary...
Farmers Exploit Loopholes to Dodge FICA, Celebrate Deduction
Mr. and Mrs. Farmer, enjoying coffee on their 320-acre $15,000 per acre-value farmstead, having never paid FICA tax because they used special farmer-only tax moves to minimize taxable income, celebrate their temporary $6,000 deduction. They earned it!
AI-Generated Checklist Demystifies Taxes and Catches Errors
Wins from using Claude Code for my taxes for the firs time: First, the document upload checklist: A while back I uploaded my prior year's 1040 to Claude and asked it to help build me a tax prep checklist: every document I'd...
Turn Tax Returns Into Strategic Profit Plans
Another tax season closed. Now the real work begins. We’re not just filing returns… we’re dissecting them. Every client gets a full financial review, identifying leaks, missed opportunities, and strategic moves. Because the goal isn’t to survive tax season. It’s to reduce liability, increase...
Proposed Elimination of Property Taxes for Seniors May Be Illegal
Next, they will try to eliminate property taxes for those 65 and over 😏 even though legally that might be an issue
Two‑owner LLC Isn’t Automatically a Tax Partnership
Simply because you have a LLC and two owners does not mean you have a partnership for income tax purposes. This will become a podcast episode at some point.
Digital Creators Can Now Receive Tax‑free Tips
Instead of getting paid as a tax advisor, can you earn tax-free tips as a "tax-fluencer"? Final Treasury Regulations include "no tax on tips" for digital content creators, such as streamers, online video creators, social media influencers, and podcasters. https://t.co/FyI6F9noBQ
IRS Clarifies $25K Tip Deduction, Adds Santa Impersonators
The IRS finalized “no tax on tips” regs—and clarified who qualifies. Yes, up to $25K in tips can be deducted. But only for certain occupations (now defined), and only for voluntary, reported tips. Santa Claus impersonators made the list. Did your job? 👀 https://t.co/q1z55eZskn
Withdraw Up to $65K Gains Tax‑Free
You can pay 0% in taxes on your investments: 0% long term capital gains rate applies if your taxable income is <= $49,450 (single) or $98,900 (mfj) After standard deduction, you can withdraw $65,550 (single) or $131,100 (mfj) of LT gains from...
Captive Insurance + PPLI: Tax‑Free Crypto Family Office
Captive insurance + PPLI = the crypto family office cheat code. Pay premiums to your own insurer, invest them in crypto, hedge funds, or real estate. Grow it tax-free. Borrow tax-free. Heirs inherit tax-free. It's straight from Buffett’s playbook.
Deferred Income May Still Be Taxed by Original State
Like many rules, there's an exception: When a person working in one state defers some of their income, then moves to a different state (where they ultimately receive the income), that income can in certain cases be taxed by the...
Section 179 Enables Massive XRP Tax Write‑Off Opportunities
Section 179 tax code allows infrastructure/software write-offs. Gas fees qualify as business expense. 1,700+ NDAs contain pre-negotiated XRP purchase options. Banks already allocated billions at low prices executables post-appreciation.
2026 Tax Bill Lets Charitable Donations Yield Deductions
Most people donate to charity and get $0 of tax benefit. In 2026, that finally changes because of the new tax bill. Here’s how to take advantage:
Shift Taxable Cash Into ISA Before 2027 Cuts
TLDR: if you have money outside of an ISA, that you are paying tax on, and you have excess ISA allowance leftover, it’s probably worth getting it inside of an ISA to avoid future tax. Especially important with the cash...
Maximize HSA Growth: Invest All, Reimburse Later
I have $500 in cash in my HSA (my plan’s minimum). The rest is invested in the S&P 500. I’m tracking all my medical expenses and plan to reimburse myself in 20 years. This is how you use HSA to its...
US Lags as Other Nations Grant Crypto Exemptions
Other countries exempt crypto already. US falling behind crypto capital narrative. Settlement exemption probable, investment exemption uncertain. Even tax-free selling loses versus holding appreciating assets. Leverage preserves upside despite interest cost.
MSG Sports Faces $50M Tax Hike, Split Could Raise $75M
Madison Square Garden Sports is facing a $50M+ bump to its annual tax bill with a new tax code provision set to start in 2027. Meanwhile, MSGS is exploring splitting the Knicks and Rangers into separate companies that would push...
2026 Charitable Deductions Available With Standard Deduction
IMPORTANT: in 2026, you can deduct charitable donations even if you take a standard deduction (up to $1,000 for single, or $2,000 married) Please track all your cash donations in 2026. They could help save on taxes (whereas you had to...
Cash Balance Plans Offer $250K Tax Deductions for High Earners
There’s a lesser-known retirement plan for high earners that almost nobody uses If you’re earning mid six figures or higher, this plan can potentially unlock a $250K+ tax deduction each year Here’s a simple explanation of how a cash balance plan works:
Unlock Early 401k Access for Tax‑Free Retirement
Many finance influencers say "get your 401k match, then invest in a brokerage" Main argument is that you can retire early with brokerage I disagree because you can access your 401k early with 72t SoSEPP, or Rule of 55. If you're a high...
ISOs Offer Wealth Potential, But Tax Risks Loom
For clients receiving Incentive Stock Options (ISOs) as part of their compensation, the potential for wealth creation can be significant – but so too is the risk of adverse tax consequences if not handled properly. https://t.co/YA6mBVn0qA #ISOs
IRS Enables Online 83(b) Election, Ending Postal Trips
The IRS now allowing you to submit an 83(b) election online is a game changer This has now eliminated my only remaining reason for going to the post office https://t.co/gjjLFqI6F4
Physicians Overpay Taxes—Learn How to Reclaim Income
Why physicians pay more in taxes and how to reclaim your income [PODCAST] http://dlvr.it/TRxTZR Podcast #PracticeManagement
S‑corp Composite Taxes Often Qualify for Resident Credit
#TaxTwitter Just a friendly reminder that state composite tax payments made by a S corp on behalf of a shareholder usually qualify for the "credit for taxes paid to other states" on the SH's resident state return.
Combine Cost Seg, Depreciation, RE Pro to Slash Taxes
Cost seg + accelerated depreciation + RE pro status (so you can use the losses to offset active income) a v powerful combo (I actually looked into starting a business helping non-working spouses get and maintain RE pro status, but couldn't...
Biofuel Lobby Urges 45Z Rule Amid Tax Credit Uncertainty
Biofuel Groups Push 45Z Rule as Delayed USDA Emissions Tool Clouds Tax Credit Value https://t.co/e4B9eUJeY4
Doctors Earn More Yet Feel Broke Due to Tax Ignorance
Physicians are expected to master complexity, but many finish training without anyone teaching them why a bigger paycheck can still feel financially tight. That is not a personal failure. It is a training gap. This episode of The Podcast by KevinMD gets at...
Stop Using LLCs to Trick Family Into Ownership
stop f’ing creating LLCs and either adding your spouse or your children as part owners and thinking you’re really clever
Easements Represent a Fractional Property Right, Valued Proportionally
https://t.co/C38z4vpXzp The ownership of land is a bundle of rights. When you donate an easement you are giving away part of the bundle not the whole bundle. So an easement will be worth a percentage of what was paid for the...
Disability Trust Deduction Stumbles Over Obsolete Cross‑References
Qualified Disability Trusts get a $5,300 deduction in 2026 under §642(b)(2)(C)(i), tied to §151(d). But both provisions rely on outdated cross-references to former §68(b)—repealed and replaced by OB3/OBBBA—raising questions about how these rules apply today.
Tax‑aware Timing Crucial when Bonus and Equity Vest Together
Stack a big bonus + equity vest in the same year and watch how fast taxes eat into decisions you didn’t plan. Most people aren't just asking about returns, they are asking about better tax-aware timing.
Kwong Decision Opens Refund Claims for Penalties, Interest
“…the Kwong decision suggests that taxpayers should reevaluate penalties and interest previously paid and consider filing refund claims targeting those amounts, even when the underlying tax liability itself is not in dispute.” Kwong Opens New Path for COVID-19 Refunds https://t.co/6OGToPBe1j...