Insights on tax, equity, and building wealth
Guides and analysis from the Harness team and the advisors on the platform.
1031 Exchange Timelines: Why Q4 Is the Riskiest Time to Start
A 1031 exchange started in Q4 can lose weeks of its 180-day window to your tax filing deadline. Here’s the rule, the math, and the fix.
Fourth-Quarter Tax Review: Close Your Books, Skip Surprises
Q4 is the last window to catch tax problems before December 31. Use this checklist to review income, estimates, and bookkeeping now.
How Much to Contribute to Your 401(k) Before Year-End to Hit the 2026
The 2026 401(k) limit is $24,500 ($32,500 at 50+, $35,750 at 60-63). Here’s the paycheck math to hit it before December 31.
Reconciling Crypto Cost Basis Before New 1099-DA Rules
Form 1099-DA cost basis reporting starts in 2026. Here’s why your broker’s numbers may not match your records — and how to fix it before you file.
Planning Q4 RSU Vesting and Stock Sales Before Year-End
Q4 RSU vests are taxed at a flat 22%/37% rate that often under-withholds high earners. Here’s how to true up before the Jan 15 deadline.
Bought Rental Property This Year? Your Q4 Cost Seg Timeline
Bought a rental property in 2026? Here’s the realistic Q4 timeline for a cost segregation study, how 100% bonus depreciation factors in, and what it costs.
Q3 Estimated Taxes Are Due September 15: A Last-Minute Checklist
Q3 2026 estimated taxes are due September 15. See how much to pay, how the Form 2210 penalty works, and what to do if you’re already late.
S-Corp Election Timing: When It Helps — and When It’s Just Extra Complexity
S-Corp election can cut self-employment tax, but payroll costs and IRS scrutiny add up. See the math, the Form 2553 deadline, and when it pays off.
Planning Alert: What Business Owners Should Do Now, Before the Fall Tax Deadline
Fall is the real deadline for year-end tax planning. See what to lock in now on entities, retirement plans, equipment, and estimates before Dec. 31.
HSAs as a Stealth Retirement Account: The Triple Tax Advantage Explained
An HSA offers a tax break no retirement account matches — deductible in, tax-free growth, tax-free out. Here’s the 2026 limits and the retirement play.
Trump Accounts Explained: The New Tax-Advantaged Savings Vehicle Launching in 2026
Trump Accounts let families save up to $5,000/year per child, tax-deferred. Here’s the $1,000 seed deposit, employer rules, and deadlines for 2026.
Mega Backdoor Roth in 2026: Who Should Still Use It After OBBBA
The mega backdoor Roth still works in 2026 — up to $47,500 in after-tax 401(k) space. Here’s who qualifies, what OBBBA changed, and the catch.
Real Estate Professional Status: Qualifying Rules and Common Mistakes
The two-part 750-hour test for real estate professional status under IRC 469(c)(7), material participation rules, and the documentation failures that sink audits.
1031 Exchanges vs. Delaware Statutory Trusts: Which Deferral Strategy Fits Your Portfolio
Compare direct 1031 exchanges and DST replacement properties — deadlines, control, minimums, and liquidity — before your next real estate sale.
Cost Segregation Studies: Accelerating Depreciation on Investment Property
How a cost segregation study reclassifies building components for faster depreciation, works with 100% bonus depreciation, and what recapture means at sale.
Crypto Tax-Loss Harvesting in 2026: Does the Wash Sale Rule Still Not Apply?
Crypto still isn’t subject to the wash sale rule in 2026 — here’s how the loophole works, why it’s survived multiple repeal attempts, and how long it might last.
New 1099-DA Broker Reporting Rules for 2026: What Crypto Investors Need to Know
Form 1099-DA is here for 2025 transactions, with cost basis reporting starting in 2026. Here’s what’s actually required — and what got repealed along the way.
How the IRS Taxes Crypto Staking and DeFi Rewards in 2026
Staking rewards are taxed as ordinary income when received, per IRS Rev. Rul. 2023-14 and a 2026 Tax Court ruling. Here’s what’s settled — and what isn’t.
The 83(b) Election Explained: Why Timing Matters for Founders and Early Employees
The 83(b) election has a strict 30-day deadline with no extensions. Here’s how it works, who qualifies, and what happens if you miss the window.
RSUs vs. ISOs vs. NSOs: Comparing Equity Compensation Tax Treatment
RSUs, ISOs, and NSOs are taxed in three different ways. Compare ordinary income, AMT, and capital gains treatment with a worked example.
QSBS Exclusion in 2026: What Founders and Early Employees Need to Know After OBBBA
If you hold stock in a qualifying startup, the rules for how much of your gain is tax-free just changed — but only if your stock was issued after July 4, 2025. The One Big Beautiful Bill Act (OBBBA) rewrote Section 1202 of the tax code, the provision behind Qualified Small Business Stock (QSBS). There are now two separate QSBS regimes running side by side, and which one applies to your shares depends entirely on when you got them — the difference between waiting five full years to sell tax-free and selling a portion, tax-free, in year three.
Qualified Opportunity Zones 2.0: What Changed for 2026 Under OBBBA
The Qualified Opportunity Zone program was supposed to be a one-time, use-it-or-lose-it deal — designate some zones in 2018, let investors pile in for a decade, and let the incentive quietly expire. (If you need a refresher on the original mechanics, see our guide to Qualified Opportunity Zone tax benefits.) The One Big Beautiful Bill Act rewrote that assumption entirely. Starting in 2027, Opportunity Zones become a permanent, recurring feature of the tax code, with a new round of designations every ten years and meaningfully better terms for investing in rural areas. If you were told a few years ago that the QOZ window was closing, that advice is now out of date — but the mechanics changed enough that old assumptions about deferral deadlines and step-up percentages don’t carry over cleanly either.
Section 179 vs. Bonus Depreciation in 2026: Choosing the Right Deduction for Business Owners
Buying equipment for your business used to come with a tax-planning puzzle: Section 179 or bonus depreciation? In 2026, under the One Big Beautiful Bill Act (OBBBA), that puzzle got both easier and more interesting. Section 179 expensing now tops out at $2,560,000, and 100% bonus depreciation is permanent for qualifying property acquired after January 19, 2025 — meaning most small and mid-size businesses can now write off the full cost of qualifying purchases in the year they’re placed in service, full stop. The real question isn’t “which one qualifies” anymore. It’s which one to actually use, and when the answer isn’t “both.”
Estate Planning in 2026: Who Actually Still Needs a Trust With the Higher Exemption
If you saw the headline that the federal estate tax exemption jumped to $15 million per person in 2026 and mentally filed “estate planning” under problems-other-people-have, slow down. The One Big Beautiful Bill Act (OBBBA) made that $15 million exclusion permanent, and for the vast majority of Americans it genuinely does mean no federal estate tax bill, ever. But “no federal estate tax” and “no trust needed” are two different questions, and conflating them is the most common estate planning mistake we see in 2026. State estate taxes, asset protection, blended families, special needs beneficiaries, and plain old control over how your money gets spent after you’re gone all live in a world the federal exemption doesn’t touch.
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