deepdive.

A new Form 1099-DA is being initiated in 2026 for tokenized‑security dispositions.  Be ready to supply records if the broker’s basis or other data are missing.

Learn how to identify Trump Account scams, spot warning signs, verify communications, and protect your child's savings from fraudsters.

Social Security is about more than choosing when to claim benefits. Learn how taxes, Medicare, spousal benefits, and retirement income planning work together to shape your retirement.

IRMAA can raise Medicare costs for higher-income retirees. Discover planning strategies for Roth conversions, RMDs, and Social Security

Your tax outcome often depends on facts and dates. A life change that happens in June — marriage, separation, a child taking a summer job, or renting your house during a conference — can determine your filing status, eligibility for credits, and what income must be reported for the entire year.

A lawsuit involving a $21 million donor-advised fund is raising new questions about donor rights, charitable giving, and tax planning.

New Jersey's proposed $900 pet tax credit is reigniting debate over whether pet owners should receive tax relief for everyday expenses.

Florida lawmakers are pursuing major property tax changes. Here's why homeowners across the country are paying attention.

CEO confidence just experienced one of its sharpest declines on record. Here's why smart business owners focus less on predicting the economy and more on planning for what comes next.

An IRS online account offers a faster, more convenient way to manage many tax tasks from your computer or phone — from checking your refund to viewing tax transcripts to setting up payments — without a trip to a post office or an IRS office.

With the federal launch of Trump Accounts scheduled for July 4, 2026, parents and family members who want to jump-start a child’s retirement savings face a rapidly approaching deadline to get accounts activated. But there are still unanswered questions.

AI tools are helping entrepreneurs launch and grow businesses faster with lower costs and fewer employees. Learn how small business owners are using AI to stay lean, competitive, and profitable.

Revenue is up—but cash is tight? Discover why your P&L can mislead you and how expense ratios reveal where your money is really going.

Converting a rental into your primary home can be a smart move — both for your living situation and for taxes — but it’s not as simple as move in, sell, and keep the profit.

A child’s and their parent’s sports expenses, from registration fees and travel to equipment and volunteer time, sit at the intersection of personal, medical, charitable and business tax rules. For tax‑minded parents, the key is sorting each cost into the correct box.

Venmo, PayPal, Cash App, Stripe, and other payment apps can create tax reporting obligations for freelancers and small business owners. Learn how Form 1099-K works, what income must be reported, and how to avoid bookkeeping headaches.

From Venmo income to freelance gigs and creator revenue, many Gen Z workers are facing unexpected tax bills. Learn how side hustle taxes work and how to avoid common mistakes.

A new, temporary federal tax break for tip earners went into law for tax years beginning in 2025 and runs through 2028. The change creates a below-the-line deduction for “qualified tips,” but it comes with a number of eligibility rules, reporting requirements, and limits taxpayers need to know.

More Americans are relying on credit cards instead of emergency savings. Learn why financial stress is rising and how small planning habits can improve financial stability.

Crowdfunding has emerged as a popular method to raise funds for various personal, charitable, and business endeavors. However, with this comes a myriad of tax implications that organizers and contributors must navigate to ensure compliance and minimize liabilities.

Inflation, high interest rates, cautious consumers, and economic uncertainty are putting pressure on small businesses. Learn how smart business owners are adapting, protecting cash flow, and staying resilient.

In the face of escalating healthcare costs, many individuals and families are seeking innovative strategies to manage expenses effectively. One emerging alternative gaining traction is the combination of Health Savings Accounts (HSAs) and High-Deductible Health Plans (HDHPs).

Starting a new business can be expensive, but the tax rules offer relief: certain start‑up and organizational expenses like market research, advertising, training, professional fees and filing costs to form a company may be deductible.

States are using sports betting to generate revenue and offset taxes. Here’s how the strategy is growing nationwide.

Portland plans to raise its arts tax while exempting thousands. Here’s what the proposal means for taxpayers.

If you've found yourself in a situation where you've repaid income that you initially reported as taxable in a prior year, you might be eligible for tax relief through the Claim of Right doctrine.

If you invested in a Qualified Opportunity Fund (QOF) using deferred capital gains, pay attention: the law requires that deferred gains be included in income no later than December 31, 2026. That deadline is real, unavoidable unless Congress or the IRS provides relief, and it can mean a large, unexpected tax bill even if your fund hasn’t paid you a dime.

The Foreign Earned Income Exclusion (FEIE) is a valuable tax provision for U.S. citizens and resident aliens living and working abroad. It allows eligible taxpayers to exclude a certain amount of foreign earned income and housing costs from U.S. taxation.

A frequently encountered issue is when an elderly parent turns the title of his or her home over to a child or other beneficiary and continues to reside in the home, thinking that it is the correct thing to do, but without considering the tax repercussions.

When engaging in business overseas, it's crucial to understand how travel expenses are treated under U.S. tax law. Unlike domestic travel, where transportation costs are often fully deductible if the trip is "primarily" for business, foreign travel requires a more granular day-by-day calculation to account for personal time. 

Individuals have many options when they cannot pay their tax liability, including setting up an IRS payment plan, tapping a retirement plan, acquiring a home equity loan and borrowing money from a friend or relative. Each option has negative implications, and some have substantial fees, penalties and/or interest.

If your federal tax refund is seriously overdue, it’s normal to feel worried — especially if you were counting on that money for bills or other expenses. Before panic sets in, here’s a clear, practical guide explaining what may be happening, why a new IRS administrative change could be the culprit, and exactly what steps you should take now.

Early 2025 tax returns filing data indicates substantial use of the new tax law’s signature middle‑class tax changes, and the average refund rose compared with last year. However, polling suggests room remains to improve taxpayer awareness and not all eligible people, especially those with tip and overtime pay, took full advantage of the new law.

Think you can afford a new hire? The true cost goes far beyond salary. Learn how to evaluate hiring decisions and avoid costly mistakes for your business.

From side hustles to creator income, Gen Z is earning in new ways—but missing key tax rules. Learn the most common mistakes and how to avoid them early.

The IRS is successfully challenging aggressive tax strategies using the economic substance doctrine. Learn what recent cases mean for your business and tax planning.

A recent federal court decision could open the door for refunds of certain IRS penalties and interest assessed during the pandemic. Learn who may qualify and why July 10, 2026 matters.

The U.S. penny is being phased out. Learn how rounding, pricing strategy, and payment trends could impact your business—and what to do now.

A former NBA executive was sentenced for embezzling millions. Here’s what the case reveals about internal controls and business risk.

Struggling with slow-paying clients? Learn how to protect your cash flow, improve collections, and get paid faster with smarter payment terms and systems.