deepdive.

Employers of all sizes can assemble a portfolio of fringe benefits that materially increase employees’ total compensation while delivering tax advantages to both the business and employees.

Many homeowners overpay by not shopping for mortgages. Learn how rates, refinancing, taxes, and cash flow can affect your finances.

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).

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