12/06/2026
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.
How Payment Apps Affect Your Taxes
Payment apps like Venmo, PayPal, Cash App, and Stripe can trigger tax reporting. Learn Form 1099-K rules and how to stay compliant.
11/06/2026
Youth sports can have surprising tax implications. Learn when sports expenses, charitable activities, medical costs, and NIL income may qualify for tax benefits.
Youth Sports, Taxes, and NIL Income
Learn when youth sports expenses may qualify for tax credits, deductions, medical expenses, charitable giving, or NIL business income.
10/06/2026
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.
Gen Z Side Hustle Tax Traps to Avoid
From Venmo payments to freelance income and creator earnings, Gen Z workers need to understand side hustle taxes to avoid costly surprises.
09/06/2026
A temporary tax break allows eligible workers to deduct qualified tips from 2025 through 2028. Learn who qualifies and the reporting rules that apply.
Tip Deduction Rules Every Tip Earner Should Know
Learn who qualifies for the new federal tip deduction, reporting requirements, income limits, and key rules for employees and self-employed workers.
08/06/2026
Quarterly Estimated Tax Payments – Reminder
If you are making quarterly estimated tax payments to the IRS, the due date for the April 1–May 31, 2026, payment period is coming up next Monday, June 15, 2026.
If you use IRS Direct Pay, payments can generally be made until 11:45 p.m. ET on the due date. If you pay by credit or debit card through an IRS-authorized payment processor, payments can generally be made until 11:59 p.m. ET on the due date.
05/06/2026
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.
The Emergency Savings Crisis Quietly Growing in America
More Americans are turning to credit cards over emergency savings. Learn why financial stress is rising and how planning can improve stability.
04/06/2026
Crowdfunding can raise capital, support causes, or launch new ventures—but it also creates tax responsibilities. Learn what organizers and contributors need to know.
Crowdfunding Tax Rules for Organizers and Contributors
Learn the tax implications of crowdfunding, including income reporting, gifts, deductions, SEC rules, and strategies to minimize tax liabilities.
03/06/2026
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.
Smart Small Business Strategies for Uncertain Times
Economic uncertainty is challenging small businesses. Learn how owners are protecting cash flow, controlling costs, and staying resilient.
02/06/2026
Learn how Health Savings Accounts and High-Deductible Health Plans can lower taxes, reduce healthcare costs, and help build long-term savings.
HSA and HDHP Strategies to Reduce Healthcare Costs
Learn how Health Savings Accounts and High-Deductible Health Plans can lower taxes, reduce healthcare costs, and help build long-term savings