Tax deadlines and penalty experience

Learn how to plan for self-employment taxes and understand how savings interest can affect your tax bill.

How can sports betting apps affect your finances? How do you set up taxes for 1099 contract work? Hosts Sean Pyles and Elizabeth Ayoola discuss self-employment taxes to help you prepare for tax season and avoid surprises. But first, senior news writer Anna Helhoski joins them to discuss the rise of sports betting and prediction markets. They break down how legal sports betting expanded after a 2018 Supreme Court decision, how app-based betting and prop bets make it easy to wager in real time, and the growing concerns around addiction risk, regulation, and the nonstop flood of betting ads.

Then, Sean and Elizabeth dig into tax prep for contract work, including how business structure can affect self-employment taxes, ways to pay during the year through quarterly estimated payments or adjusting W-2 withholding, and how to stay organized with bookkeeping, deductible expenses, and forms like 1099-NEC. They also cover what to expect tax-wise with a Roth IRA and why high-yield savings account interest is typically taxed as ordinary income (often reported on Form 1099-INT).

Use NerdWallet’s free calculator to estimate your self-employment tax: https://www.nerdwallet.com/taxes/calculators/self-employment-tax-calculator 

Want us to review your budget? Fill out this form — completely anonymously if you want — and we might feature your budget in a future segment! https://docs.google.com/forms/d/e/1FAIpQLScK53yAufsc4v5UpghhVfxtk2MoyooHzlSIRBnRxUPl3hKBig/viewform?usp=header

In their conversation, the Nerds discuss: self-employment taxes, 1099 contractor taxes, estimated taxes, quarterly estimated tax payments, Form 1099-NEC, Schedule C, Schedule SE, sole proprietor taxes, S corp vs LLC taxes, S corp reasonable salary, self-employment tax rate 15.3%, net earnings self-employment tax, W-2 withholding for side hustle, Form 1040-ES, bookkeeping for freelancers, deductible business expenses, home office deduction, business bank account, separate business and personal finances, business credit card for expenses, tax deadline for S corp, first time penalty abatement, IRS penalty abatement, Roth IRA taxes, Roth IRA income limits 2026, Roth IRA phase-out, traditional IRA tax deduction, SEP IRA, SIMPLE IRA, tax forms for freelancers, Form 1099-INT, high-yield savings account taxes, sports betting taxes, sports betting apps, DraftKings, FanDuel, prediction markets, Kalshi, and Polymarket.

To send the Nerds your money questions, call or text the Nerd hotline at 901-730-6373 or email podcast@nerdwallet.com.

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