Free tax guides · 75 in total

Every side hustle.
Every state.

7 interactive tools and 68 plain-English guides — for gig drivers, Etsy sellers, freelancers, hosts, and creators.

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Interactive tools

19 in total
★ Featured

Side Hustle Dashboard

All three calculators in one screen — your audit risk, set-aside amount, and S-corp savings projected together. Built for the moment after a client pays you and you don't know how much to keep.

Audit Shield Tax Guard S-Corp Sim
Open dashboard
Interactive tool
Audit Risk Estimator

Your IRS audit risk score with a safety checklist.

Interactive tool
Tax Guard Calculator

How much to set aside from every client payment.

Interactive tool
S-Corp vs Sole Prop Simulator

See exactly when an S-Corp saves more than it costs.

Interactive tool
Self-Employment Tax Calculator

Instant SE tax estimate — federal + state, 2025 rates.

Interactive tool
Quarterly Tax Calculator

How much to set aside and pay each quarter.

Interactive tool
1099-K Threshold Calculator

Will Etsy / eBay / PayPal send you a 1099-K this year?

Interactive tool
Can I Deduct This? — Delivery

25-card swipe game for DoorDash, Uber Eats, Grubhub, Instacart drivers.

Interactive tool
Can I Deduct This? — Etsy

22-card swipe for handmade and print-on-demand sellers.

Interactive tool
Can I Deduct This? — Airbnb

22-card swipe for short-term rental hosts on Schedule E.

Interactive tool
Can I Deduct This? — Creators

22-card swipe for OnlyFans, Patreon, and subscription-platform talent.

Interactive tool
Can I Deduct This? — Tutors

22-card swipe for VIPKid, Outschool, Preply, private instructors.

Interactive tool
Crypto Tax Calculator NEW

Short-term + long-term gains, NIIT, state — plus a hold-to-long-term scenario.

Interactive tool
Stock Tax Calculator NEW

RSU, ISO, ESPP, long-held — LTCG, NIIT, state. Compare spread, DAF gift, or SBLOC.

Interactive tool
Tax Penalty Estimator

Missed a payment? Estimate the IRS penalty + interest stack.

Interactive tool
Next Deadline Countdown

Days until your next IRS quarterly tax payment + .ics calendar download.

Interactive tool
W-4 Paycheck Calculator NEW

Set your W-4 right — every line: dependents, spouse, extra withholding. 2025.

Interactive tool
W-4 Side-Hustle Hack

Have a day job + side hustle? Up your withholding instead of filing quarterlies.

Free resource
Tax Deduction Checklist

Every deduction by hustle type — free and printable.

Gig work & delivery

8 guides

Etsy, e-commerce & resellers

12 guides

Creator economy

8 guides

Freelancing & self-employment

6 guides

State-specific guides

5 guides

Short-term rentals

28 guides
★ Featured

Complete STR Guide

The full short-term-rental landscape — platforms, tax forms, state rules, depreciation, the 14-day rule, when an LLC makes sense. Start here, then drill into specifics below.

8 platforms 12 topics 8 state rules
Open STR hub
Airbnb Host Taxes

Deductions, taxes owed, and the 14-day rule.

Vrbo Host Taxes

Whole-home vacation rental taxes explained.

Booking.com Host Taxes

Taxes for property hosts on Booking.com.

Turo Host Taxes

Car rental income, Schedule C, and deductions.

Hipcamp Host Taxes

Land and outdoor camping rental taxes.

RV Rental Host Taxes

RVshare & Outdoorsy income taxes.

Furnished Finder Taxes

Mid-term rental taxes for furnished hosts.

Neighbor Storage Taxes

Income taxes on renting out storage space.

The Airbnb 14-Day Rule

Rent up to 14 days tax-free — here's how.

Schedule C vs Schedule E for STRs

Which form you file — and why it matters.

The STR Tax Loophole

Use rental losses to offset W-2 income.

Cost Segregation for STRs

Accelerate depreciation and cut your tax bill.

STR Lodging Tax by State

What hosts owe in every state.

Airbnb Self-Employment Tax

Do Airbnb hosts owe SE tax? It depends.

Airbnb Deductions Checklist

Every deduction short-term rental hosts can take.

Mixed-Use Rental Taxes

Splitting deductions when you also live there.

House Hacking Taxes

Tax rules for renting part of your primary home.

STR Business Structure

LLC, S-corp, or sole prop — what makes sense.

Airbnb 1099-K Explained

What the form means and what to do with it.

Quarterly Taxes for Airbnb Hosts

Estimated tax deadlines and how to calculate them.

California STR Rules & Taxes

Permits, TOT, and state income tax rules.

New York STR Rules & Taxes

NYC restrictions, state and city tax obligations.

Florida STR Taxes

Sales tax, tourist development tax, and no income tax.

Hawaii STR Rules & Taxes

GET, TAT, OTAT — Hawaii's layered tax system.

Texas STR Taxes

Hotel occupancy tax, state and local rules.

Colorado STR Taxes

State lodging tax, local rules, and licensing.

Tennessee STR Taxes

Sales tax on rentals and county-level levies.

Arizona STR Taxes

TPT license, city taxes, and state filing rules.

Tell us your hustle.
We'll figure out the rest.

Pick your hustle, state, and income range. We surface every tax, license, and structure issue that applies to you — in plain English, in 60 seconds.

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