FreeYes, make 1099 season suck less — check Venmo now.

Create a free account to explore the 1099 matrix.

Stop guessing how payment providers affect your 1099s.

Instantly determine whether a payment is 1099-NEC, 1099-K, or not reportable, based on provider, funding source, and payment method.

NEW EVENT SERIES

1099Problems Virtual Road Show

Season 1 — January 16 to February 2, 2026

Join our live educational series for bookkeepers, CPAs, and accounting professionals. Learn practical 1099 workflows, decision-making frameworks, and stress reduction strategies.

6 Live Sessions

3 Free Events

3 Subscriber Deep Dives

View Road Show Schedule

Live sessions + practical guidance + subscriber replays

Distilled 1099 Knowledge. We bring IRS guidance and payment provider rules into one clear place, so you’re not left stitching together conflicting advice.

Expert led Discussion Forum

Ask a question and get answers from experts and the community. Moderated content to ensure quality and accuracy.

Global Search

Search across all content types including 1099 entries, discussions, and more.

Events

Discover and join upcoming industry events and webinars. Connect with experts, enhance your knowledge, and network with the community.

Frequently Asked Questions

Have more questions? Contact us

Do you offer a free plan?

Yes! Our free plan gives you access to Venmo and PayPal guidance. Upgrade to Pro for 70+ providers, expert discussions, and advanced search. Create an account to get started for free.

Can I cancel my subscription?

Absolutely. You can cancel your subscription at any time from your billing portal.

Who is this site built for?

Tax professionals, accountants, bookkeepers, and anyone preparing 1099 forms. We save you hours of research by consolidating verified information in one place.

View all FAQs

What Professionals Are Saying

Real outcomes from accountants, bookkeepers, and business owners

★★★★★

“Things built out of indignant rage are usually reliably great!”

Kristen Nies Ciraldo

Math for Food

Built with passion

★★★★★

“For the price of a nice dinner out, you can get a full year's access to this incredible resource for year-round 1099 management.”

Mariette Martinez

Master Your Books

Year-round value

★★★★★

“1099Problems.io is my go-to resource for 1099 season. It's saved me hours of research on my own!”

Alicia Katz Pollock

Royalwise

Saved hours of research

★★★★★

“Your software is an amazing resource. I have on occasion used it to answer questions in other groups and tell them that I got the answer from 1099problems! It has answered questions for us as well as we get questions from clients. Thank you!”

Amy McLaughry

Nonprofit Money Sense

Go-to resource

★★★★★

“One of my team members just described the decision tree as the chutes & ladders for accountants.”

Jean Zick

Juna Financial Solutions, LLC

Decision Tree

★★★★★

“The new decision tree is 🔥🔥🔥. Super helpful and easy to digest! Well done!”

Chad Pues, CPA

Double

Decision Tree

★★★★★

“Things built out of indignant rage are usually reliably great!”

Kristen Nies Ciraldo

Math for Food

Built with passion

★★★★★

“For the price of a nice dinner out, you can get a full year's access to this incredible resource for year-round 1099 management.”

Mariette Martinez

Master Your Books

Year-round value

★★★★★

“1099Problems.io is my go-to resource for 1099 season. It's saved me hours of research on my own!”

Alicia Katz Pollock

Royalwise

Saved hours of research

★★★★★

Amy McLaughry

Nonprofit Money Sense

Go-to resource

★★★★★

“One of my team members just described the decision tree as the chutes & ladders for accountants.”

Jean Zick

Juna Financial Solutions, LLC

Decision Tree

★★★★★

“The new decision tree is 🔥🔥🔥. Super helpful and easy to digest! Well done!”

Chad Pues, CPA

Double

Decision Tree

FREE RESOURCE

1099 Decision Tree Tool

A 60-second framework to determine whether a payment requires a 1099 form

Built by CPAs for anyone tired of second-guessing 1099s. This visual guide walks you through the decision-making process step-by-step.

Quick Reference Guide

Built by CPAs

Printable PDF Format

Get Free Decision Tree

Already a user? Find it in your Resources section

Start for freeKick the tires. Upgrade only if it helps.

Everything you need to stop second-guessing 1099s

Designed for accountants, bookkeepers, and business owners who dislike wasting hours untangling payment app rules during 1099 season.

Hobby

Perfect for getting started with basic 1099 information

Free

Lifetime

Access to Venmo entries in payment provider matrix
Basic discussion forum access
Access to free and public events
Basic search functionality

Popular

Pro

Full access to all features and comprehensive 1099 guidance

$11.66/month

Billed yearly

Save $27.98 (17% off)

Full access to payment provider matrix
Full discussion forum access (ask questions, get expert answers)
Advanced search with filters
App and Email notifications for site features
Global search across all content types
Access to free and subscriber only events