NEW! 1099 Filing Guide - avoid penalties and save hours. Download now
NEW! 1099 Filing Guide - avoid penalties and save hours. Download now
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Wingspan Authors
Lee @ Wingspan
For Contractors
Got Questions About Your 1099? We’ve Got Answers.
There are no dumb questions here.
For Contractors
The 1099 Checklist You Need for Tax Season
‘Tis the season.
For Contractors
This Is How to Get Your Small Business Ready for 2026
It’s time to separate your business and personal bank accounts.
For Contractors
Confused About Your Freelance Taxes? Start Here.
Yeah, it’s tax time already. Again.
For Contractors
What Contractors Need to Know About the 1099-K
Heads up: the reporting threshold is changing for 2025 and 2026.
For Contractors
How New Changes to the 1099-NEC Will Affect Contractors
Are you a contractor earning more than $600 per year? This affects you.
Compliance
These Are the Biggest 1099-NEC Filing Challenges (And How to Solve Them)
Hint: the solution involves automation.
For Contractors
Why Liability Insurance Is Worth Buying for Claims Adjusters
It’s always good to have back-up.
For Contractors
Why Contractors Should Consider Accident Insurance
Reason #1: Occupational Accident Insurance can reimburse lost income
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