My New Hire Wants to be a 1099: Is It Worth It?

January 11, 2024by Leslie Crouch

Hey there, amazing startup founders! Today, let’s chat about a situation you might find yourself in: your new hire wants to be classified as a 1099 contractor. Sounds simple enough, right? Well, grab a cup of coffee ☕, and let’s delve into why this might not be as straightforward as it seems.

Understanding the 1099 Appeal
First off, it’s not uncommon for new hires, especially in the flexible world of startups, to request a 1099 classification. They might be looking for tax benefits, more autonomy, or they simply prefer the contractor lifestyle. But here’s the catch: just because they want it doesn’t mean it’s legally correct or beneficial for your startup. There have been plenty of times a new hire has come to one of my startups wanting the 4-hour workweek, especially after COVID.

 Contractor vs. Employee: The Legal Lens 🧐
The IRS has strict guidelines distinguishing employees from contractors. It revolves around control – how much control you have over what will be done and how it will be done. If you’re dictating work hours, methodology, and providing the tools for the job, you’re probably looking at an employee, not a contractor. Check out my previous article: 1099 Audit Triggers if you want to know more.

Why It’s Usually a No-Go

  1. Legal Risks: Misclassifying an employee as a 1099 contractor can lead to legal and financial nightmares, including penalties and back taxes
  2. Control and Collaboration: As a startup, you often need your team to collaborate closely, work specific hours, or follow certain protocols – all signs pointing to an employee relationship.
  3. Training and Development: Contractors are expected to hit the ground running. If your new hire needs training or significant onboarding, that’s employee territory.
  4. Company Culture and Loyalty: Contractors may not be as invested in your company culture or long-term goals as employees are.

But Wait, There’s More! The Benefits of W-2 Employees 🎉

  1. Team Cohesion: Employees are more likely to develop a strong bond with your team and align with your startup’s vision.
  2. Growth and Development: You can nurture and develop employees to take on larger roles as your startup grows.
  3. Consistency: Employees provide a level of consistency in work and commitment that’s vital for a growing startup.
  4. Intellectual Property: It’s clearer legally that any work created by an employee belongs to your company.

The Bottom Line
While it might seem tempting to go with your new hire’s preference and classify them as a 1099 contractor, it’s usually not worth the risk. The legal implications, potential for IRS penalties, and the benefits you’d miss out on with an employee all add up to a pretty clear answer: No, it’s not worth it. Always assess each hire on a case-by-case basis, and remember, just because someone prefers to be a 1099 contractor doesn’t mean it’s the right choice for your startup. When in doubt, consult with a legal or HR professional to make sure you’re on the right track.

Cheers to building a team that’s not only talented but also legally compliant! Here’s to your startup success! 🚀🌈

And if you’re interested in more advice? Meet with me!  We’d love to help your startup:

Leslie Crouch

Leslie Crouch, a seasoned HR professional at Ravix Group, Inc. since 2014, specializes in strategic human resources for startups and mid-sized companies. With expertise spanning software, biotechnology, and SAAS services, Leslie has become a linchpin in aligning HR strategies with the growth needs of diverse clients. At Ravix Group, Leslie adeptly ensures compliance with labor laws, manages payroll, employee benefits, and oversees the entire employee lifecycle, including onboarding and complex offboarding processes. Prior to joining Ravix Group, Leslie honed her skills in contingent workforce compliance as an HR Services Manager at ICon Professional Services LLC. Her robust experience also includes a stint as an independent consultant, providing comprehensive HR services, and earlier roles at Cardica, Inc., and KPMG LLP. Leslie’s expertise in performance management, employee relations, and compensation analysis is integral to her approach, focusing on developing HR frameworks that foster operational excellence in innovative startup environments.
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