Form W-9: The Awkward Money Conversation We All Hate (And How to Nail It)

By Lisa Sretenovic, Accounting Director

Hey Visionary,

Let’s talk about one of the most cringe-worthy moments in a creative’s life: the money conversation.

You’ve just finished a brilliant collaboration. The work is inspiring, the energy was incredible, and now… you have to pay your collaborator. And they casually mention, “Just pay me cash, no need for a 1099.”

Internal screaming.

It’s awkward. It feels confrontational. And it puts you in a terrible position. You want to be supportive, but you also have a business to protect.

So, what do you do?

I’m giving you an official permission slip to blame your accountant. Seriously. That’s what we’re here for.

Your Go-To Script

Next time you're in this spot, take a deep breath and say this calmly and confidently:

"I totally get it, and I appreciate you, but my accountant is requiring me to get a W-9 from everyone I pay this year. It's a non-negotiable for them to keep my books clean, and I have to issue a 1099 if I pay you over $600. My hands are tied on this one."

It’s simple, firm, and shifts the "blame" entirely. You're not the bad guy; you're just following the rules your "strict" CPA has set.

Why This Isn't Just About Following Rules

This isn't just about being a stickler for paperwork. Using this script protects your business, your money, and your creative energy. Here’s what’s really at stake:

  • Protect Your Deductions: Without a 1099, the IRS can disallow the expense. That means the $1,000 you paid your collaborator? You can't deduct it. You'll end up paying more in taxes.

  • Avoid the Penalty Trap: The IRS charges penalties for failing to file 1099s, and they are charged per form. For 2024, the fines start at $60 per form and go up to $630 per form for intentional disregard. That’s money straight out of your pocket.

  • Dodge the Backup Withholding Nightmare: This is the big one. If you don’t have a W-9 from a contractor, the IRS legally requires you to do backup withholding. This means you have to withhold 24% of their payment and send it to the IRS yourself. It’s an administrative headache you do not want.

  • Stay Off the IRS’s Radar: Your tax return (Schedule C) literally asks two questions: "Did you have to file 1099s?" and "Did you do it?" Answering "yes" to the first and "no" to the second is a giant red flag that can invite an audit.

It’s Not Mean, It’s Professional

Handling the business side of your art isn't selling out—it's what allows you to create with freedom and peace of mind. Setting these boundaries protects your passion from being buried under tax debt and financial stress.

So go ahead, make us the bad guy. We can take it.