The Great W-9 Hunt: Stalking Freelancers for Tax Forms Before the IRS Notices

It is the second week of January. The glitter is gone. The champagne is flat. The motivation to "crush 2026" has already been replaced by the urge to nap under your desk.

You are finally settling back into a routine. You feel safe.

But then, you get an email from your accountant. The subject line is in all caps. It just says: "WHO IS DAVE???"

You freeze. You frantically search your transaction history. And there it is. August 14th. A transfer of $1,200 to "Dave."

No last name. No invoice. No LLC. Just a Venmo handle that includes the numbers "420" and a memo line that says "fix wall."

You realize the date. It is January 8th. You have until January 31st to file your 1099s. To file a 1099, you need a W-9. To get a W-9, you need to find Dave. And Dave has vanished into the ether like a mythical creature of the trades.

Congratulations. You have just involuntarily entered the most dangerous game in small business: The Great W-9 Hunt.

This is the annual tradition where business owners across America frantically stalk graphic designers, handymen, and consultants via text message, begging for their Social Security Numbers while they are inevitably on a ski trip with bad reception.

Grab your phone. It’s time to play detective.

Section 1: The Rules (Or: Why You Can't Just Ignore Dave)

Before we get into the tactical espionage required to find your missing vendors, let’s talk about why we are doing this.

I know what you want to do. You want to look at that $1,200 payment to Dave, shrug, and say, "Eh, the IRS has bigger fish to fry."

Listen to me closely: Do not do that.

The IRS computer system is not a human being with empathy. It is a cold, unfeeling algorithm that loves matching data points. If you deduct that $1,200 as a business expense (which you definitely want to do to lower your taxes), the IRS expects to see a corresponding piece of paper telling them who received that income.

If the math doesn't balance, you trigger the "Audit Flag." And you do not want the Audit Flag.

The Magic Number: $600

Here is the baseline rule for 2025 tax filings (happening now, in early 2026):

If you paid a "non-employee" $600 or more during the calendar year for services, you generally owe them (and the IRS) a Form 1099-NEC.

This includes:

• The graphic designer who made your logo.
• The IT guy who fixed your server when you broke it trying to install Home Assistant.
• The cleaning crew (if they aren't a big corporation).
• The lawyer (Lawyers are special; they almost always get a 1099, even if they are incorporated. The IRS really wants to know how much lawyers make).
• Dave. Specifically Dave.

The Loophole That Isn't A Loophole (Credit Cards & PayPal)

"But Josh!" you scream at your monitor. "I paid Dave via PayPal! Or Credit Card! I heard I don't have to file!"

Okay, sit down. Let's parse this.

Technically, if you pay via a "Third Party Settlement Organization" (TPSO) like credit card processors (Stripe, Square) or payment apps (PayPal, Venmo Business), the obligation to file falls on them, not you. They file a 1099-K.

However, relying on this is what we in the industry call "Playing with Fire."

1. Did you pay "Dave" via Venmo Personal or Venmo Business? If you sent it to his personal handle, Venmo might not issue him a 1099-K. If nobody issues him a form, and you deduct the expense, the IRS creates a "mismatch."
2. The "Belt and Suspenders" Approach: Most CPAs (the good ones) will tell you to just get the W-9 and file the 1099-NEC anyway. It is better to double-report income than to under-report it. The IRS rarely complains about being told about income twice. They get very cranky when they aren't told at all.

So, assume you need the form.

Section 2: The Anatomy of the Enemy (The W-9)

The Form W-9 is deceptively simple. It asks for:

1. Name (as shown on your income tax return).
2. Business Name (if different).
3. Business Type (legal structure).
4. Address.
5. Taxpayer Identification Number (SSN or EIN).
6. A signature.

That’s it. It takes 30 seconds to fill out.

And yet, asking a freelancer to fill one out is apparently equivalent to asking them to donate a kidney.

Why Freelancers Hate W-9s

To understand the hunt, you must understand the prey.
Your freelancer isn't withholding the W-9 because they are evil. They are withholding it because:

• A) They are disorganized creative types who lost the PDF you sent them three months ago.
• B) They are terrified of giving out their Social Security Number (valid fear).
• C) They were hoping to do this job "under the table" and didn't realize you run a legitimate business that follows the law.

Case C is the dangerous one. If Dave thought this was a cash gig, and you hit him with a W-9 request in January, Dave is going to ghost you.

Section 3: The Hunt for "Dave" (A Tactical Guide)

Okay, you have identified the targets. You have a list of 5 people who you paid over $600 last year, and your file for them is empty.

Here is your escalation protocol.

Phase 1: The "Friendly Check-In" (Jan 8 - Jan 15)

Do not start with threats. Start with administrative incompetence. It makes you look relatable.

• Channel: Email.
• Subject: Quick favor / Tax stuff for 2025
• The Script:

  "Hey Dave! Hope you're having a great start to 2026. My accountant is yelling at me to get my paperwork in order for tax season. I realized I don't have a W-9 on file for you. Can you fill this out and send it back via [SECURE LINK]? Thanks man!"

Crucial Note: Do not ask them to email it back as an attachment.
We are IT people (or at least, we play them on the internet). Sending an unencrypted PDF with a Social Security Number via email is a data breach waiting to happen. If Dave’s email gets hacked, and his identity gets stolen, and he traces it back to the unencrypted PDF he sent you... that’s bad.

Use a secure upload link (Dropbox, Google Drive File Request) or, better yet, use an automated system (see Section 5).

Phase 2: The "Nudge" (Jan 15 - Jan 22)

Dave has ignored your email. He is busy installing drywall for someone else.

• Channel: Text Message / DM.
• The Script:

  "Hey man, just bumping this. Need that W-9 by next week or my bookkeeper is going to hang me by my ankles. Let me know if you need the link again."

Note the shift in tone. We are blaming a third party ("the bookkeeper"). This preserves your relationship with Dave while creating external pressure.

Phase 3: The "Nuclear Option" (Jan 22 - Jan 30)

It is one week before the deadline. You are sweating. Dave is nowhere to be found.

• Channel: Phone Call / Stern Email.
• The Script:

  "Dave, I really need that form. If I don't get it by Jan 31st, I'm required by law to withhold 24% of any future payments for 'Backup Withholding' and send it to the IRS. I really don't want to do that. Please help me help you."

This brings us to the scary part: Backup Withholding.
The IRS creates this rule to weaponize you against the contractor. Basically, if a vendor refuses to give you their Tax ID, you are supposed to keep 24% of their money and mail it to the IRS.
Nobody actually wants to do this. It is an accounting nightmare. But threatening it is usually enough to get Dave to open his laptop.

Section 4: The Different Flavors of 1099 (Don't Mix These Up)

While you are hunting, make sure you are hunting for the right form. In 2020, the IRS decided to make our lives harder by splitting the old 1099-MISC into two forms.

1. Form 1099-NEC (Non-Employee Compensation)

This is the big one.

• Who gets it: Anyone you paid for services. Graphic designers, consultants, repairmen, coders.
• Box 1: You put the total amount you paid them here.
• Deadline: January 31st. Hard stop.

2. Form 1099-MISC (Miscellaneous Information)

This is the "Everything Else" bucket.

• Who gets it:
  • Rent: If you pay rent for your office to a landlord (who isn't a corporation), you report it here (Box 1).
  • Royalties: Did you pay someone for IP? (Box 2).
  • Attorney Fees: Even if the lawyer didn't "work" for you but you paid a settlement (Box 10).
• Deadline: technically later (Feb 28 if paper, Mar 31 if electronic), but just do it in January so you don't forget.

3. The "S-Corp" Exception (The Golden Ticket)

If you send Dave a W-9 request, and he sends it back with the box "S-Corporation" or "C-Corporation" checked... CELEBRATE.

Generally, you do not need to send a 1099 to a Corporation (S or C).
You typically only send them to:

• Individuals / Sole Proprietors.
• Partnerships.
• LLCs that file as Sole Props or Partnerships.

Note: There are exceptions (Lawyers, Medical Services), but for general trade work, the "Inc." saves you the paperwork.

Section 5: The Tech Stack (Stop Using The Shoebox)

If you are manually typing numbers into a PDF you downloaded from the IRS website, you are doing it wrong. It is 2026. We have technology.

The "Set It and Forget It" Method: Gusto / QuickBooks Payroll

If you pay your contractors through your payroll system (like Gusto), the system does this for you.

1. You enter Dave’s email in Gusto.
2. Gusto emails Dave.
3. Dave enters his own W-9 info into Gusto.
4. Gusto pays Dave.
5. In January, Gusto files the 1099.

You do nothing. You drink coffee. This is the way.
Cost: A few bucks a month. Value: Immeasurable sanity.

The "Standalone" Method: Track1099 / Tax1099

If you don't use payroll software, use a dedicated e-filing service like Track1099.

• You upload a spreadsheet of your vendors.
• The system emails them a secure portal link to fill out their W-9.
• The system e-files with the IRS and emails the copy to the vendor.
• Cost: Like $3 per form.

HatStacked Rule: Never, ever, ever verify tax IDs manually or paper file with the IRS unless you enjoy waiting in line at the post office and having your forms lost in a government basement for six months.

Section 6: What If Dave Actually Ghosts Me? (The "End Game")

It is January 31st.
You have texted. You have emailed. You have threatened backup withholding.
Dave has gone dark.
You still have a $1,200 expense on your books.

What do you do?

Option A: File with "Refused" (Risky)
Some people file the 1099 with the name and address they have, and leave the SSN blank (or write "REFUSED").

• Result: The IRS will send you a nasty letter (Notice CP2100A) saying "Hey, this ID is missing." You then have to prove you tried to get it.
• The "Reasonable Cause" Defense: If you can show you made 3 attempts (initial request, annual request, etc.), you might get out of the penalty ($290-ish per form).

Option B: The "Self-Own" (Eat the Tax)
If it’s a small amount (like $650), and you are terrified of the audit risk, some owners just... don't deduct the expense.

• They reclassify the payment as "Owner's Draw" or a non-deductible expense.
• Result: You pay taxes on that $650 as if it were profit. It costs you maybe $150 in tax.
• Is it worth it? Depends on how much you value your sleep vs. $150. I'm not telling you to do this. I'm telling you people do it.

Option C: Call Your CPA
This is the part where I remind you that I am a guy on the internet with a blog, not a licensed tax professional. If Dave ghosted you on a $50,000 payment, call a pro. Immediately.

Conclusion: The "No W-9, No Check" Rule

The only way to win The Great W-9 Hunt is to not play it.

You need to make a solemn vow to yourself for 2026. Raise your right hand. Repeat after me:

"I, [Your Name], CEO/Janitor of [Your Business], solemnly swear that I will never, ever hand a check to a new vendor until I have a signed W-9 in my hand."

Print it out. Tape it to your monitor.

When you hire a new freelancer in March, and they say, "Oh, I'll get you the tax form later, just Venmo me the deposit now so I can start," you must channel your inner bureaucratic villain.

You look them in the eye and say: "I would love to, but my system literally won't let me release funds without the Tax ID. It’s the software. Total bummer."

Blame the software. Blame the accountant. Blame me.

But get the form first.

Because frankly, stalking Dave in January is not a vibe. You have better things to do, like figuring out why your 2026 inventory count was off by three units.

Happy Hunting.

Now that you're in the mood for administrative torture, why not read The Silent Killer of Small Business: Bad Invoices or check out Do I Need a CPA for My Small Business, or Can I Keep Guessing?.