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2. The Case of the Missing Vendor Information


Walter had always been one for a good mystery. But this mystery involved higher stakes than Walter could stomach. Classify a worker incorrectly, and there would be IRS penalties to pay.
Luckily, Walter had a good head on his shoulders and some good resources in his back pocket. Now, he has no problem differentiating employees and contractors. Wondering how he cracked the case?


Walter nods hello to the new cashier, Marni, on his way to the back office of Bread, Bagel, & Butter. Marni made his life so simple. She turned in all her new hire paperwork right away.
Ernest, on the other hand … Walter draws the blinds on his office windows and sinks into his cracked leather chair. Remembering a time before fear of IRS penalties seemed to control him, Walter rubs his temples.

Walter had hired Ernest as a menu board artist for Bread, Bagel, & Butter three weeks earlier. Walter had worked long hours to discover if the IRS would classify Ernest as an employee or as a contractor. After determining that Ernest is a contractor, Walter considered the whole case closed.

A glance at the empty file on Ernest taunted Walter. With no legal name, no taxpayer identification number, and the threat of IRS penalties looming … Walter picked up the phone.

“Hello, yes … is this Tax1099? Yes, I need information on one of my new workers, and fast.”

“Yes, we can help you with that. What do you know about this worker?”

“All I have is an alias, Ernest “The Chalk” Johnson.”

“Hmm. That’s not much to go on.”

Walter groaned. It was hopeless. A cold case. Walter had given Ernest a W-9 form on at least three occasions, but Ernest never returned the form. Once, Walter found the form crumpled on the floor of the bakery.

“Walter, are you still there? I’ve got an idea.”

“Yes, yes, I’m here,” Walter exhaled into the receiver.

“Do you have an email address for Ernest?”

Walter sat forward in his chair. An email address … Flicking on his desktop screen, Walter navigated to his email account. Adrenaline coursed through his veins.

And there it was: chalkthetalkjohnson@selfemployed.com.

As Walter set down the receiver, he spun in his chair, hands rested behind his head. Then, leaning toward his desktop screen, Walter logs in to Tax1099.

Walter clicks People > Manage Recipient. Then, Walter selects “Add Recipient,” the blue button in the top left corner.

At the top of the “Add Recipient” box, Walter sees something as good as cinnamon butter on a fresh-baked bagel: W-9 Request.

Walter checks that box, and checks the “TIN not provided box” slightly below. Zeroing in near the bottom of the “Add Recipient” box, Walter types in Ernest’s email.

Walter punches “add” at the bottom of the page. A box comes up asking Walter to pre-pay the $1.00 charge for the W-9 e-solicitation.

Walter approves the charge, throws his coat over his arm, and leaves the office. It feels good to whistle again, and it feels even better to stay a step ahead of the IRS penalties.

A few steps out of the office, Walter stops cold. There, in the bakery, is Ernest. Sitting at a tall table with a cup of joe and the free wifi password.

As Walter approaches, Ernest looks up.

“Hey, boss, what’s this email I got?”

Walter clenches his jaw, anticipating the confrontation.

“It’s a W-9 request. I need your information, Ernest. Simple as that.”
Ernest stands.

“You’re transitioning to the modern age. Cutting down on paper usage. Storing my information responsibly and securely. I respect that. I’ll fill out that W-9 for you right now.”

But Walter’s no sucker for Ernest’s tricks. He peers over Ernest’s shoulder as Ernest types in his TIN, name, and address. Walter watches as Ernest e-signs the form and submits.

Walter hurries back to his office, and races to Tax1099. There, in his People > Manage Recipients screen, Ernest appears as a row in the table.

Walter makes sure the pop-up blocker is disabled for Tax1099. Then, Walter clicks, “W-9 PDF Requested.” Ernest’s form downloads. Walter opens the form.

It contains all the information Walter needs.

Just to be sure, Walter goes to the Dashboard > W-9 Requests (see all). The W-9 request populates in the screen.


Walter collected Ernest’s information via e-soliciting a W-9. All he needed was Ernest’s email address. The form was sent from Tax1099 to Ernest’s email. Ernest filled out the form, and electronically signed it. The updates to the form were sent to Walter’s Tax1099 account.


Walter has IRS compliance well in hand, for the time being.
And then his phone starts to ring. Someone’s calling in a favor, Walter can just tell.
“Yes? Yes, Grandmom, it’s me. Yes, I’ll be there.”
Just like that, Walter’s on his next case.
Walter’s grandmother has always been forward-thinking when it comes to technology. She’s co-founder of a dog walking services company, and she’s thinking about efiling 1099’s for her company this year.
She wants Walter’s help integrating her accounting software with Tax1099.
Walter has never been given a case like this before, but he’s been promised warm oatmeal raisin cookies. Walter glances at his watch, and heads for the door.
It’s time to solve the case of the accounting software integration.