Mastering 1099s

The course that takes the panic out of January.

For US business owners who pay contractors or get paid as one — and want to stop guessing every tax season.

$50 · Self-paced · Lifetime access

Get the course → $50 Instant access the moment you buy.

The part nobody tells you

1099 rules sound easy.

Pay a contractor more than $600. Send them a form. Done.

Then you sit down in January and the questions start:

Wait — did I pay them through Stripe or ACH?
Is my web designer an LLC or an S-Corp?
The attorney one — do they always get one?
I never got a W-9 from the VA who ghosted me in December. Now what?
I think I forgot to send one last year. Am I in trouble?

You google. The answers contradict each other. Three browser tabs later you close everything and tell yourself you'll deal with it next week.

It's now February. You're already late.

"Just hire a CPA"

A lot of CPAs charge $200+ per 1099. Some add a setup fee on top.

If you have five contractors, that's $1,000+ every January for a task that takes about an hour once you actually know what you're doing.

Most business owners don't need to outsource 1099s. They need to understand the rules once, build a system, and run it every year.

That's what this course is.

The 3 steps — and the one everyone skips

The actual 1099 workflow has three parts.

1. Collect a W-9 the day you hire a contractor.

Not in December. The day you hire. This is the step everyone skips and the reason January is chaos.

2. Track payments by method.

Cash, check, ACH, Zelle, Venmo → you owe a 1099 (over $600). Stripe, PayPal, Square, credit card → the platform handles it.

3. File the form.

By January 31 to the contractor. By February 28 (paper) or March 31 (electronic) to the IRS.

Nail step 1 and the other two stop being scary.

Get the course → $50

What you'll actually be able to do

By the end of this course you will:

Know who gets a 1099 and who doesn't, without googling
Have a W-9 collection process that doesn't depend on memory
Know how to file — and which service is actually worth using
Understand what the IRS does when something doesn't match
Know how to fix a mistake (because they happen)
Reduce the odds of getting an IRS letter
Decide whether to DIY or hire help from a position of knowing instead of guessing

You'll also have a year-end workflow you can repeat every January for the rest of your business.

What's inside

Who gets a 1099 (and who doesn't), including the attorney exception and the S-Corp rule
The W-9 collection workflow that stops January chaos before it starts
How to actually file — paper, IRS direct, payroll tools, Track1099, with my recommendation
Penalty breakdown — what late actually costs and what intentional costs
The fix-it playbook — corrections, late filings, wrong amounts, wrong names
State-level filing checklist, because the IRS isn't the only one watching
Backup withholding — rare but mandatory when it applies
Receiving 1099s — what to check, when to push back, what to do if it's wrong
Worker classification — when a 1099 isn't the right form at all
A repeatable year-end workflow

$50 · Lifetime access · About 2 hours of content

Get the course → $50

Why I made this

I'm Clarissa Wilson. CPA. I've run Nerdy Number Lovers for over a decade.

Before that, I worked on the side that issues IRS notices. The "your records don't match" letters? I used to write those.

I made this course because I got tired of watching business owners pay hundreds — sometimes thousands — in penalties for 1099 mistakes that would have taken 15 minutes to prevent.

The information isn't secret. It's just buried in IRS publications written for accountants. This is the version I'd hand to a friend.

But —

"I only have one contractor." That's exactly when mistakes happen. No system, one contractor too small to build one for, then you grow.

"I already use Gusto / Paylocity / a payroll tool." Good. This course covers what those tools don't catch — state filings, missed contractors, classification questions, the contractor you paid outside the system.

"I think I already messed up last year." There's a whole section on fixing past mistakes. Late is almost always better than never.

"I'm not US-based." Then this isn't the course for you. Email me and I'll point you somewhere useful.

Quick answers

Price	$50, one-time
Format	Self-paced, text-based
Length	~2 hours total
Access	Lifetime
Software needed	None
Support after purchase	Yes — every purchase includes a way to get questions answered
For non-US businesses	No
For W-2-only businesses	No (you need payroll, not 1099s)

January is coming whether you're ready or not.

The IRS doesn't care that 1099 rules are confusing. It cares whether the forms got filed.

$50 to know what you're doing, every January, for the rest of your business.

Get the course → $50