W9/1099 Workshop
Get compliant. Get confident. Move on.
This Is For You If…
Anyone in your photography business who isn’t on payroll — including:
Second shooters
Associate photographers
Editors or retouchers
Hair & makeup artists
Studio or office rent paid directly to an owner
Coaches, mentors, or educators
Virtual assistants or social media managers
Web designers or branding support
Anyone self-employed you paid by check, cash, Zelle, ACH, PayPal, Stripe, or Venmo
If you read that list and thought, “wait… that counts?” — you’re exactly who this workshop is for.
Most confusion around W-9s and 1099s comes from not realizing who the rules apply to in the first place. We clear that up immediately.
Let’s Make It Easy
to get compliant!
You’ll Learn…
This workshop walks you through the contractor side of your business from start to finish, in the right order, without overcomplicating it.
Inside, we cover:
How the IRS actually defines a contractor vs an employee
When you need to collect a W-9 — and what to review before accepting it
Which payments are reportable and which aren’t
When a 1099 is required — and which type applies
How payment method changes your reporting responsibility
What to do if you’ve already paid someone and aren’t sure what applies
By the end, you’ll know exactly what needs to be done — and just as importantly, what doesn’t.
Plus…
Bonus Walkthroughs
Once the core rules are clear, we layer in the bonuses that simplify execution and decision-making.
You’ll also get:
Simplify 1099 Compliance — how to reduce tracking and reporting based on how you pay contractors
1099-K 101 — what those forms mean and how they interact with contractor reporting
Filing 1099s Online (Step-by-Step) — a real walkthrough of electronic filing and W-9 tracking
W-8 for International Contractors (Q+A) — what changes when contractors live outside the U.S.
These bonuses are where everything clicks.
And…
Templates & Tools Included
You won’t be piecing this together on your own.
You’ll get:
A copy-and-paste W-9 request email
Optional IRS-required backup withholding (24%) language
Clear next steps once forms are returned
IRS reference links for transparency and peace of mind
Everything is designed so you can reuse this process every year.
Time Commitment & Lifetime Access
This workshop is intentionally designed to be efficient, practical, and respectful of your time — because contractor compliance shouldn’t turn into another multi-hour project hanging over your head.
The core W-9 / 1099 training (everything you need to understand contractor rules and get compliant) takes about 30 minutes total. It’s broken into short, focused lessons covering employee vs. contractor classification, W-9s, and 1099s, with clear walkthroughs and templates so you’re not guessing or Googling at midnight.
You’ll also have access to optional bonus lessons (a little over an hour) that dive into topics like 1099-Ks, international contractors (W-8s), why how you pay matters, and step-by-step electronic filing. Watch what applies to your business now and come back to the rest later — it’s there when you need it.
You also get lifetime access to the workshop. I update the content each year to reflect any W-9 or 1099 changes, so you’re not re-buying this or re-learning it from scratch every January.
Take contractor compliance off your mental list
What ‘s Included
Live Learning
☎️ Q+A Calls + Recordings
Lessons:
💻 Contractor Vs Employees
💻 Contractor 101
💻 W-9 Form 101
💻 1099 Form 101
💻 1099K 2024 Changes/Requirements
📋 1099 Electronic Filing Walkthrough (Step by Step)
📋 W-9 Electronic Requesting Walkthrough (Step By Step)
📋 W-8 Forms (For Foreign Contractors in other countries)
Resources:
📂 Blank Tax Forms with Instructions
📄W-9 Request Letter Template
Your Photography Deserves Your Full Attention
I built this workshop to take W9 1099 Compliance off your mental load once and for all,
so you can spend less time Googling and more time doing what you LOVE.
Your creativity is too valuable to waste on tax stress. Let’s handle this — and move on.
This small investment could save you thousands in penalties, hours of wasted research, and the constant stress of wondering if you’re doing this right. Put that time and money back where it belongs — into growing your business and creating work you’re proud of.
What we’ll cover:
🚧 Contractors vs Employees Dive into IRS guidelines, deciphering the distinctions between contractors and employees. Stress the vital need for accurate classification to steer clear of fines and penalties.
💼 Contractor 101 Uncover surprising insights into contractor qualifications, reshaping your understanding of this crucial distinction.
📑 W-9 Form 101 Navigate W-9 forms with precision through our step-by-step guide. Ensure clarity in receiving and collecting correctly filled W-9 forms, addressing compliance intricacies.
📑 1099 Form 101 Explore the myriad of 1099 forms and their distinctions. Walk through filing requirements, gaining a clear understanding of when and how to file.
🛠️ Handling Common Issues Tackle challenges like unobtainable W-9s or contractor refusals. Skillfully navigate the 24% backup tax withholding rules for contractors.
🔄 Navigating 1099-K Changes Stay updated on 2024 tax law changes related to Form 1099-K. Equip yourself with the knowledge to track and comply accurately.
📂 Step-by-Step 1099 Filing Walkthrough Embark on a guided session for electronically filing your 1099 forms. Ensure a seamless process with detailed instructions.
🔐 Resource Access Gain exclusive access to templates and request letters for W-9 forms. Access blanks of all tax forms and referenced IRS publications.
📈 Best Practices for Ongoing Compliance Review essential best practices to uphold consistent compliance. Ensure you're well-equipped to handle future challenges effectively.
I'm Not Your Parents' Accountant
Hi! I'm Tiffany Bastian—an IRS-certified Enrolled Agent with an MBA in accounting who exclusively serves photographers. Not photographers and other small businesses. Not photographers and some real estate agents. Just photographers.
Why Photography-Only?
Because I believe the best financial advice comes from someone who truly understands your industry inside and out. After 20+ years in accounting, I've developed a specialized expertise in the unique financial world photographers live in:
📸 I Understand Your Business Reality:
That expensive camera is both a business tool and something you'd buy anyway (let's navigate that tax line)
Your pricing isn't just about hours—it's about creativity, expertise, and image rights
Your income might be booming in May-October and crickets in January
Your business exists in a complicated web of state-to-state sales tax requirements
🗣️ I Speak Human, Not Accountant
You won't hear me saying things like "please reference section 179 of the tax code regarding depreciation schedules." I promise to never make you feel dumb for asking questions about your finances.
🤝 I'm On Your Team
My mission isn't just to keep you compliant—it's to help you build a legitimate, profitable photography business that supports the life you want. I'm the financial partner in your corner who gets what you're trying to build.
When photographers ask me for recommendations, I don't just point them to generic resources—I create exactly what they need. That's why this sales tax guide exists: because hundreds of talented photographers like you were struggling with the same problem, and deserved a better solution.
