Painless Tax Prep — Nerdy Number Lovers
Painless Tax Prep  ·  Nerdy Number Lovers

Tax Time Should Be Boring.
Not Terrifying.

The step-by-step system that turns tax season from a panicked all-nighter into a 30-minute handoff to your accountant — built for online business owners who'd rather be doing literally anything else.

Enroll in Painless Tax Prep · $400

One-time payment  ·  Lifetime access  ·  All future updates included

The painful truth about tax season for online business owners


You started your business to do the thing you love. Coach. Create. Teach. Sell. Build.

You did not start your business to spend the last week of March crying into a shoebox of receipts, googling "what is a 1099," or DM-ing your accountant at 11pm asking if Voxer subscriptions are deductible.

But here you are. Again.

If any of this sounds familiar, this course was built for you:

  • You've been "meaning to" do your bookkeeping for the last six months
  • You're not 100% sure if you're supposed to be making quarterly estimated payments (and if you are, you're definitely not making them)
  • You have a Stripe account, a PayPal account, a Shopify payout, a ConvertKit affiliate payment, and absolutely no idea how they all fit together on a tax return
  • You either pay way too much in taxes or get a giant scary bill in April that nobody warned you about
  • You hear "S Corp" and either glaze over or panic
  • Your "system" is currently a Google Doc and vibes

Here's the part nobody told you when you started your business: tax season isn't the problem. The problem is what you didn't do the other 11 months of the year.

Painless Tax Prep fixes that.

What this course actually does


This is not a tax filing course. I am not going to teach you how to fill out a Schedule C line by line.

This is a tax readiness course. By the end of it, you will know exactly:

  • What numbers your accountant actually needs (it's way less than you think)
  • How to keep clean books all year so you're never doing 12 months of catch-up in a weekend
  • Which expenses you can legitimately deduct and which ones are going to get you audited
  • How much you should be setting aside for taxes — and how to actually pay it
  • Whether your current business structure is costing you money
  • How to walk into your accountant's office (or upload your file) feeling like you have your stuff together

You'll go from "I have no idea what I'm doing" to "I know exactly what I'm doing, and I'm doing it on autopilot."

Who this is for


This course is built for online business owners who are making real money but are still treating their finances like a side hustle. Specifically:

  • Coaches, consultants, and service providers
  • Course creators and digital product sellers
  • Freelancers and contractors who've crossed the "this is a real business now" threshold
  • Membership site owners
  • Affiliate marketers and content creators with brand deals or ad revenue
  • Anyone running an LLC, sole prop, or S Corp who handles their own books

If you have employees, inventory in three warehouses, or you're trying to deduct your yacht — this isn't the course for you. Go hire a CPA.

What's inside


Nine modules that walk you from "behind and panicking" to "organized and on autopilot." Short videos. Plain English. No accountant jargon.

Module 1

Making Tax Prep Painless

The philosophy shift that changes everything — plus the Tax Prep Power Pack, your year-round checklist so nothing falls through the cracks.

Module 2

Expenses and Deducting Them

The deduction rules that actually apply to your business. What's deductible, what's not, what's a gray area, and how to document everything so you sleep at night. Includes the Ultimate Guide to Expense Deductions and the cheatsheet I send to my 1:1 clients — plus paying your child in your business and the Qualified Business Income deduction.

Module 3

Home Office Deduction

The deduction every online business owner SHOULD be taking and most are doing wrong. Simplified method vs. actual expense method, what qualifies, and how to calculate it without triggering an audit.

Module 4

Estimated Tax Payments

Why you probably owe them, when they're due, how to calculate them, and how to actually pay them. The thing your accountant assumed you already knew.

Module 5

All About 1099s

Who gets one, who sends one, the deadlines, the penalties, and how to collect W-9s without it being awkward. Plus what the new 1099-K threshold means for you.

Module 6

Red Flags That Can Cause an Audit

The behaviors and numbers that get flagged. Not to scare you — to make sure you're doing it right so you never have to find out.

Module 7

Tax Changes by Year

What changed in 2023, 2024, 2025, and 2026 — so you're not relying on a blog post from three tax years ago.

Module 8

Business Legal Structures

Sole Prop, LLC, S Corp, C Corp, partnerships. What each one actually means, what it costs you, and how to know when it's time to change.

Module 9

Catch-up Bookkeeping

For when you're behind. Step-by-step on how to dig out of the hole — and the systems to make sure you never go back in.

The bonuses


  • Tax Prep Power Pack — your year-round tax readiness checklist (PDF)
  • Ultimate Guide to Expense Deductions — the most-asked-about deductions, organized by category (PDF)
  • Expense Deduction Cheatsheet — print it, tape it next to your desk (PDF)
  • Private Facebook Group — ask me questions, get answers, see what other students are asking
  • Lifetime Access — including all future updates as tax laws change (and they will)

What waiting actually costs you


A real client story

She hired me in March because her accountant said her books were "a mess." She was 14 months behind on bookkeeping — two business bank accounts, three credit cards, Stripe, PayPal, and Square, none of it reconciled.

She owed her accountant $2,400 for cleanup just to be able to file. She got hit with a $680 underpayment penalty. And she missed roughly $4,000 in deductions she couldn't document.

Total cost of being disorganized: roughly $7,000 in one year.

Painless Tax Prep is $400. The math is sort of obvious.

Enroll today


$400One-time · lifetime access · all future updates included

For context: a single 1:1 hour with me is $300. A typical "my books are a mess, please fix them" cleanup project runs into the thousands. This course teaches you the system I'd put you on if you hired me — for less than a single session.

The guarantee


You get access to every module the moment you buy — so you'll know fast whether this is for you. Go through Module 1. Watch the videos. Download the Tax Prep Power Pack. If you're not convinced this course is going to save you time, money, and stress this tax season — email me within 3 days and I'll refund you. No drama, no "why are you leaving" survey.

About me


CW

I'm Clarissa. I'm an accountant. I am also, somehow, a person who genuinely enjoys explaining tax stuff to non-accountants — which I'm told is unusual.

I've spent the last several years helping online business owners stop being terrified of their finances. I run a CFO and bookkeeping practice. I've seen every kind of "oh no" file you can imagine, and I promise yours is not as bad as you think.

I'm not here to make you feel dumb for not knowing this stuff. Nobody taught you. That's the whole problem. Let's fix it.

Questions people actually ask


Is this a tax filing course?

No. This is a tax readiness course. I won't teach you to fill out a Schedule C line by line — I'll get your numbers, records, and deductions so organized that when an accountant files your return, it takes them an hour instead of a week.

Do I need to be in the US?

Yes — this course is built around US federal tax rules. The bookkeeping principles work anywhere, but the tax content is US-specific.

I'm not even an LLC yet. Should I take this?

Yes. The module on Business Legal Structures will help you figure out what to be, and the rest of the course works whether you're a sole prop or an S Corp.

I already have an accountant. Do I need this?

Probably more than anyone. Your accountant files your return — they don't typically teach you what they need from you. This course is the missing piece that makes your accountant's job (and yours) dramatically easier and cheaper.

I'm behind on bookkeeping. Like, really behind.

Module 9 (Catch-up Bookkeeping) is literally for you.

How long does it take to go through?

Most students do it over a weekend. Some take a week. The videos are short.

Is there a payment plan?

Reach out to me directly and we'll figure something out. I want you in the course more than I want a lump sum.

Will this be updated for the new tax year?

Yes. Lifetime access means lifetime updates.

You have two options


Option 1

Do what you did last year

Get to March. Panic. Spend a weekend you can't get back digging through PayPal and Stripe. Pay an accountant extra for cleanup. Promise yourself "next year I'll be better organized." Don't be.

Option 2

Spend a weekend with this course

Set up the system. Run your business on it. Walk into next tax season with everything done, organized, and ready to hand off in 30 minutes.

The choice is sort of obvious.

One-time payment · Lifetime access · All future updates included