Categorize My Expenses vs. FlyFin: Do You Need a CPA Bundled In, or Just Your Expenses Sorted?

FlyFin markets itself as the “#1 A.I. tax service” for freelancers, combining AI-powered deduction tracking with CPA-prepared tax filing. It's a year-round subscription that monitors your bank transactions, estimates quarterly taxes, and assigns a CPA to file your return.

Categorize My Expenses takes a different approach entirely. You upload your bank statements (or connect via Plaid), the AI sorts everything into Schedule C categories tuned to your specific business type, and you walk away with reports for your CPA or TurboTax. No subscription, no ongoing monitoring, no bundled filing.

The real question isn't which one is “better.” It's whether you need everything FlyFin bundles, or whether you're paying for services you already get elsewhere.

Side-by-Side Comparison

What You Actually Pay

FlyFin's pricing is structured as three tiers, each billed annually despite being advertised as monthly rates. Here's how the numbers break down.

Over three years, FlyFin's cheapest plan (Basic, no filing) costs $252. Categorize My Expenses costs $117 for the same period ($39 × 3). That's a $135 difference for what's essentially the same service: getting your expenses categorized.

If you compare against FlyFin's Standard plan (with filing), three years costs $576. That's worth it if you genuinely need CPA-prepared filing. But if you already use TurboTax ($89/year for Self-Employed) or have a CPA, you're paying for a service you don't need. Categorize My Expenses ($39) plus TurboTax ($89) totals $128 per year, compared to FlyFin Standard's $192 per year.

How Each Tool Actually Works

The fundamental difference: FlyFin assumes you want continuous monitoring and bundled tax filing. Categorize My Expenses assumes you want to process a year of transactions in one session and bring the results to your existing expense tracking workflow. If you already have a CPA or use TurboTax, FlyFin's bundled filing is a feature you're paying for but not using.

Privacy and Your Financial Data

Both tools need access to your bank transaction data. How they handle it is quite different.

If you're uncomfortable giving an app ongoing access to your bank account, Categorize My Expenses is the only one of the two that lets you skip bank linking entirely. Download your own CSV from your bank's website, upload it, and your credentials never leave your hands.

When FlyFin Is the Better Choice

FlyFin does things Categorize My Expenses doesn't, and some of them are genuinely valuable. If any of these describe you, FlyFin might be the right tool:

• •You want a CPA to review and file your return. This is FlyFin’s biggest advantage. A real CPA prepares your federal and state returns, catches mistakes, and e-files for you. If you don’t have your own CPA and don’t want to use TurboTax, this is genuinely useful.
• •You want quarterly tax estimates. FlyFin’s quarterly tax calculator helps you estimate and pay quarterly taxes throughout the year. Categorize My Expenses doesn’t do this at all.
• •You want year-round deduction monitoring. FlyFin’s AI scans your transactions as they happen and surfaces potential deductions you might miss. If you’re the type to track expenses consistently, this ongoing approach works well.
• •You have a complex tax situation (S-Corp, K-1s). FlyFin’s Premium plan supports complex entity types. Categorize My Expenses is focused on Schedule C sole proprietors.
• •You want unlimited CPA access throughout the year. Every FlyFin plan includes CPA advice. You can ask tax questions anytime, not just during filing season.
• •You want a mobile app. FlyFin has native iOS and Android apps. Categorize My Expenses is web-only (though it’s responsive on mobile browsers).

When Categorize My Expenses Is the Better Choice

And here's where the one-time, focused approach wins:

• •You already have a CPA or use TurboTax. You don’t need another filing service. You need organized reports to hand off. Categorize My Expenses gives you a CPA-ready PDF, an Excel breakdown, and a TXF file that imports directly into TurboTax.
• •You don’t want to pay $84+/year for something you use once. FlyFin’s cheapest plan is $84/year for expense tracking alone (no filing). For that same job, Categorize My Expenses is $39 once. Over three years, that’s $117 vs. $252.
• •You do taxes once a year and don’t think about it the other 11 months. You don’t need an AI monitoring your bank in July. You need your transactions sorted in February.
• •You use the same card for personal and business expenses. Categorize My Expenses is explicitly built for mixed accounts. You mark which accounts are “mixed” vs. “business-only” and the AI handles the separation.
• •You don’t want to connect your bank account to another app. Upload a CSV you downloaded yourself. No bank linking, no credentials shared, no third-party access.
• •Your business has a specific profile. The AI is tuned for 13 industry types (rideshare, photography, real estate, hairstyling, etc.), so a delivery driver’s gas station charges get categorized differently than a consultant’s Uber receipts.
• •You want to work on a full desktop interface. FlyFin’s experience is app-first, with reviewers noting the web interface is condensed and harder to navigate. Categorize My Expenses is built as a full desktop web app.

What FlyFin Users Commonly Run Into

FlyFin has positive reviews from many users, but certain patterns show up repeatedly across Trustpilot, BBB filings, and app store reviews. These aren't edge cases; they're things to be aware of before you commit:

What This Looks Like on Your Bank Statement

Here's what both tools are actually sorting through. If you recognize lines like these from your own statements, you know the problem:

Some of these are business (Adobe, Google Workspace, Zoom). Some are personal (Whole Foods, Target). Some could be either (Amazon, Uber, Starbucks, Venmo). And that's just 10 transactions out of the 300 to 1,000+ most freelancers accumulate in a year.

FlyFin's AI scans these throughout the year and flags potential deductions as they happen. Categorize My Expenses processes them all at once, using industry-specific AI to categorize each one into the correct Schedule C line. The end result is the same: organized expenses. The difference is whether you want it happening in the background or in a single focused session.

Common Questions