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    2. Tax Preparation

    The AutoFileEmail Blog

    Receipt organization, email-attachment filing, and tax-prep tips for solo founders, freelancers, and landlords.

    1099 vs W-2 Income: Filing Receipts When You Have Both
    MMitchel Kelonye

    1099 vs W-2 Income: Filing Receipts When You Have Both

    Day job plus side hustle? The W-2 side rarely needs receipts. The 1099 side absolutely does. Here's how to keep them separate without losing your mind.

    Jun 30, 2026Read
    What the IRS Actually Needs From Your Receipts (Boring But Free)
    MMitchel Kelonye

    What the IRS Actually Needs From Your Receipts (Boring But Free)

    The 5 things every business expense receipt must show, the retention windows, and what 'adequate records' means in IRS speak. Pubs cited.

    Jun 23, 2026Read
    Stripe + AWS + Notion Receipts: The Founder's Tax-Time Checklist
    MMitchel Kelonye

    Stripe + AWS + Notion Receipts: The Founder's Tax-Time Checklist

    The 15 vendors a typical solo founder pays every month, where the receipts arrive, and how to make sure all 15 land in one Drive folder.

    Jun 16, 2026Read
    Backfilling 3 Years of Receipts in an Afternoon
    MMitchel Kelonye

    Backfilling 3 Years of Receipts in an Afternoon

    Got an IRS letter or just years of unfiled receipts in Gmail? Here's how the 3-Year Backfill Pack turns 22 hours of clicking into one afternoon.

    Jun 9, 2026Read
    The One Drive Folder Structure Your Accountant Actually Wants
    MMitchel Kelonye

    The One Drive Folder Structure Your Accountant Actually Wants

    Your CPA doesn't want OCR or dashboards. They want a folder. Here's the exact year/vendor/month structure that survives tax season and an audit.

    Jun 2, 2026Read
    Gmail Attachments Are a Tax-Time Landmine (Here's the Fix)
    MMitchel Kelonye

    Gmail Attachments Are a Tax-Time Landmine (Here's the Fix)

    Gmail search degrades. Filters break. April hits and you can't find half your receipts. Here's why filing as you go beats archeology in March.

    May 19, 2026Read
    Receipts for Taxes: The 3 Folders That Survive an Audit
    MMitchel Kelonye

    Receipts for Taxes: The 3 Folders That Survive an Audit

    An IRS audit asks for one thing: organized records. Here are the 3 folders every solo founder needs, and how to populate the hard one without lifting a finger.

    May 12, 2026Read
    How Freelancers Actually File Receipts (No Apps, No Spreadsheets)
    MMitchel Kelonye

    How Freelancers Actually File Receipts (No Apps, No Spreadsheets)

    Freelancers don't need Hubdoc or a 12-tab spreadsheet. Here's the minimum-viable receipt system: connect Gmail, files arrive in Drive by sender. 2 minutes.

    May 8, 2026Read
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    We don't read your documents. We just file them. Receipts, invoices, statements — sorted into your cloud, automatically.

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