Meet Miles: The Freelancer, The Expat, The Cautionary Tale

If you’ve ever...

• Filed your taxes 10 minutes before midnight,
• Wondered if you could write off hot sauce as a “business expense,” or
• Moved to Portugal without notifying your state or the IRS…

…then you’ve already met Miles. Or at least a version of him.

Miles is our fictional tax disaster — a lovable expat/freelancer/small business owner who means well but files terribly. He’s the guy who screenshots his Stripe dashboard instead of sending real records. He once deducted an inflatable pool as a “wellness retreat.” He thought FBAR was a protein bar.

We created Miles because, honestly? He’s real. Not one person, but dozens — the walking, talking chaos we’ve seen over years of tax rescue missions. The client who forgot to file for three years because they were “between countries.” The founder who registered an LLC in Wyoming but banked in Mexico and filed in… Delaware?

Miles is all of them. And that’s why he’s in almost every story we tell.

Why We Tell Miles Stories

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You don’t remember IRS codes. But you will remember the guy who got audited because he Venmo’d “💅 Tax Prep Vibes” as a memo.

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Miles lets us teach tax lessons in a way that’s actually human. Through his mistakes, we explain everything from foreign earned income exclusion to 1099-K thresholds. With humor, clarity, and no boring CPA voice.

He’s not a villain — he’s the ghost of filings past. He reminds us what not to do, so you can get it right (and maybe laugh while you learn).

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Want to Stay Miles-Free?
Follow along for actual guidance, smarter strategy, and yes — receipts that don’t live in your sock drawer.

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Don’t be a Miles.
Schedule a meeting. We got you.

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