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I Uploaded My Family's Tax Return to ChatGPT. Then I Read the Privacy Policy.
Community

I Uploaded My Family's Tax Return to ChatGPT. Then I Read the Privacy Policy.

I needed a quick answer about my RRSP contribution room. ChatGPT answered in four seconds. Then I read what I'd actually sent to OpenAI's servers.

RHRob HudsonMarch 24, 20266 min read
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The Great Wealth Transfer Is Really a Document Problem
Community

The Great Wealth Transfer Is Really a Document Problem

Financial advisors talk about trillions changing hands. But for most families, the real challenge is simpler and harder: can your kids find what they need if something happens to you tomorrow?

RHRob HudsonMarch 3, 20265 min read
The Real Cost of a Missed Insurance Renewal
Community

The Real Cost of a Missed Insurance Renewal

Most families don't think about document organisation until something goes wrong. The cost shows up quietly: a renewal you forgot, a warranty you couldn't find, a tax deduction you didn't claim.

RHRob HudsonFebruary 27, 20266 min read
Why We Self-Host Everything on One Server
Community

Why We Self-Host Everything on One Server

Most startups spread their stack across a dozen SaaS platforms. We put everything -- website, CMS, database, analytics, and AI pipeline -- on a single server. Here's why, and what it actually costs us in ways that aren't just money.

RHRob HudsonFebruary 23, 20265 min read
Your Family Has a Document Problem. You Just Don’t Know It Yet.
Community

Your Family Has a Document Problem. You Just Don’t Know It Yet.

Most families can’t find critical documents when they need them most. The three common approaches all fail in different ways. There’s a better option.

RHRob HudsonDecember 8, 20253 min read
Why I Built Archevi: Two Hours Looking for an Insurance Policy
Community

Why I Built Archevi: Two Hours Looking for an Insurance Policy

A family emergency sent me digging through filing cabinets for two hours. That night I started building Archevi.

RHRob HudsonDecember 3, 20253 min read