Vendor Silo Hell: Bill.com, Stripe, Expensify All in Different Databases

I manage accounts for 8 small businesses, and each one uses a different vendor chaos: Bill.com for invoices, Expensify for expenses, Stripe for payments, Brex card, Gusto payroll, square register (legacy), HubSpot CRM. Every Friday I spend 3 hours downloading CSVs from each platform, mapping categories, spotting duplicates. The posted dates never match—Stripe shows a deposit on Thursday but the bank shows it Friday. Expensify shows the charge on card date but bill.com shows it on approval date.

Is there a way to automate this in Beancount? Can I build importers that talk to these APIs, or am I stuck downloading CSVs forever?

Bob, this is exactly why I spent 3 weeks last year building a custom importer suite. I have Stripe, Square, and a Bill.com scraper that runs daily via cron. Each one normalizes timestamps to “bank posting date” so I’m comparing apples to apples. Result: I went from 4-5 hours/week manual work down to 45 minutes. The importer handles duplicates (checks transaction ID + amount + date), flags mismatches for review, and auto-stages entries for approval.

The real wins aren’t just time saved—it’s that I catch reconciliation gaps within 24 hours instead of discovering them at month-end. Stripe payouts are now predictable; expensify submissions clear same day.

Have you looked at Plaid? It’s designed exactly for this—vendors → one normalized interface → your GL. Worth $100/month if it saves you 2 hours/week.

off-topic but: has anyone here used plaid? designed to sit between multiple vendors and your accounting system—vendor-agnostic layer. might not be beancount-native yet, but could be worth exploring for this exact problem. https://plaid.com

Most platforms have built-in GL export functions

Carlos makes a fair point. But here’s where it breaks: Bill.com exports on invoice date, Stripe exports on deposit date. That 1-3 day offset means Bob’s reconciliation is constantly fighting timing mismatches. GL exports don’t normalize timestamps, so you still get orphaned transactions.

API-based sync fixes this by standardizing on “bank posting date” everywhere. But you’re right that for small businesses doing monthly reconciliation, the GL export + manual check might be “good enough.”

The real question: at what scale does 20 minutes/week become unsustainable? 5 vendors OK, 10 vendors painful?

Every Friday I spend 3 hours

Most platforms have GL export. Just pull directly into Fava. 20 minutes a week.