What’s the biggest tax or compliance mistake you’ve made as a founder?

I’ve heard everything from forgotten 1099s to missed Delaware Franchise Tax payments, and even Form 5472 fines for foreign ownership.

And I am curious what tax/compliance mistake (if any) have you run into, and what did it cost?

We launched a tool that helps with compliance calendars and filings for early-stage startups, and wed love to make sure we’re solving for the real pain. taxhero.vc

Even anonymous war stories are welcome 😅