Friday, January 09, 2026
1099 Filing Season Has Started: Key Deadlines and Reminders
Welcome to the first briefing of 2026. If you are a founder or finance leader in the $1M to $50M revenue bracket, January is rarely about New Year’s resolutions. It is about the heavy operational lift of year-end closing and the high-stakes compliance window known as 1099 season. This month, we are moving past the administrative headache to look at 1099s as a strategic data exercise. Properly preparing and filing your 1099 forms is not just about avoiding IRS penalties. It is about the integrity of your
