I’m setting up payroll for January 1 (first time ever doing this).
I’m sharing this openly because I know a lot of you are either right behind me — or quietly dreading this step. This is brand new territory for me.I’ve never paid employees before. Until now, Monument Glamping was scrappy, seasonal, and simple. My previous business (curriculum publishing) was the same. As this business has grown — and frankly outgrown publishing — it became obvious that payroll needed to grow up too. So I finally crossed that line. 💠 WHAT I HAD TO WORK THROUGH (THE REAL CHECKLIST) • Deciding when to start (January 1 = clean reset) • W-2 employees vs contractors (especially cleaners — this matters more than people realize) • Pay periods that are predictable and easy to explain • How fast payroll gets processed after a pay period closes • Collecting W-4s from everyone (non-negotiable) • Reasonable compensation for owners working in the business • Making sure payroll syncs cleanly with QuickBooks • Choosing a system that wouldn’t turn payroll into a second job I didn’t want clever.I wanted boring, compliant, and repeatable. 💠 WHY I CHOSE GUSTO I landed on Gusto not because it’s flashy, but because it removes friction where mistakes get expensive. Here’s what mattered to me: • Full-service payroll (they handle filings) • W-2 employees and owners handled cleanly • Automatic tax calculations and payments • Employee self-service portal (pay stubs, W-2s, updates — fewer emails to me) • Easy W-4 collection and storage • Direct integration with QuickBooks • Clean audit trail (important for financing or exit) • Scales without needing to switch systems again soon I can set it up now, test everything, and not run payroll until January.That mattered. 💠 MY ACTUAL PAYROLL SETUP (FOR TRANSPARENCY) • Payroll starts January 1 • Semi-monthly pay periods:– 1st–15th– 16th–end of month • Paychecks issued within 4 days of each pay period closing • All cleaners will be W-2 employees with W-4s on file • Wendy and I will each be paid $40,000/year as salaried employees– Wendy: Operations Manager– Me: CEO