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

💠 WHY WE’RE PAYING OURSELVES SALARIES (NOT JUST OWNER’S DRAWS)

This was an important mindset shift for me.

Owner’s draws work when things are small and informal. But that breaks down when you want lenders, underwriters, or future buyers to take the business seriously.

Paying ourselves a reasonable salary does a few important things:

• Shows the business can support real management roles

• Separates labor compensation from ownership returns

• Creates cleaner financial statements

• Aligns with S-Corp best practices

• Makes the business easier to underwrite when seeking financing later

Owner’s draws say: “this is a lifestyle business.”Payroll says: “this is a company.”

The $40,000 salary level is intentional — conservative, defensible, and appropriate for where the business is right now.

💠 WHY I’M SHARING THIS

Most landowners don’t fail from bad ideas.They stall at administration fear.

Payroll was one of those invisible lines for me. Crossing it doesn’t mean the business is perfect. It just means it’s maturing.

If you’re behind me on this path, take notes. If you’re ahead of me, feel free to poke holes. If you’re avoiding it altogether, that’s exactly why I’m posting this.

We build real businesses here. That means eventually doing real payroll.

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