
This week on the Roosterwire— we’re tackling the money mess behind most newsletters. From Stripe payouts that don’t add up, to “I’ll fix it later” red flags, to the three biggest mistakes creators make when their side project becomes a business. Let’s get into it →
💡 The Reality Check
You started your newsletter to write — not to wonder where your money went. Somewhere between your first subscriber and your third brand deal, your passion project turned into a real business.
Then one day, you’re asking yourself: am I actually making money? You think so, but you’re not sure. You’re juggling PayPal exports, Beehiiv payouts, Stripe fees, and that faint sense that something’s off.
That’s the moment every creator hits — when the “creative” part starts feeling like work.

When you need two pencils, you may need a bookkeeper
🧾 The Hidden Business Behind Your Newsletter
The second your newsletter earns money — even $100 — you’re running a business. You’re managing income, expenses, marketing, and payroll (even if it’s just you). And yeah, it’s a pain in the ass. But it’s the kind of pain that comes with progress.
Most creators don’t notice until the chaos starts: payouts that don’t match, mystery fees, and profit that vanishes faster than a Beehiiv feature update.
Good bookkeeping fixes that by showing you what’s really happening — what’s working, what’s waste, and what’s worth scaling.
🚨 “I’ll fix it later” 🚨
I’ve been that person. “I’ll organize it next week.” “I’ll deal with it when I have more subs.” “I’ll set up QuickBooks once I hit 1,000 paid readers.”
That thinking is how creators end up months behind and wondering why the numbers never line up. If you’ve ever said, “I’ll fix it later,” that’s your red flag.
⚠️ The 3 Big Mistakes Creators Make (and How to Fix Them)
1. Mixing personal and business accounts
That $6 coffee might be a write-off — or maybe not. When everything runs through one account, it’s impossible to tell. Open a dedicated business checking account. (NerdWallet has a great list of options for small businesses.)
2. Ignoring Stripe and PayPal fees
A $1,000 payout doesn’t mean $1,000 profit. Those small fees, refunds, and chargebacks add up — and they distort your real revenue if you’re not tracking them.
3. Losing track of recurring expenses
Editing tools, schedulers, hosting, software — they all stack up. Clean books show you where the money’s actually going so you can cut what’s not earning its keep.

Even the sharpest roosters can get buried under Stripe fees and coffee receipts — keep your books cleaner than your inbox.
🚨 “It’s Just a Side Project” 🚨
If you’re earning money, signing contracts, or paying for tools — it’s not a side project anymore. Congrats. It’s a business. The sooner you treat it like one, the sooner you stop scrambling.
💼 What a Bookkeeper Actually Does for Newsletter Publishers

he Rooster keeps an eye on the numbers—so creators can focus on their craft.
Bookkeeping isn’t just data entry — it’s your system for seeing how your business runs. At Rooster, I use QuickBooks Online to keep everything synced, simple, and accurate.
Here’s what that looks like in real life:
Syncs Stripe, PayPal, Beehiiv, and your bank each month.
(Reconciling just means making sure what’s in QuickBooks matches what’s really in your accounts.)Categorizes income by source — subscriptions, ads, affiliates, merch — so you can see what actually makes money.
Separates personal and business expenses because messy books mean messy decisions.
Tracks recurring revenue and top sponsors so you can plan and price smarter.
Delivers a one-page summary you’ll actually read — no spreadsheets, no jargon, just clarity.
Good bookkeeping shows when you are (or aren’t) making money and (hopefully) keeps you out of jail.
🕒 When to Hire a Bookkeeper (and When to Wait)
If you’re under $1,000/month and experimenting, keep it simple — use Wave or a spreadsheet.
But once you’re earning from multiple platforms, landing sponsors, or paying contractors, it’s time to bring in help.
You don’t hire a bookkeeper because you’re “big enough.”
You hire one because you’re too busy to guess.

If your receipts have their own closet, it’s time to bring in backup.
🐓 The Rooster Difference
I started Rooster Bookkeeping after seeing too many creators trying to do it all — writing, posting, managing sponsors, and still trying to balance their books at midnight.
I get it. I write too. I know what it feels like to juggle creativity and chaos.
That’s why I built Rooster around what creators actually need:
Flat-rate pricing
QuickBooks Online only (no Frankenstein tech stacks)
Real human communication, not canned support emails
You create. I’ll keep it clean.
✍️ Final Thought: Your Newsletter Is Already a Business
Every creative project starts as an idea. But the moment it earns a dollar, it deserves structure.
You don’t need an accounting degree, you just need someone who gets the creator grind and the business behind it.
That’s where I come in.
Clean books. Clear direction. More time to create.
-Ian