Issue #1 · October 2026

Stop chasing. Let the bots ask for your money.

Subject line: Stop chasing. Let the bots ask for your money. Preview text: 4 tools that follow up on unpaid invoices so you don't have to, from $0 to $259/mo.

Hi neighbor,

Welcome to the first issue of Main Street Guardian. Each week I look out for one back-office chore and check which tools can honestly take it off your plate. You get what they cost, how long setup takes, what they replace, and whether they're worth your time. No AI headlines, no hype. Just tools for running the shop.

This week: chasing unpaid invoices. You did the work. Asking to get paid shouldn't feel like a second job.

A word on how I review: I work only from each vendor's own pricing and feature pages as of Oct 16, 2026, and I link every one. I haven't tested these tools hands-on. Anything I couldn't confirm is marked [?].

1. QuickBooks Online: built-in reminders + Payments AI

Cost: Reminders come with your subscription. Payments AI is on Essentials, Plus, and Advanced (US only). Listed prices are $19, $42.50, $70, and $170/mo. These look like promo rates, with regular prices of $38, $85, $140, and $340 [?] (plans).
What it does: Sends up to three automatic email reminders, scheduled anywhere from 90 days before to 90 days after the due date. It only covers invoices you've already emailed (help). Payments AI suggests a reminder schedule based on how each customer pays, drafts messages you can edit, and suggests late fees. Nothing goes out until you approve it (help). Intuit says customers get paid "4 days faster on average" (Intuit). "Invoicing on Autopilot" is still in beta with usage caps (Intuit blog).
Setup time: About 5 minutes. It's one toggle under Settings → Sales → Reminders (my estimate from the help steps).
Replaces: Sticky notes, calendar reminders, and copy-pasted "just checking in" emails.
My take: Turn this on first. If you already pay for QuickBooks, it costs nothing extra. It's email only and stops after three nudges, but that's plenty for most shops sending fewer than 50 invoices a month.
Pick if you… already use QuickBooks and just want polite reminders to go out without you.

2. Paidnice

Cost: Essentials is $69/mo (150 invoices, 600 emails, 2 users). Pro starts at $99/mo (300 invoices, unlimited users). SMS costs $0.10 each. Your first 20 actions are free, no card required. Month to month (pricing).
What it does: Connects to Xero, QuickBooks Online, and Stripe. It sends email and SMS reminders and automatic statements, adds late fees and interest, offers early-payment discounts, and gives customers a payment portal. Pro adds payment plans, multi-currency support, your own sending domain, and a public API/MCP server. A "Safe Mode" lets you test everything before a single message goes out (pricing).
Setup time: "Under 15 minutes," according to the vendor (pricing).
Replaces: Working out late fees by hand, monthly statements, and the collections spreadsheet.
My take: The most complete feature list for the money in this lineup. Late fees and early-payment discounts are the levers QuickBooks reminders don't give you. The vendor says it won the 2025 Xero Global Small Business App of the Year award.
Pick if you… run Xero or QuickBooks Online and want escalation, late fees, and texts without signing an enterprise contract.

3. InvoiceSherpa

Cost: $49/mo (up to 100 open invoices), $99/mo (101–500), or $199/mo (unlimited). Annual billing brings those to $41, $83, or $166/mo. There's also a 1% transaction fee on invoices paid, waived if you process payments through Propelr. 14-day free trial, no card required (pricing).
What it does: Unlimited email and SMS reminders sent from your own domain, custom workflows, a branded payment portal, autopay, installment plans, surcharging, and automatic reconciliation with QuickBooks Online and Xero (pricing).
Setup time: Self-guided onboarding on the base plan. The vendor doesn't publish a time estimate [?].
Replaces: A separate payment-link tool plus your reminder emails.
My take: A strong fit when the real problem is making it easy for customers to pay, not just reminding them. Autopay and installment plans do a lot of the heavy lifting. Run the numbers on that 1% fee first: if you collect $50K a month, it's another $500/month on top of the subscription.
Pick if you… want reminders and card-on-file autopay in one place and can avoid or absorb the 1% fee.

4. Chaser

Cost: Compact starts at $259/mo (£199) for businesses under $5M in revenue, with 4 users, 30 templates, and 4 workflows. Annual billing is about 10% cheaper ($233/mo). Core is $779/mo. "Care" plans, which add a human AR specialist, start at $1,199/mo (pricing).
What it does: Automated follow-ups and workflows for unpaid invoices. Higher tiers add a receivables forecast. Care plans give you a real person who handles follow-ups, the inbox, and disputes (pricing). Third-party reviews say it can chase by email, SMS, letter, and phone and add statutory late fees, but I couldn't confirm that on Chaser's own page [?] (accounting.events).
Setup time: Not published [?].
Replaces: A part-time credit controller, quite literally on the Care plans.
My take: The priciest option here. It's best for businesses doing $1M+ with a real backlog of overdue invoices. It's also the only one with a done-for-you human layer.
Pick if you… have outgrown simple reminders and want someone (or something) to own collections.

Side by side

Tool	Starts at	Free trial	SMS	Late fees	Human help
QuickBooks reminders	Included	—	No [?]	Payments AI suggests them	No
Paidnice	$69/mo	20 free actions	$0.10 each	Yes	No
InvoiceSherpa	$49/mo + 1%	14 days	Yes	[?]	No
Chaser	$259/mo	[?]	[?]	[?]	Care plan

Bottom line: Turn on QuickBooks' free reminders today. When you need late fees and escalation, move up to Paidnice. Bring in Chaser only once collections turns into a full-time job.

Keep your doors open and your invoices paid. I'll be keeping watch for you. — Main Street Guardian One chore, a few honest tools, every week. Hit reply and tell me which chore you'd like covered next.