#124 · How I Lost $250,000 in Four Weeks with AI Automation

youtube ↗AI & Automation

How can I set up an automated invoice‑collection system for my agency, and how should I sell it to clients?

The automation works by using a Google Sheet as a simple database of invoices you’ve sent. For each invoice you record the date, then calculate how many days have passed. Based on the age you trigger follow‑up emails: after 7 days send follow‑up A, after 14 days send B, and so on (7, 14, 21, 28, 35, 42 days). The sheet can be built in any system you prefer—Google Sheets, a CRM, Stripe, QuickBooks, etc.—as long as you can pull the invoice date and payment status. A second automation watches for incoming payments (e.g., via Stripe) and marks the invoice as paid, so only unpaid invoices continue to receive follow‑ups. The email templates are simple reminder messages that reference the invoice and ask if the client needs anything to expedite payment. This low‑cost setup automates the entire follow‑up process without manual effort.

invoice automationgoogle sheetsstripe

Related answers

youtube ↗Agency Operations

Blov 5 asks: how would the invoice collector automation work? If invoices are sent with attachments (sometimes more than one plus HTML), what would your solution be? Also, what's the best place to sell those invoices?

He describes using a Google Sheet to track invoices, checking the date sent to find overdue ones, pulling data into make.com, calculating days overdue, and routing follow‑up emails based on age; for attachments, add a column with the invoice file ID (or link) and use a Google Drive download module so make.com automatically attaches the file when iterating over overdue invoices; you can host invoices anywhere (Google Drive, etc.) and just store the file ID; the same follow‑up logic works for any pipeline, not just invoices; built‑in platform follow‑ups (Stripe, PandaDoc) are poor because they sound robotic, whereas a friendly, assumptive tone preserves relationships and improves response.

invoice automationattachmentsmake.com
youtube ↗Agency Operations

Should I stick with content repurposing or switch to AI automation, what’s the biggest mistake beginners make when selling their first automation, and how do I set up invoice reminders and track overdue invoices?

The invoice reminder is sent from your own business email—the same one you use for regular communication—so customers recognize your domain (e.g., nickleclick.ai) and assume legitimacy. To pull overdue invoices you can use Stripe, QuickBooks, Zero, or any major invoicing tool to retrieve all invoices sent up to a point (e.g., the last 100) and apply the same logic: filter for unpaid, calculate overdue amounts, and send reminders.

invoicingoverdue invoicesemail reminderstripe
youtube ↗Sales

How do you handle recurring retainer payments and invoicing with Stripe, and what tools do you use for proposals and sales workflow?

For recurring retainer payments, I rely on Stripe’s built‑in subscription/invoicing feature: create a customer, attach a recurring product to an invoice, and send it. I don’t need a fancy automated system—manually putting together an invoice takes about 30 seconds and is worth it. For the sales workflow, I use a simple form during calls to capture the customer’s name, email, phone, business, and problem details. That form triggers a make.com workflow that feeds the data into AI, which populates a proposal template on platforms like Panadoc, Better Proposals, or Quiller. Panadoc is handy because it includes payment integration that handles Stripe, though its API cost is high ($2 per document). The overall process is: sales call → form → make.com → AI‑filled proposal → send to client. You don’t need to build a custom widget or workflow; the existing tools are sufficient.

stripe invoicingproposal generatormake.com
youtube ↗Agency Operations

Which process should I automate first: outreach, nurturing, closing, onboarding, or fulfillment?

First, don’t jump straight to automation—build a solid, money‑making process first. Only automate a step if the process already works and there’s clear value in automating it. Look at each part of your workflow: outreach, nurturing, closing, onboarding, fulfillment. Closing is tough to automate without advanced AI, so focus on onboarding and fulfillment where automation is realistic. Sketch out your process (e.g., with a Whimsical mind map) before touching any automation tools. For example, a simple onboarding flow might start with a payment trigger (Stripe), then create a ClickUp folder, add a list, insert standardized tasks, send an onboarding email with a calendar link, update the client status when a call is booked, run the call, fill out an onboarding form, send a creative brief to AI to pre‑generate assets, turn those into a Google Doc and slides, and add a tracking doc. Once you have that map, see which steps can be hooked up via APIs or webhooks—like using a payment‑intent‑succeeded webhook to automatically create the ClickUp folder and list. Steps that can’t be automated via API (e.g., creating the folder or list) would instead trigger a manual action, such as a Slack notification to your project manager, which then starts the next automatable segment. In short, optimize the process first, make sure it’s profitable, then automate as much as you can.

automation prioritizationprocess optimizationonboardingfulfillment