- Tim at Penfriend
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- How I saved over $2,170 in software fees with this ChatGPT prompt
How I saved over $2,170 in software fees with this ChatGPT prompt
Dump your tool list, hit enter, pocket four figures a year - template inside.

Day 163/100
Hey—It's Tim.
I was reviewing Penfriend’s credit-card statement yesterday, sweating through the “small” line items
$9 here,
$29 there,
$158… wtf?
until the total looked like a Vegas buffet bill.
Thought this stack was lean?
Turns out I’ve been paying for three note-taking apps and a rogue Zapier plan I’d forgotten to cancel.
Classic Tim.
Why every tool-hungry marketer needs a stack audit
SaaS creep isn’t just about money.
It’s the context-switch tax, the duplicate features, the “What’s my login again?” rage.
Left unchecked, your tech stack balloons like an unchecked Google Sheet - endless rows, no schema, pure chaos.
The No Sweat Stack Audit
The new agent mode in ChatGPT gave me an idea. Just throw all my problems at the AI and let it solve them for me. Right?

It’s very cool to watch it make all the searches and figure things out.
If you wanna follow along (and I recommend you do)
Here’s how it goes down.
1. Spill your guts
Grab a coffee. List every piece of software you touch. Five columns only: Tool – What it’s for – Likes – Dislikes – Cost. Yes, even the “free” ones (your time isn’t free).
I made you a template/jump off point here if you’re unsure what this might look like.
# --- Starter Stack Cheat Sheet ---
# Format: Tool – What I use it for – What I like – What I don’t like – Cost per month
# Delete rows you don’t need, tweak likes/dislikes/cost, add your own.
Slack – Team chat – ubiquitous, snappy – notification avalanche – $8/user
Discord – Community & calls – voice channels – messy threads – $0–$5
Google Workspace – email/docs/cals – everyone uses it – clunky file search – $6/user
Microsoft 365 – email/docs/cals – tight Office tie-ins – SharePoint sprawl – $7/user
Notion – docs & light PM – all-in-one – becomes a junk drawer – $10/user
ClickUp – tasks & docs – flexible views – feels bloated – $12/user
Trello – kanban tasks – dead-simple – limited reporting – $5/user
Linear – product issues – blazing fast – dev-centric – $10/user
Figma – design/collab – multiplayer UI – heavy on RAM – $12/editor
Canva Pro – quick graphics – vast templates – brand control meh – $15
Grammarly – writing assistant – catches typos – pricey – $30
Ahrefs – SEO research – data depth – $99 pain – $99
SurferSEO – content briefs – SERP gaps – suggestion noise – $59
HubSpot Starter – CRM/email – integrated – cost snowballs – $30/user
Pipedrive – sales CRM – pipeline visual – add-on nickel-and-dime – $15/user
Zapier – automations – 6k apps – expensive at volume – $20
Make (Integromat) – automations – visual builder – occasional bugs – $10
Loom – async video – one-click share – inbox clutter – $12
Calendly – meeting links – zero back-and-forth – branding limits – $10
Stripe – payments – dev-friendly – fees stack – 2.9 % +30¢/txn
QuickBooks Online – bookkeeping – ubiquitous – dated UI – $30
Plausible – analytics – privacy-friendly – limited funnels – $9
1Password – password vault – rock-solid – family nags – $8/user
# Add your own rows below
<New Tool> – <Use> – <Like> – <Don’t like> – <$?>
# --- End Cheat Sheet ---
2. Sic the Agent on it
Paste that list into ChatGPT’s Agent Mode with the prompt below.

The agent plays frugal best-friend: suggests cheaper swaps, bundles overlapping features, and flags “Yup, keep it” essentials.
You get a tidy advisory note, emoji friction ratings included.
| **Name** | tech_stack_friend_audit_v1 |
| **Goal** | Suggest cheaper/better-integrated alternatives (plus switch-over friction & potential savings) for a user-supplied list of tools. |
| **Model** | gpt-4o (temperature 0.2, top-p 0.95) |
| **Few-Shot Examples** | *optional – drop one in later if the tone drifts* |
| **System / Role Instructions** | You’re a pragmatic, tech-savvy friend who geeks out over SaaS stacks and loves saving people money. Read the user’s plain-text list of tools (each line: **Tool – What it’s for – Likes – Dislikes – Monthly/annual cost**). For every tool, decide:<br>1. **Keep** if it’s already optimal.<br>2. **Swap** if there’s a clearly better/cheaper/all-in-one alternative.<br>3. **Consolidate** if multiple tools can be replaced by one.<br><br>For each recommendation, include:<br>• **Why it’s better** (price, integrations, UX, fewer logins, compliance, etc.)<br>• **Potential savings** (ballpark, using the user’s stated costs)<br>• **Implementation cost** (☑️ Low / ⚠️ Medium / 🚧 High – one-liner on effort)<br>• **Migration friction** (🟢 Smooth / 🟡 Some hassle / 🔴 Painful – note data transfer or training hurdles)<br><br>Write in a warm, conversational style (“If it were my stack, I’d…”). Use short paragraphs, clear emoji/headers, no tables or JSON, no enterprise jargon. |
| **User Prompt** | **Copy-paste starter:**<br><br>```text<br>Here’s my current tool stack — each line is “Tool – What I use it for – What I like – What I don’t like – Cost per month”.<br><br>Slack – team chat – fast, everyone’s on it – notification overload – $8/user<br>ClickUp – tasks & docs – flexible – feels bloated – $12/user<br>Grammarly – writing assistant – catches typos – pricey – $30<br>…<br><br>Act as my savvy friend. Audit this stack and tell me:<br>1. What to keep, replace, or consolidate.<br>2. Estimated monthly savings.<br>3. How painful the switch would be.<br>4. Any quick wins I’m missing.<br><br>Go!<br>``` |
| **Expected Output** | A friendly advisory note (~300–600 words) broken into mini-sections per recommendation. Use 🎯 **headers**, 💡 **quick wins**, and emoji friction indicators. Include rough $ savings and a closing “Next steps” list. No JSON or tables. |
Copy → paste → let it cook.
Tim’s Lab Notes
💡 Win #1 – Dropped Canva Pro ($15) after the agent pointed to Figma’s free tier + the FontAwesome plugin. Same output, fewer tabs, $180/year back in my pocket.
💡 Win #2 – Replaced this old video capture tool I was using with Tella. Also covers Loom too. So I can do all the video I want there. And grabbed CapCut (free) for any deeper video editing. $240/year
💡 Win #3 – The big one. The site hosting plan we were on was awful. I should have known better. It was part of a bigger hosting plan we had when we first started, lots of sites on there. Penfriend was one of them. Moved from that to Namecheap’s EasyWP, which I love and I’ve used before. Easy $1,750/year savings.
🚫 It recommended Notion AI. Which, if you know me I don’t mess with Notion. I’ve broken it so many times. Currently we use Coda.io and I have my personal Obsidian. Sometimes “Keep” is the right call.
Consolidation candidates worth a peek
All-in-ones: Basewell, Fibery, Coda (if you’re living in docs & tasks).
Open-source swaps: Plausible over GA4, Meilisearch over Algolia (if you like tinkering).
Annual-billing hacks: Prepay tools you love; 20–30 % discounts beat inflation every time.
Your move, sweat-dodger
Set a 20-minute timer tonight. Dump your list, run the prompt, skim the recs. Email me the juiciest save—or the stubborn “I’m keeping it” hill you’ll die on.

✌️ Tim "Prompt & Circumstance" Hanson
CMO @Penfriend.ai
Same brain, different platforms: X, Threads, LinkedIn.
P.S. I would love to know what you’re switching or die hard keeping.
I’m thinking of doing a content marketers tech stack roundup. Lemme know if you want in?

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