Hello friend,
Why you're getting this: this is my Friends Newsletter; a brain dump of weird experiments, practical tools, and overshares I send to people I like. Zero pressure to stay. Unsubscribe anytime (I won’t take it personally, I’ll just cry).
Here’s what I’m thinking about…
How I Replaced My Assistant with AI (and Saved $100K)
Let me set the scene.
January 2024.
I’m drowning in admin.
Meetings I didn’t want.
Emails I didn’t read.
Introductions I didn’t ask for.
And the worst part? I was paying someone $100K a year to help me stay afloat; and still sinking.
So I did something I didn’t think I’d ever do:
I fired myself… and built a robot to take my place.
First, let me say this: I’ve had amazing assistants.
Smart, loyal, detail-obsessed.
But there’s a dark truth no one talks about:
Admin work has Parkinson’s Law baked into it.
The more support you hire, the more chaos shows up.
Need a quick reply? They’ll draft an essay.
Need a calendar slot? You’ll get a 3-email thread and a Doodle link.
Need a bio sent over? Suddenly it’s a collaborative Google Doc with formatting suggestions.
This isn’t their fault.
It’s the job.
Admin is like laundry; it multiplies while you’re sleeping.
It started small.
I was using Superhuman and noticed I was still spending 2+ hours a day just triaging.
Not replying. Not thinking. Just sorting.
So I built a filter.
Then another.
Then a GPT prompt to categorize incoming mail.
Before I knew it, I had a little AI that could:
Game. Changed.
I call it: The Machine That Kills Email.
Here’s how it works:
Some specific use cases:
Each of these used to take 15 seconds.
Now it takes 0.
Multiply that by 150 emails a day = real time saved.
I built a “mini‑me” agent for that too.
It knows:
It integrates with:
No Calendly link. No back and forth.
Just peace.
This all sounds slick.
But I’ll be honest; it was emotionally weird.
For years I prided myself on being “accessible.”
Anyone could email me, pitch me, book me, reach me.
Then I realized: that was the problem.
I had become a bottleneck.
I was letting people into my brain without a filter.
My life had become a crowded inbox I didn’t sign up for.
The AI wasn’t just an assistant.
It was a bouncer for my attention.
And damn, it’s strict.
Not everything can be automated.
Here’s what my (human) team still handles:
But all the rest?
Booked, sorted, filed, and forgotten… by robots.
Setup:
Return:
Not bad for a duct-taped system running on caffeine and API keys.
If you want to see if you need an AI assistant, try this:
No.
But it can replace enough to change your life.
Start with triage.
Move to scheduling.
Then layer on research, social DMs, cold outreach, even writing.
Build little workflows that do one thing well.
Stack them.
Refine them.
Soon, you’ll be managing your entire life like an API.
I’m hosting a private retreat in Maui for founders running lean holding companies.
< $50M revenue, no fluff, just real ops and dealmaking talk.
DM me if you’re interested.
Still loving Beeper; combined all my DMs into one keyboard-driven app.
I actually sleep now.
Been playing with AI agents for sales follow-up. If you’ve built something that auto-follows in a human tone, I want to see it. Bonus if it knows when to back off.
Also, hiring a full-time “Automation Partner.”
You’ll live in Lindy, Notion, Superhuman, and n8n.
I’ll throw weird problems at you, you’ll solve them with flows.
Think: “Chief AI Janitor.”
Reply if interested.
1. Did this actually save you $100K?
Yes; my last full-time assistant was $96K/year. I built workflows that replaced 80% of the role.
2. Isn’t AI still too dumb for this?
It’s dumb until you give it context. Once trained, it’s eerily good.
3. What tools do you use?
Lindy, GPT-4, Superhuman, n8n, Zapier, Notion, Google Calendar, Slack, Twilio.
4. Do you still need a human assistant?
Sometimes. But far less often. My team only steps in when the AI hits an edge case.
5. Does it make mistakes?
Yes; but fewer than tired humans.
6. How long did it take to build?
6 weeks of tinkering, testing, and rebuilding.
7. What’s the ROI?
12 hours/week saved + $100K/year cost eliminated = worth every second.
8. What’s next?
AI that handles inbound opportunities—screening deals, partners, pitches.
9. Is this scalable for teams?
Absolutely. You can clone your best admin person’s logic and scale it org-wide.
10. Where should I start?
Triage your inbox. That’s where the magic is.
That’s all for now…
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