DISPATCH № 017 A FREE WEEKLY LETTER EST. 2026 AI CURIOUS → AI NATIVE

AI for hospitality. Measure output.

You run a hospitality business and you're curious about AI. Good - you should be. I write a free weekly letter that breaks down exactly how AI is changing the vacation rental game, and how to use it to increase your hospitality output - the quality of guest experience you deliver per hour of human work.

Units under management
275
Dispatches per year
52/ yr
Avg. time to read
3min
Cost
$0forever
Jack Zoppa with family
Jack Zoppa / 2026
Written by · Jack Zoppa

Building a hospitality business, managing hundreds of properties, hosting thousands of guests.

I'm Jack. I'm Founder of Stay Automated. I also run Haven - a vacation rental management business operating hundreds of properties - and Tendwell, the cleaning company I co-founded that serves short-term rental guests. I do all of that at the same time.

Alongside it, I run Stay Automated - where I help hospitality companies with consulting and AI implementation to take them from AI curious to AI native. Every week I write stories and examples straight from inside these businesses - what I tried, what broke, what actually moved the number.

If you're an operator, manager, or owner who can feel AI starting to move under your feet, you're in the right place.

Founder
Stay Automated
CEO
Haven
Co-founder
Tendwell
Inside the letter

What you'll learn.

No recycled LinkedIn takes. No “10 prompts that'll change your life.” Just the systems actually running a 275-unit portfolio - written down, deconstructed, shipped to your inbox.

01 · SYSTEMS

The guest-message stack that never sleeps.

The exact AI + human handoff we use across check-ins, damage reports, late arrivals, and 2 a.m. Wi-Fi panic - diagrammed and benchmarked.

GUEST AI TRIAGE AUTO-RESOLVE 74% HUMAN OPS 26%
02 · PLAYBOOKS

Playbooks you can copy on Monday.

Every dispatch ends with a one-page implementation: the prompts, the rules, the KPIs to track, and the 3 ways it'll break in week one.

STEP 01 → prompt STEP 02 → rule set STEP 03 → KPI ✓ STEP 04 → failure modes
03 · RECEIPTS

Real numbers from a real portfolio.

Monthly teardowns of what moved - response times, review scores, cleaning margins, payroll - with the line items that shifted after each automation went live.

▲ +42% OUTPUT Q1 → Q4 '25 AFTER AUTOMATION
What the letter is · 01

Built, not theorized.

This isn't another AI newsletter telling you what might happen someday. Every week I sit down and write about what I'm actually using and building inside a 275-unit hospitality operation - the systems, the prompts, the broken first drafts, the things that finally worked.

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I write it the way I'd tell it to another operator over a beer - no theory, no hype, just what I'm building and what it's doing.
Latest dispatch · Apr 20, 2026

Every week: a story, an example, a takeaway.

Real moments from inside Haven's operation - what went wrong at 2 a.m., the system I shipped on Monday, what it did to the P&L by Friday. No theory. Working field notes.

stayautomated.ai / keeping-a-high-standard-with-ai
MON · APR 20 · 2026 · 3 MIN READ
APR 20 · ISSUE 073 MIN READ

Keeping a high standard with AI.

We built an AI audit system to help our team rethink how we handled guest problems.

BY JACK ZOPPA · FOUNDER @ STAY AUTOMATEDMON · APR 20 · 2026

I'm actually handwriting this newsletter. Yep, with a pen. On a reMarkable. Not even sure yet how I'll get the handwriting to your email inbox. So why? I'm AI'd out for the week. Just wanted to sit down, no distractions, and write with my hand. But I know you read this newsletter to learn how I'm using AI and running my company. So without further ado…

What it audits
Every guest issue
How often it runs
Daily
What it is not
Surveillance
What this is not is a way for us to “spy” on our team. What it is, is a great way to audit our systems and process to make improvements faster.

Here's how general escalated issues work: a guest has a problem, AI escalates to the team, team and AI solve it, AI keeps the guest in the loop. So far so good? Here's where the magic happens. A daily workflow audits every single guest issue we helped solve. It catches tasks where we were about to lose money. Flags a huge bulk of them before they become a problem. It catches when we solved two guest problems but only communicated one resolution back to the guest. As it recognizes trends and successful resolutions, it learns, and holds us accountable going forward…

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