jeremiah

Builder · Founder · Learner

I build AI systems that do the work.

I am Jeremiah, 18, an owner of a short-term rental management business. I run my business with AI at the center to do all daily operations: underwriting deals, drafting invoices, talking to guests.

I don't just use AI. I build the systems that run the company.

See what I have built GitHub
$1M+ Generated for owners
15 Properties, in under a year
3 Products shipped & public
Age 11 First business founded

Selected work

Three systems doing real work right now.

Each one is live and open on GitHub, running my business every day.

No. 01

Pono

The AI company brain that runs an STR company

Pono pulls knowledge from Gmail, QuickBooks, Hostaway, and Drive, keeps it current, then turns it into executable skills an agent runs to do real work: underwriting, invoicing, guest comms. A real company brain, built and running today.

  • Agent + skills
  • Gmail
  • QuickBooks
  • Hostaway
  • Google Drive
View the repo
No. 02

Turnpoint

A full-stack cleaning-operations platform for STR managers

Scheduling, crews, checklists, inventory, owner reporting, and cleaner payouts in one place. Built to replace the patchwork tools managers stitch together to keep turnovers running. Real product, real stack, shipped end to end.

  • React
  • TypeScript
  • Supabase
  • Scheduling
  • Owner reporting
View the repo
No. 03

STR Deal Analyzer

A complete cash-on-cash underwriting model for STR investors

Give it a property and get a full return breakdown. It bases revenue on the top quintile of comps, not the median, calibrates ADR honestly, and models the real costs so the number you see is the number you can trust before you buy.

  • Python
  • Cash-on-cash
  • P80 comps
  • Underwriting
View the repo

How I build

I learn fastest by building first, then refining as I go.
Mindset

Start from the pain

Every system I build started as a manual task I was doing three times too many. Find the friction, then point the agent at it.

Method

Make it actually run

Everything I build should be able to operate in a real world with real stakes.

Machine

Ship, learn, repeat

One automation at a time, in production, learning in public on GitHub. The company runs on the same software I open-source.

Background

A founder since 11, building the boring parts so they run themselves.

I co-founded StayAscend, a full-service, turnkey short-term-rental management company, and operate it daily as the Director of Management. We allow owners to maximize their revenue while staying completely hands-off.

My real job is the system behind it. I write the AI that underwrites the deals, drafts the invoices, answers the guests, and keeps every property's knowledge in one brain. It is the same work that used to live in my head and in a hundred unread emails. Now it runs on software.

I taught myself all of it. No computer science degree, just a clear problem and the patience to keep shipping until the work got done on its own.

  • StayAscend, Co-Founder Full-service turnkey STR management. ~$1M+ generated for owners, scaling to 15 properties nationwide.
  • DECA International, 2nd place Entrepreneurship Business Growth Plan at the International Career Development Conference. Competed nationally.
  • B.S. Marketing, Western Governors University Earned the same year I graduated high school (2025). Now in WGU's M.S. Marketing program.
  • Serial founder since age 11 KoaExchange resale store, then God's Apparel, a clothing brand grown to $25K+ in revenue.

Aloha

Let's build something that runs itself.

Whether you are a founder, an investor, or just curious, I would love to show you the systems up close. Reach out and let's talk.

jeremiahlwin@gmail.com GitHub LinkedIn StayAscend