JL
Founder & CEO
Microsoft Technology Leader
2 STR Properties
Airbnb Superhost
Booking.com Award Winner
Blue Mountains, NSW
Founder's Story

Hi, I'm Jason LaGreca

I'm a technology leader at Microsoft and a vacation rental host who built GuestLoop to solve a problem I experienced firsthand: how to reduce OTA dependency and build direct guest relationships.

Tech LeaderSTR HostSuperhostAward Winner

Why I Built GuestLoop

The Problem: In my first year of running vacation rentals in the Blue Mountains of NSW, I achieved both Airbnb Superhost status and a Booking.com award. But I realized I was building someone else's business, not my own.

The OTA Trap

Despite our success—great reviews, high occupancy, happy guests—I was paying 15-20% in OTA fees on every booking. Even worse, I had zero ability to market directly to past guests for repeat bookings. The platforms owned the guest relationship, not me.

I calculated that with our two properties, we were losing approximately $4,200 per year in OTA fees. And that didn't even account for the lost opportunity of rebookings.

The Tech Solution That Didn't Exist

As someone who works with enterprise software at Microsoft, I started looking for a solution. I needed something that could:

  • Capture guest emails without being pushy or awkward
  • Provide value to guests through a digital guidebook
  • Automate marketing to past guests for rebookings
  • Track ROI so I could measure what was working

The options were either generic email marketing tools (Mailchimp) that required building everything from scratch, or property management systems that didn't focus on marketing at all.

Nothing was purpose-built for hosts who wanted to reduce OTA dependency through direct relationships.

Building GuestLoop

So I built it myself. As a Microsoft developer, I had the technical skills. As a vacation rental host, I had the domain expertise. The combination was perfect.

GuestLoop started as a simple digital guidebook that captured guest emails. But I quickly added the features I needed as a host:

  • Pre-built email templates for the vacation rental industry
  • Automated welcome and review request campaigns
  • Timing-based rebooking campaigns (6 months, 9 months, 12 months)
  • Guest segmentation by property, dates, and booking history
  • ROI tracking so I could see exactly how much I was recovering

The Results

First Year Results:

  • 90%+ email capture rate from guests
  • 12% rebooking rate within first year
  • $2,800+ recovered in OTA fees
  • 8x ROI on the tool subscription cost

More importantly, I now owned the relationship with my guests. When they wanted to come back to the Blue Mountains, they emailed me directly instead of going back to Airbnb or Booking.com.

Why I'm Sharing This With Other Hosts

After seeing the results for my own properties, I knew other independent hosts were facing the same problem. The OTAs are necessary for discovery, but they shouldn't own your business forever.

GuestLoop is my answer to the OTA monopoly. It's built by a host, for hosts. Every feature solves a real problem I've experienced. Every template is based on emails I've sent. Every automation is something I wish I had earlier.

I'm not trying to replace your property management system or become another OTA. I'm giving you the tools to build direct relationships with your guests and reduce your dependency on expensive booking platforms.

Dual Expertise: Tech & Hospitality

Technology Leader

  • Microsoft - Enterprise software development and architecture
  • Full-Stack Development - Modern web technologies, APIs, and databases
  • Product Design - Building software that solves real user problems
  • Marketing Automation - Email systems, CRM, and analytics

Vacation Rental Host

  • 2 Properties - Blue Mountains, NSW, Australia
  • Airbnb Superhost - Achieved in first year of operation
  • Booking.com Award Winner - Recognized for guest experience excellence
  • Direct Booking Expert - Built sustainable direct booking revenue

This combination is what makes GuestLoop different. I'm not a marketer selling software to hosts. I'm a host who built software to solve my own problems. Every feature is battle-tested on my own properties before it goes into the product.

My Philosophy on Direct Bookings

1. OTAs Are a Tool, Not a Strategy

Airbnb and Booking.com are great for discovery and filling calendar gaps. But relying on them 100% means you're building their business, not yours. Use them for what they're good at—new guest acquisition—then capture those relationships for direct bookings.

2. Email Capture Needs to Provide Value

Nobody wants to give their email just so you can spam them. That's why GuestLoop combines email capture with a digital guidebook—guests get value (wifi password, checkout instructions, local recommendations) and you get their contact for future stays.

3. Rebooking Is Easier Than New Acquisition

A guest who's already stayed with you is 5-10x more likely to book again than a new guest is to book the first time. Yet most hosts put 100% of their effort into getting new bookings. The math doesn't make sense. Focus on getting past guests to come back.

4. Automation Lets Small Hosts Compete

Big property management companies have marketing teams. As an independent host managing 1-10 properties, you don't. Automation levels the playing field. Set up your email campaigns once and they work 24/7 to bring guests back.

5. Own Your Data, Own Your Business

The most valuable asset in your vacation rental business isn't your property—it's your guest list. When you own the emails and phone numbers, you can market to them anytime. When the OTAs own them, you're renting access to your own customers.

Ready to Reduce Your OTA Dependency?

Join me and hundreds of other hosts who are building direct booking revenue with GuestLoop. Start with a 14-day free trial—no credit card required.

Built by a host, for hosts. Every feature solves a real problem.