Telluride Travel Rentals
Revenue $1.2M to $1.7M in 1 year, through new distribution channels and smarter revenue management.
Read the case study →Four systems. Four plans. One engine.
I'm Giacomo (Jack) Esposito. 13 years in short-term rentals: five at Booking.com, a 3,000-villa portfolio at Oliver's Travels and 500+ Guesty implementations. I fix the systems behind your revenue, distribution, operations and owner growth, so you can scale to 300 listings without the wheels coming off.
Four interlocked systems that turn a 30+ unit STR operation into a high-performance business.
Every plan builds on these four systems.
Demand is everything that drives a qualified guest to your listing before they book. OTA algorithm positioning, listing content, photography, reviews, direct booking channels, and the organic presence that makes your brand discoverable without paying OTA commission every time.
Across 30+ units, every listing ranks in the top 10% of its comp set, a direct booking channel generates 20%+ of reservations, and guests search for your brand by name.
You rely entirely on Airbnb's algorithm, have no direct booking strategy, and your listing photos were taken on a smartphone in 2022.
Revenue management is the discipline of pricing intelligently, not just setting a base rate and hoping. Dynamic pricing calibrated to local demand, comp set movement, lead time curves, seasonal patterns, and length-of-stay rules that protect your ADR.
Your RevPAR is in the top quartile of your comp set. You review pricing weekly. You have minimum-stay rules that eliminate orphan nights. You know your breakeven occupancy by unit.
You set a price in October and check it again in March. You're fully booked in peak season at a rate 30% below market.
The systems, tools, and people that deliver the guest experience without requiring your constant attention. PMS configuration, automation workflows, cleaning and maintenance coordination, guest communication, review management, and the SOPs that let you delegate with confidence.
Your guest comms run on autopilot, reaching up to 80% automation with an AI guest messaging tool. You have a cleaning team that self-manages via software. A new property can be onboarded in under a week. You could take a two-week holiday without the business breaking.
You're manually sending check-in instructions at 11pm. Your cleaner finds out about checkouts via text. Every new property adds 8 hours per week to your workload.
Growth is not just adding units. It's building the ownership model, capital structure, and acquisition strategy that lets you expand without breaking the systems underneath. Portfolio construction, owner acquisition, market selection, and knowing when to say no.
You have a documented model for evaluating new properties. You have a pipeline of property owners approaching you. Your margins improve as you add units, not deteriorate.
Every new listing is a heroic effort. You're growing revenue but not profit. You're saying yes to every property because you're scared to say no.
Built for property managers and operators with 30+ units. Every plan runs on the four systems; you choose how deep we go.
Fix your single biggest leak, fast.
Two systems, implemented and tuned.
Full 4-system build-out.
Embedded fractional partner for the year.
Payback assumes a 30-unit portfolio at about £150 ADR and 65% occupancy (about £1.07M a year in room revenue), over one year.
By application, for founders who want a sounding board rather than hands-on delivery.
Giacomo works with a maximum of 5 clients at any time, one dedicated day per week per client. Limited availability.
“Jack (Giacomo) disrupted our business and we couldn't be happier.”
Five years inside Booking.com. Three years at Guesty delivering 500+ global projects. A portfolio of 3,000 luxury villas at Oliver's Travels. Now independent, helping operators build businesses that scale.

6K+ operators and industry peers follow along on LinkedIn.
Spent five years inside the world's largest OTA learning how distribution, algorithm and commercial strategy actually works, from the platform side.
Managed a portfolio of 3,000 luxury villas across Europe and beyond. Operations, revenue, owner relationships and guest experience at serious scale.
Implemented over 500 Guesty projects across 40+ countries. Built operational playbooks now used by some of the largest STR operators in the world.
Independent STR consultant. Deploying everything learned inside those three organisations for growth-minded operators.
Revenue $1.2M to $1.7M in 1 year, through new distribution channels and smarter revenue management.
Read the case study →Guesty implementations across 40+ countries, 2021 to 2024.
Operations set-ups that took client projects from 40 to 500+ listings without operational breakdown.
Airbnb and Booking.com are distribution tools. Treating them as your entire business limits your growth and margin.
Most operators underinvest in operations software. A well-configured PMS pays back in staff hours within the first quarter.
I've never met a failing STR operator who wasn't working hard. The issue is almost always a systems gap, not a motivation gap.
A pricing tool is one input. Real revenue management touches pricing, LOS, distribution mix, and demand forecasting together.
Adding units without fixing your operational foundation doesn't multiply revenue. It multiplies problems.
If your business requires your daily presence to function, you own a job, not a business. The goal is a machine that runs without you.
The Guesty setup mistakes I find most often when I compare a PMS to what guests see on Airbnb, Booking.com and Vrbo, and how to fix each one.
ReadWhat a Guesty consultant does, when to hire one, and how expert consulting helps property managers optimise PMS setup and scale operations.
ReadPractical playbook for STR operators with 30+ properties, multi-channel distribution, reducing Airbnb dependency and activating direct bookings.
ReadFive quiet mistakes that compound into a revenue ceiling for short-term rental operators, from Smart Pricing dependency to misconfigured dynamic pricing tools, over-automation, stale seasonal pricing, and OTA over-reliance.
ReadHow short-term rental operators and property managers acquire owners: channel economics, acquisition cost benchmarks, churn rates, conversion and retention.
ReadPick a slot that works for you. No forms, no back-and-forth. We'll use the 30 minutes to find your biggest revenue constraint.
See available 30-minute slots and pick the one that suits you.
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Book a 30-minute fit call to find out which system is your biggest constraint.
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