About RentalMind | The operating system for rental managers

RentalMind is the operating system for rental managers.

It puts your property details, SOPs, policies, and team tasks in one place, with Macaw AI Assistant answering your team’s questions straight from your own documentation. It’s built to keep you organized and to make it so your team, your human and AI agents, can support your business as it grows.

An operator and a cybersecurity technologist.

Michael Dinwiddie

Founder & CEO

Operates a Washington Coast rental company, which he scaled from 1 to 25+ properties.
Former Expedia Group employee building customer support systems, so he knows how the largest travel companies operate, and what a small operator actually needs from that playbook.

Michael built RentalMind because he needed it. When his portfolio jumped from three rentals to seventeen in one month, the answers stopped fitting in his head, so he built the system his team could run from. He still does most of the demos himself, and takes Wednesdays off with his kids.

Matthew Weir

Co-founder & CTO

Former CTO of a cybersecurity firm he scaled to eight figures
Fractional CTO of a 250-person European development firm
Advisor to a global non-profit foundation and a $1B+ AUM investment firm

Matthew has spent two decades running technology where an outage or a breach is not an option. He founded Fulcrum Insights, the engineering firm that has built RentalMind from the first commit, and owns the platform’s architecture, security, and AI. His rule: the AI only acts when a person asks.

A team isn’t a system.

Hiring help doesn’t free you. Until the knowledge lives somewhere other than your head, every question still comes back to you.

No team

It all fits in your head.

You know every guest, every quirk, every lockbox code.

With a team

Everything routes through you.

You hired help. Now you’re the bottleneck.

With a system

Your team asks the system.

Answers come from your documentation, not your phone.

“I went to Hawaii and let my team run the business. It kind of blew my mind.”

Michael, three months after going from 3 properties to 17

Three things we won’t budge on.

The build

Built for rentals, not a blank canvas.

Blank tools make you invent the structure, and most people stall at 30%. RentalMind ships with property pages, owner records, SOPs, and task templates on day one.

The AI

Macaw answers from your business, not the internet.

Macaw AI Assistant reads your SOPs, property details, and policies. Your cleaner asks where the water shutoff is and gets your answer, not a text to you.

The company

Human built, with AI in the loop.

Real data security, real user management, a lot of deliberate design. People made every decision. AI helped us move faster. That order stays.