The Story

I've been in real estate related fields most of my life. I grew up in my family's carpentry and home improvement business, swinging a hammer before I could drive. Later, I've spent more than 20 years in the mortgage business, focused mostly on first-time buyers with credit or financial situations most lenders wouldn't touch. I also helped build and scale a rent-to-own PropTech company, where we bought homes for people who couldn't qualify for a traditional mortgage. We built individual credit action plans and coached them toward successful homeownership.

In the middle of all that, I am also a landlord — at one point, owning 15 long-term rental units personally, all close enough to home that I could handle most of the repairs myself, or at least supervise, even with a property manager in place.

In 2021, I bought a my first short-term rental over 800 miles away.

I hired Vacasa to handle everything — bookings, guest issues, repairs, all of it — for 25% of the rent. Six or seven months in, they told me the service plan I was on was being discontinued, and I'd need to either switch plans or end the relationship. At eight months, I flew out and inspected the property myself. What I found was enough to make the decision for me — I terminated the contract on the spot.

The property isn't in a populous area, and finding reliable contractors out there is genuinely hard. I remember sitting with that problem afterward, wondering how I was supposed to handle guest issues and repairs on a property I couldn't easily drive to — on top of a full-time job, four kids, and a marriage I intended to keep intact.

At the time, voice AI was mostly being used to cold-call leads and book sales appointments. It seemed obvious to me that it could do something far more useful: actually pick up the phone, actually solve the problem, actually be there at 2am so I didn't have to be. That's the whole reason HelpingRE exists.