Three years in, operating with
fifteen years of knowledge.
I got into short-term rentals the way most people do: one unit, a lot of questions, and a guest arriving on Friday. The difference was who I learned from. Peter LoPresti of The Stoic Team had already spent more than a decade building one of the largest hosting operations in the country, and he showed me the systems before I had a chance to learn the expensive way.
Three years later I run more than twenty units across Chicago, Indianapolis, Orlando, and Costa Rica. The Chicago portfolio is fully registered with the city, which puts me in a small group of operators who can say that. That is the part I am proudest of, because it is the part most managers cannot do.
Today I take on three kinds of clients: owners who want their property handled, investors who want to buy right and launch legal, and landlords who would rather lease to a licensed operator than a tenant. On the investor side I work alongside The Stoic Team, so the deal analysis and the operation come from the same playbook.
Four things I will not compromise on.
Dynamic pricing that reads the market daily, guest screening that protects the asset, cleaning and maintenance routines built for turnover at scale. Not trial and error at your property's expense.
Regulation is where most short-term rentals die. I start the licensing file on day one and run it in parallel with everything else, so the property earns without shutdown risk.
Local cleaners, maintenance, pricing, guest operations. I have built that stack in four markets and I will build it in yours.
The reviews read the way they do because there is no difference between how I run a client's property and how I run mine.
Licensed, registered, and fully legal. Even in the hardest markets.
Chicago BACP registered, running fully compliant units in the city today.
From first application to final approval. No shutdown risk, fines, or delisting surprises.
BACP · Shared Housing