I’ve opened them. Reopened them. Fixed them. And sold them.

2013 — 2026Concurrent operations · U.S. & México

Three businesses at once, in two countries, for eight years.

A 300-capacity music venue with a full staff in Portland, Maine. Fifteen rental units — seven short-term, eight long-term — across the United States and México. Four buildings bought, renovated and sold. Not one after another. All of it live in the same week, with separate P&Ls, separate tax and licensing regimes, and separate failure modes.

For four years I flew to Mérida almost every month to run renovations, then went back to the venue and the U.S. buildings in between. I bought in South Portland while Portland was the market everyone wanted, and in Progreso and Mérida before either was on a list. Every building ran above a ten percent cap rate while I held it — the market moves the exit price, it does not move the cap rate.

• 2021A four-unit I converted into a five-unit. Profitable throughout, sold after three years of ownership for a large six-figure gain.
• 2022A three-unit on long-term tenancies. The market I bought into did not develop for the first three years — I ran it above a ten percent cap anyway, on long rents alone, which is the hard way to get there. It turned the year before I sold. We were moving to México, and of everything I was already running from a distance, this was the one I chose to let go. Two and a half times the purchase price.
• Oct 2024A four-unit run as three short-term units and one long-term tenancy — profitable in operation, and the last of the U.S. buildings. Sold at two and a half times the purchase price.
• Jan 2026A Mérida duplex that had already paid for itself. When the market saturated and revenue softened, I sold it at twice what I paid.

2006 — 2013Owner / Operator

I took over a 140-capacity music venue that could not pay its owner.

I bought in, ran it, and it kept struggling. So I made the call to close for two weeks, rebrand, and reopen — then rebuilt the programming, the systems and the staff from there. Sales grew nearly 300% across seven years of ownership, and I built it to a six-figure owner salary. I added a cold-serve food menu with no kitchen to build it in, and the talent relationships that let a 140-cap room compete against substantially larger venues. By the end I had managers who could run every part of it without me in the building. I ran it until the lease came up in 2013.

2015 — 2022Founder / Owner

Not a rescue. An empty flower shop I turned into a 300-capacity music venue.

Portland House of Music and Events, built from nothing at 25 Temple Street — concept, buildout, licensing, staffing, systems and programming. It became one of the city’s premier independent live-music rooms. I listed it in early 2020 to slow down. It closed seventeen months and reopened in July 2021 with most of the same team back — then sold a year later, on earnings, to a career booking agent and promoter, because I wanted it still standing in ten years.

Between opening and listing it ran at roughly double the industry-average profitability for an independent venue its size, on a team of twenty-plus. I retired the acquisition note early and bought out the minority partner from operating cash. It sold on earnings, after paying me a six-figure owner salary.

The margin came out of how the deals were written. Artists got the better end of the door — splits ran from 60/40 to 100/0 in their favour — and bar was never split with talent, not once in seven years. Guarantee exposure stayed deliberately low, so a soft night cost me a night and never cost me a quarter. On that structure the room averaged close to one sellout a week.