Name: Gaetano Morello
Company: High Street Properties
Hometown: Andover, MA
Dream Job as a Kid: Entertainment Lawyer
Tell us about your family business, High Street Properties.
My father started the company in the 70s and focused primarily in the Back Bay, investing and developing what are now considered trophy properties on Commonwealth Avenue and Newbury Street. He has continued to acquire buildings over the years and has assembled a great portfolio. Today, we still focus on multifamily properties. We own apartment buildings throughout Boston and I’m really diving into the historic brownstone world, where I’m buying these brownstones and converting them to luxury condos, predominantly in Beacon Hill, Back Bay, and the South End.
Did you know you wanted to be involved in the family business when you were a kid?
I started working for my father painting fences and turning over apartments when I was a teenager. I always knew I wanted to be in real estate, it’s always been a passion of mine. I love building things and seeing the transformation of properties take place. I was always the kid pulling apart his toys and trying to put them back together, and I feel like that pairs well with what I do now, buying these buildings, ripping them apart, and putting them back together.
Real estate might’ve been pre-ordained, but what was your education like?
I got my real estate license at 18, and started renting apartments to the fraternities at BU. I kind of got the itch for sales and a love for real estate, and after graduating BU, I worked for the family business for a couple years doing condo conversions in Cambridge and Somerville, then realized I wanted to grow, needed to step out and see what I was made of. I moved to New York City and got my master’s in real estate development from NYU, and there I worked for the number one team at Sotheby’s in Manhattan.
You must’ve gotten a ton of experience with luxury listings.
My first exclusive listing was a $12.5 million dollar listing in the West Village, I think I was 24. So I’ve had a lot of experience in different areas of real estate — brokerage, development, investment, even worked for a hotel developer in Manhattan, and played around with retail in Brooklyn and the Bronx, but ultimately decided to come back to Boston to take over the family business. I’ve been back in Boston for five years, and over those years, I’ve worked on several successful brownstone projects, and that’s where I’m at today. I love what I’m doing, and am always looking to raise the bar with each project that I work on.
From frat houses in Boston to Sotheby’s in Manhattan — how tough was it to make that leap?
I was fortunate to have some really good mentors, like Robin and Jeremy Stein at Sotheby’s. I’m a pretty quick learner, I think on my feet, and I’ve always had an appreciation for luxury and an eye for design. I think I was able to pick up those skillsets. I don’t know. Everything sort of fell into place, but breaking into luxury brokerage in New York is super challenging and it can eat you up and spit you out, so you have to find great mentors and keep sharpening the axe.
With such a diverse set of experiences under your belt, how’d it feel to come back to Boston to High Street?
When I came back, I was then a partner or principal at High Street Properties, which was fantastic, so I was taking an equity stake in these deals and fully responsible for the acquisition and development and eventually the sales of those units. I hired brokers for them, but just managing the whole process. In large part, I can thank the time I spent in New York, because when I came back, I incorporated a lot of what I saw in New York into my projects in Boston. I still do, and I try to stay ahead of things in terms of design, the things people appreciate. A lot of the buyers of our properties are usually from New York, which I think is kind of interesting.
Speaking of design inspiration — as you get further removed from your time in New York — how do you stay ahead of the curve on design?
I look towards a lot of established developers and projects going on around the world and see what people are doing. I’m also really close with my design team. We have group chats, and we’re always sending inspo images and having that constant conversation. I love reading Architectural Digest, I love traveling and taking inspiration from places that I travel. I try to keep my head on a swivel and look for cool things to incorporate. We have a Pinterest board for every project we do.
On a project, what part of the process do you love the most?
I think it’s demolition. I like the first month, because I love seeing the bare bones of the building, and the volume of the space. It’s kind of like looking at a blank canvas. It’s a sense of possibility. And then of course, the end — screwing in the lights and polishing the stone. Sending in the cleaners for the last time. But by that time, there’s so much deal fatigue, you’re ready to move on. And I’m always looking, but we’re super specific about the properties we acquire.
What characteristics would make you really chase a property?
It’d probably be a double-wide limestone building between Arlington and Berkeley on Comm Ave, or waterside Beacon Street, with an opportunity to do garage parking, some amazing finishes, great ceiling heights, historic details. Historically significant properties with great bones, gorgeous views, and the potential to create something that’s one-of-a-kind.
When funding a deal, how do you weigh self-funding versus raising capital?
It’s all positive. Even if we go the route of taking on partners, they’re going to be strategic partners — people that we trust and want to build a long-term relationship with. So I don’t think it’d be that different from funding it ourselves.
What do you think separates a mediocre developer from a great one?
To be a great developer, I think you have to be an expert communicator. It’s less about being great at one thing. It’s just like being a film producer. You need to be able to communicate to all the different players, and orchestrate it all. You also need to be decisive. Opportunities come and go and you need to move quick. You also need a great imagination, a strong vision.
Switching gears a bit — are there any particular features that are really helping to move properties right now?
A really great outdoor space. That is so important right now. And in the luxury brownstone world, garage parking and an elevator too. Checking those three boxes, outdoor space, garage parking, and elevators, puts you in a whole other pricing category. People aren’t loving stairs so much. They want horizontal living. That’s a huge value-add, whenever you can buy a wide building, or combine two buildings. That’s one of the most coveted features, specifically in the brownstone world.
Imagine it’s 2032. There’s a new hottest area to develop in or near Boston. Where would you guess it is?
I’m going to say Revere Beach. I think that could be super cool.
If you had to start over in another city in the United States, where would you go? Where do you see a lot of opportunity?
I might go up to coastal Maine. It’s a really beautiful state with some great opportunities. Portland. There’s a lot of tech going there. I think that would be an interesting play.
You’re the founder of the Level Up mastermind group. What’s the spirit behind that?
I find my success comes from my relationships. I thought that building a community of people in real estate who are there to support one another and push each other to succeed is just such a great thing. Having a group of people who you can always go to to ask a question, bounce an idea off of, or get support, is a wonderful thing. And when you’re surrounded by people who are constantly working on themselves and want to take their business to the next level, it’s contagious and it takes you to the next level. They say a rising tide lifts all boats, and I think that’s true with this mastermind group. It’s goal-setting accountability mixed with professional growth in real estate.
How does membership work? Do you need a referral to join?
Yeah, so we take on a few members every quarter. You don’t need to know anyone within the group. You can apply right on the website. We’re just trying to bring on members who fit the fabric of the community we have now, which means getting a diverse range of professionals in different fields. So if you offer something unique and can deliver good value, you have a great shot at getting in.
What’s still on the to-accomplish list for you?
On the residential front, I want the next one to be that much better. Always raising the bar on quality and design. Not necessarily bigger, but something I’m increasingly proud of. Commercially, the next thing for me is to break into the hospitality space. I’d love to do a hotel and enter that arena.
Do you have any words of advice for someone looking to break into the industry?
It sounds cheesy, but you’ve got to believe in yourself. If you want it badly enough, you will make it happen. You don’t even need a lot of capital starting out — you just need to build good relationships with people, work on yourself, work on your communication skills, and you can raise money and find the players. You can enroll people in your vision.
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