Steve Whalen and Fred Starikov | 6 Boston Developers to Watch in 2025

NAME: Steve Whalen + Fred Starikov
COMPANY: City Realty

Steve, Fred, let’s start by taking it all the way back, would what you're doing now have made sense to your 16 year-old self?

Steve Whalen: In college I was a history major, thinking about law school but really undecided. I had an uncle in real estate, so that always intrigued me. I grew up in Maine but couldn't go back after college because there were no jobs. So I ended up in Boston working at a grocery store. A lot of real estate guys came in there and I’d chat with them. It was a bad economy, so they weren’t exactly like “Get in there, kid”. But I studied for my real estate license, started in rentals and moved up from there.

Fred Starikov: My mother actually tipped me off about how the rental business worked. I'd grown up in Allston and you couldn't miss the hundreds of real estate offices around Allston-Brighton. As soon as I had a chance I got my license. 

I thought I had a job lined up through a friend's older brother who had an office, but one of the partners nixed it, so that was a shock. Then I was driving home one day, past this little office in Cleveland Circle and figured I'd stop in. The guy immediately hired me—though later I found out he didn't have authority to hire anyone. But still, I just started going in. The owner wasn't around much so you had to figure it out for yourself how to do a deal. And that’s where I met Steve.

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What kept you pushing through before that first deal landed?
Fred: It took three or three and a half weeks before I made a rental. I was only 18 so no one took me seriously. All the clients were older. But once I broke the ice, everything changed. There was so much opportunity—I could do multiple rentals a day, and they were nice hits for a young kid.

Steve: Yeah, the office definitely had a lack of hiring standards when Fred and I got in. It was 240 square feet, maybe seven desks, but in summer there were 12 agents crammed in. They hired everyone who walked in. It was a fun time. That challenge with older clients was real though, we looked young. Fred especially looked ridiculously young!

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So you were mostly dealing with rentals early on too?
Fred: We were doing everything and anything to make money. Steve was already doing property management and that experience helped us move from rentals into sales. At that time it was managing and selling a lot of student housing—four to eight-bedroom units—which are really difficult properties to manage, but Steve was able to deal with it.

Steve Whalen: Yeah managing student housing was nuts. Every weekend it felt like they were trying to kill themselves. One time I went over and in the basement it looked like blood, like somebody had been tied up. I freaked out and called the cops. But it turned out they'd been filming a movie in the basement. There were endless stories like that, but it all gave me experience for when we started owning property.

Like Fred said, we were doing anything and everything to make money. The office owner had buildings he managed, and when his trash guy quit, I even took over that too.

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And so you guys were a team pretty early on there?
Fred: Yeah so I started in college during the dotcom boom. I'd do rentals in summer, then go back to school. Steve had already worked at the office, then went into commercial leasing at a large company before coming back to residential. After I finished college I went into rentals full-time and we teamed up shortly after at Green Line Realty, which is now long gone.‍

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Got it. So once you’re out of school and working full-time, how did things start to evolve?
Fred: We began leveraging the relationships we'd made with landlords. We started selling property for them and creating investment sales out of that. Even if it meant managing a building for a year, we'd make a big commission selling it later. The numbers were so good that landlords were compelled to invest, and we'd manage or resell it for them.

That built up our bankroll so we could start finding our own opportunities. We started buying condominiums and doing small conversions of existing properties.

Steve: Fred loved to live on the construction site. He'd buy a condo and I'd go over to see him. I remember looking over at a bathroom with no door, and a Ukranian guy was in there smoking while working. I was like, "Hey, what's up?" The place wasn't usable, but Fred was always in the mix.

Fred: Yeah, that was my first place—a studio on Commonwealth Ave near BC. My parents were ten minutes away, so for the couple of days the bathroom was down I showered at their house. 

The 2000 block of Commonwealth was so dead at night I didn't even have parking. I'd just double park my car overnight, get up early, and move it. I’ve racked up so many tickets doing this job over the years, visiting sites, driving around to meet clients, I’d sometimes leave the old ones on hoping they wouldn't give me another. Didn't always work.

Steve: I think he added it up once. It was like a hundred grand over his rental career. His car always had a bouquet of tickets on it.

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That’s funny. So you were both working at Green Line Realty. How long were you there before planning to go out on your own?
Steve: No more than two years. We had a call with the owner while he was skiing in France. We'd just crushed it that month, I think we grossed $100,000 in sales, so we offered to partner with him and grow together. He didn't see the value, so we moved on and opened another office.

Fred: We bought a dormant existing office around the corner, called City Realty Associates, and we changed the name to City Realty Group. There were two years left on the lease, but we knew we could make that back in a month or two and have a roof over our heads. We eventually bought the unit next door too, which was three or four times the size and gave us a proper office.

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So it's the two of you to start. How do you build the business?
Fred: At first we focused exclusively on sales—larger deals, bigger commissions. We filled the office with younger brokers, built a presence across the city, and grew smaller sales listings like condos.

We also sold our own small condo conversions through the office, giving the new brokers deals to cut their teeth on. A lot of offices actually spawned from ours—people worked with us for a few years then went out on their own and often we still did business with them. Plus we were opening more of our own offices.

Then after a few years, we had all these offices and properties popping up and realized it wasn't what we wanted. So we sold some of the offices and transitioned from brokerage to ownership.

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And managing brokers was just too much?
Steve: Yeah, it was like herding cats. Good ones stayed a year or two then left. We were always rebuilding the team. We got tired of it and decided owning real estate was the better path. The challenge was making that switch to what's essentially a different business while supporting ourselves during the transition.

How many years in were you when this switch happened?
Fred Starikov: Maybe four. By late 2007 into 2008, the crash hit. Before that, we'd built a pretty good portfolio in Lynn, Massachusetts. It was a long commute, but when Boston was too competitive, Lynn was where we could find larger properties. Some were mixed-use—retail and office as well as residential. We had successes, like taking a 50% occupied building to 98% and then selling it.

Steve Whalen: Before that we landed a 32-unit building in Brookline. We got it at a good price, but the owner wanted to back out after getting a higher offer from Harold Brown  the next day. There was some litigation, but we eventually settled. 

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How did you actually manage to hold that deal together?
Fred: The bank initially agreed to finance both the purchase and construction, then backed out of the construction and said we had to put more down. But we still had to close.

The litigation was resolved when we reached a settlement. As part of the agreement, the sellers kept their two units—about 4,000 square feet with beautiful city views. We adjusted the price accordingly, and everyone was satisfied with the outcome.

But we didn't have construction financing. We didn't have the cash to fix up all the units. It was a tight time—other investments weren't performing well either. We sold some assets, raised money, and focused on interior renovations.

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Was that a turning point in how you thought about what to renovate and what to leave alone?
Fred: Definitely. We cobbled it together and started selling the units as condos. Then we found out Brookline buyers often prefer to renovate themselves. We realized that for us, it wasn't worth doing a high-end renovation. Sometimes just painting, redoing floors, fixing common areas, and selling for a little less was faster and more profitable. It was counterintuitive, but it worked. Brookline was—and still is—a strong market.

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So selling that building gave you money to reinvest during the real estate disaster of 2008–2012. What did that period look like for you?
Steve: We got going before the crash in '08, but tightened our belts through that and came out able to buy a lot of property around Boston. We built up our portfolio quickly with residential—mostly three-families—by assembling partners and investors and buying distressed property across the city and beyond. Real estate wasn't sexy then. 

I remember standing in a foot of water in a basement of a three-family and we'd just bought 10 of these and thinking, are we doing the right thing? All the older landlords told us we were crazy. But we looked at the prices and thought, this is so cheap we have to figure this out.

At that time we got good at zoning, learning how to add value by getting approvals for more units. And then we started building. Without even noticing, we'd become a construction company.

What do you think separates developers who can scale by juggling multiple projects at once, and those who never do?
Steve: It's a lot of different skill sets—hiring the right people and realizing what teams you need. A lot of our people stay for either a couple of weeks or 15 years. We have stellar employees who've been with us many years, some growing into new positions. For example, our CFO started as an unpaid intern while he was at UMass getting his finance degree. He became a rental agent, then moved into the office, and now he's one of the best in the city. Mentoring and giving people runway brings loyalty—and great work.

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What do you think makes people stay with you for the long haul?
Steve: Everybody feels confident to have their voice at the table. There's a book we give to everyone who onboards—Team of Teams by Stanley McChrystal. He refined the approach in Iraq and Afghanistan, trying to get ahead of the problems they faced there. We onboard with that—it's about communication so information doesn't get lost, and making sure we get feedback from everyone. People feel comfortable speaking and making decisions. Once they have autonomy, the company's stronger—we're not answering a hundred thousand questions on things that are already handled.

Fred: It's really hard and expensive to scale. A lot of very talented landlord-developers purposely keep things small. Small staff, doing a lot themselves, operating their portfolio. Maybe they don't have the desire to grow—or they grow very slowly. We took a higher-volume approach, which means you have to scale, expand, hire and manage teams.

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Let's talk about some of the bigger projects in recent years. Was there one in the last 8–10 years that felt like a gamble?
Fred: I wouldn’t say there’s one that felt like a huge gamble, it’s more that we’ve naturally progressed to larger deals—and moved into other commercial sectors. We still do smaller deals.

We have a hotel conversion of an office building we're working on, with the opening about two and a half years away. We also own some bars and restaurants, including a high-end sushi restaurant in Chestnut Hill called XOXO Sushi. We partnered with an amazing chef. It opened about 15–17 months ago and he's already received a lot of awards and accolades.

We also bought a portfolio of bars from a legendary bar owner, Henry Vara. At one point he owned 60–70 liquor licenses in Boston, plus clubs and bars. He was even a co-owner of Studio 54 in Florida. He passed away a few years ago. From him we got some famous dive bars in Boston, and a couple others we later sold off.

That’s very cool. And you’re still investing in offices too, even given remote work?
Steve: Yeah. We still think offices are necessary so people can learn by osmosis, have real team interactions, and bring younger people up in the business. So there's a place for offices. Will it be a reduced market? Yeah. What I fear in Boston is a doom loop where downtown gets uglier and uglier, we're hoping the city takes that seriously with promotion of retail tenants and keeping the city alive through transition.

In class B real estate, which is where we're investing, a lot is getting converted. Not much new is being built. We think supply will reduce and that'll tighten things up eventually. 

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Can you share a bit more on your approach or strategy there?
Fred: We're buying commercial office buildings in downtown and other towns. Some of them we're converting to other uses, but others we're keeping as office. A lot of owners get stuck where they don't have money to do the buildout for tenants or to pay the broker. They can't really rent their space. They're in a catch-22. We're buying these office buildings at 50% of what the current owner paid. Sometimes these are equivalent to 20-years-ago pricing.

It's a precarious market because some buildings have no path. There's too much competition, too much vacancy. If you're in an office park in a suburban town, for example, and nine out of nine of the buildings around you have 50% vacancy and tenants looking to leave, you've basically got a building you're paying taxes and operating expenses  for without tenants. You have to be smart about what you buy.

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I saw on your site it mentioned being a partner to communities. How do you approach that?
Steve: It’s important to us to keep the flavor of the town, so we always want to work with local people and local businesses. For example, Orchard Skate—a respected Allston skateboard company—left for the North End. We courted them back to Allston for one of our projects because they add so much to the area. We also work with local artists. We commission paintings for all our buildings—each floor has a piece. It adds vibrancy and you can see it in the results. Rentals or sales move quicker after that. Listening to what people want in the neighbourhood is key, and it helps support local people too.

City Kids came out of that. What first sparked the idea—and how has it grown since?
Steve: Once we started making a little money, we wanted to give back. The millennials on our team didn't just want jobs, they wanted to contribute, and we really liked that. In the beginning we didn't know what direction to take. But I’d notice in some of our apartments there would be kids without books or computers at home—no fertilizer for intellectual growth. So we started small, buying every child in our apartments a subscription to National Geographic, thinking it might spark their curiosity and discover something that interests them.

From there we looked at other ways to engage. We support all kinds of sports, and because a few people in the office surf, we started surf camps up in New Hampshire at Cinnamon Rainbows. We've been doing that for about 10 years, bringing city kids up there. Some don't even know how to swim—it blows their minds. Even a simple drive out of the city to try something new is huge.

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That’s awesome. What’s the main focus for City Kids today?
Steve: Right now we're focused on financial education. Our mantra early on was that financial education is more important than algebra, because so many kids don't have those basic skills and they fall behind. We've embedded in a number of public schools to engage kids. We have someone who teaches the curriculum twice a week for open periods, and students sign up. It's been really good. At Brighton High, average attendance is 50%, and the ones who show up aren't always engaged. It's eye-opening. Our hope is that Boston Public Schools adopt it as a curriculum once they see results.

We're also focused on arts. They've been neglected, but we believe they're essential for well-rounded development. We've teamed up with local artists for seminars and projects with kids. One project connects with Nepal. In Nepal, if a mother goes to prison, her kids go with her. Conditions are terrible—disease, trafficking, no support. A woman there takes the kids out and puts them into group homes and schools. We've been supporting her for nearly 10 years. Now we're planning an arts collaboration between artists in Nepal and Boston, with kids from both places.

Anything under City Kids you haven't done yet that excites you?
Steve: You just have to know your limitations. Right now, it's a good size—manageable. We've got people working from all kinds of disciplines—education, finance, arts. Finding the right person with the right passion. For example, in our Nepal–Boston artist exchange, we want a good videographer to document it. Boston's full of talent—it's just about finding the right people who get the project.

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Looking ahead—how do you see the trajectory?
Fred: We focus on multifamily residential, rental or condo. Like Steve mentioned, there's been a lot of opportunity in offices, although very few deals make sense right now with high interest rates and construction costs. We've still managed to find enough worthwhile deals, sometimes with conversion opportunities. And then there's City Kids, which we’re always excited about and proud of, so we want to keep scaling the impact of that.