New York City moving season is officially here—and if you’ve ever moved in this city, you know it’s not for the faint of heart.
Last year, we shared a three-part blog series covering everything from Prep Before the Move and Moving Day Tips, to Post-Move Strategies, filled with practical insight to help make the process feel a little less overwhelming. But while we know a thing or two about transforming and settling homes, there’s no one who understands the realities of moving in NYC quite like the movers themselves.
So this time, we went straight to the source. We sat down with Matt Fiore of West Side Movers to talk about the biggest mistakes people make during a move, the smartest ways to prepare, and the insider advice that can make the difference between a chaotic moving day and a seamless one. This is the kind of insider knowledge only years of experience can bring.
Jolin: Hi, Matt. Thanks for sitting down with us today. I’m so excited to hear all your insider secrets on how you create such an amazing moving experience for your clients!
“How did you get started in the moving industry, and what led you to where you are today?”
Matt: West Side Movers was founded by my dad in 1972, so I really grew up around the business. Over time, I realized moving is much more than transporting furniture. People are usually going through a major transition when they call us, and the real value is helping make that process feel calm, coordinated, and predictable. Today, a big part of my focus is creating a more thoughtful and personalized moving experience where clients feel genuinely taken care of from the earliest planning stages through final setup.
Jolin: It’s so nice when you can actually connect with a real person through a process as stressful as moving and not just feel like a name on a roster. That’s great.
“What do you love most about helping people through this major life transition?”
Matt: I love bringing structure and calm to something that can otherwise feel overwhelming. A move is often tied to a major life transition - growing families, renovations, downsizing, preparing a home for sale, estate transitions, career changes, or new beginnings. The best feedback we receive is when clients say the process felt easier and more under control than they expected. That’s always the goal.
Jolin: Absolutely! Isn’t that the dream? Ok, I know people want to know…
“What’s the craziest or most memorable move you’ve ever had?”
Matt: NYC always keeps things interesting. One memorable project involved coordinating a large-scale move and staging setup at The Plaza Hotel for a home that was later featured on a Netflix real estate series. Projects like that require a significant amount of planning, timing, and coordination behind the scenes, which is often the part clients never fully see. When everything comes together smoothly, it’s incredibly rewarding for both the client and our team.
Jolin: That’s so fun! Now I want to go find that episode!
“Have you ever encountered an unexpected challenge on moving day? How did your team handle it?”
Matt: Unexpected challenges are honestly part of moving, especially in New York City. Parking issues arise, elevators go offline, weather shifts, or timelines suddenly tighten. The difference is how you respond. Our approach is always to stay calm, communicate clearly, and solve problems proactively before the client feels the stress of them.
Jolin: I can imagine your client’s feel so much better knowing they have a team around them that will keep their cool, no matter what comes up.
“What do clients tend to underestimate the most about the moving process?”
Matt: Most people underestimate how many moving parts go into a successful move. Moving is really a coordination project - timing, access, packing, elevators, parking, building requirements, and dozens of small decisions all happening simultaneously. When nobody is actively managing those details, stress compounds quickly. A well-planned move should feel controlled, not reactive.
Jolin: I couldn’t agree more. There often seem to be so many things that slip through the cracks when there isn’t someone to act as a project manager.
Sage Wisdom: Let the experts handle it! We offer concierge Move Management Services and partner with movers like Matt to make sure every part of your process is taken care of, leaving you stress-free and at peace in your new home.
“If you could give clients one piece of moving advice, what would it be?”
Matt: Start planning earlier than you think you need to. The smoothest moves are always the ones where there’s enough time to think through decisions before things become urgent. Moving day itself should really be the execution of a good plan, not the beginning of one.
Jolin: Yes! Planning ahead is SO important for moving. That’s why I literally wrote the book on it!
Sage Wisdom: Looking for a more detailed roadmap to navigating your move? Our digital guide The New Yorker’s Guide to Moving is packed with expert timelines, planning strategies, packing guidance, checklists, insider tips, and everything you need to make your move feel significantly more seamless and less stressful. Whether you’re relocating across the city or settling into your forever home, this guide was designed to help you stay organized, prepared, and one step ahead throughout the entire process.
“How does hiring a professional organizer before, during, or after a move improve the overall experience?”
Matt: A great organizer can add a tremendous amount of value because they help clients make decisions before the move becomes overwhelming and help the new home function more quickly afterward. Depending on the client’s needs, that may mean decluttering before packing, creating systems after delivery, or helping prioritize key spaces during the settling-in process. When movers and organizers communicate well together, the entire transition feels more seamless and far less stressful for the client.
Jolin: We love working with clients for moving projects. I think they’re actually my favorite kind of projects, honestly. We get to help people set-up their homes up for success and ease from the first day, instead of breaking down old habits and systems that weren’t working. We love moving days!
“Are there any NYC moving insider secrets that most people don’t know?”
Matt: Most people don’t realize that NYC moves are often won or lost before the truck even arrives. Building logistics play a huge role - elevator reservations, certificates of insurance, parking, service entrances, hallway protection, and timing restrictions can completely change how a move needs to be approached. Good planning prevents surprises.
Jolin: Oh my gosh, yes. The last thing you want is zero access to an elevator when you live on the tenth floor and have two hundred boxes and eight rooms of furniture to haul. What a nightmare!
“What do you think makes a moving company and a professional organizing Company such a powerful team?”
Matt: They support different parts of the same transition. A moving company manages the logistics, protection, and execution of the move itself, while an organizer can help clients make decisions and settle into the new space more intentionally afterward. When both sides communicate early and collaborate well, the experience tends to feel much smoother and less overwhelming for the client.
Jolin: It’s always so nice to work with a moving company to fill in those gaps of service that we don’t offer. We pick up right where you left off and settle people into their space like they’ve lived there for years. Eliminating the stress of moving for people feels like such a gift. We’re so lucky to love what we do!
Lightning Round:
Jolin: Freight elevator or fifth-floor walk-up?
Matt: Freight elevator, assuming the building actually reserved it properly.
Jolin: Packing tape: best invention ever?
Matt: Right behind stretch wrap and coffee.
Jolin: Weirdest (but also coolest) item you've ever moved?
Matt: A life-size model DeLorean - the Back To The Future car.
Jolin: Coffee: before a move or during a move?
Matt: Before for planning, during for survival.
Jolin: One word to describe moving in NYC?
Matt: Layered.
A successful New York City move ultimately comes down to preparation, coordination, and having the right team in place. The difference between a chaotic move and a smooth one is often the planning that happens long before moving day arrives.
A huge thank you to Matt Fiore and West Side Movers for sharing their expertise with us for this edition of our Expert Q+A series. Stay tuned for more conversations with professionals who help make homes — and life transitions — run more seamlessly behind the scenes.
Want to know more about our Home Organizing Services, learn all about our process and the services we offer here!
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