Keys to the Office | Jonathan Wasserstrum from SquareFoot

The COVID-19 pandemic has made remote work common—but most companies still need physical space, and finding it isn’t easy. You need to find a good broker, see dozens of spaces, and engage in a bureaucratically complicated process that makes the entire experience rather dreadful.

Jonathan Wassrstrum recognized this problem and saw an opportunity to create something better. So he founded SquareFoot, a company that offers businesses a streamlined office space rental experience, which includes comprehensive listings, experienced brokers, and easier paperwork.

On this edition of UpTech Report, Jonathan offers his take on the pros and cons of remote work, current trends in flexible workspaces, and explains why ultimately he feels having a physical office is an important need that won’t go away.

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SquareFoot Founder/CEO Jonathan Wasserstrum began his career in commercial real estate as part of the International Capital Group at industry leader Jones Lang LaSalle (JLL), where he advised foreign and domestic clients on more than $3 billion worth of transactions globally. He attended Columbia Business School, where he earned his degree in May 2012. He also has a BA in Economics from Emory University.

Founded in 2011, SquareFoot is a new kind of commercial real estate company that helps companies solve their office space needs, providing transparent access to inventory, brokerage services, and flexible space offerings. SquareFoot also provides top-of-the-line lease consultations, advises on subleasing spaces, works closely with and recommends reliable vendors to ensure a seamless move, and more. SquareFoot’s veteran brokers always put clients’ needs first.

SquareFoot’s online platform features over 300,000 office listings, with 5,000 new listings posted monthly. The company has executed over 1,300 leases to date. SquareFoot is headquartered in New York City, and also serves 30 other national big-city markets.

DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Jonathan Wasserstrum 0:00
Zillow doesn’t make it better for you to live in your house on a day to day basis, Zillow makes easier to find and transact that house. And we’re that peace of

Alexander Ferguson 0:13
Welcome everyone to UpTech Report. This is our AppliesTech series. UpTech Report is sponsored by TeraLeap. Learn how to leverage the power of video at Today I am joined by my guest, Jonathan Wasserstrum, who is based in New York, co founder and CEO of squarefoot. Welcome, Jonathan. Good to have you on.

Jonathan Wasserstrum 0:30
Thanks for having me.

Alexander Ferguson 0:31
Now, your core product is office space search technology, aiming to give transparency like Zillow has done for residential. Now along with that you’re offering concierge service having brokers in house to help with actual transactions along with technology to make the whole process easier and simpler. Now, for those out there, maybe you’re trying to find office space, whether it’s two desks and a co working or all up to 300 people with 50,000 square feet, this might be a platform you want to check out, though this is unique times and because of the pandemic. And that’s where I’d love to hone in first, Jonathan, of what was the problem you initially saw instead of to solve with square foot. And now how is that change and changing? And we’ll go into then the future of office space. But let’s start, what was the core problem you initially saw?

Jonathan Wasserstrum 1:18
Yeah. And it’s even easier because the core problem, the initial problem is still the same problem, which is, companies need space, and we want to help them right. And the that search, that journey always starts with wanting to actually see what’s available. The same way when you look for a house or apartment, you’re on Zillow. So that’s how we start, we bring transparency to the market with square foot Comm. And everybody needs help with the transaction. So we have a bunch of brokers.

Alexander Ferguson 1:47
What’s the problem not being solved before? Or like, Did you just have a different take on it just it wasn’t easy enough.

Jonathan Wasserstrum 1:53
There was no transparency, that traditional brokerage experience is pretty shitty. No technology. There’s a whole bunch of culture issues that we can get into that aren’t terribly interesting. So we probably won’t get into them. But there’s a much better way to go through the commercial real estate leasing process. And that’s what we bring here at square foot.

Alexander Ferguson 2:13
Gotcha. And would you say that, that the commercial side, I was a lagging on compared to the residential side as far as technology adoption, 10 years on a good day behind sheet. Nice. So that’s your aim to solve that bring technology, make it more transparent, and still offer the concierge part? Because people don’t want to, they still want handheld throughout the throughout the whole process?

Jonathan Wasserstrum 2:34
It’s a transaction you’re not doing very frequently. It’s a big one, it’s messy. Why do by yourself,

Alexander Ferguson 2:40
got it. And interesting that you’re not just doing larger space, even doing co working space.

Jonathan Wasserstrum 2:45
everything right, we get back to that same problem, right, which is businesses struggle, finding transacting and occupying real estate. And we’re here to solve that. And the nice thing for us because of technology, we’re able to do things a lot more efficiently. So we can profitably and economically work a transaction for the two of us when we’re just the two of us in a co working space. And then the nice thing for us is then the two our company grows with square foot. Now I’m talking about myself on both sides of the table here. But it works.

Alexander Ferguson 3:18
The target market that you’re helping is it just New York at the moment.

Jonathan Wasserstrum 3:26
Our main market is New York, we platformers live all over the country, we’ve done deals at all the top 20 markets, most of the top 30 markets. First part of next year, we’ll be officially launching from a brokerage perspective, a couple new markets, which we’re really excited about.

Alexander Ferguson 3:43
Awesome. Now, transitioning to the second part of conversation where a lot of people’s minds are, what is the new type of mindset when it comes to office space, both small, mid and enterprise. We’ll start off with what you have heard and seen, we can dig into what does that look like?

Jonathan Wasserstrum 4:03
We’ve heard and seen everything, especially if you look, I don’t think the past and the future look too terribly different. They look different. But it’s not like there was not this tidal wave of change that’s washed over us. I don’t think that the average person wants to work from home. I think the average person wants to work in an office. I don’t necessarily think the average person wants to work in the office every day. And that’s before we even talk about like, how longer commutes and all this other stuff. But I don’t believe that the average person now I’m gonna say something provocative. The average person who wants to do a good job at their job, if they’re being honest, thinks that they’re doing that best in their pajamas, on their couch or even in their home office.

Alexander Ferguson 4:57
That I like you said that it could be a A provocative question because there’s there are some people that may disagree with that. But I would agree that that’s not everyone’s.

Jonathan Wasserstrum 5:07
And by the way, if that’s actually how you think you do the best work, then that’s where you should work. I don’t believe most people do their best work in their pajamas on their couch. That doesn’t mean there’s not a ton of benefits working from home, I get to see my seven month old kid like six times a day, when I go into the office Tuesdays and Thursdays, I don’t. So that sucks. I really like my seven month old kid. I’m a lot more productive in the office. So there’s trade offs. And I the thing that pisses me off about this whole conversation, not the one you and I are having, but the conversation that we are having, which is that there’s no perfect solution. And both have trade offs. inviting people who think remote is the future, say, Oh my god, you know how bad it is to work in an office and then you commute and then they like punch you in the face when you walk in the door? And then on your way out, they trip you? And can you imagine that we’ve actually lived our lives like this. as some people like going to the office, some people don’t have, it’s a pretty first world thing to say to which is like, not everybody can like have a comfortable place to work from their home or their apartment. And then the people, you don’t have too many people yelling from the rooftops that the offices do, I don’t think anybody believes that everybody should be back in the office five days a week

Alexander Ferguson 6:26
going forward. That leads us nicely into this next part. I mean, I’ve been speaking to as far as the tech side companies, throughout this year, through apptech. And I’ve been kind of sneaking in that question every once in a while. So what’s your plan? I what is next year look like? Are everyone coming back? What is it? And the most common answers is a hybrid. And I think it sounds like everywhere, it’s just gonna come back to a hybrid model. So looking at that for a moment, what do you think is the realistic? Kind of next step? Are people going to change? Either the quantity of space they have like the the size of the space? They’re going to have more? more locations and different places?

Jonathan Wasserstrum 7:08
I don’t know yet. Right. My job to note, I don’t know yet. So I think it depends on the size of business. Like if I have a seven person company? Do I have three offices? I don’t think so. Okay, if you have a 17 person company, do you have two offices? Probably not at 70. Also, probably, if you have like, so we’re a 70. We were pretty COVID, a 70 person company. And we actually were remote in the sense that not everybody was in New York, we had an office in Belfast, who worked out of an office in Belfast. So we believe that talent is everywhere, not just in New York. By the way, we had a woman who was working with us here in New York, and she wanted to move to Seattle for personal reasons. And she still worked with square foot when she lived in Seattle. So I, we’ve been doing the remote thing, or hybrid or flight. I mean, everybody makes up words as they go forever. Now, when we just had one person in Seattle, and that person was a designer, and she actually liked working from home, to work from home, otherwise, we’d have gotten her one desk at a we were in Belfast, they wanted to be in an office. So there’s an office. It remains to be seen. But then if I’m IBM, right, and I have I don’t. I have no idea. Like, if you’re a big financial services company in New York, do you now have five offices in like different parts of the city to cut down on commute time? I don’t think so. I think you just have people come in three days a week instead of five days a week. I don’t think JP Morgan is like gonna, we’re out. We live in Westchester. I don’t think JP Morgan opens up a Mamaroneck office. More should they I don’t think

Alexander Ferguson 9:08
you’ve been you mentioned also earlier about, you know, we work or our co working space. Do you think there’s going to be a rise in in CO working space?

Jonathan Wasserstrum 9:17
Yeah, absolutely. Yeah. Look, I think that there’s no better time looking forward. For co working and co working is also one of these like, everybody’s is different definition. I think the rise of flexible space is enormous. I will continue. flexible space can mean what some of your listeners have in their mind’s eye, which is there’s a whole bunch of people in an open office don’t work at the same company and there’s dogs and kegs and stuff. That’s part of flexible that’s not all flexible. A lot of flexible is also you go to wework. There’s a ton of private offices, right for person companies or for person side offices. I think you’ll see a lot more That, by the way, I think you’ll see for 40 and 400 person companies, too, I think more people will want more flexibility. And that was a that was people like to talk a lot of trash about we were one of the things we worked at very well was show that if you offer people, the option between a long term lease a short term lease, they will take a short term, even at a premium, right, they’re willing to pay for flexibility. And that’s only going to increase going forward, especially as there’s really like the question is like, how much does one have to believe that like a hub and spoke system turns into it, where I have like a downtown headquarters, and then siloed offices in the periphery, not like within the same city, but like, great, we’ll put one in Connecticut and one in Jersey and whatever. Two is very new york tri state exam, you don’t have to have that much movement at the margin, to have a pretty seismic impact on what the real estate market actually looks like.

Alexander Ferguson 11:01
Have you seen anybody making decisions now, or fairly recent to make changes,

Jonathan Wasserstrum 11:07
we’re seeing more and more people enter the market, and more and more people are getting ready to we’re actually starting to make decisions. And we saw that kind of a couple of no pun intended wave. So the first wave start actually pre vaccine, where, again, not we read on Twitter, or in the New York Times, but there’s a lot of people who wanted offices. And we see that because people when they want offices, leave or not the first day to do is actually not called the New York Times, and not tweet about it, they go online and Google downtown office space. And we saw a bunch of that start to pick up pre vaccine, because I think that first wave of people were tired of the current environment. Right, and then it said, we don’t know how long this is going to be. And we need to start getting back to some semblance of normalcy. We’re gonna look for more space than we might have. And also less, more, because we need more per person, but less because not everybody’s coming back to the offices regularly. And then we’ve now seen another wave post virus started post vaccination, where people like, Great like, by q2, and if q2, this is hopefully everybody’s rearview mirror, by the way, if you’re a company of any size, you’re making real estate decisions, three to six months in advance. So we’re now three months from where, even like, the average scenario plays out. We’re done with this not like done done, but like everybody. Everybody should get vaccinated. But everybody who wants to get vaccinated, vaccinated, a lot of people haven’t gotten vaccinated will be safe by then, hopefully, recovered as well. But you get to this point where enough people either have had it by then four months from now, or have been vaccinated, so that you can now like probably still were masked, by the way, I think masks will be with us for a while. I’m ready to get back, like, closer to what normally used to look like.

Alexander Ferguson 13:19
Interesting, a timeline you shared. So you’re actually seeing that data, even on your own side of the searches and people are looking at this type of stuff.

Jonathan Wasserstrum 13:25
Yeah. Maybe I should start tweeting about that more.

Alexander Ferguson 13:31
Once the people have the data, they need to share that it’s happening because you’re right. When someone is searching, if I was searching for office space, I’m not going to start telling everyone Hey, I want to get back to an office. You’re just gonna be doing it.

Jonathan Wasserstrum 13:42
But remarkably, the people who think that remote is the future don’t stop tweeting about it.

Alexander Ferguson 13:48
Talking about wanting to talk about a change, but not everyone is desiring it and I agree with you feel like there was a certain amount of time it was novelty. It was a novelty. And then you realize, wow, I could really use some quiet dedicated space

Jonathan Wasserstrum 14:06
plus and minuses right. And, look, I have a little less than our key move from where we are into my office now. I’m glad I’m able to do that twice a week and not five days a week. I’m glad that it snowed a lot yesterday usually going on Thursdays I didn’t go in on Thursdays

Alexander Ferguson 14:24
going back to your platform and technology what what do you see is the future though of commercial space office space interchangeably use that when it comes to making it easier what’s the future look like?

Jonathan Wasserstrum 14:41
Um, there’s a bunch of things we don’t spend much time with which is like the day to day occupancy of the space where I’m sure they’re not sure there are tech solutions that are making stuff better there. Look, the stuff we care about is the like, same way think about Zillow. Zillow doesn’t make it better. For you to live in your house on a day to day basis, it makes it easier to find and transact that house. And where that piece of it, that’s where you spend all our time. Luckily for us, there’s a ton of very crappy things that happen between when you say I want office space, and when I get office space, and when you get office space, that gives us plenty of work to keep busy from a fire perspective.

Alexander Ferguson 15:22
What would you say is the most interesting or exciting features that you guys have worked on or released or about to release that you would want to share?

Jonathan Wasserstrum 15:30
Well, I mean, so we’ve been bullish on flexible space for a couple of years now. And we think that only picks up steam coming out of this. We have a product called flex by square foot, we have a platform called pivot desk. Both of which enable more flexible lease solutions for our clients. And as excited as we are as excited as we were about those February 15 of this year, a whole hell of a lot more excited about them a couple days after December 15.

Alexander Ferguson 16:04
Talk about particularly like the the pivot desk is and how does that change? Cuz that’s in the CO working space roller? How’s that? Where’s that play roll?

Jonathan Wasserstrum 16:14
Well, that like? I don’t know, we’ll call it code sharing.

Alexander Ferguson 16:21
co sharing. Okay, because it’s a ticker, you can lease out smaller pieces of it.

Jonathan Wasserstrum 16:25
Yeah, so it’s technically co working has this like, co working when I think of CO working. There’s 50 companies in 300 desks in this like massive open area. That’s not really a pivot desk is pivot desk is I have a lease of 1000 square feet. And where we have kind of 20 extra desks, which is our growth space. And we invite one other company to be our roommate for a few months.

Alexander Ferguson 16:54
And you’re effectively providing an option for people to search through and our list said spaces. Under that

Jonathan Wasserstrum 17:02
pivot desk is both the supply side and demand side. It’s the marketplace, right? So just like Airbnb is going to people who want to rent the house for a weekend and the people who have a house rent that weekend,

Alexander Ferguson 17:12
what’s what’s your competition look like on that type of business model opportunity?

Jonathan Wasserstrum 17:19
Nobody really direct but a ton of indirect right? In the sense that like, when we think about competition, it’s what’s the job to be done, to quote that whatever business cliche, and then how else can somebody go about doing that. So if somebody is looking to go rent 20 desks, they can go to the reorg, they can go get direct space, which we can help them with both of those things? Or the right answer for their real estate solution for the real estate problem might be 20 desks, and cohabitated with one other company.

Alexander Ferguson 17:50
The the benefits of cohabitating with a company versus just getting some space at a co working space. If you look from the one who would want to get it, is there any benefits that you can see the direct benefits?

Jonathan Wasserstrum 18:03
It’s generally cheaper. It’s more personal, right? Then you have one roommate, it’s the difference between like, this is a good analogy, like standard hotel where you have like 50 roommates. And then like, just now we have a two bedroom apartment. Mm hmm. And it’s generally more customized, not in the sense, it’s customized for you with the 20. But like, if you walk in an aisle I, whether you like it or don’t i don’t care, where you walk into work, it looks like we work when you walk into industry. So it looks like an industrial, when you walk into convene. It looks like it could mean they all look fine. But when you walk into 10 different offices, they all run with each other, but they’re not like carbon copies. So

Alexander Ferguson 18:53
as far as then the those who are supplying the space, what’s the benefit for them? Or because I see potential negatives of like, okay, you have another person inside your organization. But I guess it’s the cost benefits, as long as it’s a good fit.

Jonathan Wasserstrum 19:09
Yeah, I’m lucky. I think there’s a lot more benefits than costs. Like I don’t knock on wood. I don’t think we’ve had or heard of many horror stories where like, when you meet the person first and just like roommate, like, probably millions of people find roommates on Craigslist. And there are clearly psychopaths out there, both from a residential perspective and commercial perspective. But anyway, so it’s not really an issue. Now that you have somebody else who’s not you in the space. the plus side is you don’t look at a bunch of empty desks and the plus side is you make a couple of dollars on it. So I mean, look, we’ve been on both sides of it, and we think it’s great. That doesn’t mean just like with everything else. I’ll tell you what I do. I’ve never provided advice and once you say Jonathan, what should I do with my particular situation.

Alexander Ferguson 20:00
Got it. But I appreciate that the lay of the land and if anything going forward, I feel like people are going to look for new options, new solutions, new ways to make it work. versus just a traditional a let’s get off a space for 510 years and and roll with it. Yeah. What if you were to give a word of wisdom to someone that is trying to decide plan, getting a new office space changing just a word of wisdom overall? What would you share?

Jonathan Wasserstrum 20:37
offices are great.

Unknown Speaker 20:43
That period, but yeah,

Jonathan Wasserstrum 20:45
I believe in the benefits of an office, I’m probably biased. But also, like I’ve talked to enough people who are not biased to can’t wait to get back to the office. That doesn’t mean there’s not a lot of people who don’t want to go back to the office, I think it gets back to what we said at the top of the hour, like maybe I should start being more provocative, I’ll get more clicks. But I think the average person when they want to do work, is not doing it from their couch. Which by the way, for more, we’re concerned, like, if everybody starts writing, co working, that’s close to where they live, that’s still great for me. The only that’s not great for me, is if everybody sits on their couch. But I think that’d be bad for everybody because we as a country, we as a society will be less productive.

Alexander Ferguson 21:37
We like to the actual see people and commune with people, we’re human beings.

Jonathan Wasserstrum 21:43
But what they’re saying what people say is that, should you let your HR department decide who you get to see.

Alexander Ferguson 21:53

Jonathan Wasserstrum 21:54
in my opinion,

Alexander Ferguson 21:57
well, I love your very point blank, just how your delivery and not extremely verbose in your answers, but you you say it, how you see it, and I appreciate the perspective. For those that want to check more, you can go to square, correct. Pivot desk,

Jonathan Wasserstrum 22:18

Alexander Ferguson 22:19
pivot And then they can just jump right in what’s a good first step that they can take and what can they expect when they get their instructions? The instructions should be pretty straightforward. Why easier

Jonathan Wasserstrum 22:31
than building IKEA furniture

Alexander Ferguson 22:32
there, which that may be the next step once you get office space to devise some of that furniture as I can imagine the whole technology stack to the whole office experience. Thank you so much John’s for joining us. Definitely go to squarefoot comm to see more of their platform apptech is sponsored by TeraLeap. If your company wants to learn how to better leverage the power of video to increase sales and marketing, head over to and learn about the new product customer stories. Thanks everyone. And we will see you guys next time. That concludes the audio version of this episode. To see the original and more visit our UpTech Report YouTube channel. If you know a tech company we should interview you can nominate them at UpTech Or if you just prefer to listen, make sure you’re subscribed to this series on Apple podcasts, Spotify or your favorite podcasting app.


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