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Becoming a Real Estate Angel Investor with Jonathan Wasserstrum

The BiggerPockets Business Podcast
47 min read
Becoming a Real Estate Angel Investor with Jonathan Wasserstrum

Jonathan Wasserstrum, founder of SquareFoot likes to say that he was working in PropTech before PropTech was a thing, and he’s right! For the past few decades, many industries were seeing expansive growth, new ideas, and upgraded technology. One of the industries that didn’t see that tech growth was real estate.

Jonathan found that many commercial real estate customers were looking for a consumer-facing option to view commercial spaces from the comfort of their own homes. Why were there so many residential real estate sites, but no commercial real estate sites? That’s where Jonathan’s company SquareFoot came in!

SquareFoot took off and over time was becoming a staple product for those looking for commercial real estate spaces. Due to its success, Jonathan was in a great position, which allowed him to become an angel investor for real estate deals and different startups, passing on his knowledge and capital to other new businesses!

Jonathan talks syndications, funds, and investing as a whole. For any investor who wants to see their industry grow and advance forward, Jonathan is a great success story showing you have the power to change your industry for the better!

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Listen to the Podcast Here

Read the Transcript Here

J:
Welcome to the BiggerPockets Business Podcast, show number 86.

Jonathan:
As a founder, do you know what you’re getting yourself into? Which is both that your balances start running a marathon. You have no idea how long that marathon is going to last, and by the way, most days, while you’re running that marathon, you’re going to get punched in the face.

Recording:
Welcome to a real world MBA from the school of hard knocks, where entrepreneurs reveal what it really takes to make it. Whether you’re already in business or you’re on your way there, this show is for you, this is BiggerPockets Business.

J:
How’s it going, everybody. I am Jay Scott. I’m your co-host for the BiggerPockets Business Podcast, and I am here again this week with my beautiful co-host and my beautiful wife, Carol Scott, how are you doing today, Carol?

Carol:
Oh, doing so well, and thank you for always talking me up, I appreciate you more than you know. I’ve got to tell you, we are closing in on the end of 2020, and we have some absolutely awesome guests lined up for the rest of this year, and on into 2021. We are always looking for more entrepreneurs, business owners and founders with great pro tips.
If you’ve got a great story to share with actionable advice, we’d love to hear from you. If you’d like to be on our show or know somebody else who would just go to biggerpockets.com/guest. That’s biggerpockets.com/guest, we would absolutely love to hear from you.

J:
Absolutely. We have a great show today. We have another show that I refer to as Real Estate Adjacent, meaning it’s related to real estate. The person we have on is not a real estate investor, but he runs a real estate related business, and actually he is a real estate investor in a way, he invests in real estate businesses. On this episode, we talk about both.
His name is Jonathan Wasserstrum. He is the founder of a company called SquareFoot. SquareFoot, they’re a marketplace. They’re a marketplace that brings together commercial real estate owners and companies that are looking for commercial real estate space. He brings the two together in a way that’s so much more efficient than was possible in the past, and he does it using technology.
Jonathan is a big fan of property related technology. There’s an industry that’s been growing over the past decade called prop tech or property technology, which is essentially, this whole emerging industry of technology related to real estate. In addition to running SquareFoot, which is a prop tech company, Jonathan also is an investor in other prop tech companies. He’s essentially an angel investor. He’s one of those people that makes investments in early stage companies in hopes that they do well, and then he gets a big return.
On this episode, in addition to talking about the evolution of SquareFoot and what SquareFoot does, Jonathan also talks to us about being an angel investor and how that whole industry works. For all of us real estate investors, it’s actually interesting, it’s very analogous to investing in certain types of real estate. For you real estate investors, I think you’ll like that analogy.
On this discussion, we talk about SquareFoot, we talk about angel investing, we talk about how to get into angel investing. We talk about if you just want to be a small angel investor. I do want to make a quick disclosure, Jonathan talks about his prop tech investing funds, his angel investing fund, Carol and I are investors in his fund. So, I do want to make that disclosure. We don’t get paid anything if you decide to invest in it, or if you decide not to, or if you decide to invest in anything else, there’s no benefit to us. But I do want to make that disclosure that we are an investor in his fund, and that’s how I met Jonathan, and that’s why we chose to have him on the show because he’s a great guy and he has an amazing story.
I am going to say one other thing, if you are sensitive to curse words, Jonathan does use the S word and the F word just a couple of times in this episode. I do want to throw that out if that’s something that’s going to discourage you from listing, please know, ahead of time, and also if you have little kids around and you want to quiet it down, you might want to listen with headphones on. It’s only a couple of times, but I also wanted to mention that as well.
Now, if you want to learn more about Jonathan, more about his company, SquareFoot, or any of the things he invests in, check out our show notes at biggerpockets.com/bizshow86. Again, that’s biggerpockets.com/bizshow86. Okay, without any further ado, let’s welcome, Jonathan Wasserstrum to the show.

Carol:
Jonathan, welcome to the BiggerPockets Business Podcast. We are so absolutely looking forward to hearing your story, learning about all the great things you’ve done and just getting all kinds of great pro tips for our listeners. Thanks for being here.

Jonathan:
Thanks so much for having me, guys.

J:
Absolutely. Jonathan, you have a great background and I think we’re going to touch on a whole lot of really interesting things today. You come from a real estate background in a sense, you come from a business background, you also come from an investing background. Your company has raised a lot of money, but you also invest in other companies as an angel investor. I want to talk about all these things today, but let’s start with your backstory. Tell us, how did you get into the real estate industry? Tell us about your company, SquareFoot that you started a bunch of years ago, and just the evolution of you in the real estate industry.

Jonathan:
Yeah. My quick background, I grew up in Houston, I went to college in Atlanta, lived in D.C. for a handful of years after that, most of the time was doing capital markets work at JLL. This was 2007 to 2010 in a group called the International Capital Group. This is 13 years ago and that group started a handful of years before I got there, because this is now 20 years ago, which is crazy. But at the time it was really novel idea to think that there would be foreign buyers of US real estate and US buyers of foreign real estate.
So, JLL set up this group called The International Capital Group that had a senior and a junior in each of the world’s capitals, right? We were here in D.C., in the States here in D.C., and there was analogous pairs in London, Sydney, Shanghai, and Dubai.
It was awesome. I learned a ton. I had a lot of fun. It was not the most lucrative few years of my life because we were trying to do capital markets work in the middle of the great recession or whatever they called that few years, but it was awesome, and that’s how I got started real estate. I was very fortunate when I started that job, this was, I guess, one of the benefits or silver linings of work not being so fast paced because the markets were slow. My boss let me shadow some other people around the organization.
I got to spend a little time doing some leasing, not actually working transactions, but shadowing some of the senior people in a few different groups. Gave me at a very, very, very shallow level, a lot of experience into what it means to be in commercial real estate. So, leasing, development, our group was capital markets, within capital markets, there was both investment sales, which was buying and selling the buildings as well as real estate investment banking, which was helping put debt on these transactions, and actually a group called Corporate Capital Markets that did big sale lease backs for big corporate users. I learned a ton. It was awesome.
The plan was always to go back to business school, which I did, which is what brought me to New York, got my MBA at Columbia. But shortly after I got here, I got a call from a friend of mine who was looking for space for his last company. He had gone online to try and do that, thought you could find office space online the same way you could find an apartment or house online. Sure as… I can’t say that word-

J:
Sure you can. You can say it.

Carol:
Just say it.

Jonathan:
Sure as shit, you can. My phone rang, “Jonathan, how the heck do I do this?” After a couple of those conversations, we saw there was a whole bunch of pain points that growing companies feel finding, transact and occupying real estate. We decided to fix that with SquareFoot.
It was the summer between my first and second year of business school, which would have been May, June, July, August of 2011, we pulled up in my parents’ attic in Houston, and we started SquareFoot. During my second year of business school, taking classes full time and doing this nights and weekends, we saw there’s enough meat on the bone to continue doing this full time. By the time we graduated, by the time I graduated in May of 2012, we were full-time on SquareFoot, and the rest is history.

J:
SquareFoot is basically, it’s a real estate company, but you help companies find office space. If you were going to use an analogy in the residential world, who are you like in the residential world, but on the commercial side?

Jonathan:
Yeah. Redfin or Compass.

J:
Perfect. You decided to focus on this industry. You started SquareFoot in 2011, you were still in business school. Was this something you were doing part-time, did you raise money? Were you self-funding, did you have a team around you? Was it just you? What did it look like in the early days?

Jonathan:
Early days is me and two guys I knew from home. We self-funded it to build a prototype. I think we’ll talk about this more soon, but prop tech wasn’t a word like VC is more on funding, real estate startups. More importantly than that, we couldn’t convince tech people that the future for them should be in helping us build a real estate tech company. We started by using a firm to build the initial prototype, and then after we did that, we were able to get some initial clients and customers. By that point, the snowball was starting to build, albeit, very small, and then we were able to recruit a CTO to help join us full-time, to help build out the product going forward.
Then we got into an accelerator here in New York called ERA, Entrepreneurs Roundtable Accelerator, the beginning of 2013, and then off to the races since then. That’s technically, we got a few dollars from them, that was the first institutional capital we took.

Carol:
Cool. Real quick, Jonathan, just to help some of our listeners just who might not be quite as familiar with the terminology, what exactly is prop tech, and can you give us some examples of what that means?

Jonathan:
Yeah, I smile because I take a very, very broad definition of prop tech. For me, prop tech is anything that impacts the built environment. Easy stuff is like a commercial real estate leasing platform, like SquareFoot, or on the residential side, Compass or Redfin, who do what we do, except for people buying and selling houses. It can also be like energy management solutions, either for a house or for a building. It can be self-storage marketplaces. That’s a very big and growing part of the world is self-storage. Well, how do you find the self-storage unit that you use? By the way, how do those self-storage providers run their business? There’s a whole software platform for them.

J:
Got it. Property technology is basically any company that’s focused on building technology and infrastructure around real estate.

Jonathan:
Yeah.

J:
Perfect. Okay. You’re still in business school, you’re growing a little bit, you joined an incubator, they give you some money, what’s the next steps? At what point do you say, okay, this is going to be, if not my life’s work, this is going to be my next decade of work, and maybe longer than that, when do you decide to plant that stake in the ground and say, SquareFoot is the place I’m going to focus for the next, however many years of my life.

Jonathan:
Yeah. On some level, I wish that there was actually that conversation never happened, as opposed to, just one foot in front of the next, and now 10 years later, we’re 10 years in. There’s a very, very high mortality rate with startups. By the way, this is not my first startup, it’s my first, even exposure to startups as a way of life, a business, whatever you want to call it. I worked at JLL, which has a 20,000, 30,000, 40,000, 50,000 global employees. It was great place to work. It still is a great company, but it’s not a startup. I had no idea when I was starting this and I didn’t have friends who were in startups.
I grew up in Houston, went to Atlanta for college, New York for business school. This was before startups were popular in New York. I really had no idea what I was getting myself into. I didn’t know… By the way, if you’d ask me, do you want to spend the next 10 years doing this? I think I probably would’ve said yes, but that conversation never happened.
Now, when I sit on the other side of table, investing and advising companies, a lot of whom are prop tech, I do have that conversation with them. As a founder, do you know what you’re getting yourself into? Which is both that you’re about to start running a marathon, you have no idea how long that marathon is going to last. By the way, most days, while you’re running that marathon, you’re going to get punched in the face. Just know what you’re signing up for. Nobody had that conversation with me, which is not somebody else’s fault, I just had no idea what I was getting myself into, but it’s been awesome.

Carol:
Okay. Jonathan, clearly you absolutely have your finger 100% on the pulse of real estate technology. Where are you seeing innovation and technology happen in this space, and what are some of, I guess the current trends that you’re seeing these days?

Jonathan:
It’s a bit of a bullshit answer, but it’s literally everywhere. There’s really not a single portion of the industry that isn’t being touched by technology right now, or where there’s two guys in their parents’ attic or basement or garage, depending on what part of the country they live in, thinking about the next thing. I know you all spend a lot of time on the residential side, I spend a lot of time on the commercial side, there’s three or four other property types that are pretty interesting. If we look at the day-to-day experiences that you have as a client or a tenant or customer, in any of those, if you look at the ownership, the buy sell process of any of those, if you look at the management of any of those, it’s not that silly.
The statement to say that across the board, there’s been almost no innovation in the last 50 years. When you pick up your iPhone or your Android, whatever kind of phone you have, I don’t care, you have 100 apps that do 100 different things. The way you book a plane, completely different. By the way, the way that the airlines do pricing, completely different.
When you want to go from place A to place B, you’re not putting your arm up like a putz on the street corner, you’re pulling up an Uber. How you bank is completely different. When was the last time you walked into a bank branch? You might still do it, but with a lot less frequency than you used to. Not to sound like a 2011 Verizon commercial, but there’s an app for that, for literally everything that’s not real estate. Over the last now, 10 years, you’ve seen a lot of the innovation really in the last three or four or five years, I think everything is in play. Across property types, across geos. I’m friendly with, and we’re investors in a residential brokerage in Korea, residential marketplace in Latin America. As far behind as we are in the US, other markets are even further behind.
There really isn’t something that is being done in real estate that technology shouldn’t be able to do better. That doesn’t mean everybody should be a trillion dollar business, it doesn’t mean every business should be venture-backed, which is a whole separate conversation. But if you wake up in the morning and you’re a tenant, an occupier of any type of space, your life should look different three years from now than it does today. If you’re the owner of that property, your life should look different a few years from [inaudible 00:16:09]

J:
Yeah. I love that. It’s so true, it’s like the pace of technology evolution, well, not… It is obvious, is not just a linear thing these days, it’s very much exponential growth. What we’re seeing over the past year is the same thing that we saw over the past many years before that and what we saw the many years before that was the same growth that we saw in the 50 or 100 years before that.
It’s really interesting to think that as the pace of innovation is increasing, what we’re going to see in just the next couple of years. Can you talk to us a little bit about how SquareFoot has evolved over the last nine years? I imagine just with the pace of innovation increasing what you originally envisioned in 2011 has probably changed a little bit and the original goal of the company might be the same, but I’m guessing your product and evolution has been impacted. What’s gone on over the last nine years?

Jonathan:
Yeah, I couldn’t have phrased it any better, rather. The goal has always been the same, which is growing companies, struggle, finding transact not prime real estate. When we started, we said, let’s just do like Zillow for office space. The main problem that somebody feels is, I just want to see inventory. Again, getting back to that, when you go look for a house or an apartment, you go to Zillow, and then Zillow historically made money selling ad units to brokers, and whoever else wants to get in front of you when you are trying to buy a house.
That’s actually what we started with. We only did that for about six months because we saw pretty quickly, was that even more so than on the side, where everybody still uses a broker, on the commercial side, you need twice as much, because it’s a transaction that’s infrequent, very big. It’s like the second largest line item on your P&L as a company. Granted, that’s an order of magnitude less than your people cost, but it’s still the second biggest expense. By the way, it’s more of a fixed cost than your people, because you can let people go, it’s hard to get out of a lease.
It’s big, it’s infrequent. Because it’s infrequent, it’s not something you do very often, obviously. The markets move and the process of how to do it, it doesn’t change, but it’s not something you’re familiar with. It’s not something that a lot of people in your friend group have done. If you want to buy a house, all of your friends have bought houses or rented houses, or your mom, your cousin, your sister, somebody that you know has gone through that process. That’s not the case with commercial real estate. If you call your 10 closest friends, “Have any of you guys done a commercial lease?” I’m willing to bet that fewer than two of them will say yes.
Then where are you supposed to look for help? That’s why we launched a brokerage, and that was again about six months. Then the last call it three or four years, which now looks [inaudible 00:19:04] or dumb luck, or some combination. Well, actually neither, it’s all based on the data that we get through our system. Flexibility is the future.
Going back, I guess, a little more than two years ago, we bought a company called PivotDesk. PivotDesk, you could think of like Airbnb for office space. We have an office of 8,000 square feet. We’re not using all of it because some of that’s our growth space, and this gets back to great, you have to sign a long-term lease because that’s how the industry sets itself up. Anyway, what do we do with these extra 20 desks? You put them on PivotDesk. We did that.
Middle of last year, or early last year, we launched a program called FLEX by SquareFoot, which is another service that we offer our clients that helps unlock shorter lease terms. Because what we saw, again, from a data perspective, the last few years, even pre-COVID, more and more clients, more and more tenants wanting shorter term leases. Because in commercial real estate, the average lease is five or 10 years, but the way they companies are being built these days doesn’t really lend itself to five or 10 year lease cycles. When we get the big drawing board in the office out, and you say, well, what should we be building from a product perspective, from a service perspective to help our clients solve their real estate needs, how do we do that? That’s PivotDesk helps that, FLEX by SquareFoot helps that.

J:
Got it. You said yourself though, that a lot of us don’t deal in these types of transactions. Your customer demographic is probably smaller than a residential real estate prop tech company. The cycle for leasing office space tends to be longer than residential. Residential you’ll lease month-to-month or more commonly annually. In commercial, it could be two years, five years, 10 years, 30 years for a triple net, but you have a marketplace. Your company is a marketplace, and like any marketplace, you rely on network effects, basically this whole idea of you need a lot of buyers and you need a lot of sellers to come together for your company to gain enough traction, to actually start making a lot of money.
If you can’t get enough buyers, you can’t get enough sellers, the company is not going to gain traction and take off. How do you reconcile this whole, we need network effects in this business, we need lots of buyers, we need lots of people that are looking for leases, we need lots of sellers, people that have commercial space to lease. With the fact that there are fewer buyers and sellers in this space, and the sales cycle, the lease cycle is longer. How did you focus on building those network effects and getting customers on both sides?

Jonathan:
Yeah. One of the things that we’ve gotten very good at here at SquareFoot is aggregating tenant demand. What does that mean? It means that when you’re looking for office space, especially in our main market of New York, we’re about to launch two or three markets the first quarter of 2021. If you’re Googling New York city office space, any of the neighborhood office spaces like Chelsea office space or [inaudible 00:22:02] office space, downtown office space, you’re finding us. Because taking two steps back, what is the customer journey for somebody looking for a space, commercial space? Historically, it’s still, if we look up the block and Midtown, it’s a bunch of kids just out of college, cold calling companies saying, “Hey, do you need help with office space? I’d love to come tell you about the market.” Very, I don’t know if it’s push or pull, but that way, right?
Most things don’t work that way anymore. Everybody, for whatever they want picks up their phone or their laptop and Googles it. When your air conditioner breaks, maybe you’re calling your friend to say, “Hey, your air conditioner broke the other day. Who’d you use?” You’re sure as shit not waiting for the air conditioner repairman to call you saying, “Hey, it’s been pretty hot today, is your air conditioner working in order?” What you’re doing is you’re Googling air conditioning repair, and then wherever I live. That’s where we start.
When you’re looking… Because when you’re thinking about how do you acquire users, you think about, well, if I was a user, how do I want to be a [inaudible 00:23:05] It’s going to be in the comfort of my own office, or the comfort of my house late at night after work, and I’m going to Google, fill in the blank, office space. We built the business from the ground up, making sure that, that works. Luckily for us, that’s not nearly as competitive on the commercial side, as it is on the residential side. We’re also very, very good at it, but it’s also not as competitive.
That’s on the demand side. Then the really nice thing about the commercial real estate brokerage industry or landlords, they love doing deals, and they can only do a deal if they have a tenant. You say, “Knock, knock, knock Mr. Landlord, Mrs. Landlord, I have this tenant. Are you interested?” Demand creates supply in a very nice way for us there.
Now, if I’m being provocative, I’ll say you’re a moron if you don’t have your property listed on SquareFoot. Because do you think more people are going to know about your space if it’s listed on a publicly pasted listing portal or if it’s not? Pretty easy question. It’s a self-serving question, and most landlords know the right answer to that question, thankfully.

Carol:
Excellent. I have to ask though, Jonathan, and I suspect a lot of listeners are wondering the same thing. You’ve talked about your business model. You’ve talked about a couple of new markets you’re expanding into, you’re talking about growing demands on both sides. I’m curious to know what other types of things have you set your company up to do that have enabled you to continue thriving through everything that’s happened in 2020, especially looking into the future when you’re able to expand? What were the differentiators that you built into the infrastructure of your company that have enabled you to keep going and keep growing?

Jonathan:
Look, it’s both tried, but 100% correct, but we have an amazing team here, and that enables you to roll with the punches. If 2020 has been anything, it’s been a ton of punches. Commercial real estate has been very impacted, to say the least. We’ve made a lot of decisive decisions over the last nine months to make sure that we’ll still be here nine months and nine years from now.
Very fortunate to have a president who’s been through, I don’t know, three or four recessions, not to age him too much, because then you can count… Well, it’s four recessions, how old must he be? I remember sitting here in the office, this was early March. We’d already suggested most people start working from home. This was literally the last week before we said, okay, nobody can come back to the office for now. I said, “All right, Mike, what should we do? What have you seen work? How have you managed to get through three or four recessions very successfully at your previous brokerage company?”
That necessitated some really tough decisions, especially early in this, but it set us up well to fight another day, which is really the name of the game. This will not be our best year ever, but with that being said, we’ve made a ton of progress. We’ve brought on… A lot of this is, always, but especially this year is how do you set yourself up for the future? Not so much, like when we’re sitting in June, it wasn’t like, how do we make sure we have an amazing November? We were sitting here in June, it was like, how do we make sure that November 2023 is amazing? Because there’s very little stuff that we can be doing today that impacts tomorrow, but there’s a ton of stuff we can be doing today that impacts next year, and the year after that.

J:
I love that, and I think it’s a great lesson for all entrepreneurs and business owners out there that, yeah, there could be struggles today, but your struggles today are opportunities in the future. As long as you’re thinking long enough term, whether that’s six months out or a year out or three years out, basically there’s going to be opportunities and whatever roadblocks you’re running into today are going to be different roadblocks in a couple of years. Now’s a great time to start preparing for those.

Jonathan:
By the way, if I’ve learned one thing is that there’s always something broken. If there’s one thing I wish somebody told me about when we started this 10 years ago, it’s not like be prepared to wake up and still be doing this 10 years from now, but that stuff broken or on fire is the norm.

J:
Yeah. I love that. Okay. I want to pivot a little bit because we can talk about SquareFoot for a long time. You probably would love to, but I have something else that I’m really interested in. So, I’m going to force you to pivot here a little bit. Back in 2011, you saw an opportunity in this emerging area called prop tech, property technology. You’ve now built a decade old company around this emerging market, prop tech, but you haven’t just done that, you’ve taken a step further and you’ve started investing in other companies that are in this space. You saw an opportunity, not just to build a company around prop tech, but also to become an investor at other companies. I’d like to dig into that, because I know a lot of our listeners have heard this whole idea of there’s venture capital, there’s angel investors, there are these people out there that invest in companies.
We’ve talked in multiple episodes with people who are building companies and getting these investments, but I’ve never had anybody or we’ve never had anybody on the show who is actually one of those investors, somebody that actually invests in these companies. I’d love to get your perspective both for our listeners who are building companies that might want to get investment at some point, I’m sure you can give some insight to them about how the other side works. But also we have a lot of people who are entrepreneurs, they’re investors in the real estate space, and they may be saying, “Hey, at some point I want to get into investing and being an angel investor, being a venture capitalist maybe one day.” I think this is a great topic. Are you willing to go into that line of questioning?

Jonathan:
Happy to. I find them to be very symbiotic with my day job. So, it’s great.

J:
Yeah, and that’s what I see here in this discussion. I guess walk us through your evolution as an investor in other people’s companies. When did you make your first investment? What led you to do that and how have you grown in that industry?

Jonathan:
Yeah. The crappy joke I’ll make is that we’ve been doing prop tech since before prop tech was a word. Winding the clock back, not 2012 when we started, but within a couple of years after that, once… To say we were established is stupid, but once we were a thing and I started having friends and whatever, I would start getting people reach out to me either from my old life in commercial real estate or from business school or friends of friends or whatever saying, “Hey, I’m trying to start… ” I don’t know what they called it the time, but we’ll call it prop tech now. “I’m starting this prop tech company. Id love to bend your ear on what the industry is like.”
I like to learn about new things. It’s as selfish as it is selfless. I’d always take those meetings. Happy to hear about what you’re building. Over a few years, some of these I thought were pretty cool, and they’re reaching out to me for advice. There’s this old joke, if you want money, ask for advice, if you want advice, ask for money.
A couple of these, I said, “Hey, Billy or Sally, I really like what you’re doing. Can I write a small check? I’d love to be a part of what you’re building.” I did that a few times and I learned a lot and it helps me be better at my day job because I get to see what kind of parallel parts of the industry are doing with technology. I get to see just parallel companies being built because I have a sample set of one when it comes to seeing what it’s like to build a company.
It’s having fun and learn a lot. Then just from an evolution perspective, middle of 2018, somebody told me about AngelList. AngelList is a talent platform, which I had already known about, but there’s also the other part of AngelList, which is, I guess we’ll call it equity crowd funding for venture deals. I started participating in some syndicates. Syndicate being, somebody has a deal, not their company, but George’s company is raising capital and then I get an allocation for it and I go take it to my syndicate.
I started participating in a couple of syndicates writing really small checks. Again, learning, having fun. I took a step back and said, “Wait a minute, these deals that I’m participating in, don’t look very different from the deals that are coming to me, the ones that I’m helping out with, why don’t I try and be a syndicator?”
I started doing that the end of ’18. Now, I’ve done probably almost 30 deals in the last, I guess now two and a half years. Most of which have been prop tech, probably three quarters have been prop tech. Then the other stuff, just things I think are interesting and potentially be really big businesses. Invest in a direct-to-consumer meat company called Porter Road. I was a customer first, and then I heard they were raising money and now I’m an investor too. COVID has been very kind to Porter Road.
Actually over the summer, the syndicate didn’t really evolve, but I also launched a prop tech specific fund where with a group of committed capital LPs, investors who say, “Great, I really like what you’re doing here. I now have committed capital to do these same investments, same types of companies, except only in prop tech.” The really special thing is that maybe 90% of my LPs there are real estate and prop tech executives. It makes my life a lot easier, in that I have this brain trust of people across the industry. Again, the industry being residential, commercial, multi-family just everything who know their parts of the world, a whole hell of a lot better than I know their parts of the world.
That helps with sourcing, because there’s always somebody saying, “Hey, Jay and Carol, I have this idea.” Then that winds up on my desk, or there’s something that winds up on my desk and I say, “Hey, this is in this part of the world that you spend all your time in. What do you think of it?” Then the best thing about it actually is after we decided to part of the company, the brain trust can be value value-added investors in a real way. We’ve already made a lot of customer introductions, strike partnerships and all this other stuff. I’m sure you’ll want to dig in on some of that, but that’s been the narrative arc.

Carol:
I love it. Jay is much more well versed in these types of topics. But as we talked about earlier, this is all very new to me, Jonathan, and I suspect it is to a lot of our listeners as well. I’d really like to know, just from a starting perspective, since you’ve done over 30 deals, you’ve launched some of your own funds. Does that mean I, as somebody starting out in this arena would have to have millions or tens of millions of dollars available to invest by myself, or can I somehow become some type of angel investor without having millions? How does that all work together? Just give me some more perspective on that.

Jonathan:
I don’t have anywhere near any of those numbers you just said. Look, the easiest way and the cheapest way you can back angel is syndicates. I’d love to have any of your listeners be a backer of mine. We’ve got more than a thousand backers. All that being a backer means is that you get access to my deals, and there’s a lot of other syndicates that are great too. I’m a member of a lot of other syndicates where I participate, where I’m not the lead. You can get started for as little as $1000 a company.
That’s how I really… I did a few of these deals where I knew the people, the CEOs myself, but I got really active writing those $1000 checks into random companies. Random, not in the sense of like, oh, here’s a company, here’s $1000, but random in that, I didn’t know the CEO of one-on-one.

J:
Yeah. Just to use an analogy that maybe a lot of our listeners will get in the real estate world, we can go out as real estate investors and we can buy deals, and we can spend our own money. We can borrow money and use that money. But for a lot of us, when we want to do big deals, like Carol and I recently participated in a multi-family syndication, it was a $20 million deal. Yeah, we could borrow a lot of that money, but at the end of the day, down payment was $7 million, $8 million. We didn’t have $7 million or $8 million to put in the deal ourselves, so we went out and we started, again, the word you used, a syndication.
This was basically, we started up a company where Carol and I, and a couple of our partners run the company, we’re the general partners, and then we bring in passive investors that pool all their funds and they’re called limited partners. Basically, each one can put in a little bit of money, but at the end of the day, that company has now raised $7 million or $8 million, and all of those limited partners together with the general partners can take that money and put it into the deal.
It sounds like what you’re saying is you kind of do the same thing. You’re the general partner. You bring together all of these investors that can put in a $1000 or $2000 or $20,000, whatever the number is, and at the end of the day, you have this big pot of money that you then take and you allocate to invest in startup companies. Do I have that right?

Jonathan:
99% right.

J:
Oh, okay. Well correct me on the other 1%.

Jonathan:
Yeah. The 1%, and I trip a lot of people up myself included with it. There’s two things, which is the syndicate, and then there’s the fund. The syndicate is opt-in to any individual deal. It’s actually the same thing in real estate finance. It sounds like you all just pulled together a syndicate for a multifamily thing, that was a one-off transaction, and you wrote up a deal memo and you email it to all your buddies and said, “Hey, who wants to pass the chips?” That’s one way to buy, and I do that too on that syndicate side.
Then the other way, which happens very commonly in real estate is you raise a fund, which then you get the commitments up front and says, okay, everybody, this is my thesis. This is what I’m going to do. Put up your chips, and then I’m going to go make us all some money, and that’s what I do for the fund structure.

J:
Got it. On the syndicate side, you say, you’ve talked to the CEO of cool new product LLC. He’s got this technology company and you say, okay, I’m going to raise money for you. So, you start a company that raises money that is specifically to fund cool new product LLC, and the CEO that you know. Everybody that’s investing in that syndicate knows exactly what company their money’s going into, as opposed to a fund where you’re saying, okay, trust me to go do my due diligence, pick the right companies. I’m going to invest in a whole bunch of companies. You put money into my fund, and then you trust me because I have the experience and the knowledge and the connections and the network to go out and deploy those funds in various things.
I might invest in five companies or 50 companies or 100 companies. At the end of the day, your money is going to get doled out across all those investments in the fund. Is that better?

Jonathan:
That’s exactly right. There’s benefits to both the GP and the LP in both of those, both benefits pluses and minuses, rather.

J:
Got it. Let’s say somebody’s listening to this thing. Oh, that’s really cool. I could go out and do a real estate syndicate, buy a 500 unit apartment complex and raise $40 million. That seems like fun. But I really like this idea of investing in companies, and I want to know how to get started doing this. How could somebody… How did you get started, how could somebody that’s listening right now get the… What are the first steps that they would need to take to go out and start one of these, either syndications or funds, maybe you can talk about the differences, and actually assuming they can raise the money, how do they get the relationships with the people they’re investing in and how do they make the decisions on what to invest, and what’s that whole ecosystem look like?

Jonathan:
Yeah. Just like in real estate, everything’s predicated on deal flow. If one of the listers already has great deal flow, and they’re just like, I have more deals than I know what to do with, and I can’t write all these checks myself, that makes sense for you to try and start a syndicate or a fund. More likely, I’m guessing, they don’t, which is… You just have to be in the ecosystem that have it. By the way, the way I got started was I participate in other people’s syndicates. That’s what I would do if I was most people. Happy to have your listeners in my syndicate, and I can also point people to other syndicates that I like as well.

J:
Yeah. That makes sense. I guess again, just using that real estate analogy of investing in big multi-family apartments syndicates, a lot of us started by investing in other people’s apartment complexes, and we were limited partners, we didn’t have any say in it, we would put the money in and we would get our return back, and then we graduate to, oh, okay, now I understand what’s actually going on here. I want to run one of these deals so I become the general partner and I start raising money from other people, and I’m now the operator who makes all the decisions, but I’m pooling money in from other places. I guess it’s a pretty good analogy there.

Jonathan:
Yeah, and that’s exactly right, because… By the way, I’ve never done any GP real estate work, but I’ve done some LP stuff. In real estate, hopefully these famous last words for anybody listening, but it’s really hard to lose all your money in real estate transaction. It doesn’t mean they all perform amazingly, but it’s really hard to buy a multi-family apartment complex for $100 and have it go to $0. It might go to $80, but it’s not going to go to zero.
Most venture investments go to zero. A couple of things to take in to account there is, don’t put all of your eggs in one basket, you should have a very diversified portfolio. Two, you want to be in the good deals. Two things about that one, you should align yourself with people who have access to the good deals. Then two, this gets back to diversification thing, you want to be in as many deals as makes sense, because even the people who do this professionally for the last 30 years, never know which company is going to be the company.
They have portfolios. There’s no VC out there who’s like, yeah, this is my one company. VCs have portfolios of dozens of companies. Even then… By the way, when they first write those checks in those companies, they all have the potential to be trillion dollar businesses. Otherwise they don’t write the checks. These are people who do this professionally and are a lot smarter than I am, and they’re still wrong, 70% of the time, which is not a bad thing. It just means you need to have the portfolio because you never know why companies don’t work. It’s easy after the fact, to be like, oh, this was too early, or the guy was too stupid or whatever. There’s 100 things that can kill a company.

J:
Yeah. That’s one of the things I love about real estate is I know when I get into a deal, typically I can bound my returns pretty well. I know that if things go really poorly, I might break even, or make a little bit of money. Obviously, you can always risk losing some money. If things go really well, I know I might make 10% or 15% IRR. Obviously, diversification is always important. But when I go and do an investment in an early stage startup company, for example, basically every time I read a PPM, a prospectus, or I get involved in a syndicate, I will read the words, you are going to lose all your money. Basically, they want you to know that that is a risk, and in a lot of cases, that’s what’s going to happen.
But by the same token, in a real estate deal, I’m never going to make 100 times my money, I’m never going to make 500 or 1000 or even 5,000 times my money. But in the early stage company investing world, making 50 or 100 or 1000 times your money, it happens. It doesn’t happen often, but it’s also not a never happen sort of thing. You can make 1000 or even 5,000 times your money if you happen to pick the right company; Uber, Airbnb. Can you talk to us a little bit about that whole risk versus returns in the angel investing world. How diversified does somebody need to be? Should I invest in three companies or 300 companies, and should I be expecting to make 5% returns or 50% returns or somewhere in between? Can you talk to us a little bit about that risk and reward?

Jonathan:
Yeah. Actually, AngelList does a lot of good research on this. I think you probably want to be in at least 20 to 30 to have enough diversification there. The way I talk about is like, if you’re going to have… Let’s say you have… This is a lot of money. You have $100,000 that you want to do this. If it was me with $100,000, I would write probably 100 $1,000 checks, maybe 50, call them $2,000 checks. I don’t think I’d write 10, 10s. This is me personally. Everybody has slightly different strategies. By the way, with diversification as… By the way, with public equity stuff and probably real estate private equity to, the absolute best performing funds are going to be concentrated in the winners.
By the way, the absolute worst performing funds are going to be concentrated in the losers. By the way, whoever was writing those checks at the time, didn’t say, oh, I think there’s going to be the losers. I’m going to go bet on them. In my estimation, and I think the math backs all this up, the best chance of having a very good performing portfolio is to be in a lot of deals. That’s one thing. The second thing is expected returns. All I know is you can look at historic performance. The average VC investment goes to zero, the top, top performing funds are literally stupid. I just read something yesterday, Sequoia who is one of the top one, two or three firms, period, they’re an investor in Airbnb, and I think also in DoorDash, both of which are about to go public. They’re definitely an investor in Airbnb, I think. How’s that for a stupid statement. But whatever they’re invested in, in that fund is going to be a 10X fund. Which means if you put in $100, it turns into $1000. It’s stupid.

J:
Yeah, I heard 2020, they’ve already returned 11 times in their fund, which… This is a tough year, this is a year where a lot of companies have gone out of business and yet they’ve returned 11 times the share.

Jonathan:
That’s your 10X, if it’s 11 times… Yeah, that’s 10X. You’re very, very lucky if you’re an LP there. Granted, all their LPs, they’ve been amazing for the last 30 years. All their LPs are nonprofits, I think actually, and that’s one of the things they pride themselves on. But yeah, a 10X return, to be abundantly clear, that’s not 10% return over the life of the fund. Let’s say it’s a 10 year fund, that’s crazy.

J:
Yep. Okay. We shouldn’t expect-

Jonathan:
To be real quick, I’ll do stupid math. If you put $100 into a real estate investment that earned 7% a year, that doubles in 10 years. One goes to two… Here, one went to 10 over that exact same time. Literally, five times as good.

J:
Got it. I assume nobody should expect 10X returns in this. But by the same token, because it’s more risky than real estate, you’re probably expecting more than 5% or 6%, which is what we see in the typical deal, typical cap rate in real estate these days.

Jonathan:
I think if you have a well-diversified portfolio and there’s an asterix there, what is well-diversified mean? I think 10% to 20% is a fair gut check, but over time. 10% to 20% annualized over a bunch of years.

J:
Got it. What is the typical deal… Again, let’s use the real estate analogy. Typical multifamily deal is going to be four to six years before you buy, renovate, stabilize, and then resell the asset. What does an investment in a company look like? Is it a two-year investment, a 20 year investment, somewhere in between?

Jonathan:
I think you should assume five to 10, and the longer, the better, right? Because the thing with real estate versus venture, real estate, the returns don’t compound in a way that they do in venture. In real estate, you buy your multifamily, let’s say it’s a value add multi-family. You put in your new stainless steel appliances, and now it’s worth a whole bunch of more money. On a percentage basis, it’s worth 20% more. So, you refinance out and payback everybody and you’re gaining your coupons going forward.
By the way, you’re getting those coupons because there’s nothing that the multi-family operator can do with that excess cash flow that makes the asset more valuable. However, in venture, you don’t get dividends, because you hope, and this is the case, that the company has much better uses of that extra $100 every year to reinvest in the business, that $100 is now worth $200 the next year and $300 the next year, and $400 the next year.
Airbnb, for an example, an Airbnb is one of 20 or 30 once in a generation companies, that’s a 30 plus billion dollar business, probably the more now. It took them 13 years to do that. At any juncture between here and then, then and now, if I was an investor in Airbnb, I would much rather have Airbnb have $100 than me have $100, because Airbnb was able to show… Because all of this is the power of compounding. Warren buffet talks about till he’s blue in the face, a lot of people talk about the power of compounding, and venture is that.

J:
Right. I might be able to take that $100 in dividend and turn it into $200 in five years. If I leave it in the startup, they could turn that $100 into $10,000 in the next five years.

Jonathan:
That’s exactly right.

J:
Got it.

Carol:
Cool. I have a follow-up question on that, Jonathan. How many deals do you invest in per year, and how do you find them and what are the types of things you are looking for that gives your fun confidence in a company?

Jonathan:
Yeah, a few questions. There’s three things that matter. Let’s start there. The three things that matter with the venture investment is team, product and market. In inverse order, is the market big enough to support a venture sized business, right? The second is that whatever the product is, so the solution that’s being brought to that market, does that product solve the needs of the market? Then probably most important, but they’re all the most important is, is this the team that can do that?
Different people ask in different ways, why is this the team that’s going to win? What secrets does this team know that nobody else knows? That’s going to be something, some secret about the market, and it’s not a real secret, but a secret, why do they know this space better than anybody else? Why are they able to build a product better than anybody else?
When a company checks all three of those boxes, you have the potential for a nice business, and then this gets back to every… Not every, but 90% of these go out of business. That’s why you have to have a bunch of them. Those three things. For me, personally, the things that I have to be vaguely interested… More than vaguely, I have to be interested.
Lucky for me, I think, or lucky for the types of companies I work with, a lot of things interest me, especially when it comes to real estate. Here with real estate, we’re all in the ice ages or maybe the stone ages, I don’t know which one came first, but we’re definitely not in the industrial age. As we were talking about earlier, across property types, across geos, across business models, there’s a ton of really, really interesting innovation happening.
Then for me personally, one of the things that’s really important to have to really like the team. Not just because the team has to be very good at their job, but because if I’m again, involved with a company, I need to be happy if one of them calls me at 11 O’clock on a school night saying, “Hey, I got this problem that I’d like your help with.” If you don’t like the person calling you, you don’t want to pick up the phone. That plus, the investing thing for me is a hobby. If you don’t go… I don’t golf, because this is my hobby, but you wouldn’t go golf with somebody you didn’t want to spend five hours with, even if they’re the best golfer in the world, because it’s not worth it. Same here. If the companies that we partner with aren’t companies that we want to be spending time with, it’s an easy pass, actually.

Carol:
Awesome. Thank you for that. I just want to know, Jonathan, what’s next for… You’ve got so many great irons in the fire, what is next for all of them? What is on the horizon for SquareFoot? What is on the horizon, and coming up for your AngelList syndicates, for your prop tech fund, what is coming up in your world? What’s going on?

Jonathan:
Look, my favorite part about what I… Again, none of this… I didn’t have, I don’t know, they call it a dream board or something. I never had this 10 year vision when I sat down 10 years ago, like 2010 going to business school saying, I want to wake up 10 years from now and have these three things. By the way, if you asked me then my wife, maybe you should listen to this, and not like… I didn’t think I’d be in New York 10 years then when I went to this business school.
I don’t know that I have a 10-year vision board from here. It’s been a lot of chance favors that prepared and I’ve been, I think, very prepared and very lucky with everything. The nice thing also, sorry, I know I went on a tangent there. For me, all three of those things, which really is just two things, which is SquareFoot, and my angel investing are extremely symbiotic. I have seen tremendous returns, not necessarily from a dollars and cents perspective, but also from a dollars and cents perspective with me doing both. Me investing makes me a much better operator. Me investing makes me better prepared when we go through our financing processes, because I know what investors look at and what their hot buttons are and what you need to be speaking to.
Thankfully, for me, my hobby makes me better at my day job. Going back to golf, and no offense to golf, I used to golf, maybe I’ll start golfing again. But if I golf on the weekends, it doesn’t make me better running SquareFoot. Here, doing all my angel investing actually does and vice versa, running SquareFoot makes me better angel investor.
A lot more rambling than you wanted, but going forward I’ve never been more bullish or excited about what we’re building here at SquareFoot. There is an enormous market dislocation, which anybody who’s alive for the last year knows about. Commercial real estate has been very impacted. Market dislocations are really scary, but they’re also the most exciting times, because market dislocations mean opportunity. We could talk about 10 examples of historic market dislocations and the fortune that were made coming out of them. Whether or not we get a fortunate, we’ll see, but there’s a very fun time for us to be doing what we’re doing.
We’re having tremendous success with hiring brokers, both in New York and in new markets. These are brokers extremely experienced, call it 10 to 30 years who’ve been doing things a certain way at the big shops, and they say, it’s stupid that everything in my life is done one way. But when I walk into my office, real estate is still done another way.
then we come knocking on their door and they say, “Oh, this is actually pretty interesting.” We’ve had a lot of success there. We will be launching new markets, which we’re really excited about. I mentioned we have PivotDesk and FLEX by SquareFoot which are options that help services and product that we have here at SquareFoot only, that bring flexibility to the market. We saw this coming. We didn’t think that there was going to be this catalyst with a global pandemic, but it’s not just us, everybody in the industry has been talking about 10 years from now, a third of the world will be flexible. That’s what people were saying at the beginning of 2020, that third, I think have probably grown, and that 10 years has gotten shorted and we’re ideally primed to execute on that in the coming months.
That’s my day job, super exciting. The nights and weekends hobby, look, this is the first core I’ve been doing in the fund, so the syndicate will slow down a little bit because most of this stuff I have always looked at as prop tech. If it’s prop tech, it goes to the front first. It’s working out even better than I thought it was. Getting back to the whole, my life appears to be a lot of chance favoring than prepared, as my grandma says, it’s better to be lucky than good. We have more than 45 LPs in the fund this quarter. It’s like a murderer’s row of real estate and prop tech executives, which has been, like I said, a superpower for the fund. Makes my life a lot easier, what should be even better returns for the LPs, and I think we’re going to have a lot of fun doing it.
For the fund… Well, first off, we’re always accepting new LPs. If anybody’s interested in getting involved in prop tech, I guess we can put that in the show notes, syndicate as well, that we’re looking for a bunch of people to still get involved from the LP perspective, and then we’re always looking for new great companies that are doing new, great things, and like I said, anything that touches the built environment, which is broad and expansive, but a ton of opportunity. We’re still in maybe the bottom of the first inning, as an industry, not as the fund, the fund is in the top of the first.

J:
Awesome. Okay. Well with that said, I think this is a good place to jump into the final segment of our show, which we call the four more. That’s where we ask you the same four questions that we ask all of our guests. That’s the four part, and then the more part, let you tell our listeners where they can connect with you, where they can find out more about you, your company, your fund, anything else you want to talk about. Sound good?

Jonathan:
Yeah.

J:
Okay. I’m going to take the first question. Jonathan, what was your very first or your very worst job and what lessons did you take from it that you still use today?

Jonathan:
I’ve been pretty fortunate from a job perspective, but I’ll say what was my first job was delivering pizzas. This was right after I had a learner’s permit… Sorry, I don’t what they call it, whatever. I was 15 or 16 and I delivered pizzas for a summer, and then part of whatever a year after that in high school was. First off, you’re working in retail, which I think everybody should do at some point in their life, customers likes to complain, everybody likes to complain, and I think that’s an important lesson in life.
You interact a lot of people. I learned that you’re not supposed to use the Parmesan that’s on the table in most places because they don’t clean the insides of it.

J:
Make sure that goes in the show notes.

Carol:
That is fantastic.

Jonathan:
The red pepper flakes are fine, but I wouldn’t use the Parmesan in most pizza places.

Carol:
Very unique piece of wisdom there. I love it. Okay. Jonathan, I would love to hear what is the best piece of advice you have for young entrepreneurs or new business owners that you haven’t shared yet today?

Jonathan:
What I haven’t shared yet today.

J:
Have you told us everything you know?

Jonathan:
No, but my favorite one is that, fucking up is normal.

Carol:
That’s great.

J:
Yeah.

Carol:
That is great, seriously. You’re normalizing fuck up. You just said it, I said it. Yes. You’re normalizing fucking up in business and that’s exactly right. That’s huge.

Jonathan:
That it’s important to know that most F-ups aren’t catastrophic, but they happen all the time. I think the challenge that a lot of people have, by the way that I had until pretty recently, actually unfortunately is not recognizing that was part of it. When I used to make a mistake, I was like, “Oh, shit, I suck at my job.” Nobody else is making mistakes, you just pick up the paper, and everybody’s worth a trillion dollars and they’re hiring a billion people and they’re on these planes looking so happy and here I am, I can’t tie my shoe. But that’s not the case. Everybody struggles.

J:
That’s great. Love it. Okay. Question number three, favorite book, favorite business book or book that you would recommend that our listeners be reading, maybe something that hasn’t been mentioned a million times by a million different people.

Jonathan:
I’m trying to think of any of the cliché answers, Power Broker, which is not about a real estate broker, but it’s about this guy, Robert Moses, who aggrandized a ton of power in New York and essentially built the city. Real Estate Nerds. The book I read recently that I really like is a book called Higher H-I-G-H-E-R, which was about the skyscraper races in the, I guess, late-’20s or early-’30s here in New York with the Chrysler Building, which was built by Walter Chrysler of Chrysler, and then downtown a building call 40 Wall Street, and it was these two architects that were partners and then archenemies, and they were building the two tallest buildings. Then by the way, out of nowhere, you have the Empire State Building, but it’s a really fun book to read. It’s also a historical piece because it talks about the go-go ’20s and then ’30s are not as go go. Yeah, that was a good one, especially for real estate folks.

Carol:
Super, thank you. Okay. I’d love to ask this question of all of us with an entrepreneurial mindset, see where it leads us. What is something along the way, Jonathan, you have splurged on either in your work life or your home life, just however, wherever, whenever, whether it be a thing or an experience that was totally an entirely 100% worth it.

Jonathan:
To my wife’s consternation, I’m pretty miserly. I’m seven months into having a kid, and that seems to be pretty expensive and the best thing I’ve ever have done.

J:
Look, congratulations on the baby, and yes, they get more expensive as they grow up.

Jonathan:
That’s what I hear. Or you have to put them to work. He’s going to have to start doing diligence for me.

J:
Absolutely.

Carol:
That’s right. Got to earn it.

J:
Absolutely. Awesome. Well, thank you for that, Jonathan. That was the four part of the four more, now for the more part of the four more, can you tell our listeners where they can connect with you, where they can find out more about SquareFoot, your company, maybe where they can find out more about your syndicates or your prop tech fund, anything you want our listeners to know?

Jonathan:
Yep. SquareFoot is easy, it’s www.squarefoot.com. As I mentioned, PivotDesk a couple of times, that’s www.pivotdesk.com. I’m trying to be more active on Twitter. That’s @jmwass J-M-W-A-S-S. Actually, you can make it even easier, we can also move it the show notes. But in my Twitter bio is a link to both my syndicate and my fund. I’m pretty active on LinkedIn, not so much in posting, but I check my LinkedIn multiple times a day. So, feel free to connect with me there as well. Then yeah, in the show notes, I’ll give you the direct links for the syndicate and the fund. Would love to have any of you all along for the ride.

J:
Awesome. Jonathan, this has been absolutely fantastic. We appreciate you being here with us, and this has been a great topic. This is something that we haven’t discussed on our show before. So, I know our listeners are really going to get a whole lot out of this. I look forward to having you back in a couple of years to talk about both how your fund is doing and how SquareFoot is doing and growing. Thanks again for being here.

Jonathan:
Yeah, thank you all for having me.

J:
Absolutely.

Carol:
Thank you, Jonathan, great talking with you.

J:
Thanks.

Carol:
Oh my goodness, loved it. Absolutely loved all of his discussions about SquareFoot as well as AngelList. Jay, I think there was one thing Jonathan said… There are so many things, of course, but one thing that resonated with me so well in terms of real estate and prop tech, he said that because of technology, everything in our life has changed so substantially, but real estate really is just done the same. We are at this time right now, where we are on the cusp of prop tech just exploding, and there is so much opportunity at this time. I think that’s really cool.
I also think it is exceptionally cool that you, of course, have been talking about angel investing, you’ve been involved in angel investing for a long time. I, on the other hand, it’s not my thing, that is not my wheelhouse, now my area of expertise, but Jonathan broke it down in a way that now I can understand what you do. I thought it was phenomenal all the way around.

J:
Yeah. I thought it was great too, and Jonathan is somebody I’ve known for a little while, which was the reason I chose to bring him on the show because what he’s doing both with SquareFoot and his investing has been amazing, and he’s a great guy. Yeah, just a fantastic episode and a little bit different than some other stuff we’ve talked about in the past, but in a good way.
Anyway, everybody, thank you so much for tuning in. I hope you have an amazing week and yeah, we’re winding down this year, so go get your Christmas or Hanukkah or other holiday shopping out of the way and tune in again next week, and we’ll see you next week on the BiggerPockets Business Podcast.

Carol:
Let’s wrap this up, baby.

J:
All righty. She’s Carol, I’m Jay.

Carol:
Now, go diversify where you invest your money today. Have a super week, everybody can’t wait to-

J:
Thanks, everybody.

Carol:
… see you soon. Bye.

J:
Bye-bye.

 

Watch the Podcast Here

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In This Episode We Cover:

  • How to start a self-funded venture, even at a young age
  • Why real estate is such a great industry (residential and commercial!)
  • Why startups have such a high mortality rate
  • Why PropTech is so important to investors, tenants, and all real estate professionals
  • Why “flexibility is the future
  • The difference between syndications, funds, and more
  • Why investing can make you a better business owner
  • How angel investors think when investing in a new business
  • And So Much More!

Links from the Show

Books Mentioned in this Show:

Connect with Jonathan:

Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.