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How Can A Proptech Platform Assist In WFH Whilst Making Underwriting Real Estate Deals Easier? with Roger Smith


In this episode of The Propcast, Louisa talks with Roger Smith, CEO of TermSheet, about how productivity in real estate deals can be maximised through centralised data, workflows and collaboration tools to bring together all functions of a firm, saving time, increasing efficiency and extrapolating data in meaningful ways. 


Key Insights From This Episode

  • The power of Excel and the excessive use of Excel is interesting, but like the amount of insight and data that’s generated, because of my data background, like generated in those Excel spreadsheets is massive and it’s untapped right now. – Roger Smith
  • First and foremost, our core problem we’re trying to solve is to build workflows that help real estate professionals manage their deals better. – Roger Smith
  • So our purpose is really to help them surface insights from their own data. Not necessarily for us as a company to surface insights from their data. – Roger Smith
  • What we’re hearing on is like platform fatigue, where I have to go to all these different places to understand one thing. – Roger Smith
  • When you build a tool inside a private equity firm, it’s great because you have access to all the problems. But that’s not great because you think the world thinks exactly like that. – Roger Smith

About Our Guests

Roger Smith

Roger Smith is the CEO of TermSheet, which he co-founded in 2020. He is a seasoned entrepreneur with extensive experience in technology companies and deep roots in proptech.

Prior to founding Term Sheet, Roger served as Chief Technology Officer for a real estate-focused private equity firm based in Kansas City. He was responsible for the creation and maintenance of internal, advisor-facing,and investor-facing technology systems.

Previously, Roger was chief technology officer at Groundbreaker, Inc., where he built the firms white-label real estate crowdfunding product, which powers a number of current applications. Prior to Groundbreaker, Roger was lead engineer for PlotWatt, Inc., a start-up energy disaggregation technology company, growing the client base from zero to several thousand.

Roger earned a Bachelor of Science in Math and Computer Science from the University of North Carolina at Chapel Hill, was a Researcher in Duke Universitys Computational Neuroscience Laboratory, and earned a Master of Science in Machine Learning from Columbia University.

Sahil Rattan

Sahil Rattan is the COO of TermSheet, which he co-founded in 2020. He spent the early half of his career focused on real estate private equity covering diverse transactions on both the acquisitions and asset management side.

He spent the latter half doing technology investment banking in Deutsche Bank’s San Francisco office focusing mergers and acquisitions, and debt/equity capital raises for leading software businesses.

He holds a Bachelor’s degree in economics from the University of Southern California where he graduated with honors.

About Our Host

Louisa Dickins

Louisa started her career in property working at a well-known estate agency in London. Realising her people skills, she moved over to Lloyd May to pursue a career in recruitment. She now is a Director at LMRE, who are a specialist recruitment firm driven by PropTech and recruitment professionals, and Louisa oversees their 5 core areas. Louisa co-founded LMRE and provides a constructive recruitment platform to the new disruptors in real estate. Louisa is also on the board of Directors at UK PropTech Association (UKPA).

About LMRE

LMRE believe there is a better way to recruit. LMRE focus on a more comprehensive, client led focus delivering exceptional talent to the place at the time. They are passionate about the industry and passionate about people’s careers. LMRE spend time with each client to become and an extension of the business, and their transparency and core values help them grow with the sector. LMRE simplify recruitment and innovate with our clients and evolve the people driven, PropTech community.


Resources Mentioned





Platform Ventures

CRE Tech 

Lincoln Property Company

Episode Transcript

Louisa: Today on the Propcast we will be delving into the future of how to manage and underwrite real estate deals. And we’ll be speaking with one of the co-founders of TermSheet Roger Smith. 

For those listening TermSheet is a single platform for managing and underwriting real estate deals, communicating with lenders and collaborating with partners. And this is previously developed in-house. Which is awesome. Congratulations. You’ve rolled out a standalone platform to help other sponsors and investors, so without further ado, welcome to the show Roger.

Roger Smith: Thank you so much for having me, Lou, I’m happy to be part of the Propcast and I’m excited to talk to you today. 

Louisa: It’s a pleasure to have you. Now, everyone who’s listening to today’s show, we’ll hear about TermSheets mission. We’ll learn a little bit more how the product came to be, where it’s at now.

We’ll talk about how it can help. It’s your better collaboration between employees. We’ll talk about the working from home topic, which everyone’s talking about at the moment. How to extract better insights when it comes down to real estate deals, which I’m sure lots of people listening, and especially in the real estate world, you want to learn how to do.

But for a quick introduction to Roger who is the CEO of TermSheet, she co-founded alongside Sahil in 2020, Roger is a seasoned entrepreneur with extended experience in technology companies and deep roots in PropTech. Now prior to founding TermSheet, fairly recently, Roger served as a Chief Technology Officer for real estate focused private equity firm based in Kansas City.

He’s responsible for the creation and maintenance of internal advisor facing and investor facing technology systems. And before that, Roger was Chief Technology Officer at GroundBreaker, which we’ll hear a little bit more about later. At GroundBreaker, he built the firms white labeled real estate crowdfunding product, which hails a number of current applications.

Roger was involved in various other businesses as well, but I’m going to stop talking cause it’s best to hear from Roger. And from this introduction, it’s very clear that Roger, you’ve obviously had firsthand experience of issues when it comes to underwriting real estate deals.

And hopefully I’ve worked out really how technology can help solve that. So why don’t you start by telling the audience a little bit more about your journey to creating this incredible product and maybe some issues you came into before TermSheet.

Roger Smith: Yeah, it’s funny you say seasoned entrepreneur, that’s like a euphemism for on the slightly older, but, I appreciate that introduction, Lou, and just to give you a quick sort of condensed history of me and how I got here, and hopefully that gives you some insight into how I think about the space. The unique perspective I believe that I bring to our company and the industry as a whole. I went the traditional, what I would consider technology route, study math computer science undergrad, did my Masters in machine learning.

I really was of the belief of, data being like, the internet 3.0 thing, where we were having this proliferation of data. And obviously at some point in time, we’re going to have to make sense of it. And that’s turned out to be pretty true. And from that point on, I was really involved in a lot of traditional enterprise SaaS companies in the productivity space, the energy management space, not really around proptech, actually, this is probably before proptech the term even existed, or, that I even would have considered this as a career path.

As through a colleague of mine from grad school who had come from a traditional real estate background teamed up shortly after the jobs act was passed in the US, which if you’re not familiar with the jobs act, that was really the passage of a bill under the Obama administration that really like unlocked equity-based crowdfunding around the time when angel lists was born, where you could invest in startups. Prior to that, real estate deals were always backroom buddy type of deals, broadcast to the world.

“Hey, I’m raising capital. Come invest with me.” The jobs act really changed that. And so that’s around the time when you saw this, inception of companies like Fundrise, RealtyMogul, CrowdStreet shortly thereafter, this is GroundBreaker.

We were trying to do the same thing. but unfortunately we didn’t have the advantage of syndicating our own deals. We didn’t have our own portfolio that we were essentially being like a matchmaker. And, lesson learned at that time, the people, the sponsors who needed the money or the capital were really the ones who, wanted the money, were really the ones who probably most needed it and maybe at that time, maybe didn’t deserve it. And the people who want to invest in real estate, or had the money to, pretty well understanding of what a good real estate deal looks like. So it was hard to make that sort of match. 

But what was happening was that people were all asking us to do this white label platform to manage your own investments and investors, because we were bootstrapped. That could be a whole another show of how that was. We pivoted to that sort of model, and then that’s where I met the Platform Ventures guys through that relationship. Private equity real estate firm, started by two brothers, very entrepreneurial. 

And I was listening to your previous podcasts. I think it was with Alex and Jack and talking about the difference between entrepreneurial and innovative in the real estate space. And that really resonated. These guys are super entrepreneurial. Real estate investors are really entrepreneurial, and that’s what really attracted me to the space.

They’re willing to go do things, in real estate there’s a lot of money floating around. That’s one of the things like you want to be where money’s being made. I said, wow, this real estate thing is interesting. And that firm, Aqua, hired me to go build another platform within them for helping wealth advisors access quality, real estate. The thesis being if a client of a wealth advisor wanted to invest in real estate, typically the wealth advisor to put them in some publicly traded rate or some sort of fund to funds, without direct access to real estate. So we’re trying to give them direct access to real estate. 

I moved to Kansas city and I really became embedded in this firm, and that’s where I became CTO of the firm. Where solely responsible for guiding, what would now be called the innovations team. But also building tools to help the company as a whole. So sitting with accounting, sitting with legal, sitting with acquisitions and asset management, and really having this perspective of watching them work and learning myself on how large scale commercial real estate gets done.

The last thing I’ll say here is that I think is difficult as an entrepreneur, and why I was particularly interested in starting GroundBreaker is when you have that entrepreneurial mindset, you’re always looking for problems, like looking for gaps in markets and saying, “oh, I can fill that gap or I can solve that problem”.

I think the bigger issue is not having exposure to those problems. So that’s why I was able to work with my colleague at GroundBreaker and then have access to the team at Platform Ventures, really you see things from a different lens and having the opportunity to see, you’re talking about like, we’re moving billions of dollars and that’s how it works.

Louisa: I was going to say, what was one of the most baffling things that you probably experienced firsthand in your career? 

Roger Smith: I’ll talk about this later, but obviously power of Excel and the excessive use of Excel is interesting, but like the amount of insight and data that’s generated, because of my data background, like generated in those Excel spreadsheets is massive and it’s untapped right now.

So that’s one thing. And then also just other smaller things, like how marketing, SCC registered marketing, is done within firms. How money is moved within these firms. How the access controls required to move money and data from properties back to the proforma and the actuals.

Everything’s very manual. But at the end of the day, people are used to doing things a certain way, that’s just how they do it. And so that’s where having the opportunity to live inside of a firm, live with it. Honestly like 20 companies, I could start just from there. 

Louisa: How did you meet Sahil? Talk us through a little bit more through TermSheet, and also how the products changed. So are you in year two and growing the business?

Roger Smith: Yeah. So Sahil was an intern at that firm shortly after I joined. We met that summer.

He finished school and he went back and did a stint in investment banking. Really got the exposure to SaaS business on the flip side, on the investor side, and understanding that part of the business, how they’re valued and underwritten on that side.

So when we had started building TermSheet internally to help the deal team, the asset management team, better manage their workflow and data, we realised that, “Hey, while we build a lot of tools internally this one might actually have some legs beyond these four walls.”

And we had decided we’re going to try to make a business out of this. And I had stayed in touch with Sahil over the years and we reconnected to say “Hey, why don’t you come back and we’ll go take this business outside and go start it on its own. Our first, official thing we did was we went to CRE Tech, in New York in October 2019. And we really just booked as many of those

Louisa: 15 minute chats. Yeah. 

Roger Smith: And talk to anyone and everyone who had talked to us, to try to understand does this thing actually have legs and what do those legs look like? How will this work, what are you trying to solve? And so that was our, really our first thing.

Louisa: I’m glad you mentioned CRE Tech because that’s also where I went out before we officially launched LMRE in the US, and I literally set up 15 minute meeting to startups, the agencies, the VCs to really work out is there like a massive market, and this was obviously pre-Covid. 

Shout out to Michael Beckerman, because I think he’s done wonders for the industry and just connecting people as well. And I can’t wait for the next CRE Tech, there’s one in London and there’s one in New York. I can’t wait to be back out in the states.

Presuming I get double vaccinated and I don’t have to quarantine for two weeks in a hotel room, I think I would drive myself mad. 

Whilst we’re talking about your product, we spoke about this before we hopped on the podcast, you’ve been obviously growing your team, been growing your product, is there any massive lessons you learnt that you can take from the last two years of doing this? 

Roger Smith: One of the things that we pride ourselves on, I learned this when we were at CRE Tech and I think we’ve built it into our sort of company values that holds true today and will continue to hold true, is that having empathy for our customers is really important. And I don’t mean empathy necessarily in the emotional sense of the word. I mean in really understanding the problems they’re trying to solve, and it’s not enough for me to say “I’m selling you this software product, and it’s going to make your life better”, it’s “I want to understand the exact things you’re doing today.” 

We’re looking to shave hopefully like seconds off of people’s time. And what I mean by that is, I think we have this unique perspective of having been part of a private real estate company, and obviously still access to that team, to really understand like all the things that people do. Let’s face it, especially in this COVID world, like we’re all super busy.

So helping people do minor things quicker, simpler with less thought, I think we have this advantage of thinking like that. So I guess to answer your question is, having team members who aren’t just great technology people, or great entrepreneurs, but also have this perspective of coming from a real estate background so they can speak the language, right? That’s super important. And I think it’s been taken for granted where, you talk to groups and it’s “wow, these guys just don’t get it”. So I got to spend an hour trying to educate them on X, Y, and Z.

When one of the things with us is we already know what you’re doing. We understand the tools, we understand the pain points that you’re struggling with and the problems you’re trying to optimise. And so I would say continuing to have members like that, is really important for us.

Louisa: And so obviously you spoke about your own employees. so talk me through with your product. How can it help employees of your clients to collaborate or to get back to this new normal working from home or whatever it means to these businesses. 

Roger Smith: Yeah. We launched at an interesting time, right around when COVID hit. And first and foremost, our core problem we’re trying to solve is to build workflows that help real estate professionals manage their deals better. And so if you’re an investor, that means, from the acquisitions perspective, getting your deals into a centralised platform that gives anyone and everyone on your team, not only your colleagues, but also executives, a perspective on the deal more efficiently, manage the process to make it faster. Consolidate all tasks, documents, and things that go around a deal. Just to make that process more efficient and, easy to report on. So now you think about from that perspective, what is the Monday morning pipeline meeting look like? Because that’s like the classic meeting, right?

Like how does that work over zoom? It’s great now for like probably like TermSheet, you can all be going in the same tool. You can all talk in the same language. You can see the latest status, all the files everything’s there. You don’t necessarily have to have that one person who’s building up all the reports the day of the meeting.

I think in that sense, it really helps. The longer-term thing we look at is building this sort of platform of data, right? So groups, and I’ve experienced this firsthand, have all this data that they’re either collecting themselves or are building data warehouses to collect. How do we surface that information in a place again, where that real estate professional can take advantage of it?

And that’s just on the acquisition side. We’re solving the same problems on the lease management side, the buy-side, broker side, helping all of those groups better collaborate. And then, add mobile to that. Where now you don’t actually have to sit in front of a computer.

When you think about going to site visits, we can help facilitate the process of getting data, pictures and videos back from the site visits back to the tool. So it’s becoming this single platform where all the deals and data can be collected. 

Louisa: Yeah. So on the topic of data, is that any sort of major trends that you’ve extracted from your data, which you’d like to share with our audience?

Anything that you’ve seen in the past two years? 

Roger Smith: Yeah. So, one of theses of the company is that we’re not trying to build a marketplace of our users’ data. So, we look at it, and I get that our clients are very sensitive to that, it’s their sort of Glengarry Glen Ross of leads, right? That is their significant advantage, not just in terms of deals, but in terms of data they may have collected from target assets that they’re looking to acquire.

So our purpose is really to help them surface insights from their own data. Not necessarily for us as a company to surface insights from their data. I will say one of things I can take away from what I’m seeing is that data is very important. And go back to the previous podcast I listened to with Jack and Alex, where, I would say Prop tech 1.0 was all these sort of point solutions, right?

You’re still seeing that today where you have third-party data over here. You have another data set over here. You have another data set over here. What we’re hearing on is like platform fatigue, where I have to go to all these different places to understand one thing.

And then forget about the whole fact that as I’ve mentioned, they themselves are creating their own data sets, that also have value. Maybe even more valuable than any of these third party datasets. And so we are now seeing that firms are recognising that and saying, we need to do something about this. Whether that means that they’re building their own data warehouse internally or trying to find a solution to consolidate all these things.

I think everyone, previously, I would’ve said everyone recognised the value of data, but hadn’t done anything about it. I think we’re now at the point where they not only recognise it, but they’re actually doing something about it.

Louisa: Agreed. And talk us through your sort of partners and clients. And also if there’s any sort of partnerships you’re looking to develop, maybe it’s another part of your product. I don’t know. I’m here to learn. 

Roger Smith: Yeah. I’ll mention this a little bit later, but one of gold clients that we always refer back to is Lincoln Property Company, LPC. They were at their large industrial investor. 

Louisa: Eric Rosen and the team there, fab team.

Roger Smith: Their Chicago office, and I’ll mention her name in a second, but the Chicago office was really one of the early adopters of TermSheet in that sort of January timeframe.

We really quickly brought them on the platform and understood, or worked with them through June of last year to… When you build a tool inside a private equity firm it’s great, because you have access to all the problems. But that’s not great because you think the world thinks exactly like that.

And what we realised after bringing up BC was like, “wow, that was a bad assumption”. And so what we realised from a platforms perspective is that we have to build a plan. It can’t be just an investor management acquisition tool. It can’t be that, we’re building something bigger than that.

We’re building a platform that can help that process, but also help groups manage their data, build on top of, right? And the LPC team were the ones who like really worked with us on that. The LPC Chicago team was really the ones that helped us understand that. And that’s when like June, July is where we were like, holy cow, like the current platforms current assumptions is wrong. 

Like it has to be, not rebuilt from scratch, but we have to build it in a way that’s more flexible. And they’re still customers of ours today and one of our biggest advocates and, our customer referral, we always refer back to them, continuing to grow with them.

They’re bringing on more users. I think, then obviously along with the Platform Ventures team, who is really continuing to support us, was one of the clients that I think almost as like a partner. And that’s how we look at our clients. We have this unique advantage where we can our clients are actually telling us what the deal, right?

Like how many startups are in a position where they’re telling you what you need to do? As opposed to us just always guessing.

Louisa: A lot of what I’ve heard from other of startups I’ve worked with, or I’ve spoken with, is that when a client or partner doesn’t give clear communication and proper feedback, it’s very hard for a business to adapt to it as well. So the fact that you have clients like Lincoln, who are giving you that clear feedback, so you can only improve, that’s amazing. But you have to have that relationship and that crossover the whole time, otherwise, that’s where you start getting a bad reputation or, word spreads quickly that you went into the market to hot and you don’t make assumptions, which you shouldn’t naturally.

We’re coming to the end of The Propcast, but this is coming on perfectly to the LMRE part. So L is lessons you’ve learned. Maybe you have another one other than not make assumptions on market fit. M, mentioned anyone, or another product out there. R is any regrets, and E what are you most excited about the future of PropTech?

So without further ado, if you would like to kick start us. Actually, no we’re going to change the regrets to rewarding, because regrets is too negative. I don’t think we should have regrets, so the R is what’s the most rewarding part of working in prop tech. Kick us off. 

Roger Smith: All right. So lessons I’ve learned, I think I have two lessons and this ties back to what we were just talking about, which is the value of listening.

And I don’t mean just hearing, I mean actually listening to what they say. And I think if you can listen to people, especially in this space, there’s so much value to be extracted from that. Oftentimes like the most valuable tidbits, if you’re speaking to someone for 20 minutes, it might come in three seconds snippet of what someone may have said it.

If you’re zoned out for that three seconds, you could have missed something that would alter the course of your life or your business. And then that’s how we’ve talked our customers. Like we just want to listen and be available while also understanding that they have businesses to run.

Like it’s not their job to be our product team. And then, I think it goes without saying. I think it’s hard when you come from an engineering-like background, like I do is networking. Some people, if they don’t come from an engineering background, like that’s just part of the work.

But when you come from an engineering technical background, like I did, oftentimes networking goes undervalued, right? And especially in this space, it’s a small space. Being, like you said, a standup sort of person listening to people being honest and open. but being out there and, I think is what would be, obviously I encourage someone if they were getting into this would be network.

Louisa: Yeah. It was very difficult for the past year, but I think everyone’s so keen to out there. Right, who do you want to mention? You already mentioned a couple of people.

Roger Smith: Yeah. I already mentioned Platform Ventures and the guys there in helping us get started, continue, go. Lincoln Property Company, especially the Chicago office.

And specifically call out, Jordan and Jacob. So Jordan Kovalsky, I had mentioned her previously. She’s actually now at Faropoint. She continues to make time for us as a company, really aid in our growth like, I can’t say thanks enough.

And obviously her partner in crime, Jacob who is still at LPC is still one of our biggest advocates. We certainly appreciate, their support.

Louisa: Okay. Now what’s the most rewarding aspect of working in Proptech? 

Roger Smith: I’d actually thought about this from the regret perspective. I will say not getting into real estate sooner would have been like one of my biggest regrets.

I think one thing that I have learned in being in this space is that it’s not that hard, right? It’s it’s once you’ve got to understand the basics, underwriting and valuing real estate, you can focused on a specific asset class or a specific thesis and you go all in, like it’s pretty repeatable.

So I would say that’s probably my biggest regret, if I could go back, let’s say getting to real estate sooner. Or if you flip it and say rewarding aspects, I will say it was working with all of our clients, I think is really rewarding and seeing them take a tool that was just an idea a little over a year ago, to actually like building their business on top of, and in fact I’ve been on demos with clients, customer calls with clients and they’re actually teaching me how the product works. Maybe cause like I forgot, I don’t remember that particular feature. So that’s rewarding.

It’s like “wow. I didn’t even know that it did that” or “I forgot, thank you for showing me”. That’s pretty, it’s a pretty amazing feeling. 

Louisa: Yeah. It’s pretty powerful. Last but not least. What are you most excited about for the future of proptech, other than getting out there and actually meeting your clients in person potentially?

Roger Smith: Yeah. Again, I’m a machine learning data guy. So that’s where I love, so you think about what’s happening, in GPT3 on the consumer side and how can we apply those sorts of technologies to all of the data that we’re collecting both again, third-party and internal on the property side.

So I’m really excited to continue to see how machine learning will come into the space. And I don’t mean just from like AVM perspective. I really mean helping groups better understand how to buy assets, but ultimately as well, better manage assets. I think I personally am a big believer in the blockchain, from revolutionising the world perspective.

So I’m excited to see how we can move beyond how we’re thinking about it today. That’s one of the biggest, that’s one of the hardest things I think, to educate groups on is like, what that is and how it can change the industry. And I don’t mean just in terms of the blockchain itself, but like fundamentally change how real estate is purchased.

I’m particularly excited about that. And I’m really bullish on that space 

Louisa: Going into that whole education piece is a whole other podcast. I think there’s a whole other series actually. so we might have to get you back on for that. 

Roger it’s been an absolute pleasure talking through your whole journey. Also what you’re doing in this space as well. And I’m looking forward to hopefully seeing you out in the states in a couple of months, and I will catch up with you after the show, but thank you for joining me. 

Roger Smith: Thank you so much for having me. And I think we’ll hopefully see you at CRE Tech in October. Hell yeah. All right. Thank you so much.

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