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Anshul Ruparell On Raising Over $100 Million To Change How People Buy And Sell Homes

Anshul Ruparell has raised a significant amount of financing and capital for his venture that is transforming one of the biggest and most entrenched markets. His startup Properly has raised more than $100 million in finance from top-tier investors like Silicon Valley Bank, 1984 Ventures, Daniel Curran, and i80 | Group.

In this episode, you will learn:

  • How Properly is transforming the real estate transaction
  • How to pick your investors
  • Going through a major pivot
  • Debt versus equity fundraising
  • The importance of real focus
Alejandro Cremades · EP 312 Anshul Ruparell On Raising Over $100 Million To Change How People Buy And Sell Homes


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Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Anshul Ruparell:

Anshul Ruparell is the co-founder and CEO of Properly.

Properly uses modern technology to accurately predict what a home will sell for on the open market and enables homeowners to sell directly to Properly at that price and to close a sale on their schedule.

Prior to Properly, Anshul Ruparell was an Entrepreneur in Residence and venture capital investor at FJ Labs (an early investor in companies like Airbnb, Dropbox, Palantir, Uber and others), where he led investments and helped build startups including Poncho and Merlin.

Earlier in his career, Anshul Ruparell worked as a private equity investor at the Canada Pension Plan Investment Board and as an investment banker at Merrill Lynch. Anshul Ruparell is from Calgary, and comes from an extensive family background in real estate.

Anshul Ruparell received an MBA from Columbia Business School and an HBA from Ivey Business School.

Connect with Anshul Ruparell:

  • Crunchbase
  • LinkedIn
  • Twitter

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Alejandro: Alrighty. Hello everyone, and welcome to the DealMakers show. Today is very exciting. Today is the very first time that we’re doing this via video, and we have a great founder. We’re going to be learning a lot from building, scaling, pattern recognition. He’s gone from the other side of the table as an investor to now being an entrepreneur. But without further ado, let’s welcome our guest today. Anshul Ruparell, welcome to the show.

Anshul Ruparell: Hi. Thank you so much for having me.

Alejandro: Originally born and raised in Calgary, Canada. How was life growing up?

Anshul Ruparell: Life was good. Calgary is very cold. It goes to 40 below zero in the winter, so that was an adjustment. My parents are both immigrants. They grew up in Africa, and so it took them quite a bit of time to adjust to that, but Calgary, in Canada, is a great place to grow up.

Alejandro: And growing up there to parents that had to build their own future, coming from a different country as immigrants, building their own business, you having exposure to the entrepreneurial life, and the hustling mentality, so how was that for you?

Anshul Ruparell: I saw my parents, my grandparents, and all my relatives build themselves into something from nothing. That was pretty inspiring. I think that grounded me in the type of grit and hustling that it takes just to succeed generally in life, but it was fun. There were some successes, and there were some failures. I’ve been around entrepreneurs from the day that I was born. I think, to be honest, it’s part of what inspired me to do what I’m doing today. A lot of the entrepreneurial work that my family did was involved in the real estate sector. Now, the company that I’m building is trying to transform the real estate industry in Canada, so I think there has to be some cause of that back there.

Alejandro: Absolutely. Looking at them and seeing them going through the ups and downs, what were some of the key lessons that you got from them, from being there with them because you were sharing the same roof? So, you were able to share their good times and the bad times, as well, to a certain degree, so I’m sure you got your lessons from that as well.

Anshul Ruparell: Yeah. There are a couple of things that immediately come to mind. I think the first is that you need to be emotionally resilient to the ups and downs that are the life of an entrepreneur. When things go well, they are euphoric and exciting, and when they go poorly, it can be quite stressful. If you can’t numb yourself to those ups and downs, then it’s going to be difficult to endure in life for too long. I certainly think that I learned that lesson both through osmosis with my family, and then I learned it first-hand as an entrepreneur thereafter. I think the other is that there is an incredible importance in surrounding yourself with the right people to succeed. Knowing where your strengths are and then finding people to complement you where you don’t have those direct strengths is critical. My dad and his brothers are in business together in many parts. They all just played different roles. They divide responsibility with it cleanly, and so I’ve taken a lot of that into the relationships with my co-founders today where if you’re standing on top of each other and trying to do the same thing, it’s going to bring tension and friction and results in you moving a lot more slowly than you would otherwise.

Alejandro: Absolutely. In your case, you did your undergrad. Then after your undergrad, you went at it and did banking. Why banking?

Anshul Ruparell: [Laughter] Yeah. It doesn’t quite follow the narrative art that I would have expected for myself, having seen what my family went through. To be honest and totally transparent, I went and studied business and undergrad, and everyone in my program was going into banking or consulting or accounting. To a degree, I just followed the herd, I think, more than I perhaps should have. I did my first job as an investment banker. I learned a lot, but it was a grueling couple of years. Then I transitioned after investment banking into private equity, where I started to see the opportunity to learn what it takes to evaluate companies and what it takes to work with entrepreneurs and management teams that I thought that actually could just be a good experience for me to learn what it takes to build a company over time. It was my step in the direction to something entrepreneurial. I realized after a couple of years of that, despite the fact that I learned an incredible amount from amazing people and got the chance to see executives and companies both succeed and fail gloriously. I just realized eventually that the only way to be an entrepreneur is to learn by watching others. After a couple of years of that, I decided to go and set out more on my own.

Alejandro: Got it, and that was the time that you eventually met Fabrice Grinda who has also been on the show, and that was coincidentally, as well, with the time that you were in New York City, and you were doing your MBA program at Columbia. So why, out of all the places, did you decide that New York would be a good stop for you?

Anshul Ruparell: I had this idea in my head that I wanted to go and do something entrepreneurial. I didn’t know if that meant I was going to join an early-stage company or if I was going to start a company of my own. But what I wanted to ensure is that I had the opportunity just to be surrounded by people doing interesting things and building. I did my MBA, and so I knew I would be spending part of the time in school, and I wanted to be in a position where I could spend the rest of my time working with companies and entrepreneurs. So, New York gave me the ability to spend literally one day a week in school and then six days a week working with startups. They’re not just startups. I worked with other companies, too, but I ended up taking roles on the side in products, marketing, and ops. I had a sense from these different companies and entrepreneurs as to what it takes to succeed and, in some cases, things to avoid if you want to succeed. It gave me an amazing amount of experience and perspective very quickly, and then I serendipitously met Fabrice Grinda. For those who don’t know, he’s a multi-time entrepreneur, and he’s built, scaled, and sold some very successful companies. He headed the venture capital fund with his partner, Jose Marin, called FJ Labs, who is now one of the preeminent marketplace investment firms globally. I met Fabrice, and I was talking about what I wanted to do, and he said, “You should just come and work for me.” I can teach you what it’s like to invest in companies, and I give you some experience in building them. So I ended up joining the team of FJ Labs in a bit of a hybrid capacity. I spent half my time working with them to meet early-stage entrepreneurs that are raising primarily seed rounds of financing and ended up helping the team make investment decisions and then supporting those companies afterward, so I was involved in investing in 30 to 35 companies over a couple of years. Then, the other half of my time I spent supporting entrepreneurs that were incubating businesses within FJ Labs. Every year after, he supports one or two companies to go and create an idea from nothing and provide them with the financial backing and some of the expertise to do so. I was involved in helping two companies, one of which was Poncho, work with an entrepreneur named Mike Lloyd. He’s amazing, and he was building a D2C and price consumer insurance brokerage focusing on D2C insurance. I think Mike will be the first to tell you that it was a solution in search of a problem. It was a really interesting lesson learned like you have this amazing idea for properties that should exist but forget to talk to users first. No one would actually want to use it. It became very clear that this was a vitamin and not a painkiller and one that didn’t necessarily see a clear path to building a venture-skilled outcome. We ended up shutting it down after a little while, but it was an amazing experience and set of learnings on how to build product, how to do customer discovery effectively, how to build a sales channel when you’re traditional or digital online advertising channels don’t work effectively. Then, after that company transitioned to being sold to an acquirer, there were a couple of other entrepreneurs working at FJ. They were working on this idea for what eventually became a marketplace connecting hourly workers in small businesses. The company is called Merlin and they worked from zero to a couple of hundred employees in a few years, and I was involved in helping those guys in the early stages do that customer discovery work and decided what is my product vision, etc. That was another really amazing experience where I got first-hand, or rather, I got to sit in the passenger’s seat and be involved in some of the early-stage decisions and getting a sense of what it takes to go from zero to one, which was a really rewarding and exciting and fulfilling experience. I think that combination of experience of working with amazing entrepreneurs and then seeing what it’s like to start something from nothing is what ignited the flame while I was at the campuses, but I wanted to go and build a company.

Alejandro: It’s interesting because I think you’ve hit it on every single angle when it comes to deal making, which I’m sure has helped you to develop that pattern recognition, so we if take a look, and we go back through your journey, first, you started with investment banking, so there, you were able to see what really makes a deal click and a deal go forward. Then, you also went into private equity, so a little bit more on the later stage, but you were able to see what it looks like in going through financing cycle to financing cycle to get it to that level. Then, you go all the way to the initial stages, which is what you did with FJ Labs, with Fabrice, which is more focused on the early stages, seed, Series A. So, when it comes to pattern recognition, what were you able to develop during all those different experiences that led you to believe this is what separates something that is going to work versus something that is not going to work when it comes to pattern recognition?

Anshul Ruparell: Yeah. I think that when I came into my experience in the early stage, I brought a lot of experience that was helpful, and a lot of bias, as well. I had seen how to assess success once it’s there: assessing a market opportunity for your business, assessing the economics of the business model with a high degree of granularity. That later-stage company analysis I brought to the table, and that is what I think helped me to build a set of tools to both define and assess successful company strategy, which is really helpful. Then, when I transitioned to early-stage, I realized that assessing a market opportunity is critical, but the path to capture that market opportunity is going to be an indirect one as an early-stage company. What mattered the most is if the people who are seeking to build toward that vision have what it takes to manage the adversity to overcome to attract incredible people to come and work with them. What I came to realize is that when I was evaluating early-stage entrepreneurs and evaluating myself as a potential entrepreneur for co-founders to work with, there were a couple of things that just had to be there. One was an obsession with the customer and understanding their needs and pain points that you can design for them instead of for yourself and superimpose that on my work in the industry. The second is that you need to be an exceptional salesperson. You need to convince investors that they should give you money to go pursue this vision. You need to convince customers that they should take a bet on you to go and even test out your product and service, and then you need to convince amazing people to come and work with you to make that vision a reality, whether it’s to your co-founders to eventual employees. And you need to get people who have the resilience, grit, and drive to get through the inevitable downs that will come alongside the ups in those first couple of years. I think that combination of experience was really helpful to me, and I’m sure there’s a bit of hind-sight here, where I’m able to articulate us a lot better now having been through the experience of building a company for a little while, but I certainly hope that those were helpful lessons that I learned.

Alejandro: Let’s talk about Properly at the point where the idea of Properly really comes into place, and how was that process of incubating the idea, putting the team together, and bringing it to life? What was that like?

Anshul Ruparell: In our third-year anniversary a couple of days ago, it’s nice to reflect back on the early days. I mentioned before that my family are all entrepreneurs. They’re almost all entrepreneurs in the real estate industry. I grew up immersed in this industry my whole life. Then I moved to the U.S., and I realized that despite the fact that the industry’s structure is similar, there had been a lot of innovation in the United States, and there’s been basically no innovation in decades in Canada from the early parts of the home-buying journey where you’re dreaming about that perfect home, and the planning of how you’re going to make that a reality for yourself and actually executing. There’s this incredible amount of information, opacity, stress, expense. It almost seems like you have this industry that has been designed to serve itself more so than it is to serve customers. So it became really frustrating when I started to realize this, and I wanted to go investigate why that was the case, but it became very clear that a lot of this comes down to the fact that no one has taken the big bold step that’s necessary to transform the home buying and selling experience in Canada. So, that’s what really inspired me to go and start to look into potential solutions to go and solve these problems in the Canadian market.

Alejandro: Tell us about what was that event that pushed you over the edge to say, “I’m going to go and do this thing”?

Anshul Ruparell: At the time I was doing this work, the city that I’m from, Calgary, was going through a severe recession. The city itself is highly [13:44] industry. All prices collapsed, and all the sudden, you had the city go into recession. I have a lot of friends and members that had houses, and they were incapable of going through the process of selling them. I realized that for people that have the majority of the network tied up in an asset that are going through the experience of buying or selling something, that would be one of the most significant milestones in their life, it’s so emotional and so personal, and for that process to be designed in such a way that makes it so difficult for them to do the most basic things, and to have the confidence that they can achieve the outcome that they can achieve, it was a problem that I felt this burning drive to want to go and solve. That’s what inspired me to take the first step. Then I convinced my two co-founders, Craig and Sheldon, to join me. I think as you touched on, I bring the depth of experience and finance, and I wanted to make sure that I wasn’t overly biased for that experience. Sheldon brings the experience from operations. He’s part of the team that built and scaled Uber in Canada, and then Craig is the technologist, and he literally invented Blackberry Messenger and was in motion when there were 35 employees until they were at 15,000. The three of us felt like the right group of people to go and try and solve these problems and transform the real estate industry in Canada.

Alejandro: What were the early days like?

Anshul Ruparell: [Laughter] Honestly, they were fun. There are three of us at a desk in a co-working space, and Craig, who is an OG technologist, was coding our first website himself. I was running around trying to get access to the first capital we needed to run the business. Just for context, Properly is trying to create an end-to-end partner for payees as they go through the home buying and selling process. We have these free digital products you can use to go and find your perfect home online where you can track the existing value of your home, like you track the value of your stock portfolio. And we offer services that help you go through the purchase and sell process in a way that minimizes stress and reduces friction. For example, we have a service called Sale Assurance that lets our customer buy their next home first and then sell their existing home later without the listing process. To offer that service, we needed a lot of capital, so I was raising my first credit facility when it was just an idea. We were trying to raise the first capital. We were trying to put together our first operational flows, and it was fun; it was exciting. I had taken something from an idea to reality. I remember our first meetings with customers where it was literally us, the vendors at the kitchen table with our customers saying, “You should work with us to manage your first sale despite the fact that we have no track record and no online reviews.” It’s a very different way of going through a process that you can condition your whole life to believe needs to be done in the traditional path.

Alejandro: Absolutely. I know that the business model has shifted or shaped up a little bit, so where are you guys today with Properly? How do you make money?

Anshul Ruparell: The company has changed a lot. We launched our service focused on a single city, and it has since expanded to multiple cities. We went from three of us at a desk to now 50+ people, and the team has grown quickly. We had another to join us this week and a couple more next week. We make money by providing our customers with the ability to buy their next home and sell their existing home. We get paid when we help them to find their next homes. We get paid a commission like a traditional agent would get paid; then again, we help them sell their existing home successfully. In addition to providing the traditional services that a real estate agent would provide their customer, we provide a number of other superpowers to a customer to make them more likely to achieve their desired outcomes in the purchase and sell. We offer a service called Sale Assurance that lets them buy their next home without any conditions and sell their existing home without living through all the process. We offer a service called Properly Polish to let them get access to a $20,000 interest-free advance so they can get their home renovated before it goes on the markets and can sell for the highest possible price. Over time, we provide additional services like financing, and insurance, and otherwise.

Alejandro: How much capital have you guys raised, Anshul?

Anshul Ruparell: We’ve raised just over $15 million of equity and $100 million of debt.

Alejandro: It’s interesting here because you’re not the typical founder. The typical one that comes up with an idea goes out there and tries to understand the fundraising process because the fundraising process is quite a beast. You’ve got the strategy, you’ve got the psychology, the storytelling, understanding the process. But in your case, you knew all that, so how did you approach the whole fundraising process, and also, what kind of people you knew that you wanted to participate in this journey with you guys?

Anshul Ruparell: I think that in the early days, the thing that matters the most is the quality of the team and the vision when raising that early pre-seed capital just to go and test the initial idea. In our case, it required quite a bit of money just to test the idea because our first business model involved us actually buying homes from customers. But then, at every stage thereafter, what mattered the most was our track record, so if we could take the money the investors gave us and turn it into actual results. On the equity side, that process went pretty well. On the debt side, it meant even more. We went from having equity investors, who all they care about is returning their funds and changing the future, and then investors want to protect their capital; they want to minimize risk. In the case of selling to those investors, the strength of execution and a consistency of our track record is what mattered the most. We operate the business with a lot of discipline. That process was relatively straightforward to go through. If you go to investors and say, “Here’s what we’ve done, and we’re proving it to you.” We wanted to raise our credit facility, and then we spoke to 12 investors, and we see around nine term sheets. On the equity side, it’s a lot more difficult; it’s a lot more of a relationship. It takes a lot of time. In terms of picking the right investors, we always look at where we’re strong as a team and where we can complement ourselves with the strengths and experiences of others. We thought about that both in taking equity investors as well as debt investors. On the equity side, we have one investor who was a founding investor in Compass, a big real estate platform in the U.S. He brought this depth of experience in profit/debt in understanding how the industry evolved and what it takes to scale real estate sales teams. That was massively valuable to us. Then another entrepreneur who has built and scaled marketplaces before. Then on the debt side, we’re looking for partners that know what it’s like to evolve the model of the time in the contents of an early-stage company, and then also have the ability to scale with us as we moved to the next level. So, can they take us to $100 million, to $500 million, and beyond? That will make our lives a lot easier if we can grow with the same partners instead of having to replace them.

Alejandro: It’s interesting that you mention the founding investor of Compass because I find that entrepreneurs are always about, “Oh, I’ve got to raise money; I’ve got to raise money.” One thing that they don’t really realize is that it’s not about the money; it’s about the network; it’s about turning it around, and it’s the network that is giving you the money and how you can leverage that. So, when it comes to network, or when it comes to perhaps assessing an investor because, obviously, they’re doing due diligence on you from the investor to the founder, how should the founder be doing the due diligence on the investor, and more specifically on the network side of things?

Anshul Ruparell: I can tell you what I’ve done if that’s helpful.

Alejandro: Right.

Anshul Ruparell: I’m sure that some other guys will have some other ideas, but what I’ve done are deep references on my investors the same way that we would do on a new employee joining the company. You almost treat an investor like they are a new employee joining. They’re actually ones that we can’t fire if it doesn’t work out, so you must be even more diligent in your process of assessing them – and speaking to the founders that those investors have backed before, and to the debt side as well – so, speaking to the companies that have been supported by certain debt investors. We look for, how has that investor provided you value over time? What are the things you hope to receive from them? What are the things they promised you, and what did they actually do? I want to see if those things actually match up. I look for what the specific strengths are that this investor brings. We want people who bring specific strength, not just a lack or weakness, so what do they bring to the table that nobody else brings. A lot of that, oftentimes, is network. Then, how do they act when things don’t go exactly according to plan? We transitioned our business model over the last year, and it took incredible conviction from our team but also from our investors to stand by us and say, “We’re comfortable bearing some short-term pain in the interest of long-term gain. Not all investors are going to be supportive of that, of being aligned with the vision of the founders to make changes that are necessary for the business. Those are the three things that we look for. I referenced investors and said no to them based on those references.

Alejandro: What was the most shocking that you heard, without disclosing any names, like something shocking that you discovered from that investor that was like, “This is a big no-no.”

Anshul Ruparell: I’ve heard of investors berating founders for not hitting target metrics and being completely unwilling to allow for the team to shift strategy as they learn what’s going on in the market. At the end of the day, the entrepreneur and the team are the ones that are closest to the market. They’re the ones that are closest to tapping on the ground, and they’re going to learn things in real-time that are going to result in them shifting strategy, changing the product, changing the service, changing the brand. The role of the investor is to say, and the board, specifically, “Is this the right team? Is this the right CEO to go and execute against this vision?” And they need to have faith in that person and that team to go and take all those inputs and turn it into their own strategy. We want people to have strong opinions that are loosely held – people that are willing to change their minds in the face of new information. An investor that has strong opinions that are strongly held can be very dangerous and result in your moving slower and can be a destructive force in the company. I’ve heard a lot of scary stories about that.

Alejandro: I can imagine. In your case, though, you were touching on this earlier. There was a pretty nerve-wracking moment, which was doing a pivot in August. Tell us about this, and basically, what was the breakthrough and the turning point there?

Anshul Ruparell: We had an original service that many in the industry refer to as [25:12], so customers would sell their homes directly to Properly, and then they’d avoid the experience of having to list their home in any other market. We were doing really well. We went from a $50 million runway to $159 million between November and March. Then the pandemic hit, and all of a sudden, we hit the pause transactionally. We didn’t know if the market was going to go down by 10% or 50%. The real estate market effectively shut down for a couple of months. In this period where we weren’t really able to operate, we started to talk to our customers and get a sense from them as to where we were adequately solving their problems. It became clear that we were solving half the problem. We were helping them sell more easily; we weren’t really helping them buy their next [25:49]. So, we came up with a variation of our service that we thought would better address those problems. We tested it in the summer in a pilot, and the pilot went exceptionally well. It became clear to us that we were onto something. Then we had to make the decision of: do we operate both services or do we just pick one and go all-in? We made the decision to go all-in on this new service that we call Sale Assurance. It required incredible conviction from the team. It required us to change all of our messaging and a lot of original processes. You get to build new functions that didn’t exist before, and it required patience on the part of our board. We went from being a rapidly-growing company, scaling very quickly, to raising capital, to basically being a pre-seed company again in the span of a month. That was a stressful experience to go through, but one that we felt confident in. Then when we actually launched the business, and things went, to be honest, better than we expected them to. We got an incredible amount of media attention. In our first week of launching, we had so much demand from customers that every person on the team, including all of our software developers, were on the phone with customers answering calls. There was a degree of luck involved in that, of course, but things went well afterward. That period of transition was certainly a difficult one to go through.

Alejandro: As they say, luck is preparation meets opportunity. So you guys were very well prepared. For Properly, imagine you were to go to sleep tonight, and you wake up five years later. You wake up in a world where the vision of Properly is fully realized. What does that world look like?

Anshul Ruparell: I think I touched on it a little bit before, where we have a vision to create a future, a world in which real estate transactions aren’t stressful, complicated, and expensive. They’re managed with dramatically less friction and surprising simplicity, and where you don’t need as a customer to engage with 10 or 15 intermediaries. Rather, you can work with a single trusted partner to manage everything from the beginning, from home search through to home sell. Then, more specifically, from a Properly perspective, we think that there’s a future, not too far from now, where every Canadian has an account with Properly, where they can check the value of their home or they can check the value of their stock portfolio. And with a few clicks of a button, they get access to best-in-class services that help them manage everything from dreaming and identifying with that new home through the managing the sale of their existing home. That’s the future we have to create.

Alejandro: I love it. Imagine if I put you into a time machine, Anshul, and basically what I’m doing is I’m bringing you back in time, maybe to that point where you were still working with Fabrice and thinking about that business that you were going to build. Based on what you know now – I mean, you’ve been at it for quite a while now with Properly; you’ve done a bunch of good stuff, pivots, financing rounds, hiring, all of the above. If you were to have that ear of that younger Anshul that is actually listening, and you were able to give your younger self one piece of advice before launching a business, what would that be and why based on what you know now?

Anshul Ruparell: That’s a very good question. If I could think of one thing, it would be to narrow your focus. I think it’s very easy to procrastinate by declaring multiple priorities, and during this, you can make yourself thoughtful, and considerate, and measured, but lack impact. When you realize what focus means, it’s especially very difficult. It’s defining all the things you’re not going to do and being very clear about that. So, doing this is incredibly difficult, but if you do it well, it enables really clear thinking, and it allows you to make decisions very swiftly; it allows you in the contents of Properly saying, we’re not going to operate two businesses; we’re not going to operate in multiple cities; we’re going to focus on one. When I look back at all the things that I wish we had done differently, thankfully, the list is not that long, it almost always comes back to having allowed ourselves to dilute our focus and attention for longer than we should of and to let things drag out instead of being really swift, really clear, and very focused.

Alejandro: Absolutely. Laser-focused. I love that. Anshul, for the folks that are listening, what is the best way for them to reach out and say hi?

Anshul Ruparell: I’m on Twitter: @AnshulRuparell. If you’re interested in learning about Properly, it is,

Alejandro: Amazing. Anshul, thank you so much for being on the DealMakers show today.

Anshul Ruparell: It’s been my pleasure. Thanks for having me.

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