Matias Recchia On Raising $45 Million To Provide AI-Powered Solutions For The Real Estate Industry

Matias Recchia has undergone bold transitions, gained global experiences, and developed a deep conviction in the power of technology to modernize traditional industries. He helped pioneer social gaming in Latin America and transformed how real estate professionals discover and manage assets in the US.

Matias’ latest venture, Keyway, has secured funding from top-tier investors like Camber Creek, Graph Ventures, Great Oaks Venture Capital, FJ Labs, and Thomvest Ventures.

In this episode, you will learn:

• Matias Recchia’s global upbringing shaped a strong network and cross-cultural entrepreneurial mindset.
• His transition from McKinsey to startups highlighted the value of structured problem-solving in chaotic, high-growth environments.
• IguanaFix showcased how technology can bring efficiency and opportunity to traditional, underserved industries.
• Keyway was born from Matias’ frustration with the opaque real estate investment process and his drive to apply data and AI for better decision-making.
• He prioritizes founder-aligned investors over the highest term sheets, valuing true partnership over headline valuations.
• Selling software in traditional industries like real estate requires long cycles but leads to long-term customer stickiness.
• With the rise of AI, Keyway is making real estate software seamless and intelligent, enabling professionals to focus on high-impact work.

 

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About Matias Recchia:

Matias Recchia’s work experience includes positions at various companies, starting with his current role as the Co-founder & CEO of Keyway since September 2020.

Prior to this, he worked as an Entrepreneur In Residence at Schmidt Futures from July 2020 to July 2022, and at Harvard Business School from September 2019 to July 2022 in the same role.

Before his roles in venture capital and entrepreneurship, Matias was involved in the startup scene. He served as a Board Member at IguanaFix from July 2020 to April 2022 and as the Co-founder and CEO from February 2013 to July 2020. Previously, he held the position of President and COO at Vostu from July 2010 to February 2013.

Matias started his career at McKinsey as an Engagement Manager from September 2007 to June 2010. Before that, he worked as a Corporate Finance Manager at Procter & Gamble from an unspecified date in 2003 to 2005.

Matias has a solid educational background with studies conducted at reputable institutions. From 2005 to 2007, Matias attended Harvard Business School. This indicates two years dedicated to advancing their knowledge and skills.

Prior to that, from 2000 to 2001, Matias enrolled in The London School of Economics and Political Science (LSE), concentrating on Financial Markets & International Markets Classes. This educational experience allowed him to delve into the field of business for a year, gaining insights into financial markets and international dynamics.

Connect with Matias Recchia:

• LinkedIn
• Crunchbase
• TheOrg
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: Alrighty, hello everyone, and welcome to the DealMaker Show. Today we are going to have an amazing time. We have a repeat founder joining us, and we’ll be talking about building, scaling, and financing—he’s done it all.

Alejandro Cremades: In today’s episode specifically, we’re going to dive into working with people you already know versus new people. In his case, he’s collaborated with many people from his previous startups. We’ll also talk about AI—why it’s so important and how to think differently when starting a business today. We’ll cover why he chose the least high term sheet—not the highest, but the one that was more compelling given other factors. We’ll also explore what it’s like selling software in a very traditional industry.

Alejandro Cremades: So again, brace yourself for an impactful and inspiring conversation. Without further ado, let’s welcome our guest today, Matias Recchia. Welcome to the show!

Matias Recchia: Hi Alejandro, thank you so much for having me on the show today.

Alejandro Cremades: So Matias, I know you were born in Argentina but raised all over the place—your dad was in the oil industry. Walk us through memory lane. What was life like growing up?

Matias Recchia: As you said, I grew up all over. I’m originally from Argentina, but even within Argentina, I lived in several cities. My father was in the oil and gas industry, so we moved every two or three years. When I was seven, we moved to Venezuela, which is really where I grew up, in several cities there as well.

Matias Recchia: Then I moved to the UK, then to the US. And for the last 15 years, I’ve been living back and forth between New York and Buenos Aires.

Alejandro Cremades: That’s amazing. Your education too—the London School of Economics and Harvard Business School. I’m sure you built quite a network at those schools.

Matias Recchia: For sure. A lot of the businesses I’ve started, the people I’ve worked with and hired, have come from those schools and those formative years. They were great educational experiences and also a great way to find partners—people to work and have fun with.

Alejandro Cremades: How do you go from McKinsey—a great place to learn how to break big problems into smaller ones—to entering the venture world with a social gaming company in Brazil?

Matias Recchia: As you said, McKinsey is a fantastic place to learn. I see it as a continuation of my education. It was a great place to meet smart people. My office mate during my McKinsey years in New York is now one of my advisors and was a board member when we started Kiway.

Matias Recchia: That network of impressive people is very helpful when starting businesses and gives you a shared language. While at McKinsey, I began helping some friends who had started a social network for Latin America called Vostu. This was back when Facebook was still limited to Ivy League schools in the US, and these guys were building the same for Latin America.

Matias Recchia: I joined them when we pivoted the business model to focus on social gaming. We became the largest social gaming company in Latin America, and the third largest in the world, with 20 to 25 million daily active users. The team grew from 10 when I joined to 400 people.

Matias Recchia: You think you’ve seen it all from business school cases or McKinsey, but the reality of a high-growth startup hits you hard. It was an incredibly exciting time. I worked with close friends from business school, including Mario, who’s also been on your podcast.

Matias Recchia: It was exciting but very different from my time at McKinsey. Mario and I had both worked there, and I believe that gave us a common framework for tackling problems and tough situations.

Alejandro Cremades: For those wondering, Mario is the founder of Oscar Health—you can check out his episode. Now, Matias, Vostu was eventually acquired. What visibility did that give you into the full business cycle?

Matias Recchia: It was a great experience. We went through high growth, restructuring, and close work with partners. In social games, you often operate on platforms you don’t own—so we partnered heavily with Facebook and Google in the region. We also worked with advertisers for brand positioning, so it wasn’t just B2C—it involved a lot of business development.

Matias Recchia: It was also a lot of people management—working with developers, designers, finance, and strategy teams to figure out monetization. It was a powerful experience, managing a complex business with just three or four years of work experience. A real crash course. You make a lot of mistakes, but hopefully you learn and don’t repeat them. The thrill is incredible, and I think that’s why, once you’ve been an entrepreneur, it’s hard to go back to a regular job. That adrenaline is addictive.

Alejandro Cremades: So how do you go from Vostu to IguanaFix, your next venture?

Matias Recchia: IguanaFix was fundamentally different. I started it with Vostu’s former CTO, someone I had a great working relationship with. After years in the virtual world, selling virtual cows and assets, we felt the urge to do something in the physical world—something where we could bring technology to a more traditional industry.

Matias Recchia: That theme—bringing efficiency and tech to traditional industries—has stayed with me. Real estate, for instance, is slow to adopt technology. Home improvement services are the same. We asked: Why can’t hiring a plumber be as easy as calling an Uber?

Matias Recchia: In Latin America, there’s a big divide between social classes. Often, workers doing important jobs don’t get to scale their businesses or become entrepreneurs. We loved the idea of using tech to help them do that. We launched IguanaFix and scaled it significantly.

Matias Recchia: We had over 80,000 independent service providers doing millions of jobs each month. We worked with both B2C and B2B clients, including some of the largest corporations in the region that used our platform to manage all their maintenance services.

Alejandro Cremades: Instead of a full acquisition, you did several transactions. Walk us through how you engineered the M&A outcome for IguanaFix.

Matias Recchia: Our last round was led by Temasek, which brought a private equity mindset and new thinking about the exit. There wasn’t an obvious exit path, so we split the transaction.

Matias Recchia: Black & Decker acquired the technology platform. They went on to do other things with it. We were already providing software to major retailers and corporations for property management—that was very valuable.

Matias Recchia: But the B2C operations weren’t of interest to them. So we sold that part of the business to Madeira Madeira, a SoftBank-backed company in Brazil—kind of like the IKEA of Brazil. IKEA had acquired TaskRabbit in the US, and Madeira followed that strategy.

Matias Recchia: Another Matias, our COO at IguanaFix, stayed on and built an even larger business within Madeira’s ecosystem.

Alejandro Cremades: After those transactions, you launched your current venture, Keyway—your third time around in the venture world. Why did you feel this problem was meaningful enough to build another company?

Matias Recchia: When I was leading IguanaFix, I got very close to the real estate world. We were building tech for property management, working with JLL, CBRE, and other major institutions. I saw that tech adoption was happening in logistics and operations—but not in property sourcing, transactions, or management.

Matias Recchia: I was investing in real estate myself and realized I only saw what brokers wanted to show me. I asked, “Why can’t I access the full landscape of real estate opportunities and filter them to meet my specific goals?”

Matias Recchia: Whether I was looking for wealth preservation, higher risk for higher return, or a cash flow play—I wanted data-driven answers. I tested every tech platform out there and didn’t find one compelling enough.

Matias Recchia: That’s when I decided to build a platform that brings data and technology to the sourcing, underwriting, and transaction management of real estate.

Matias Recchia: And I was like, if this doesn’t exist in the U.S., then it does not exist anywhere. I think for several of these businesses where you’re trying to bring more liquidity and more technology to a traditional industry, it first happens in the U.S. Then, if you’re interested in expanding internationally or building a business in other countries, you sort of adapt—or as we like to say in Latin America, “tropicalize”—that solution. But in this case, I was like, alright, there’s no platform yet that does this well in the U.S.

Matias Recchia: And I was like, alright, let’s do this.

Alejandro Cremades: So then, for the people listening to get it, what ended up being the business model of Keyway? How are you guys making money?

Matias Recchia: At Keyway, we license software to asset managers, investors, and property managers. We aggregate all public information that’s available about every property in the U.S. and we make that data talk to each other—whether it’s traffic patterns, credit card spending, census numbers, real ownership of the assets, lending associated with a particular asset, rent evolution in different markets, and so on. So we acquire data that can be resold.

Matias Recchia: We also scrape tens of thousands of websites every day. We normalize that data and make it talk to each other to inform customers—large funds or medium funds—that are deploying a specific strategy. We also support asset managers optimizing revenue management of a particular building or developers thinking about building in an area who want to figure out what tenants appreciate—is it amenities, convenience, larger apartments? So we also help developers think about the configuration of new units.

Alejandro Cremades: And how much capital have you guys raised to date for the company?

Matias Recchia: We’ve raised a little bit over $45 million so far.

Alejandro Cremades: And how did you go about raising this? Because I know that, for example, for your Series A, you didn’t take the term sheet with the highest valuation. Why?

Matias Recchia: So we did a Series Seed of a little bit over $15 million, and then we did a Series A of a little bit over $25 million. When we received the term sheets for the Series A, we were not actually looking to raise money—which turns out to be when you get the best term sheets. It’s not when you’re trying to raise money—it’s when you’re growing fast, people figure out what you’re doing, and they reach out to you.

Matias Recchia: At that point, we had several funds reach out and offer term sheets. And when you’ve been around in the startup world, whether through direct experience or by talking to other founders, you start to realize what really matters to you when dealing with investors. I don’t think there’s a right answer—but there are preferences and different types of investors.

Matias Recchia: Some of the term sheets we received were from funds where the folks doing the work and who were excited about our company were not principals or partners. They were not going to be sitting on our board or making decisions for their fund.

Matias Recchia: And in my experience, what I really appreciate is having investors who also think like founders—investors who are taking low salaries in their funds and whose compensation comes from the performance of their investments. They’re personally invested in the success of the company.

Matias Recchia: Because I think those investors behave like entrepreneurs. They are entrepreneur-centric and not trying to play politics or just look good in front of their investment committees. They’re focused on one thing: how do we grow faster, and how do we ensure a successful exit? Those folks are problem solvers too—they’ll sit with you and say, “Let’s solve these problems.” So I prioritize that entrepreneurial aspect in my investors. I don’t think of them as just capital.

Alejandro Cremades: Obviously, when you get investment, people are betting on the future. I think the same goes for employees. Now, if we’re thinking about the future, and let’s say you go to sleep tonight and wake up in a world where the vision of Keyway is fully realized—what does that world look like, Matias?

Matias Recchia: It’s a world—and I think the vision of Keyway has only been enhanced in the AI era. When we started Keyway in 2020, ChatGPT wasn’t out yet. When ChatGPT-3 came out in 2023, my first reaction was, “Oh my God, this is going to completely reshape the software world.” Now every company has a real reason to rethink its software stack.

Matias Recchia: For the first time since the invention of Excel—not even the web—real estate professionals have a reason to start using technology. Now software can be built to adapt to how you work, freeing up your time so you can focus on what matters. And for real estate professionals, that’s doing deals.

Matias Recchia: Real estate people want to be out there shaking hands, closing deals, touring properties, getting to know their tenants. It’s actually a very creative industry.

Matias Recchia: If Keyway is successful, we’ll see much more of that. The mundane tasks that were done by analysts, associates, or outsourced to consulting firms will be fully automated with thoughtful AI—AI that replicates human criteria while having access to all the world’s structured information to help real estate professionals make better decisions tailored to their goals.

Matias Recchia: In an ideal world, people using Keyway don’t even realize they’re using it. It’s frictionless. It adapts to how they work. They’re just doing deals, optimizing their investments, managing properties better, and building better buildings for their objectives.

Alejandro Cremades: How is it to be selling software in a very traditional industry?

Matias Recchia: Well, it’s tough. Real estate—similar to law or medicine—is a traditional profession. There are a lot of similarities. When I think about selling software to real estate, I often think of people who’ve sold software to the medical profession.

Matias Recchia: Similar to doctors, real estate professionals don’t have a lot of time. In their own time, they’re making money—by seeing patients or closing deals.

Matias Recchia: So there’s not a huge appreciation for software, and they don’t have much time to listen to pitches. They’re not rethinking their tech stack every year. People using tools like Argus to underwrite buildings have been doing so for a decade—and they’re not actively seeking alternatives.

Matias Recchia: So it’s a long sales cycle. In large firms, we start by speaking to heads of innovation or heads of technology.

Matias Recchia: In mid-sized firms, we talk to principals or managing directors. We explain how we can impact their business—top-line (finding new opportunities, better monetization), and bottom-line (requiring fewer resources and cutting costs).

Matias Recchia: Next, we usually run a pilot. Junior team members test the product, explore functionalities, and report back to senior leadership with feedback—what worked, what didn’t.

Matias Recchia: Then you enter a longer sales cycle with legal, compliance, etc. These real estate investors have proprietary data—tenant data, asset data—and they want to ensure their data is secure, responsibly used, and not used to train your models. And that’s important.

Matias Recchia: This makes the sales cycle closer to six months, unlike CRMs or marketing software where someone clicks a link, inputs a credit card, and starts testing software the next day.

Matias Recchia: It’s a more painful sales process, but I believe that’s directly correlated to stickiness. If they go through this process, enjoy the software, and it delivers—once they adopt it, they’ll likely stay. Easy come, easy go.

Matias Recchia: Painful sales cycle—but if you build a great product, it becomes very sticky. And in real estate, sticky means a decade—not six months.

Alejandro Cremades: Talking about decades and time, let’s say I put you in a time machine and take you back to that moment when you were thinking about launching your first business. You were part of the founding team at Vostu, but your real first journey from idea to outcome was IguanaFix. If you could show up and give that younger Matias one piece of advice, what would it be and why?

Matias Recchia: I’ll give you two answers to that question—one technical and one more soft or emotional.

Matias Recchia: Let me start with the soft one. Don’t congratulate yourself too much when things go better than expected—some of it was luck. Do the work to understand what really worked so you can replicate it.

Matias Recchia: And on the flip side, when things don’t work out, don’t punish yourself too much. Get to the radical truth. Was it the thesis, the idea, the execution?

Matias Recchia: We tend to be very results-oriented and mix idea, execution, and market dynamics into one judgment.

Matias Recchia: So stay aware as you execute. What’s lagging, what’s real traction, what are the headwinds or tailwinds in the industry?

Matias Recchia: And if things take longer or are harder, if you stick through and keep your eyes open—stay real about the situation and your value proposition—things tend to work out.

Alejandro Cremades: I love it. Matias, for the people listening who want to reach out and say hi, what’s the best way?

Matias Recchia: I’m on X, @MatiasRecchia. That might be the easiest. Or LinkedIn—I’m actually quite good at responding to my LinkedIn messages, even though I get a bunch of them.

Alejandro Cremades: Amazing. Well, Matias, thank you so much for being on the DealMaker Show today. It’s been an absolute honor to have you with us.

Matias Recchia: Thank you so much, Alejandro. I really appreciate you taking the time today to talk a little about my experience.

*****

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