This Repeat Entrepreneur Raised $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’ path has been anything but linear, but always intentional. In this engrossing interview, he talks about preferring to work with people he has worked with before, AI, and why it’s crucial to adopt a unique perspective when starting a business.

Matias also traces the reasons behind his preference for choosing the lowest term sheet for his latest venture, Keyway, because it offered more compelling benefits. And what it means to sell software in a very traditional industry.

Listen to the full podcast episode and review the transcript here.

A Global Upbringing

Born in Argentina but raised across Venezuela, the UK, and the US due to his father’s career in the oil and gas industry, Matias developed a global perspective from a young age.

His academic foundation, established at the London School of Economics and Harvard Business School, shaped his business thinking.

But, more importantly, helped him build a lifelong network of collaborators, many of whom would later become co-founders, partners, and team members in his ventures.

Matias started his career at McKinsey, where he learned to break down massive problems into structured solutions, a skill that would prove invaluable. He considers his time at McKinsey to be a continuation of his education, and he met with several incredible people.

One of Matias’ colleagues is now an advisor and board member of Keyway. At McKinsey, Matias learned a common language that he would use to talk to people when starting his company. Soon, the startup world came calling.

Working in a Hypergrowth Company–Vostu

Matias joined Vostu, a social gaming company that was initially conceived as a Facebook-like network for Latin America, just as it pivoted to focus on gaming. At that time, Facebook was living through Ivy League schools in the US. When Matias joined, Vostu pivoted its business model.

What followed was hypergrowth. Initially, Vostu was a social gaming company with a focus on gaming on the Google platform. It had become the largest in Latin America.

Eventually, it became the third-largest social gaming company globally, with 25 million daily active users and a team that scaled from 10 to 400. The experience was a “crash course” in business building, one that left Matias addicted to the adrenaline of entrepreneurship.

Working at Vostu gave Matias a powerful, first-hand experience of the full cycle of a company. It underwent hypergrowth, restructuring, and collaboration with partners.

The company partnered with giants like Facebook and Google, while also collaborating with avid advertisers to achieve brand positioning. Thus, Vostu was not just a B2C business, but it was also undergoing significant business development.

Matias recalls managing teams comprising developers, designers, financiers, and strategists, and working out how to monetize the business.

IguanaFix: Bridging the Physical and Digital Worlds

Matias co-founded IguanaFix with Andres Bernasconi, Vostu’s former CTO. Matias had built a fantastic working relationship with Andres, and the duo wanted to create a company together.

The objective was to tackle the inefficiencies in home improvement services across Latin America–to make hiring a plumber or electrician as seamless as calling an Uber.

Matias and Andres wanted to bring technology to traditional industries, such as real estate, which had been slow to adopt technology. They wanted to apply the marketplace mindset to all services and bridge the vast divide between social classes.

As Matias points out, folks doing this critical work often struggle to scale their businesses and become entrepreneurs. Matias and Andres wanted to help small entrepreneurs grow into medium-sized or even large-scale enterprises in these sectors. Thus, they started IguanaFix.

IguanaFix connected over 80,000 independent service providers with both consumers and large corporations, including both B2C and B2B customers.

Soon, the company was performing maintenance work for some of the largest corporations in the region while utilizing its platform to hire the necessary services.

The venture stood out not only for its tech-forward platform but also for its social mission. The company did several small M&A transactions to spur growth and secured funding from Temasek Holdings and Qualcomm Ventures.

Eventually, IguanaFix’s technology was acquired by Black & Decker, while the operations were sold to SoftBank-backed MadeiraMadeira, which is a multi-billion-dollar corporation and Brazil’s answer to IKEA.

The exit was strategic, structured across multiple deals, and highlighted Matias’ evolving expertise in navigating mergers and acquisitions (M&A).

Enter Keyway: Bringing AI to Real Estate Investing

Matias’ exposure to the real estate industry during IguanaFix planted the seeds for his next startup, Keyway. At IguanaFix, they had been building technology for property management for JLL, CBRE, and other huge institutions.

However, Matias noted that very little technology, data use, and data science were being used for sourcing, transacting, and managing properties. Frustrated by the manual, broker-driven process of real estate investing, even in the US, he saw an opportunity to transform it with data and AI.

Matias began to think about eliminating geographical limitations and identifying the best opportunities available to him based on his objectives. For instance, wealth preservation pressure and his risk appetite when faced with large investment rewards.

Or, cash flow plays versus an investment in which he was open to taking zero cash flows for several years in exchange for a large payout at the end of the day.

Matias started exploring all the available technology platforms and couldn’t find any that brought data into sourcing, underwriting, and transacting the management of real estate. It simply did not exist, either in the US or anywhere else. That’s when he decided to build Keyway.

The Keyway Business Model

As Matias explains, Keyway licenses software to asset managers, investors, and property managers. The platform aggregates and normalizes public and scraped data on properties across tens of thousands of real estate websites in the US every day, enabling interactions.

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, or more, Keyway acquires data that can be resold, bringing clarity to one of the most opaque asset classes in the world.

The platform offers software that empowers customers, large funds, medium-sized funds, investors, asset managers, and developers, who are configuring new units, to make more informed and personalized decisions.

Any entity looking to deploy a specific strategy, optimize revenue management for a particular building, or construct a new structure in a specific area can use Keyway. They can identify what tenants are looking for in that area, as well as the amenities, conveniences, and sizes they want.

The Fundraising Philosophy: Pick People, Not Just Valuations

In raising over $45M for Keyway, Matias stayed true to his principles. When multiple Series A term sheets landed on his desk, he turned down the highest valuation in favor of partners who were “founder-first” or investors with skin in the game and entrepreneurial empathy.

Matias recalls how they raised a seed round of just over $15M and then a Series A round of $ 25M. For him, the ideal investor isn’t just capital; they’re co-builders who solve problems, roll up their sleeves, and are aligned not just financially but philosophically.

Storytelling is everything that Matias Recchia was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.

Matias was keen on bringing on board investors who take low salaries in their funds, along with compensation sourced from the performance of their investments. He wanted people who were truly personally invested in the success of the company.

Matias strongly believes that investors who behave like entrepreneurs and are entrepreneur-centric are not trying to live through the politics of marking their investment to market or just looking well in front of their investment committee.

Instead, they are focused on ensuring the company grows faster, how it grows, and how they can ensure a successful exit.

The AI Revolution: A Once-in-a-Generation Shift

The launch of ChatGPT in 2023 reaffirmed Keyway’s mission. For the first time since Excel, there’s a clear incentive for real estate professionals to embrace new software.

Matias remembers reacting to ChatGPT as “a tool that would completely reshape the software world. Every company out there needs to rethink its tech stack.”

With AI, software becomes adaptive to user workflows, freeing up time for higher-value activities, such as deal-making and relationship-building. As Matias points out, real estate is a very creative industry, and people want to tour properties and interact with tenants in person.

Matias envisions a world where real estate professionals don’t even realize they’re using Keyway, it’s just embedded seamlessly into how they operate. Keyway is frictionless and adaptive, enabling real estate investments, property management, and objective-optimized construction.

Mundane tasks that were previously performed by analysts, associates, or consulting firms outsourcing these projects would now be automated. Thoughtful AI can replicate the criteria of human beings.

At the same time, AI can access all the world’s information in a structured manner, helping real estate professionals make informed decisions that adapt to their needs, dreams, or visions of what they want to build.

Selling to a Traditional Industry: Real Estate’s AI Moment

Selling software into the real estate industry isn’t easy. The sales cycles are long, and stakeholders are busy and don’t have the time to listen to pitches. Because of this, legacy systems are entrenched, and software upgrades lag.

Matias draws a parallel to healthcare. Both sectors are highly specialized, relationship-driven, and slow to adopt change until the benefits become undeniable. Folks are resistant to change and don’t see the need to update their tech stacks.

Keyway’s entry strategy involves proving value through pilots. They start by talking to the heads of innovation or technology in very large organizations. In medium-sized firms, they talk to the principals or managing directors, explaining the impact Keyway can have on their business.

Benefits are in terms of the top line, which is finding new opportunities and monetizing opportunities more effectively. And, in terms of the bottom line, this means requiring fewer resources or spending less money on many of their processes.

Next, they target and win over junior users by allowing them to test the product and check its functionalities before informing the more senior members of their experiences and perspectives.

All that remains is navigating the compliance-heavy environments of institutional buyers. That’s because many large real estate investors have a lot of proprietary data and tenant data, and data is an asset.

They want to make sure that their data is safe and is being used responsibly. They also want assurance that the data is not being used to train Keyway’s systems. The upside? Once adopted, these tools stick, sometimes for decades.

Matias also points out that the sales cycle is closer to six months. It is unlike CRMs, marketing software, or simple AI co-pilots, where users can simply click on a link, enter their credit card information, and begin testing the software the next day.

Advice to His Younger Self: Stay Grounded, Stay Curious

Looking back, Matias offers two key pieces of advice to aspiring founders:

1. Don’t ride the emotional rollercoaster. When things go better than expected, stay humble. When they worsen, remain objective. Learn from the outcome either way.
2. Stick with it through the hard times. If you’re honest about your value proposition and market dynamics, persistence often leads to breakthroughs.

Final Thoughts

Matias Recchia’s career is about the power of reinvention–of industries, companies, and even oneself. He has transformed real estate with AI and his journey reflects a rare blend of intellectual rigor and entrepreneurial gut.

Through Keyway, he’s not just building software; he’s reshaping how a multi-trillion-dollar industry thinks, invests, and grows.

Listen to the full podcast episode to know more, including:

• 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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Keep in mind that storytelling is everything in fundraising. In this regard, for a winning pitch deck to help you, take a look at the template created by Peter Thiel, the Silicon Valley legend (see it here), which I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash. 

Remember to unlock for free the pitch deck template that founders worldwide are using to raise millions below.

 

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