NVC@30 Fireside Chat with Sebastian Rivas Explores Building Andes from NVC Winner to Real Estate Asset Platform

As part of the NVC@30 Fireside Chat series, the Polsky Center welcomed Sebastian Rivas, MBA ’21, founder and CEO of Andes, to discuss his entrepreneurial journey, his experience in the New Venture Challenge, and how his company has evolved from an early-stage idea into a rapidly scaling real estate asset platform.

Moderated by Mark Tebbe, adjunct professor of entrepreneurship at Chicago Booth and entrepreneur-in-residence at the Polsky Center, the conversation followed Andes’ path from its origins, including launching during the COVID-19 pandemic, to its expansion across the United States and Latin America.

Andes was built around a simple, but difficult, problem: institutional real estate owners knew short-term rentals were an opportunity — but didn’t know how to operationalize them.

“With short- and medium-term rentals, it’s the same asset, but completely different work,” Rivas said. “Traditional property managers don’t know how to price nightly stays, manage guests, or operate across platforms like Airbnb.”

At the same time, demand was shifting. Remote work and digital nomadism were reshaping how people lived, creating a growing segment of renters looking for flexibility.

“If even a small percentage of the population is demanding something—and no one is offering it at scale—that’s a problem worth solving,” he said.

Rivas first recognized this gap before Booth while working in real estate investment banking. After testing short-term rentals on his own property and seeing significantly higher returns than traditional leasing, he began to see a larger opportunity.

Sebastian Rivas and Mark Tebbe.

Still, when he pitched the idea to institutional investors, the response was: interesting, but too difficult to execute at scale.

Andes was built to solve that challenge — helping property owners integrate short- and medium-term rentals into existing portfolios and unlock value from underutilized units. Today, the company operates as a platform layered on top of existing real estate infrastructure, combining local operators with centralized technology to drive revenue and efficiency.

Rivas chose Chicago Booth specifically for its entrepreneurship ecosystem and used his time to build Andes while deepening his understanding of business.

At Booth, he immersed himself in entrepreneurship coursework, taking as many classes as possible and applying those lessons directly to his company. From marketing to strategy and operations, those classes helped him identify and fill critical gaps in his knowledge.

That growing confidence carried into the New Venture Challenge. Rivas entered with a working business but initially struggled to communicate its full potential.

“I got destroyed in the first round of pitching,” he said. 

Rather than double down on his original approach, he leaned into feedback from faculty, mentors, and judges, focusing on being coachable and shifting his mindset.

“The biggest thing I took from the experience was to be coachable,” he said. “Don’t fall in love with the solution you create — fall in love with the problem.”

By the final round, Rivas had significantly refined both his pitch and his vision for the company, ultimately winning the NVC and receiving what was at that time the largest first-place investment in the competition’s history.

After graduation, Rivas faced an important decision – pursue a traditional career path or fully commit to building Andes.

Despite offers that would have provided financial stability and a clearer path to remaining in the United States, he chose entrepreneurship.

“I asked myself what I would regret more,” he said. “If I didn’t take the opportunity, I would always wonder ‘what if.’”

In the years since NVC, Andes has grown steadily, raising capital, expanding into new markets, and evolving its business model.

One of the company’s most significant shifts was moving from a traditional, operations-heavy property management model to a more scalable platform approach.

“We realized managing everything ourselves wasn’t scalable,” Rivas said. “So we built a platform — more like an Uber model — where local operators handle hospitality, and we manage the digital layer.”

This transition improved margins and enabled faster geographic expansion, with the company growing from a handful of markets to more than a dozen in a short period.

Rivas also discussed how broader market forces — including rising interest rates, shifting real estate dynamics, and advances in artificial intelligence — are shaping the company’s strategy.

“What used to be a ‘nice-to-have’ solution is now essential,” he said. “For many property owners, vacancy is a major issue — we’re helping them solve that.”

The company integrated AI into its operations, building internal tools that allow team members to optimize workflows, simulate outcomes, and make more informed decisions using proprietary data.

“We reorganized the entire company, from top to bottom, to put AI at the core,” Rivas said. “Everything from operations, product and engineering, sales and marketing, and data science was reimagined from the ground up.”

“This isn’t off-the-shelf AI,” Rivas continued. “We made it possible to manage every single aspect of the company digitally and enabled our operators, who have deep subject matter expertise, to train and deploy AI agents to solve their problem and execute their workflows.”

Rivas called out that one of the most overlooked aspects of entrepreneurship is effectively communicating with customers — particularly in industries resistant to change.

“The key is empathy,” he said. “You need to speak their language and show them that if they had the same tools and time, they would create the solution that you’re providing.”

As Andes continues to grow, Rivas sees significant opportunity to expand beyond short-term rentals into a broader platform for managing real estate assets.

“My vision has evolved over time,” he said. “The market evolves, technology evolves, and you need to evolve with it.”

The event was part of the NVC@30 Fireside Chat series, which celebrates three decades of the New Venture Challenge and highlights founders who have turned early-stage ideas into high-growth companies.