Bystreet Is Building the MLS for Caribbean Hotel Deals

The Macro: Hospitality Deal Sourcing Is Still Stuck in the Relationship Era

Commercial real estate has been slowly digitizing for two decades. CoStar dominates US commercial property data. Crexi handles online auctions and listings. Reonomy does property intelligence. For office buildings, retail spaces, and multifamily apartments in major US markets, there is a reasonably functional digital infrastructure for finding deals, running comps, and connecting buyers with sellers.

Hospitality is different. Hotels, resorts, and mixed-use hospitality properties trade on thinner information. The datasets are smaller, the properties are more unique, and the deal flow is relationship-driven in a way that office leasing has mostly moved past. A 200-room resort in Cancun is not interchangeable with a 200-room resort in Punta Cana, even if the financials look similar on paper. Location, brand affiliation, renovation history, management contracts, and seasonal demand patterns all matter in ways that resist standardization.

The Caribbean and Latin American hotel market takes all of these problems and amplifies them. The region spans dozens of countries with different regulatory frameworks, currency dynamics, and ownership structures. Deal flow happens through a network of brokers, developers, and family offices that communicate primarily through personal relationships. There is no MLS equivalent. There is no CoStar for Caribbean hotels. If you want to find a hospitality deal in the Dominican Republic, you need to know someone who knows someone.

This is the kind of market that looks small from the outside but moves real money. Caribbean tourism generated over $60 billion in GDP in recent years. Hotel transactions in the region regularly hit nine figures. The buyers are institutional: private equity firms, hotel management companies, sovereign wealth funds. They have capital to deploy and no efficient way to source deals.

The Micro: Harvard CS, Government Sonar Systems, and a Scaled Startup

Bystreet is a hospitality deal sourcing platform focused on the Caribbean and Latin American hotel market. It provides a database of properties that users can filter by country, asset type, and ownership structure. Think of it as a vertical search engine for hotel deals in a region where that search engine did not previously exist.

The value proposition is straightforward: instead of flying to conferences, working your broker network, and hoping the right deal crosses your desk, you log into Bystreet and search. The platform aggregates property data that was previously scattered across broker decks, government records, and personal networks into a single queryable interface.

This is a data business more than a technology business. The hard part is not building the platform. The hard part is getting the data. Who owns that resort in Jamaica? Is it actually for sale or just “testing the market”? What did comparable properties trade for last year? In the Caribbean hospitality market, this information lives in people’s heads and in PDF attachments on email threads. Digitizing it is unglamorous, painstaking work that creates a genuine moat once you have done it.

The founding team is a three-person group. Charlie Maki is a co-founder and Harvard CS graduate. He previously launched and scaled a startup from zero to $1M ARR and 10,000 paid users as a founding engineer. Corey Anderson is co-founder. Cameron Hake studied CS and data science at UW-Madison and previously worked on sonar systems for the US Government. They are part of YC’s Winter 2025 batch.

The competitive landscape is thin, which is both a validation and a warning. CoStar does not meaningfully cover Caribbean hospitality. STR (now part of CoStar) provides performance data but not deal sourcing. HVS does consulting and valuations but is not a marketplace. JLL Hotels and CBRE Hotels handle brokerage but do not offer a self-serve deal sourcing platform. The fact that nobody has built this yet could mean the market is underserved, or it could mean previous attempts failed for reasons that are not obvious from the outside.

The Verdict

I like vertical SaaS plays in fragmented markets, and this is about as vertical and fragmented as it gets. The Caribbean hotel deal market is opaque, relationship-driven, and ripe for a data product. If Bystreet can assemble a comprehensive property database and keep it current, that is a genuine competitive advantage that is difficult to replicate.

The risk is chicken-and-egg. The platform is only valuable if it has deals. Deals only show up if the platform has users. In a market driven by personal relationships, convincing the first hundred brokers and developers to list their properties on a new platform is a cold start problem that no amount of technology solves. This is a sales and relationship-building challenge, not an engineering challenge.

There is also a geographic expansion question. The Caribbean and Latin American hospitality market is a reasonable starting point, but it is small enough that the total addressable market could cap out quickly. Can Bystreet expand to Southeast Asia, the Mediterranean, or African resort markets? Those regions have similar information opacity problems. Or does the platform stay regional and build depth instead of breadth?

Thirty days, I want to see the property count. How many listings are in the database, and how many of them represent real deal opportunities versus stale data? Sixty days, show me a closed transaction that originated on the platform. Not a lead. A deal that actually closed because a buyer found a property on Bystreet that they would not have found otherwise. Ninety days, the question is whether the data is getting better or going stale. A deal sourcing platform with outdated information is worse than useless because it wastes time. If the data stays fresh and the property count grows, Bystreet could become the infrastructure layer for an entire market that currently runs on handshakes and WhatsApp.