Land Investing From Across the World w/ Max and Lucas Canevaro

Max and Lucas Canevaro are brothers with Italian heritage born in Argentina, raised in Italy, and now based in Europe and South America respectively. They operate a U.S. land investment business remotely, specializing in subdivisions and land-home packages. Max works for a major American company while running the business from Italy, while Lucas is fully committed to the business from Brazil. They also have a third brother, Mauro, managing finances and operations.

The brothers initially questioned why pursue U.S. land investing when their family had real estate experience in South America. Max wanted to recreate childhood memories of land ownership, but Lucas convinced him that South American markets lack the stability and remote-work infrastructure of the U.S. Lucas explained that while he built a successful company scaling to 200 people across five countries in South America, entrepreneurship anchored him to those locations. The U.S. land market, with its data systems and technology infrastructure, allowed him to achieve the "second divorce"—working and living in different places—which was essential to his vision of freedom.

The brothers began with house flipping but quickly realized margins were insufficient. They explored tax liens and tax deeds before being directed by Emmanuel toward raw land investing. They scaled rapidly, eventually doing 70-100 transactions annually, but discovered this quantity-based approach was unsustainable. They were working extreme hours (sleeping 5 hours daily for 4 years), incurring massive infrastructure and team costs, and receiving thin margins despite high volume. The turning point came at the end of 2025 when they realized they needed to shift from quality-to-quantity strategy to focus on larger deals with better margins.

The critical innovation was implementing AI agents to move the underwriting bottleneck from after lead generation to before mailer deployment. Rather than sending 7,000 mailers to receive 500 leads and then underwriting them, they now use AI agents to:

- Scan regulations across multiple counties

- Map parent and child parcel relationships for subdivision potential

- Perform full underwriting and subdivision sketches before any marketing outreach

- Design underwriting protocols that perform better than their senior human underwriter

This required approximately 4 months of training the AI system (1-2 months for initial development, 2-3 months for refinement), with the final 20% of accuracy taking the longest. The complexity arose from the infinite variability of individual parcels and unforeseen situations, requiring continuous prompt refinement. The investment in AI training is cumulative—each hour improves the system permanently, unlike managing human employees who require repetitive training.

The results have been dramatic: they can now identify 500 highly qualified leads through continuous mailers to the same three counties rather than blasting mailers across six counties. This concentration strategy builds local expertise and relationships, eventually leading to off-market deals from real estate agents who trust their business. They've shifted from hiring acquisition managers and building bloated teams to a lean two-person operation that generates better bottom-line results.

However, the brothers emphasize that AI is not a complete replacement for human judgment. When they attempted to delegate acquisitions to hired managers, deal flow dropped significantly despite those managers' experience. They found that the personal connection, trust-building, and ability to understand seller motivations—skills developed over years—directly impact conversion rates. They returned to closing deals themselves, recognizing that paying an acquisition manager to buy at market value (rather than discount) made no economic sense.

On the future of AI in land investing, Lucas argues that AI will quickly become commoditized and won't provide lasting competitive advantage. History shows that each innovation (letters, email, eventually inbound marketing) initially provides advantage but eventually becomes baseline. The real competitive advantages will come from operational innovation—doing different things rather than using the same tools better. Examples include: pursuing more complex markets (major subdivisions, building roads, bringing utilities), paying market value while creating value through development, novel value propositions (partnership models), or niche specialization (solving title issues).

The brothers also discuss their evolution in identifying what only they can do. After repeatedly seeing deal flow drop when they attempted to leverage out of acquisitions, they recognized their personal involvement in seller conversations was irreplaceable. This led them to reconsider their position: rather than scaling through teams, they focus on larger deals where their expertise commands better margins, and they maintain personal involvement in critical relationship-building activities.

On pivoting versus persisting, Max emphasizes becoming an expert first, as expertise enables recognizing when genuine market changes require adaptation versus grass-is-greener thinking. Lucas advocates for the "80/20 rule"—dedicating 80% to proven systems while dedicating 20% to continuous exploration, preventing both scattered focus and dangerous stagnation. He argues that human nature defaults to laziness once survival is achieved, causing people to stop learning and become vulnerable to disruption. The best scenario is defeating yourself through continuous innovation rather than being defeated by competitors.

Both brothers acknowledge the current market downturn and industry consolidation as a rare opportunity window. As less adaptable operators quit and the next boom hasn't yet attracted new entrants, today's market rewards those willing to unlearn and relearn. This window likely won't persist once the market recovers and new operators enter.