If you were at VRMA in Nashville this year, you may well have come home with a pack of trading cards featuring a hundred familiar faces from the vacation rental industry. Jan Sahagun is the person behind them, and in this episode he explains where the idea came from, how the cards were chosen and produced, and why a $7,000 marketing experiment ended up booking far more demos than he ever expected.

Jan has spoken with thousands of property managers over the past three years, and he hears the same complaint everywhere: too many tools, none of which talk to each other. Heather and Jan talk about how AI agents are starting to change that, moving beyond guest messaging into day-to-day operations, and what this means for traditional property management software.

Jan also makes a case some listeners may find surprising: don't switch your PMS right now.

The conversation closes with a reminder that applies to all of us using these tools. Use AI to sharpen your thinking, not to replace it.

About Jan Sahagun

Jan Sahagun is co-founder of Trellis, a Y Combinator company building AI agents that run operations for property management companies, and founder of STR Tech Report, a free directory of the tools available to vacation rental operators. 

Originally from Barcelona, Jan studied at McGill University in Montreal, played hockey along the way, and worked in investment banking and procurement before moving into sales. He joined the industry selling AI guest communication software, and co-founded Trellis with Lodovico Benvenuti, who runs a 150-listing property management company in Milan.

Key takeaways

• The most common complaint Jan hears from property managers is tool fragmentation: separate systems for guest messaging, operations, pricing and the PMS, with no single place to manage it all.
• Jan doesn't recommend switching PMS right now. If you must, compare the API documentation of each system (the technical detail of what other tools can connect to) and choose the one that allows the most. Then hand those documents to Claude to do the comparison for you.
• AI guest messaging often falls short because it lacks operational context. An agent that knows who is working, where they are and what they can fix can resolve an issue end to end, rather than sending an apology and escalating.
• Direct booking websites remain essential, because AI booking assistants can only offer your direct rate if they can find your site. They now need to be built so these assistants can read them.
• The cards worked because they were about people, not the brand. Personal, thoughtful marketing gets kept; generic giveaways get thrown away.
• Use AI to build on your own ideas, not to have them for you. Keeping your own thinking active is what protects your expertise.

‍Resources and links mentioned

• Trellis: trellistech.com
• STR Tech Report
• Jan on LinkedIn: linkedin.com/in/jan-sahagun-str
• Apaleo: a hotel property management system built API-first, mentioned as an example
• Hospitable: mentioned for expanding its API and MCP connections
• Claude, Claude Code and Codex: the AI tools Jan's team uses day to day
• VRS666: The Seven Deadly Sins of AI

Connect with Jan Sahagun

Jan is a regular at industry conferences, and he says the easiest way to spot him is the mustache. Go and say hello, and you may even leave with a pack of cards.

Trellis: trellistech.com

LinkedIn: linkedin.com/in/jan-sahagun-str

‍