Paul Kromidas didn’t just pivot a startup—he changed the vehicle mid-race and still pulled ahead. Summer began as an asset-heavy “own an STR without the risk” model: Summer found the house, bought it with their capital, operated it for two years, and sold it back with a book of business. It worked—until the capital stack and rate environment made venture-scale returns incompatible with real estate velocity. So Paul did the brave thing founders talk about but rarely do: he sold the homes, kept the brains, and rebuilt Summer around the software that had quietly powered V1.

That software—Summer OS, now supercharged by Sunny AI—acts like a true asset-management layer for short-term rentals. It stitches market underwriting to unit-level P&L, pipes into your PMS, flags issues before they become reviews, and guides both pros and serious first-timers from “where should I buy?” to “how do I out-operate the comp set?” It’s not a wrapper around generic answers; it’s a working analyst that shows its work.

Today on the show, I’m joined by Paul Kromidas—founder of Summer—on building tools that help operators decide, buy, and perform.In this episode, we:

If you’re building a portfolio—or rebuilding your ops stack—this one will sharpen how you underwrite, staff, and scale.