The AI rollup transforming property management

This week on Riding Unicorns, we sit down with Dan Lifshits, Co-Founder & COO of Dwelly — the AI-first lettings and property management platform reinventing how landlords, tenants, and agents interact.

Dwelly is on a mission to modernise the UK rental market by acquiring traditional letting agencies and rebuilding them with technology at their core. The business is growing fast, backed by General Catalyst and other leading investors, combining the operational rigour of real estate with the scalability of AI.

Before founding Dwelly, Dan was one of the youngest associates at McKinsey, then helped scale Gett (the ride-hailing company) from early stage to over $1bn in GMV and 1,000+ employees — experience that now shapes Dwelly’s operational DNA.

In this episode, we dive into:
🏢 The rollup model — why Dwelly is buying agencies instead of building from scratch
💡 Applying AI to traditional services — from lettings to maintenance and communication
🌍 Moving to Hull — and why the founding team relocated to be closer to their first acquisition
🚀 Turning investor scepticism into conviction: why rollups might define the next decade
🤖 Using data to discover the “perfect process” across thousands of lettings
💼 How to balance being a product builder, operator, and M&A organisation
🔥 Lessons from Gett and McKinsey on scaling complex, real-world businesses

Dan also shares his view on the coming wave of AI-enabled rollups, why the UK rental market is “crying out for disruption,” and what founders can learn from industries still running on manual workflows.

Wanna see a CSS magic trick?

The Stack Overflow Podcast

The web's evolving security landscape

The AI-powered Podcast Player