Riding Unicorns: Venture Capital | Entrepreneurship | Technology · Riding Unicorns Productions

Pioneering the AI-rollup model in the property management space with Dan Lifshits, Co-Founder @ Dwelly

November 12, 2025·45 min·2 clips

Dan says landlord acquisition is the hard part, not finding tenants, and that roll-ups solved the growth problem.

1. Riding Unicorns: Venture Capital | Entrepreneurship | Technology focuses on Dan Lifshits and Dwelly's AI-first lettings and property management model. 2. Dan Lifshits is the co-founder of Dwelly, and the hosts frame him as someone building a UK-based platform with acquisitions and partnerships. 3. The episode asks how an AI company can use a roll-up model to change lettings and property management. 4. Dan says his path ran through McKinsey, Get, and earlier operational roles before Dwelly. 5. He describes childhood in Israel and Russia, then moving to the UK and studying mathematics and law at the London School of Economics. 6. He says his career in consulting and at Get gave him exposure to tech-enabled operational businesses that scaled fast. 7. Dan says his former business scaled to more than 1 billion in GMV and more than 1,000 people. 8. He says the earlier business gave him experience in operations, product engineering, and UK general management. 9. Dan says he met his co-founders more than 10 years ago while competing at Uber. 10. He says he and his co-founders looked for other markets with two-sided fragmentation, large operations, and weak technology adoption. 11. Dan says founding was never a question of if, only when, because he felt a strong desire to build something. 12. He says personal impact, legacy, culture, and control over work-life boundaries all pushed him toward founding. 13. Dan says his advice for hesitant founders is to try if they would regret never doing it. 14. He says Dwelly grew from the insight that finding tenants is easier than acquiring landlords. 15. He says landlords rarely switch agents, which makes organic growth structurally hard in lettings. 16. Dan says the roll-up model means buying existing incumbents to acquire customer books in bulk. 17. He says VCs such as RedBus and Episode One passed repeatedly before the model became more accepted. 18. Dan says he moved to Hull with the team and worked in person with the first partner agency to rebuild the operating model. 19. He says the interview style is conversational and detailed, with practical examples from lettings, AI, and venture fundraising. 20. People interested in AI-enabled services and roll-up investing would fit this episode, while listeners wanting light entertainment probably would not.

As heard by us

An AI-first property management story that uses acquisitions as a go-to-market tool.

Riding Unicorns spends this episode on Dwelly's push to build a UK-based, AI-first lettings and property management platform, using acquisitions and partnerships with older agencies to improve service and experience.

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Why you'd press play

For the mechanics behind an AI-first lettings platform that grows by buying and partnering with agencies, press play.

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