Ilya Drozdov from Dwelly on AI in Lettings and Building High-Margin Businesses

Ilya Drozdov, is the CEO at Dwelly, an AI-enabled Lettings & Property Management Marketplace, that boosts 3x margins of the letting agency in 2 months only. He previously co-founded the largest tech-enabled letting company in Eastern Europe that managed 10,000+ properties and reached $50M GMV in three years. In this episode, Ilya Drozdov, former Uber GM and CEO of Dwelly shares his journey from scaling Uber Russia to building tech-enabled property management platforms. He dives into lessons from managing fierce competition with Yandex, what made Uber’s playbook effective, and how Dwelly uses AI to transform traditional letting agencies. Ilya also discusses why culture mirrors founders, the balance between innovation and tradition in real estate, and the critical role of timing in startup success. He explains Dwelly’s acquisition and partnership strategy, the importance of product-market fit before scaling, and how founders can detach personal identity from company outcomes—and much more! Timestamps [02:15] – The general manager role at Uber and how it trained him for entrepreneurship. [03:40] – Uber’s entrepreneurial culture under Travis Kalanick and the motto: “Make big, bold bets.” 04:50] – Growing Uber Russia from 5 to 1,000 people and focusing on market share over team size. 06:05] – Uber’s expansion across 17+ Russian cities and the dominance of Moscow and St. Petersburg. 08:00] – Yandex’s advantages: local product teams and integration with existing services (maps, navigation). 09:30] – Uber’s city expansion playbook: choosing based on market size, competition, and local partnerships. 12:00] – How Yandex was equally aggressive in pricing and competition. 12:30] – Why Ilya transitioned into property lettings and how marketplaces shaped his lens. 13:30] – Challenges of building a marketplace in lettings due to lower transaction frequency. 14:50] – Dwelly’s unique edge: leveraging AI, especially LLMs, to automate communication-heavy property management. 16:00] – Dwelly's two-pronged growth: acquiring agencies and partnering with existing ones. 17:10] – Why traditional agents won’t disappear: AI + human hybrid model is the future. 18:30] – Targeting small-to-mid-sized agencies (500–3,000 properties) for scale and partnership. 19:45] – Dwelly aims for 35–40% EBITDA margins, significantly higher than traditional agents. 23:15] – Real estate innovation: evolution vs. revolution; building on top of existing industry norms. 24:30] – Why timing plays a critical role in startup success—compared to catching waves while surfing. 25:50] – On simplicity in product: it depends on the market’s cultural context (e.g. China vs. US). Ilya’s Links  LDN– https://www.linkedin.com/in/ilyadrozdov/ Website - https://dwelly.group/ My Links  Podcast: https://lifeselfmastery.com/itunes Newsletter: https://partner-grow.beehiiv.com/subscribe YouTube:  youtube.com/lifeselfmastery Twitter: https://twitter.com/rohitmal LinkedIn: https://www.linkedin.com/in/rohit857/ Agency: https://bit.ly/41YuNnx