Alexander Edward Chesterman

Alexander Edward Chesterman is a highly successful British serial entrepreneur and a prominent angel investor, widely recognized for founding and leading several transformative companies. His entrepreneurial journey includes co-founding Lovefilm, which was later acquired by Amazon, and founding Zoopla Property Group (ZPG Plc), a FTSE-250 listed company that revolutionized the UK property market. Most recently, he founded and served as CEO of Cazoo, an online used car retailer that achieved unicorn status and listed on the NYSE.

Transitioning into angel investing, Chesterman primarily focuses on disruptive technology companies, often within sectors he has deep expertise in, such as PropTech, FinTech, and consumer tech. He seeks out strong founding teams and scalable business models with the potential to significantly impact their respective markets. His investment strategy typically targets early-stage opportunities, with a notable preference for Seed and Series A rounds, where his operational experience can provide significant value beyond capital.

Chesterman is known for being a strategic and engaged investor, leveraging his extensive background in building and scaling businesses to support his portfolio companies. He has made at least 11 known angel investments, according to public records, often participating in substantial funding rounds alongside institutional investors. For instance, he was an early backer of Hometree, a home services platform that later secured a £25 million Series B round, and Nested, a property technology company that raised a £100 million Series B. His involvement suggests a long-term view and a willingness to follow on in subsequent funding rounds.

His investments underscore his continued commitment to fostering innovation within the UK tech ecosystem, backing the next generation of entrepreneurs. While specific individual check sizes are not always publicly disclosed, his participation in significant early-stage rounds suggests that his typical first cheques range from approximately $125,000 to $1,875,000, reflecting his status as a substantial and influential angel investor.