Alex Chesterman – The Visionary British Entrepreneur Who Built Zoopla, LoveFilm, and Cazoo
From Innovative Success to Hard Lessons in Business Transformation
Introduction
Alex Chesterman is widely regarded as one of the most influential figures in the UK’s digital business landscape. Known for his ability to spot opportunities and transform consumer experiences, he built successful companies such as LoveFilm, Zoopla, and Cazoo. His story is a mix of remarkable achievements and valuable lessons, offering both inspiration and caution for future entrepreneurs. As a British entrepreneur and former CEO of Zoopla, his legacy continues to shape how people think about technology-driven industries.
Born in London in 1970, Chesterman developed a passion for economics and business early in life. Over the years, he grew into a pioneer who disrupted multiple sectors—first in entertainment, then property, and finally in the automotive market. His career reflects both the highs of billion-pound valuations and the lows of business collapse, making his journey uniquely powerful and instructive.
Quick Bio
| Attribute | Details |
|---|---|
| Full Name | Alexander Edward Chesterman |
| Date of Birth | 9 January 1970 |
| Birthplace | London, United Kingdom |
| Nationality | British |
| Education | St Paul’s School, BSc Economics at University College London |
| Occupation | Entrepreneur, Angel Investor |
| Known For | Founder of LoveFilm, Zoopla, and Cazoo |
| Net Worth (Est.) | £750 million (2021 estimate) |
| Marital Status | Married |
| Children | Two sons |
| Awards | OBE (2016), EY Entrepreneur of the Year, Debrett’s 500 |
Early Life and Education
Alex Chesterman was born in London, where he was raised with a strong focus on academics and discipline. His early years at St Paul’s School shaped his analytical mindset, which later played a vital role in his entrepreneurial ventures. From a young age, Chesterman displayed curiosity about technology, business, and problem-solving.
He went on to pursue a Bachelor of Science degree in Economics from University College London (UCL). This academic background equipped him with both theoretical knowledge and practical insights, which later proved essential in building businesses that disrupted traditional industries.
The Start of His Career
Chesterman began his career with a corporate role as Executive Vice President at Planet Hollywood. While this position provided him with valuable leadership experience, he soon realized his real passion was in creating ventures that solved consumer problems.
By the late 1990s and early 2000s, the rise of digital platforms offered fresh opportunities. Chesterman identified gaps in how consumers accessed entertainment and soon launched himself into entrepreneurship.
LoveFilm – Revolutionizing Entertainment
One of Chesterman’s first major ventures was ScreenSelect, which later became LoveFilm. The service pioneered online DVD rentals, offering convenience at a time when video rentals required physical store visits.
The platform gained rapid popularity, eventually merging with rivals and becoming the market leader. In 2011, Amazon acquired LoveFilm for around £200 million, marking Chesterman’s first big success. This exit established his reputation as a digital innovator and gave him the confidence to explore new industries.
Zoopla – Transforming the Property Market
In 2007, Chesterman founded Zoopla, a property search and information platform designed to make real estate more transparent and accessible. At a time when buyers and renters faced limited data, Zoopla provided property values, area insights, and listings in one place.
The company grew rapidly, going public in 2014 with a valuation close to £1 billion. Under his leadership, Zoopla became part of ZPG plc, a broader digital group that included uSwitch and other property-related services. In 2018, ZPG was sold to Silver Lake for £2.2 billion, cementing Chesterman’s reputation as one of the UK’s leading entrepreneurs.
Cazoo – Ambition and Collapse
Chesterman’s next venture was Cazoo, launched in 2018 to disrupt the used-car market. The idea was bold: to enable customers to buy or finance cars entirely online with confidence. The company quickly raised significant funding, and by 2021 it achieved a $7 billion valuation through a SPAC listing in New York.
Initially hailed as a groundbreaking success, Cazoo later faced severe financial struggles. By 2022, it reported losses exceeding £700 million, and in May 2024 the company entered administration. The collapse highlighted the risks of rapid expansion, particularly in highly competitive industries. While a setback, it also demonstrated the volatile nature of tech-driven ventures.
Investments and Angel Roles
Beyond his major companies, Chesterman has played an important role as an angel investor. He has supported a wide range of startups, including Graze, Secret Escapes, CarWow, Farewill, Farmdrop, and UniPlaces. His investment approach often focuses on businesses that challenge traditional models and improve customer experiences.
This part of his career shows his lasting commitment to innovation and his belief in supporting younger entrepreneurs. Many of the startups he has backed have gone on to achieve significant recognition in their respective fields.
Recognition and Awards
Alex Chesterman’s impact has been widely recognized. He received an OBE in 2016 for his contributions to digital entrepreneurship. He was also named Ernst & Young Entrepreneur of the Year in 2013 and included in Debrett’s 500 list in 2017, which honors influential figures in British society.
These awards highlight not only his business achievements but also his influence on the UK’s broader digital economy.
Latest News
The most recent chapter in Chesterman’s story centers on Cazoo’s collapse in 2024. Despite its early promise and billion-dollar valuation, the company struggled with mounting losses and ultimately entered administration. This marked a significant turning point in his career, showing the fine line between rapid success and unexpected failure.
While some critics focus on the downfall, others view it as part of the entrepreneurial journey—proof that risk and reward go hand in hand. Even with this setback, Chesterman remains respected for his past successes and his role in shaping multiple industries.
Legacy
Alex Chesterman’s legacy lies in his ability to disrupt traditional markets and create platforms that transformed consumer experiences. His ventures—LoveFilm, Zoopla, and Cazoo—changed how people rented films, searched for properties, and bought cars.
Although Cazoo’s decline was a major setback, it does not erase his achievements. Instead, it underscores the unpredictable nature of entrepreneurship. He is remembered as a visionary British entrepreneur whose bold moves left a lasting mark on the digital economy.
Conclusion
Alex Chesterman’s journey demonstrates both the highs of entrepreneurial success and the challenges of over-expansion. From selling LoveFilm to Amazon, floating Zoopla on the stock market, and leading Cazoo to a multi-billion-dollar valuation, his achievements are undeniable. Yet, the failure of Cazoo reminds us that even the most visionary leaders face setbacks.
His story is one of ambition, resilience, and reinvention. For future entrepreneurs, Chesterman’s career serves as both inspiration and a reminder that innovation requires courage, adaptability, and an acceptance of risk.
FAQs
Q1: Who is Alex Chesterman?
Alex Chesterman is a British entrepreneur known for founding LoveFilm, Zoopla, and Cazoo. He is recognized for disrupting multiple industries with digital solutions.
Q2: What is Alex Chesterman’s net worth?
As of the 2021 Sunday Times Rich List, his net worth was estimated at around £750 million.
Q3: What companies did Alex Chesterman found?
He founded LoveFilm (sold to Amazon), Zoopla/ZPG (sold for £2.2 billion), and Cazoo (collapsed in 2024).
Q4: Has Alex Chesterman received any awards?
Yes, he was awarded an OBE in 2016, named EY Entrepreneur of the Year in 2013, and included in Debrett’s 500 in 2017.
Q5: What is Alex Chesterman’s legacy?
His legacy is that of a bold, visionary entrepreneur who disrupted industries and shaped the UK’s digital economy, despite facing significant business setbacks.
