Let’s dive in and get to know Rory McIvor — a rising star in finance, a scholar at Cambridge, and the new boyfriend of reality TV star Olivia Bentley. Rory’s life is full of interesting stories, from his successful career to his exciting personal life. If you are curious about who he is, what he does, and why people are talking about him, you’re in the right place. Here’s everything you need to know about Rory McIvor.
Rory McIvor’s Early Life And Education
Rory McIvor was born in Ireland and had a passion for learning from a young age. He studied at the University Of Edinburgh, one of the top universities in the world. In 2017, he graduated with a First-Class Honours degree in History And Politics. His studies were not just about books — Rory loved learning about how history, economics, and politics shape the world we live in.
During his time at university, Rory was very active outside the classroom too. He took part in sports and public speaking, which helped him build strong leadership and communication skills. His final year project focused on the role of the United States in the Irish Peace Process. This showed early signs of his deep thinking and his ability to connect big ideas to real-world issues.
By the time Rory left Edinburgh, he had built a strong foundation for a future filled with possibilities. His interest in history, people, and society would later help him become a voice not only in finance but also in education and public discussions.
Career Beginnings At Ruffer LLP
After graduating, Rory did not waste any time. In 2017, he joined Ruffer LLP, a respected investment management company based in the United Kingdom. His first role was as an Investment Associate in the Private Wealth team. Here, he worked closely with wealthy individuals and families, helping them manage and grow their investments carefully.
Rory’s work was not just about numbers. He listened to his clients, understood their goals, and created smart plans for them. His calm nature and clever thinking made him stand out quickly among his colleagues. It was clear that he had a special talent for turning complex financial ideas into something simple and easy to understand.
Working at Ruffer gave Rory a deep understanding of how financial markets work. It also gave him a new passion — teaching others how to understand and manage money better.
Rising To Leadership
It didn’t take long for Rory to rise through the ranks at Ruffer. He was soon promoted to Director, where he took on even bigger responsibilities. His main job was leading the firm’s investment communications, helping clients and the public understand markets, risks, and smart investment strategies.
Rory became the Editor of the Ruffer Review between 2021 and 2024. Through this platform, he shared insights on behavioral finance, market history, and smart investment thinking. He also led Ruffer’s podcast and short video series, interviewing famous figures like Louis Theroux and Joanna Lumley.
More than anything, Rory’s leadership made finance feel less scary for many people. He used real-life examples, humor, and easy language to explain complicated topics. His goal was simple: make financial education open to everyone.
Founding Pretty Penny
In early 2025, Rory made a big decision — he left Ruffer to start his own company, Pretty Penny. This move showed his desire to change how people learn about and think about money. Pretty Penny is designed to make financial education simple, fun, and accessible to everyone, not just experts.
Pretty Penny plans to launch in Summer 2025 and is expected to offer tools, advice, and content that make investing and managing money easier. Rory wants to break the idea that finance is only for a few. Instead, he wants to show that everyone can understand and use smart money strategies.
With Pretty Penny, Rory is blending his finance background with his talent for storytelling and media. It’s a big step, but one that fits perfectly with his vision of helping people live smarter, more confident financial lives.
Academic Pursuits At Cambridge
Even while building his career, Rory never lost his love for learning. In 2025, he started a Master Of Philosophy (MPhil) program in History at the University Of Cambridge, one of the most respected universities in the world.
At Cambridge, Rory is studying Modern British And Irish History. His research focuses on Irish Nationalism and how history shapes the way societies grow and change. His studies show that Rory is not just about money — he cares deeply about ideas, cultures, and how people understand their place in the world.
Balancing his studies with running a company is not easy, but Rory’s passion for both fields keeps him moving forward. It also adds a unique depth to his work, combining real-world finance with a deep understanding of history and society.
Relationship With Olivia Bentley
In 2024, Rory’s personal life came into the spotlight when he started dating Olivia Bentley, a well-known star from the TV show Made In Chelsea. Olivia had a colorful dating history on the show, including relationships with Francis Boulle, Fredrik Ferrier, Digby Edgley, and Tristan Phipps.
Rory and Olivia’s romance became public in May 2024 when Olivia posted a sweet photo of them together on Instagram. They were reportedly introduced by a mutual friend named Cat, a Pilates instructor. Their relationship quickly caught attention because it seemed genuine and grounded.
Even though Olivia is used to public life, Rory has remained more private. They have shared a few special moments on social media, like dressing up with skeleton makeup for Halloween. Fans love the fact that Rory brings a sense of calm and stability into Olivia’s life.
Private But Influential
One thing that stands out about Rory is how he handles fame. Despite dating a reality TV star, Rory keeps his life mostly private. He has no public social media accounts and rarely appears in interviews focused on his personal life.
This private approach has earned him respect. In a world where many people chase fame, Rory focuses on meaningful work, education, and building a lasting impact. He believes that real success is not about how many followers you have, but about the value you create for others.
This quiet confidence is part of what makes Rory so interesting — and why more and more people are starting to notice him.
Public Speaking And Media Work
While Rory prefers privacy in his personal life, he shines when it comes to public speaking and media work. At Ruffer, he hosted podcasts and events that made financial discussions interesting and easy to follow.
He believes in making financial literacy fun. Whether it was explaining market crashes through stories or discussing behavioral finance with humor, Rory found ways to connect with audiences who might otherwise be intimidated by financial topics.
Through Pretty Penny, he plans to continue this style — using clear, relatable language to teach people how to take control of their financial futures.
Commitment To Philanthropy
Beyond finance and media, Rory also believes in giving back. During his time at Ruffer, he was part of various charitable projects. He understands that true success includes helping others along the way.
His girlfriend Olivia also shares a passion for philanthropy. Together, they have supported different causes and used their public platform to raise awareness. This shared value adds another layer to their strong bond.
Rory’s view is simple: real wealth is not just about money. It’s also about using your success to make a positive difference in the world.
Future Plans
Looking ahead, Rory has big dreams. Pretty Penny is just the beginning. He hopes to expand the platform into new areas, offering more educational resources, videos, podcasts, and community tools to help people around the world understand finance better.
He also plans to keep studying, learning, and growing — both in business and academically. His goal is to make financial education something people enjoy, not fear.
By mixing finance, media, history, and education, Rory is building a career that is not only successful but also meaningful. He is determined to leave a lasting impact.
Final Thoughts
We hope you find this article helpful and inspiring. Rory McIvor’s story shows that success is not just about working hard — it’s also about thinking big, staying curious, and helping others along the way. From leading in finance to studying history and building a new business, Rory’s journey is full of lessons for anyone who dreams of making a difference.
As he continues to grow Pretty Penny and build his public presence, one thing is clear — Rory McIvor is a name we will be hearing a lot more about in the future.
(FAQs)
Is Rory McIvor really dating Made In Chelsea star Olivia Bentley?
Yes, Rory McIvor and Olivia Bentley went public with their relationship in May 2024. They were introduced by a mutual friend and have been seen together a few times, including celebrating Halloween with matching skeleton makeup.
Did Rory McIvor leave a top investment firm to start his own company?
Yes, in 2025, Rory left his high-ranking role at Ruffer LLP to launch Pretty Penny, a bold new platform aiming to make financial education simple and fun for everyone.
Is Rory McIvor also studying at Cambridge while building his business?
Shockingly, yes! Rory is studying for a Master’s degree (MPhil) in History at the University Of Cambridge while also running Pretty Penny full-time.
Was Rory McIvor already interviewing celebrities before founding Pretty Penny?
Yes, during his time at Ruffer, Rory hosted podcasts and events with famous guests like Louis Theroux and Joanna Lumley, making finance more entertaining and accessible.
Does Rory McIvor plan to change how people learn about money forever?
That’s the goal! Through Pretty Penny, Rory is working to completely change the way people learn about finance, making it easy, fun, and available to everyone — not just experts or the wealthy.
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