Rory McIvor: Investment Professional, Writer, and Founder of Pretty Penny
The name Rory McIvor has begun to appear frequently in financial circles, media publications, and even lifestyle headlines. Known both for his professional achievements and his personal life, he represents a new generation of financial thinkers who bridge the gap between traditional wealth management and modern communication. From his years at Ruffer LLP to his current role as Founder and Writer at Pretty Penny, McIvor has carved a career that combines investment expertise with a flair for storytelling. His relationship with Made in Chelsea star Olivia “Liv” Bentley has also attracted public attention, adding a celebrity dimension to his growing profile.
This article explores Rory McIvor’s journey—covering his education, career at Ruffer, his new venture Pretty Penny, his personal life with Liv Bentley, and the qualities that make him an emerging voice in finance and beyond.
Early Life and Education
Friends’ School Lisburn
Rory McIvor’s academic journey began at Friends’ School Lisburn, one of Northern Ireland’s most respected institutions. During his time there from 2004 to 2011, he displayed both academic and sporting prowess. Excelling in subjects such as English Literature, History, Mathematics, and Physics, he left school with top grades including multiple A* and A results. His extracurricular involvement was equally impressive: Deputy Head Boy, 1st XV Rugby Captain, 1st XI Cricket player, Irish Schools Badminton competitor, and participant in theatre and debating. These early achievements revealed a mix of leadership, intellectual curiosity, and creative expression that would characterise his later career.
University of Edinburgh
Between 2011 and 2015, McIvor pursued a Master of Arts in History and Politics at the University of Edinburgh, graduating with First Class Honours. His academic focus included the Scottish Enlightenment, 20th-century United States history, African state politics, and modern Irish history. His thesis, on the United States’ involvement in the Irish peace process, was awarded a first-class mark. Beyond academics, he was active in the university’s rugby club, boat club, Shakespeare Company, and journalism through The Student. He also represented Edinburgh at the Harvard Model United Nations.
University of Cambridge
In 2025, McIvor embarked on a new academic challenge by enrolling in a Master of Philosophy in Modern British History at the University of Cambridge. His research centres on the life of Sir Roger Casement, a controversial figure in Irish history. This academic pursuit demonstrates his enduring commitment to intellectual study and historical inquiry, even while pursuing professional ventures.
Professional Journey
Ruffer LLP
Rory McIvor’s professional career began at Ruffer LLP, a London-based investment management firm, in 2017. Initially joining as an Investment Associate in the Private Wealth team, he managed portfolios for individuals and families. Over time, his career shifted towards communications and business development.
By the early 2020s, McIvor had become Director of Communications and Markets at Ruffer, a role that allowed him to combine finance with storytelling. He edited the Ruffer Review (2021–2024), hosted the firm’s podcast, fronted short-form video content such as The Green Line, and chaired weekly investment meetings. His approach was creative—using fairy tales, playground games, and historical analogies to explain complex investment strategies.
He also represented Ruffer at high-profile events, interviewing public figures such as Louis Theroux, Joanna Lumley, and Dominic Sandbrook. This public-facing role cemented his reputation as an articulate communicator who could translate financial insights into engaging narratives.
After nearly a decade at Ruffer, McIvor announced in early 2025 that he was leaving the firm to pursue new ventures, expressing gratitude for the opportunities and support he received there.
Pretty Penny
In March 2025, McIvor founded Pretty Penny, a new platform aimed at making stock market education engaging and accessible. The venture also seeks to help fund managers navigate the noisy world of social media to connect meaningfully with retail investors. With a planned launch in Summer 2025, Pretty Penny represents a fusion of his financial expertise, media skills, and creative vision.
Pretty Penny positions itself not just as an educational tool but as an entertainment-led brand. McIvor’s ability to bring humour, narrative, and history into financial communication is expected to set it apart from conventional platforms.
Licenses and Certifications
To complement his academic and professional achievements, Rory McIvor has acquired several respected qualifications in the world of finance:
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Investment Management Certificate (CFA Institute, 2017)
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Private Client Investment Advice and Management Award (CISI, 2018)
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Chartered Wealth Manager – Merit in Applied Wealth Management (CISI, 2019)
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Investment Decisions and Behavioural Finance (Harvard Kennedy School, 2023)
These certifications demonstrate his technical proficiency and his interest in the psychological side of financial decision-making—a theme that often appears in his writing and public speaking.
Founder & Writer
Beyond finance, Rory McIvor is also a writer. Following his departure from Ruffer, he began working on a novel titled Tainted Glory, a story exploring modern masculinity, friendship, addiction, and secrecy through the lens of two young Irishmen. This project underlines his versatility as both an analyst and a storyteller. His dual role as Founder & Writer captures the essence of his career: blending financial expertise with creativity.
Personal Life: Rory McIvor and Olivia Bentley
Meeting and Relationship
In May 2024, McIvor became publicly linked to Olivia “Liv” Bentley, a well-known personality from the reality TV series Made in Chelsea. The couple made their relationship “Instagram official” when Bentley posted a photograph of them together at a Chelsea lunch. Introduced through a mutual friend, their relationship quickly attracted media attention.
Liv Bentley on Rory
Bentley has spoken openly about the positive impact Rory has had on her life. In interviews, she described him as “amazing” and credited him with changing her perspective on relationships and family. Previously uncertain about having children, Bentley revealed that being with Rory shifted her outlook. The couple’s communication and shared values appear to be central to their relationship, making them one of the more intriguing celebrity-finance pairings in recent memory.
Public Attention
While McIvor has built his career largely in the financial sector, his association with Bentley has introduced him to a broader audience. Articles in lifestyle and entertainment publications now mention him alongside Bentley, demonstrating how his personal and professional worlds have intersected in the public eye.
Age and Profile
Based on his academic timeline—finishing school in 2011, graduating from Edinburgh in 2015, and starting at Ruffer in 2017—Rory McIvor was born around 1993 or 1994. That makes him approximately 31–32 years old in 2025.
This age reflects a career trajectory that combines early success in wealth management, a high-profile communications role, and a new entrepreneurial chapter as the founder of Pretty Penny.
Conclusion
Rory McIvor stands out as a modern financial professional: a historian by training, a wealth manager by career, a communicator by talent, and now an entrepreneur by ambition. His journey from Friends’ School Lisburn to the University of Edinburgh and Cambridge illustrates both intellectual depth and academic rigour. His eight years at Ruffer LLP established him as an articulate voice in investment strategy and financial communication.
Through Pretty Penny, McIvor is now seeking to democratise stock market education and help reshape how finance interacts with the public. At the same time, his personal relationship with Olivia “Liv” Bentley has brought him a degree of celebrity visibility.
At just 32, he already has a CV that spans wealth management, academic research, public speaking, writing, and entrepreneurship. Whether through his financial insights, his upcoming novel, or his new venture, Rory McIvor is a name that will continue to resonate in both financial and cultural conversations.
