Paul P. O’Leary bought his first stock (Gulf and Western) with paper route earnings around the age of ten, which began a lifelong study on the topic of investments and building investment wealth. After 20 years in finance and operational roles in corporate America, he read Unconventional Success, by David Swensen, the legendary chief investment officer of the Yale University endowment.  This book offered a radically different approach for individual investors:  a simple, yet sophisticated portfolio constructed from a select few index funds.  Persuaded by the clarity of Swensen’s thinking and the detailed supporting research he offered, Paul saw the powerful investment framework this offered to individual investors and their families.  Importantly, he also saw the ability to offer the model as a business, where the cost savings could flow through to investors in the form of lower fees. With that vision, Paul founded Unconventional Investor in 2007.

Paul challenged himself to solve the pervasive frustrations that traditional asset management options cause individual investors, from excessive costs and conflicts of interest to poorly chosen securities and confusing pricing. From day one, Paul’s primary goal was to build a better, more personal advisory business. UI delivers sound investment strategy at extremely competitive fees, supported by a low overhead business model that is still highly individualized and responsive. In practical terms, this means many things, including a non-custodial approach, no expensive office spaces, the use of very low-cost index funds, unusual transparency, and unrivaled service.

From a business standpoint, UI is very similar to when it was founded.  The investment strategy has evolved slightly, and we have responded to changes in the market and in our clients’ needs, but little has changed about our fundamental approach. Every decision we make is based solely upon our clients’ best interests, maximizing their returns over time, and helping them achieve their financial goals.  

As of the end of the 2019, Unconventional Investor manages over $180 million for about 80 families. 



Our founder, Paul O’Leary, held senior level finance positions at several companies during his career. After business school at the University of Michigan, he worked for TRW in various finance and marketing capacities. From 1997-2002 he was Director of Finance, then Vice President of Finance for Score Educational Centers, a subsidiary of the Washington Post Company (WPO). He held the title of Director of Finance at Scientific Learning Corporation (SCIL) from 2004 through 2006. He left Scientific Learning at the end of 2006 to pursue his dream of starting this business and making high quality investment advice available to normal people at a reasonable cost.  




BA, Political Economy, 1987; Johns Hopkins University, Baltimore, MD
MBA, 1991; University of Michigan’s Ross School of Business, Ann Arbor, MI

Paul passed the Level I CFA Exam in 2003. He is not a CFA Charterholder.



Matt is a graduate of the College of Holy Cross with a double major in French and math (so he really understands the importance of compound interest!).  After graduation, Matt served for 6 years as an aviator in the US Navy, achieving the rank of Lieutenant and flying several different aircraft, including F/A-18s. After separating from the Navy, Matt worked for 5 years in consultative sales for Keyence Corporation, a global supplier of industrial automation equipment. Matt and his wife Amanda, a physician, live in Charlotte, NC with their dog Penny.