Trained at MIT as a computer scientist, Bob's analytical talent has led him to become an experienced investor with a track record of identifying opportunities in areas of outsized potential growth. He began his investment career on the floor of the American Stock Exchange and went on to develop quantitative research-driven trading strategies at JPMorgan Chase, Soros Fund Management, and Bloomberg, where he managed a team of quantitative engineers.

In 2013, Bob established Uji Capital LLC, a family office focused on quantitative opportunities in global equity capital markets. One of the first investors to identify the growth of the Canadian legal cannabis market as a strategic investment opportunity, Bob took early equity positions in Tweed Marijuana Inc. and Aphria Inc., which have since grown into two of North America's most successful cannabis companies. Subsequently, Bob made a private investment in and served as a board member for Tokyo Smoke, an award-winning cannabis lifestyle brand, which merged in 2017 to create Hiku Brands, where Bob served as chairman. Hiku Brands was acquired by Canopy Growth Corporation in 2018.

In 2019, Bob made a donation totaling $9 million to Harvard and MIT to fund research on the effects of cannabis on the human body and brain. His hope for the gift is to enable world-class researchers at these institutions to delve into a new area of scientific research that could have bearing on a rapidly growing industry, and to lend credibility to an area of science that has been stigmatized in the past. At the time of the donation, the gifts to MITs Picower Institute for Learning and Memory and Harvard Medical School combined represent the largest gift towards cannabis research in history.

Bob holds a Bachelor of Science and Master of Engineering in computer science from the Massachusetts Institute of Technology, and a Master of Arts in East Asian studies from Harvard University. He lives in New York with his wife, Yuka, also an MIT alum, and their two children.