Scott Samuel

An early Internet pioneer, who Reid Hoffman credits with helping PayPal get off the ground, eyes cannabis – specifically the sale of pipes and related devices to discreet consumers over the web – as the next digital frontier. As co-founder and chief strategy officer of ShopHitly, a Chicago-based ecommerce platform set to debut later this year, Samuel is planning to attract 35-to-65 year-olds for whom stigma or professional reputation issues would not feel comfortable walking into a headshop. The founder of – which in 1998 was among the top the top 25 trafficked websites in the world – believes there is an opportunity to build a big, socially-minded enterprise before the Amazons of the world invariable jump in. Stay tuned. 

James Yi

In 2019, James Yi and partner Michael Piermont raised $4.5 million for their cannabis software company Hyde Park Angels, an investor group comprised by University of Chicago alumni and stakeholders, led the investment round. The company plans to connect dispensaries with brands to optimize supply and demand. According to’s online origin story, the company concept emerged as Yi and Piermont observed dispensary professionals texting photos of suppliers of orders written on napkins. 

Jessi Rae

As Eugene, Oregon-based chief operating officer of CannaConnections, Jessi Rae is co-hosting the 10th CannaGrow Expo in Chicago on April 17 and 18. This education and networking conference will focus on the “art and science” of growing cannabis and will include panel presentations and expert talks from leading local and national proprietors.

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Brad Spirrison is a journalist, serial entrepreneur and media ecologist. He lives in Chicago with his son. Interests include music, meditation and Miles Davis.