While still attending Cal, John began working at Farallon Computing - a vibrant and creative startup where he refined his skills and clarified his ambitions. In 1992, he launched his own award-winning boutique interactive design firm, Midnight Design, Inc. Following the dot-com crash and the events of September 11, 2001 (he and his wife were just 40 blocks away from the Twin Towers), he spent time reflecting on the future. A brief foray into voice-recognition technology with his brother led to the co-founding of Letters and Arts, Inc., a successful digital publishing company that continues to thrive.

After 2006, he stepped away from daily operations at Letters and Arts but remained involved as a shareholder. Since then, he has become more deeply engaged in private equity investments across software, oncology, and the wine industry, including notable investments in the ed-tech company LetsGoLearn, Inc., and the oncology startup Presage Biosciences.

In his personal time, he enjoys being with his family, mountain biking, exploring additional investment opportunities, teaching at Southern Oregon University, sampling wines, producing music, fundraising for charitable causes, and volunteering as a patient advocate for individuals with high-grade cancers. He was publicly elected to the Ashland School Board, where he served for six years. He has also served as board chair for the Rogue Gallery (a regional community art foundation), the Ashland Water Advisory Committee, and the Ashland Forest Lands Commission, and has held board positions with several nonprofit and governmental organizations.

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