My Friend Bob Cringely

A personal memoir of a long friendship with Bob Cringely, told by a former Ph.D. student who wrote an early Java book and was recruited in 1996 to build Bob’s startup prototype “Pronto.” Pronto was a concrete technical idea: a small daemon that would opportunistically download full-color magazine PDFs during idle dial‑up time and trigger a home printer at 2 a.m. so subscribers would wake to a printed issue. Bob funded the work and paid reliably, but Pronto never reached market. That project kicked off roughly 30 years of exchanges - about 320 emails over 13 years - during which Bob repeatedly circulated new startup ideas, often with precise revenue projections. The narrator joined two ventures (home-account and Sonisafe) and kept pitch decks and idea writeups from many more collaborations.

The account emphasizes Bob’s charismatic public persona and a mismatch between his strengths and ambitions: he was magnetic on screen, an excellent writer and TV host who made nerd culture comfortable and glamorous, yet he pursued the role of serial startup founder with mixed results. Anecdotes highlight that dynamic: a late-night C# rant became a Bob blog post and a surprise trip to Sun Microsystems with its CEO; a VH1 casting email yielded the narrator eight minutes on TV; and classic Cringely specials like Plane Crazy and The Transformation Age remain available online. The piece concludes with a warm goodbye and admiration for Bob’s gifts.