Dot-Com Crash, the $63M Exit and Conquering Enterprise IoT (Eric Simone, ClearBlade CEO) - Episode 24

from WORK IN PROGRESS · host Wes Botman, Ian Piepenbrock

Silicon Valley runs on stories. Reality runs on systems.Eric Simone has lived through multiple tech eras, from mainframes to the dot-com crash to modern IoT hype, and built ClearBlade while others chased narratives that collapsed under real-world scale.This episode is about what actually breaks companies: bad timing, fragile platforms, and founders who confuse momentum with durability. Strip away the mythology and what’s left is execution, patience, and uncomfortable tradeoffs.Chapters(0:00) Eric Simone’s background and perspective(4:30) Early Silicon Valley before startups were cool(13:40) IBM, mainframes, and learning the hard way(27:50) Bootstrapping Compete and surviving the dot-com bubble(40:10) Bad timing, good ideas, and why Webvan failed(54:00) Selling a company does not mean you are set for life(1:10:30) The painful birth of ClearBlade(1:23:00) Why IoT platforms keep failing at scale(1:32:40) Google IoT shutdown and ClearBlade’s breakout moment(1:39:00) Industrial IoT, edge computing, and real use cases(1:44:00) Fear, naivety, and why action beats certaintyOur GuestEric SimoneFounder & CEO at ClearBladeWebsite: https://clearblade.comThe WORK IN PROGRESS podcast hosted by Ian Piepenbrock and Wes Botman,two founders who are scaling and refining their businesses every day.Wes Botman is founder and CEO at Eli5 (https://eli5.io), a software studio making complex ideas simple and accessible.Ian Piepenbrock is CEO at Noco (https://noco.agency), an agency dedicated to helping B2B SaaS and tech companies grow through strategic web design and branding.Watch/listen on YoutubeFollow us on X for more raw insights, thoughts, and a good dose of founder reality:Wes: https://x.com/wesbotmanIan: https://x.com/lamswolprins

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This episode was published on January 21, 2026.

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