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Dot-Com Crash, the $63M Exit and Conquering Enterprise IoT (Eric Simone, ClearBlade CEO) - Episode 24
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 certainty
Our Guest
Eric Simone
Founder & CEO at ClearBlade
Website: https://clearblade.com
The 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 Youtube
Follow us on X for more raw insights, thoughts, and a good dose of founder reality:Wes: https://x.com/wesbotman
Ian: https://x.com/lamswolprins
View all episodes
By Wes Botman, Ian PiepenbrockSilicon 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 certainty
Our Guest
Eric Simone
Founder & CEO at ClearBlade
Website: https://clearblade.com
The 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 Youtube
Follow us on X for more raw insights, thoughts, and a good dose of founder reality:Wes: https://x.com/wesbotman
Ian: https://x.com/lamswolprins