In this episode, Jeremy Toeman sits down with John Biggs—whose career spans from hand-coding HTML at Carnegie Mellon to writing over 11,000 posts for TechCrunch, to founding startups and hosting the Keep Going podcast. John explains how he learned to pivot from tech journalism into building products of his own, why he believes in testing ideas quickly (even if they fail), and how he turned countless “side experiments” into actionable lessons. You’ll hear:
How early web tools at CMU taught him to build fast and fail fast
The story behind launching CrunchGear at TechCrunch and scaling into a separate gadget site
What prompted him to leave full-time journalism to become a startup founder
Why he launched Keep Going, and how recording hundreds of founder interviews reshaped his view of “success”
No hype here—just honest talk about learning through failure, leaning into your network, and staying curious in a world where everything changes overnight.
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