# Brex 3.0: An 18-Month Operational Evolution & the Brex Hacker House “AI Startup within a Startup" experiment w/ James Reggio #236

Page: https://stenobird.com/podcast/the-engineering-leadership-podcast-743839/brex-3-0-an-18-month-operational-evolution-the-brex-hacker-house-ai-startup-within-a-startup-experiment-w-james-reggio-236
Text version: https://stenobird.com/podcast/the-engineering-leadership-podcast-743839/brex-3-0-an-18-month-operational-evolution-the-brex-hacker-house-ai-startup-within-a-startup-experiment-w-james-reggio-236.md
Podcast: [The Engineering Leadership Podcast](https://stenobird.com/podcast/the-engineering-leadership-podcast-743839)
Published: 2025-11-12T22:51:46+00:00
Episode link: https://sfelc.com/podcasts
Audio file: https://pscrb.fm/rss/p/afp-942744-injected.calisto.simplecastaudio.com/4d87e711-78c0-43f3-9633-fa05520e07f2/episodes/185edc0a-cd8e-4bb0-8da2-2ad049abb5fc/audio/128/default.mp3?aid=rss_feed&awCollectionId=4d87e711-78c0-43f3-9633-fa05520e07f2&awEpisodeId=185edc0a-cd8e-4bb0-8da2-2ad049abb5fc&feed=Z8Dl_qAv
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JSON: https://stenobird.com/v1/public/podcasts/the-engineering-leadership-podcast-743839/episodes/brex-3-0-an-18-month-operational-evolution-the-brex-hacker-house-ai-startup-within-a-startup-experiment-w-james-reggio-236
Duration seconds: 2730

## Resource

James Reggio (CTO @ Brex) shares the story of "Brex 3.0", an 18-month journey behind their operational evolution. We explore how they rewound their org from a Series E to a Series C mindset, and replaced siloed OKRs with seasonal "marquee initiatives." James deconstructs the “Brex Hacker House”, an AI-focused startup within a startup experiment aimed to disrupt their core business. This conversation is all about evolving operational rhythms, layers of management, product building, and culture change!

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## Transcript

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