Issue No. 43Week ending Sunday, October 25, 2026636 episodes · 2800 articles
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Measure Engineering Like You Measure Sales (w/ Dan Bender & Kirby Montgomery, Code & Co.)

With Jim Milbery, Dan Bender, Kirby Montgomery · Sunday, October 25, 2026

Jim Milbery hosts Dan Bender and Kirby Montgomery from Code & Co. to explore how private equity investors can measure software engineering with the same rigor as sales and finance. The conversation covers the evolution of technical due diligence shifting left before LOI, the risks of 'dark factories' and vibe coding, why classic metrics like lines of code and story points fail, and how investors can evaluate AI resilience, DORA metrics, and unit economics during the hold period.

Key takeaways

  • Dan Bender and Kirby Montgomery at Code & Co. track the rise of dark factories, where automated AI agents generate software without human oversight or verified test suites. Read more →
  • Dan Bender of Code & Co. points out that middle-market software targets often rely on Delphi fat clients where presentation and business logic layers intertwine, making standard continuous deployment impossible without a complete rewrite. Read more →
  • Less than 30% of enterprise production tokens (roughly 28%) now run through proprietary frontier models, with open-weight models absorbing the rest. Read more →
  • Raw volume metrics punish efficient developers: Dan Bender notes that strong engineers routinely delete code to refactor systems, making gross code output an inverse signal of software health. Read more →
  • Technical diligence shifted from a confirmatory check three weeks before signing to a pre-LOI gating item focused on software durability. Read more →

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