Ep. 77 | Winning with transparency - Norman Coburn

Jack sits down with the co-founder and CTO of Darien Technologies, Norman Coburn, in Panama City to unpack 11 years of building a “software factory” across banking, fintech, and startups. They contrast capital-rich comfort in the U.S. with the scrappy, bootstrapped edge of LATAM, then dig into how AI shifts the craft from deterministic builds to generative experiments, plus when to use each. Beyond code, they cover senior product coaching, ruthless scoping, and early user feedback loops that turn specs into MVPs people actually adopt. The team’s operating principles come through: transparent proposals, radical candor with partners, annual reinvention to stay relevant, and addressing misalignment or underperformance early.

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(01:17) LATAM vs US funding realities
(02:50) “Software factory”
(04:54) Annual reinvention to stay relevant
(05:20) AI shift
(06:55) Generative vs non-generative
(07:32) What a “software factory” actually does
(09:59) Coaching clients
(15:05) Senior “reality checks” that change roadmaps
(16:23) What separates winners from the rest
(22:58) Transparency over black-box proposals
(28:56) Radical candor with partners keeps momentum
(32:14) Address underperformance early