What happened to you in Mexico? Justin is back from his co-founder retreat with Jon on Holbox Island. He gets vulnerable about the drift that naturally happens in a remote co-founder relationship, the big conversations they'd been avoiding, and the realization that alignment isn't a one-time thing (it requires constant investment!). Jordan and Brian weigh in on co-founder dynamics, decision-making in a 50/50 partnership, and why strategy has to belong to a key decision maker.
The conversation then spills into the "Mexican standoff" happening on teams as AI reshapes who does what and whether that's something to fear (or lean into).
Timestamps:
(00:06) - Introduction
(01:47) - Justin and Jon's founder retreat
(06:44) - Using video as an example of how to communicate with cofounders
(09:45) - It's not a marriage, it's a dictatorship
(12:12) - What do goals look like for a company?
(20:48) - Video is hard and heavy... should we do it?
(24:22) - What Jordan's done to help alignment on his team
(29:46) - What about Jon's side of the conversation?
(39:46) - Navigating new work dynamics with the speed of AI
(46:56) - There are smart developers resisting AI - why?
(54:24) - A Mexican standoff on teams
(01:06:47) - Company design and system design
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Links mentioned in this episode:
Holbox Island
Photos from co-founder retreat
Article: The five stages of losing our craft
Article: Will Claude Code ruin our team?
Jack Dorsey lays off 931 workers
Polsia - this weird AI driven SaaS making $2m! (You give it an idea, provide a budget/credit card, and it autonomously launches the business)
More on Ben Cera, founder of Polsia
The Amazing Money Machine book cover