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