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A software release plan that works is not a timeline. It is a coordination document that makes explicit what needs to happen and who owns each decision.
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Two-sided marketplace product organizations need to solve two fundamentally different problems simultaneously. Most structure them wrong from the start.
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The most expensive go-to-market mistake is trying to create a new category and sell into it simultaneously. PermissionTV did both at once. EditMe did not. Here is what the contrast teaches.
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EditMe pivoted three times - wiki to CMS to collaboration software. What each pivot taught me about when to change direction vs. avoiding a harder conversation.
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You can build something real without quitting your job - not as a side hustle but as a structured business. The distinction between a backup plan and a practice is the decision that actually matters.
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Most leaders with transparency problems are not lying. They are managing information. The gap between what people are told and what is actually happening is what erodes trust — not the bad news itself.
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