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At PermissionTV, detailed wireframes kept producing features users did not need. The problem was treating UX artifacts as deliverables instead of hypotheses.
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The EditMe acquisition happened over beers, not in a boardroom. What it taught me about co-founder dynamics, customer development, and knowing when to sell.
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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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Ed-tech marketplace failures almost always trace back to the same problem: the user and the buyer are different people. BetterLesson figured this out through iteration, then built something durable by accepting the constraint.
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Most SaaS companies plateau between $5M and $20M ARR for the same reasons. Here is what separates the ones that break through.
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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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