Founder Secondaries: When to Take Money Off the Table
Founder secondaries let you sell shares before the exit. Here is when taking money off the table makes you a bolder founder, and how much is far too much.
Lessons, frameworks, and stories from the trenches of building companies.
Founder secondaries let you sell shares before the exit. Here is when taking money off the table makes you a bolder founder, and how much is far too much.
AI runs the happy path and quietly erodes recovery, the one skill you cannot delegate. Why recoverability decays as reliability rises, and how to keep yours.
The delegation threshold is the line where buyers stop testing your AI and start depending on it. Here is how to read it in revenue, and how to cross it.
The real moat question is not whether AI can do what you do. It is whether anyone still pays you after it does. Here is the Absorption Test and how to pass it.
AI is great at the how and silent on the what. The skill that atrophies is initiative: deciding what to do when nothing prompts you. Here is how to protect it.
AI agent costs do not just shrink payroll. They change its shape, turning a fixed salary into variable metered compute. Here is the margin trap and the fix.
AI burnout is not about working too little or resting too much. It is the bar for enough rising faster than you can meet it. Here is how to define enough.
Revenue per employee became the number investors trust, and headcount growth turned into a warning sign. How the signal inverted, and how to hire lean.
Decision fatigue is the hidden tax on AI output. Cheap execution multiplies your decisions, and deciding is the one skill that gets worse the more you use it.
Automation bias is the operating risk that shows up when your team quietly stops checking AI output. How it compounds, and where to make checking mandatory.
Building something interesting? Looking for an investor who’s been in the trenches? Or just want to say hello? I’d love to hear from you.
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