Why Bootstrapped Companies Win
VC funding creates misaligned incentives. Bootstrapped companies often build better products and more sustainable businesses....
Hard-won lessons from 45+ years in the trenches.
No optimism theater What actually works
VC funding creates misaligned incentives. Bootstrapped companies often build better products and more sustainable businesses....
Slack users spend 1 hour 42 minutes daily on the platform. Power users hit 3.1 hours. The communication tool designed to save time became the biggest drain on it....
Knowledge workers spend 4.3 hours per week fact-checking AI outputs. 47% of enterprise users made major decisions based on hallucinated content. The costs are mounting....
Running BBSs in the 1980s meant handling hardware, limited connections, users gaming the system, moderation, and community - with no cloud, no scaling, no support tickets. Lessons that still apply....
Legal terminology, manufacturing jargon, call center scripts - each requires specialized training. The myth of 'one model to rule them all.'...
Series A funding often kills more companies than it saves. The pressure to scale before ready destroys sustainable businesses....
The architecture mistakes that kill startups: premature microservices, wrong database choices, god objects, missing observability, and more. Patterns that repeat across failed companies....
First-person account of running Core Logic Software during the 2000-2002 dot-com crash. When the NASDAQ fell 78% and 4,854 internet companies died, what it looked like from inside the ecosystem....
During the Gulf War, Iraqi troops surrendered to the USS Missouri's Pioneer UAV - the first surrender to a drone in history. Connecting military autonomous systems history to today's AI debates....
ORMs hide the database until they don't, create performance traps, and solve the wrong problem. SQL is the better abstraction. A contrarian take from 30 years of database work....
The AI wrapper economy mirrors dropshipping: low barriers to entry, no moat, platform dependency. With 90% failure rates and platforms absorbing successful features, the model is broken by design....
The security industry profits from fear. Most breaches have minimal impact while companies overspend on exotic threats....
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