The Archive

Led a $45M investment at the height of the dot-com bubble despite partner opposition. Lost everything when the market crashed 6 months later.

Partnership with college roommate imploded over relocation decision. No formal agreement. Lost major client, company value, and a 20-year friendship.

Ignored warnings and deployed $23M in real estate just before 2008 crisis. Lost everything trying to meet deployment deadlines.

Hired big-company executive to run startup. Culture clash destroyed momentum, team morale, and growth trajectory.

Scaled from 12 stores in one state to 37 stores in 6 states in 18 months. Different markets destroyed our model.

Compromised analysis to keep major client. Deal failed spectacularly. Lost client, reputation, and entire firm.

Missed customer concentration in due diligence. "Diversified" revenue was 75% dependent on one funding source that collapsed.

Pivoted profitable media company to video based on Facebook's "future is video" push. Facebook's metrics were fake. Lost everything.

Tripled SaaS pricing based on consultant analysis. Lost 80% of new sales and 45% of existing customers.

Invested $9M in fintech without verifying regulatory compliance. Founders were operating illegally in 12 states.

Ordered 3x inventory after previous year's stockout. Market shifted, competitors emerged. Lost $5M liquidating.

Built entire business on Instagram API. Instagram cut access overnight. Company went from $25M valuation to zero in 8 months.

Tried to "productize" high-touch consulting firm. Clients paid for humans, not software. Lost clients and $4M.

Acquired startup for $11M. Imposed our corporate processes. Destroyed their culture. 60% of team quit within a year.

Switched from proven ML model to LLM after AI hype. LLM was worse. Lost $14M in revenue and customer trust.