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Our company: 150 employees, structured, process-driven, quarterly planning cycles. Target: 25-person startup, scrappy, move-fast culture, achieved product-market fit we wanted.
My Role: Acquirer CEO
Acquired company for $11M—$6M cash, $5M earnout over 2 years. Strategic acquisition to accelerate our product roadmap. Due diligence focused on tech, financials, customer contracts. Cultural integration was "we'll figure it out." Post-close plan: target team stays autonomous, reports to our CTO. Seemed respectful of their culture.
Within weeks, clash emerged. Our: formal code reviews, security requirements, privacy protocols, compliance checks. Them: "just ship it, iterate fast." Our procurement: 45-day vendor approval process. Them: used to buying tools with credit card instantly. Our planning: quarterly roadmaps locked 6 weeks in advance. Them: used to pivoting weekly. Their founder-CEO reported to our CTO who had zero startup empathy. Every decision required "alignment" with 4 stakeholders. By month 4, their founding team was frustrated. By month 7, their CEO quit. By month 10, 15 of 25 original employees had left—including the entire product team we'd acquired them for. Earnout was never achieved. We got the code but lost the people who understood it. Took us 18 months to rebuild, cost us $7M in additional hiring and delayed roadmap.
Acquisition discussions begin
Deal closes - $11M ($6M cash, $5M earnout)
Integration begins, friction emerges
Process conflicts escalate
Acquired CEO expresses frustration
Acquired CEO quits
15 of 25 employees have left
Earnout period unlikely to be achieved
"You're acquiring people and culture, not just technology. Culture clash kills value."
$11M acquisition price + $7M to rebuild = $18M total for nothing.
Guilt for destroying a great team. Felt like a corporate villain.
Acquired team hated us. Word spread—hurt ability to do future acquisitions.