Rainmakers #18 Joe Liemandt: Startup Founder turned Buyout Billionaire
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Aug 21, 2025 Witness the journey of a billionaire who thrived amidst the chaos of the dot-com era. Discover his unique approach to buying and revitalizing struggling software companies, turning distress into profit. The conversation dives into innovative business strategies focused on cash flow and customer value. Learn about the evolution of ESW Capital and their game-changing contrarian tactics. Plus, get insights into how Trilogy University trains the next generation of entrepreneurs through rigorous challenges and a strong corporate culture.
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Early Breakthrough With A Last-Minute Demo
- Joe Liemandt built Trilogy by solving a painful sales/configuration problem he observed while interning and studying at Stanford.
- A last-minute demo for Silicon Graphics succeeded and turned into the first big client that launched Trilogy's growth.
Facing The Dot‑Com Bust And Customer Criticism
- Trilogy hit the dot-com downturn and faced customers who said the product didn't deliver measurable value.
- Liemandt responded by restructuring, buying back stock, and focusing the company on delivering real ROI to clients.
Enterprise Software Is Exceptionally Cash Generative
- Computer Associates showed enterprise software can be massively cash generative through frugality and acquisitions.
- Liemandt studied that model and realized cutting costs plus retaining engineers turns bought software into fast cash engines.
