Rainmakers #19 Chris Sacca: Venture Cowboy
10 snips
Aug 28, 2025 
Chris Sacca, a renowned venture capitalist and founder of Lowercase Capital, shares his remarkable journey from being fired as a lawyer to investing in giants like Twitter and Uber. He discusses the evolution of venture capital, emphasizing the Netscape IPO's impact on Silicon Valley. Sacca also reflects on navigating the dot-com boom's highs and lows and the strategies that led to his success. His insights on pattern recognition and collaboration with innovative founders reveal the secrets behind his influential career in tech investments.
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From Student Loans To Silicon Valley
- Chris Sacca used grad-school loans and day-trading leverage during the dot-com boom to fund ventures and lost millions when the bubble burst.
- He then moved to Silicon Valley, worked at small startups and Google, and learned generalist skills that shaped his VC career.
Repetition Built VC Pattern Recognition
- At Google Sacca saw 40–50 proposals a day, giving him massive pattern recognition about what makes startups compelling.
- He turned those repetitions into the confidence and taste needed to spot founders early and invest as an angel.
Be The First Check For Engineers
- Do target exceptional engineering talent and be the earliest check to secure favorable economics and real influence.
- Add value as a generalist operator so founders view you as a partner, not just a capital source.