Tim Guleri is a former serial entrepreneur who built Scopus Technology (IPO 1995) and founded Octane Software (acquired by Epiphany for $3.2 billion) before becoming a VC, giving him credibility with founders as someone who has personally built and exited large-scale enterprise software companies. He has developed a distinctive five-layer AI layered cake framework for investing that maps opportunities from core infrastructure to novel AI-native business models, and spends nights and weekends learning and testing generative AI to bring fresh reports and frameworks to Sierra Ventures' investment decisions. Tim Guleri is a former serial entrepreneur who built Scopus Technology (IPO 1995) and founded Octane Software (acquired by Epiphany for $3.2 billion) before becoming a VC, giving him credibility with founders as someone who has personally built and exited large-scale enterprise software companies. He has developed a distinctive five-layer AI layered cake framework for investing that maps opportunities from core infrastructure to novel AI-native business models, and spends nights and weekends learning and testing generative AI to bring fresh reports and frameworks to Sierra Ventures' investment decisions.