cloudmark
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Karl Jacob
Karl Jacob is a Silicon Valley serial entrepreneur and the co-founder and CEO of LoanSnap, an AI-driven mortgage startup that pitched itself as the fix for a $13 trillion industry. Over more than two decades he founded or led companies including Dimension X (sold to Microsoft), Keen/Ingenio (sold to AT&T), Cloudmark (sold to Proofpoint) and Coveroo (sold to Zazzle), became one of Facebook's earliest advisors in 2005, and angel-invested in dozens of startups. LoanSnap raised roughly $100 million from backers like True Ventures, Richard Branson's Virgin Group, Reid Hoffman and Joe Montana before unraveling amid lawsuits, regulatory fines and an eviction between 2022 and 2024.
Vipul Ved Prakash
Vipul Ved Prakash is a serial entrepreneur and technologist who co-founded Together AI, an AI acceleration cloud platform valued at $3.3 billion after a $305M Series B in February 2025. Previously, he built Topsy (acquired by Apple for $200M+), co-founded Cloudmark (acquired by Proofpoint), and created Vipul's Razor - one of the internet's first collaborative anti-spam systems. A self-described cypherpunk with a table-tennis past, Prakash has been dismantling bottlenecks - from spam to closed AI - for over two decades.