We are a small team. We are not lone wolves: we value personal relationships, not personal brands, and work together on every investment.
Raymond Tonsing
Partner
Raymond founded Caffeinated in 2008. As one of the first solo GPs, he pioneered the single-partner fund model and scaled the firm to billions in AUM. Raymond has backed companies from seed to IPO (Affirm, Opendoor) and others acquired by BlackRock (FutureAdvisor), Google (Appurify), JPMorgan Chase (WePay), Meta (Parse, Blueprint Labs), and Spotify (Betty Labs).
Raymond serves on the boards of Onebrief, Saronic, Seneca and Twenty. He lives between San Francisco and Aspen and enjoys cycling, jiu-jitsu, and coffee.
Raymond serves on the boards of Onebrief, Saronic, Seneca and Twenty. He lives between San Francisco and Aspen and enjoys cycling, jiu-jitsu, and coffee.
Our founders do not have to deal with a rotating cast of partners or complex partnership dynamics.
None of our investments are options; we invest when we genuinely want to work with you for decades.
Varun Gupta
Partner
Varun joined Caffeinated in 2020. A generalist investor, he has sourced companies like Saronic and Twenty. Previously, Varun was a data scientist and machine learning engineer at Affirm (pre-IPO), where he led the development of multiple novel credit underwriting systems, one of which made the Affirm Anywhere mobile product newly profitable. Before that, Varun worked at Expanse (acquired by Palo Alto Networks) and Wealthfront and studied applied math, computer science, and AI at Stanford University.
Varun serves on the boards of Federato, Amca, and Luzern. He lives in New York.
Varun serves on the boards of Federato, Amca, and Luzern. He lives in New York.
Matthew Volosin
Partner
Matt began working with Caffeinated in 2009 and joined full-time as partner and COO in 2013. He helped scale the firm's pioneering single-partner fund model and now leads the operationalization of the firm's evolution into a multi-partner platform. Matt oversees all non-investment functions at Caffeinated, including operations, fund administration, legal, finance, compliance, deal execution, and LP relations.
He lives in Cleveland and enjoys golf, skiing, and traveling.
He lives in Cleveland and enjoys golf, skiing, and traveling.
We pride ourselves on knowing what it takes to build exceptional companies after decades of personal partnerships with some of the world’s best founders.