We are a small team with no internal politics or promotion ladders.
We value personal relationships, not personal brands, and work together on every investment.
Our founders do not have to deal with a rotating cast of partners or complex partnership dynamics.
We value personal relationships, not personal brands, and work together on every investment.
Our founders do not have to deal with a rotating cast of partners or complex partnership dynamics.
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. A generalist investor, 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).
He currently serves on the board of the following Caffeinated portfolio companies: Cloudtrucks, Onebrief, Saronic, and Twenty. He lives between San Francisco and Aspen and enjoys cycling, jiu-jitsu, and coffee.
He currently serves on the board of the following Caffeinated portfolio companies: Cloudtrucks, Onebrief, Saronic, and Twenty. He lives between San Francisco and Aspen and enjoys cycling, jiu-jitsu, and coffee.
Varun Gupta
Partner
Varun joined Caffeinated in 2020. A generalist investor, Varun sourced companies like Saronic and Twenty and currently serves on the board of the following Caffeinated portfolio companies: Federato, Amca, and Luzern. 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.
He previously worked at Expanse (acquired by Palo Alto Networks) and Wealthfront and studied applied math, computer science, and AI at Stanford University. He lives in New York.
He previously worked at Expanse (acquired by Palo Alto Networks) and Wealthfront and studied applied math, computer science, and AI at Stanford University. 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.