FTX founder Sam Bankman-Fried was not only a tireless fundraiser from venture capital firms including Paradigm and Sequoia Capital, but also quietly made investments in those same funds, according to two people familiar with the matter. The unusual moves show how entangled Silicon Valley VC firms are in Bankman-Fried’s collapsing crypto empire, which has already forced these firms to mark down the value of their FTX stakes—previously worth hundreds of millions of dollars—to zero.

Bankman-Fried’s trading firm, Alameda Research, which had close ties with his crypto exchange FTX and which shut down this week, invested at least $20 million in Paradigm last year, according to two people with direct knowledge of the matter. Separately, Alameda Research and FTX Ventures, a venture arm backed by Bankman-Fried’s personal money, committed hundreds of millions of dollars to Sequoia Capital, Altimeter Capital Management and Multicoin Capital, according to four people familiar with the matter. Funds connected to Bankman-Fried also backed K5 Global, an advisory and investment fund run by Michael Kives, a close adviser to Bankman-Fried.