Private equity firm GSR Capital will invest up to $374.6 million in online retailer Overstock.com Inc. and t0.com Inc. under term sheets signed among the parties.

GSR Capital will buy up to 3.1 million shares of Overstock's common stock at a 5% discount to the Aug. 1 closing stock price. The firm will also invest as much as $270 million for up to 18% stake in tZERO at a post-money valuation of $1.5 billion. In addition, GSR Capital agreed to buy $30 million worth of tZERO security tokens from Overstock. GSR Capital has rights to allot a portion of the investments to third parties.

The transactions are contingent on definitive documentation, among other closing conditions.

TZERO is a blockchain subsidiary of Overstock.