Jeff Housenbold, a Managing Director for the last four years at Softbank Investment Advisors, where he led one of the six investment teams that deployed the $100 billion Softbank Vision Fund. Prior to joining Softbank, Jeff worked at sixteen companies, including eleven years as CEO of Shutterfly. four years in the early days of ebay, four as Special Industry Advisor to KKR, and one as Entrepreneur in Residence at Sutter Hill Ventures. He’s also served on the Boards of dozens of companies, including Caesars Entertainment, Memphis Meats, DoorDash, Compass, Opendoor, Wag, and Groupon.

Our conversation starts with Jeff’s true rags to riches story and then turns to a whirlwind of lessons learned as an operator at eBay during its hypergrowth and Shutterfly overseeing a successful turnaround. We then dive into the Softbank Vision Fund, including the original investment thesis, sourcing ideas, valuation discipline, decision making in groups, portfolio structure, and results. We close by talking about the SPAC market, capital market expectations, the characteristics of successful organizations, and succession planning.