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.   Please enjoy the countless nuggets of wisdom in my conversation with Jeff Housenbold.   Learn More Subscribe: Apple | Spotify | Google   Follow Ted on Twitter at @tseides or LinkedIn Subscribe Monthly Mailing List  Read the Transcript 

Jenny Heller is the President and Chief Investment Officer of Brandywine Trust Group.  Brandywine formed 25 years ago to manage the capital for a small group of families that all share a long-term, multi-generational time horizon. Today, it oversees almost $9B for those same families, much of it from compounding over a quarter century. The Group invests flexibly across asset classes, with a focus on partnering with people who they believe have sustainable competitive advantages, share their long-term vision, and have highly aligned interests.  These elite managers often start with great ideas, but limited capital.  Before taking the helm at Brandywine five years ago, Jenny worked at the Sloan Foundation, Stanford University Management Company, and Merrill Lynch in its investment banking program. She is a graduate of Williams College, where she serves on its Investment Advisory Committee, and Stanford Business School. Our conversation starts with Jenny’s frustrating experiences with a non-profit micro finance in India and South Africa and turns to her career allocating money on behalf of non-profits and families. We touch on subtleties in picking managers for taxable investors, challenges in executing a long-term strategy, learning from mistakes, and mentorship. Jenny’s clear and deep thought process provides pearls of wisdom throughout our conversation. Learn More Subscribe: Apple | Spotify | Google   Follow Ted on twitter at @tseides or LinkedIn Subscribe Monthly Mailing List  Read the Transcript