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. For more episodes, go to capitalallocatorspodcast.com/podcast Follow Ted on twitter at @tseides

Today’s show is a little different from my ongoing series of conversations with Capital Allocators.  As you probably know, about 9½ years ago I made a bet with a certain Oracle, in Omaha, that pitted the performance of a group of five hedge fund of funds against the S&P 500. In this year’s annual letter to Berkshire Hathaway shareholders, Warren wrote extensively about his views. You can find that letter at www.berkshirehathway.com/letters. Now I haven’t said a lot about the bet, although fairly often I’m asked how it came about, why I made the bet, what I really think about hedge funds and the market, and of course, who's winning. I thought long and hard about whether to share my views publicly, and had been leaning towards staying out of the limelight.  But my guest on Episode 2 of this podcast, André Perold, convinced me that I should share the many other investment lessons the public can learn from this exercise. I thought a podcast would be a perfect venue to discuss my thoughts, so I asked my friend Patrick O’Shaughnessy to discuss the bet with me, and that conversation follows. Before we dive in, I thought it might help to let you know where to find answers to some of those common questions I’m asked. For starters, Carol Loomis, the legendary and recently retired Fortune columnist, wrote a wonderful piece called “Buffett’s Big Bet” back in 2008 that described in detail how the bet came to pass.  You can find her piece at www.capitalallocatorspodcast.com/bet. On that same page, you can find links to some of my written thoughts – both at the time of the bet’s inception and two years ago. Next week, I’ll add another link with some concluding thoughts.   For more episodes go to CapitalAllocatorsPodcast.com/Podcast Follow Ted on twitter at @tseides