Andy Redleaf is the Founding Partner of Whitebox Advisors, a $5.5 billion multi-strategy hedge fund launched in 1999 with primary offices in the metropolitan hubs of Minneapolis, Austin, and Sydney, Australia. Before founding Whitebox, Andy spent twenty years trading options, for two years at Gruntal & Comes mpany alongside Stevie Cohen, fourteen on the CBOE, and five as a Founding Partner at Deephaven Capital Management. He has an irrepressibly creative mind and, alongside his partners, writes one of my favorite manager letters.  Our conversation covers Andy's nuanced view of the evolution of trading markets and financial instruments over his forty-year career, including arbitrage trading in the 1970s and 80s, unintended consequences of the deregulation of trading commissions, segmentation of market participants, importance of liability management, growth of orphaned securities, and the pending shift from decentralized to centralized market systems over the coming years.   Learn More Join Ted's mailing list at CapitalAllocatorsPodcast.com Write a review on iTunes Follow Ted on twitter at @tseides For more episodes go to CapitalAllocatorsPodcast.com/Podcast   Show Notes 1:52 – Andy’s background and the founding of Whitebox 5:34 – The math of options in the late 70’s, early 80s  13:44 - The decentralization of markets 16:34 -  Andy’s transition into trading other strategies 18:31 – The launch of Whitebox 20:08 – The meaning of the firm name Whitebox 23:38 – An example of a transitioning security from one group of investors to another 28:31 – Has it gotten harder to find arbitrage opportunities 32:29 – The driver of the financial crisis 32:44 – Gary Gorton, Misunderstanding Financial Crises: Why Don't We See Them Coming 34:28 – His purchase of a bank 38:17 – How he got involved in the structured credit markets 42:39 – What is that Whitebox does differently from others 47:14 – Principles that guide the investment activities he likes to take part in 50:03 – How will the financial system evolve over the next 10 years 55:29 – Closing questions

Wayne Wicker is the Senior VP and CIO of ICMA Retirement Corporation, an asset manager that oversees $50B across more than a million retirement accounts of City and County public sector employees throughout the country. Before joining ICMA-RC in 2004, Wayne had a distinguished career as an allocator and manager, starting as an allocator at the corporate pension fund of Dayton Hudson (now Target Corporation) in the 1980s and the Howard Hughes Medical Institute endowment in the mid-1990s, after which he moved to direct investing in large cap growth equities for seven years at Cadence Capital Management in 1998. Our conversation covers Wayne’s career path, multi-asset investing, and the ins and outs of managing defined contribution plans as a fiduciary and as a business. We discuss asset allocation strategies, regulatory limitations, stable value products, retirement shortfall risks, active vs. passive on large pools of capital, and managing internal and external teams. This episode took place at a recent Institutional Investor conference for Corporate Funds and Insurance Portfolios, with the core discussion about ICMA-RC occurring in front of a live audience.   Learn More Join Ted's mailing list at CapitalAllocatorsPodcast.com Write a review on iTunes Follow Ted on twitter at @tseides For more episodes go to CapitalAllocatorsPodcast.com/Podcast   Show Notes 2:01 – How Wayne first got into the investment business 3:58 – What he did after getting his MBA 7:25 – How he learned about the pension business as a staff of one 9:18 – Key investment lessons from his early career 11:08 – Decision to move on from Target/Dayton Hudson 12:44 – Key differences between overseeing a corporate pension vs a hospital endowment structure 14:25 – How much did the difference in the investing strategy come from the mission of the funds vs the boards overseeing them 15:50 – What could Wayne do on the margin at Howard Hughes 17:28 – Transition to CIO 22:40 – Live Show Begins 23:00 – Defining ICMA-RC 23:32 – How does Wayne think about setting investment objectives with such a diverse group of clients 25:02 – Is it frustrating to have a more finite universe of investing options compared to previous work at Howard Hughes and Dayton Hudson 26:08 – Views on active vs passive 27:50 – The manager selection process 28:49 – Managing risks with external managers vs an internal team 30:34 – How does the team at ICMA-RC put their best ideas forward without governance getting in the way 31:34 – What constraints are imposed on investment decisions by the various regulatory bodies that ICMA-RC faces 32:40 – Their outlook on the market 34:08 – How does ICMA-RC’s constituents respond to market performance             35:32 – Closer examination using 2008 stock performance 36:23 – How does Wayne educate investors 38:00 – Next steps for ICMA-RC 38:51 – Most challenging aspect of Wayne’s work life 39:41 – Is there a looming pension crisis 40:53 – How do the Financial Planners help the employees if things don’t work out 42:10 – How do they think about financial planning for clients when there’s a chance defined benefit plans could come up short in the future  45:06 – How does Wayne address manager selection differently today given some of the constraints that he faces 47:19 – What has led Wayne to want to exit manager relationships 49:46 – Is there a point where Wayne would decide the optimal strategy is to go passive 51:28 – How does Wayne think about technology and the way it will be disrupt the industry 52:58 – Balancing the internal/external dynamic when hiring people 54:30 – Wayne’s greatest success and failure over the last 14 years 55:50 – Where will the move into emerging markets come from  56:27 – What does Wayne think of the new products that can help younger constituents meet their retirement objectives 57:41 – Live Show Ends/Closing questions