Making Mistakes – Josh Steiner (EP.503)
Capital Allocators – Inside the Institutional Investment Industry
Release Date: 05/18/2026
Making Mistakes – Josh Steiner (EP.503)
Capital Allocators – Inside the Institutional Investment Industry
Josh Steiner is a polymath of the New York and D.C. power corridors across government, media, and finance, and co-author of From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You. Josh rose to national prominence as the youngest-ever Chief of Staff at the U.S. Treasury in the Clinton administration, where he made a high-profile mistake he unpacks in the book. He pivoted to finance as a media investment banker and co-founder of private equity firm Quadrangle...
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Will England, Derek Drummond, and Tony Caruso – Disintermediating Pod Shops (EP.501)
Capital Allocators – Inside the Institutional Investment Industry
Today’s show discusses an innovative joint venture between asset owners and a multi-manager hedge fund that seeks to deliver smooth, equity-like returns at a lower cost than available in the marketplace. My guests are Will England, Derek Drummond, and Tony Caruso. Will is the CEO and CIO of $12 billion multi-strategy hedge fund Walleye Capital. Derek is head of external public markets investing at the State of Wisconsin Investment Board, and Tony Caruso is Managing Director of hedge funds at...
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Sloane Payne and Dave Joerger – Why Culture Matters (EP.500)
Capital Allocators – Inside the Institutional Investment Industry
Sloane Payne and Dave Joerger are the COO and CCO of WCM Investment Management, a firm chronicled over the years for its remarkable culture and growth to $120 billion in assets under management. This special conversation was hosted by Scott MacDonald on our affiliate Investment Management Operations podcast. Their conversation describes WCM’s culture in practice that includes hiring for character over credentials, trust as an operating principle, overtrusting before proof exists, generous compensation and shared equity, values as a daily practice, connection through...
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Alex Sloane & Matt Perelman – Buy-and-Build Playbook in the Core Economy at GSP (EP.499)
Capital Allocators – Inside the Institutional Investment Industry
Alex Sloane and Matt Perelman are co-founders of Garnett Station Partners, a $4 billion private equity firm focused on buy-and-build investments in founder-led, core economy businesses. Alex and Matt are lifelong friends who took an unconventional path out of business school, acquiring a 23-unit Burger King franchise in North Carolina that they scaled to 1,100 locations before selling it back to the franchisor. That operating experience became the foundation for their investment firm. Our conversation traces that evolution from operators...
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Rodney Comegys – The Mechanics of Indexing at Vanguard (EP.498)
Capital Allocators – Inside the Institutional Investment Industry
Rodney Comegys is the CIO of Vanguard Capital Management and its Head of Global Equity Indexing, where he oversees $8.5 trillion in index assets across domestic, international, and multi-asset strategies. Rodney joined Vanguard twenty seven years ago and has worked across operations, customer service, risk management, and investing. Our conversation covers the philosophy and mechanics behind running one of the world’s largest index fund operators. We discuss Vanguard’s ownership structure, values, product selection, and mechanics of...
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Randall Stutman – Giving Feedback, Followership, and Admired Leadership (EP.497)
Capital Allocators – Inside the Institutional Investment Industry
Randall Stutman is the founder of Admired Leadership and one of the most sought-after executive coaches in the world. He’s known across Wall Street, the hedge fund community, professional sports, the Olympics, and the White House entirely by word of mouth. Randall was a past guest on the show six years ago in a rare public appearance, and that conversation is replayed in the feed. Our conversation covers the framework for uncovering the behaviors and best practices of admired leaders and then dives into examples around giving...
info_outline![[REPLAY] Randall Stutman - Admired Leadership (EP.150) show art](https://assets.libsyn.com/item/40803060?height=50&width=50)
[REPLAY] Randall Stutman - Admired Leadership (EP.150)
Capital Allocators – Inside the Institutional Investment Industry
Randall Stutman is founder and co-head of the Leadership Practice at CRA. and the Admired Leadership Institute. Randall is probably the top executive coach that you’ve never heard of before. He’s spent 30 years coaching and learning about the behaviors and routines of extraordinary leaders. To give you a sense, he was worked in the White House and the Olympics, with something like 2,000 senior executives and 400 CEOs, and in our world, the most senior executives at JPMorgan, Goldman Sachs, Morgan Stanley, and Blackstone. Randall is also well known among the titans in the hedge fund...
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Promote Giving – A New Model for Performance-Driven Giving (EP.496)
Capital Allocators – Inside the Institutional Investment Industry
My guest on today’s special episode is Joel Holsinger, Co-head of Ares’ $50 billion Alternative Credit strategy. In addition to his long and stellar career in the credit markets, Joel spearheaded the launch of Promote Giving, a philanthropic initiative similar to Warren Buffett and Bill Gates’ Giving Pledge, designed for alternative asset managers. Our conversation covers Joel’s path to engaging in philanthropy, starting from humble beginnings to now making grants of $5 million in 2025 through Ares and launching Promote...
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Bruce MacDonald – The Playbook for Building a Mid-Sized Endowment from Scratch (EP.495)
Capital Allocators – Inside the Institutional Investment Industry
Bruce MacDonald is the CEO and CIO of the Virginia Commonwealth University Investment Management Company, which runs $2.5 billion for VCU’s endowment and health system. Bruce joined the University in 2015 and shortly thereafter, had the opportunity to sell the portfolio and start fresh. Since being promoted to CIO in 2022, VCU has been a top decile performer with a team of just five investment professionals. Our conversation covers Bruce's unconventional path from a religion major at Wesleyan to fixed income investing at Putnam and endowment roles at Columbia and UVIMCO before arriving at...
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Kieran Goodwin – Private Credit Concerns (EP.494)
Capital Allocators – Inside the Institutional Investment Industry
Kieran Goodwin is a Partner at Saba Capital, a $6 billion hedge fund manager that seeks to identify dislocations in credit and equity markets to generate convex returns in volatile times. Kieran has been one of the top credit traders on the Street for the last three decades across roles at investment banks in the ‘90s and early 00’s, King Street, his own hedge fund, Panning Capital, and most recently, Saba that he joined in 2024. Our conversation covers a tour of Kieran’s background, including early experience with credit derivatives, growth at King Street, lifespan of...
info_outlineJosh Steiner is a polymath of the New York and D.C. power corridors across government, media, and finance, and co-author of From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You.
Josh rose to national prominence as the youngest-ever Chief of Staff at the U.S. Treasury in the Clinton administration, where he made a high-profile mistake he unpacks in the book. He pivoted to finance as a media investment banker and co-founder of private equity firm Quadrangle Group in 2000, worked as an operator at Bloomberg in the 2010s, has served on Yale’s Investment Committee for nearly a decade, and five years ago returned to private equity as co-founder of SSW Partners managing capital for a few families.
Our conversation focuses on mistakes, quite a contrast from other discussions on the podcast. We kick it off with Josh’s big mistake at Treasury and analyze the nature of mistakes and what happened to Josh. We then turn to his mistakes in investing across deals, managing an investment business, managing people, and serving on Investment Committees. We close with frameworks to avoid mistakes and with Josh turning the table on me to discuss an impactful mistake I made that I’ve never discussed before.
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