Alex Gentilli is the Director of Investment Operations at the Colby College Office of Investment Management. He came to Colby after spending time in trading and investment operations at places like Arrowstreet Capital and The Baupost Group before moving to the allocator seat.
We get into building an operating model from a blank slate — digitizing the investment book of record, selecting a portfolio management system, standing up a research management system, and putting cash controls and capital call discipline that had been part of the college treasurer’s office for years.
Alex describes the common tech stack build as a New England farmhouse — rooms added one at a time as the need came up — stepping back and decided it was time to redesign the house than do another addition.
We also dig into how he actually runs vendor selection: a weighted rubric, scoring each product immediately after the debrief to beat common organizational challenges and best ways to run a process.
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Natalie McIntyre is the Global Head of Consulting at Cutter Associates, a research and consulting firm that is focused exclusively on the investment industry.

In today's conversation, Natalie talks through how she got to Cutter from Bridgewater Associates, and how she took that knowledge base to help other organizations be the best version of themselves. We dig into what separates a good consulting firm from the rest and what a typical engagement really looks like once you get past the pitch.

Natalie shares the stories and the tipping points, those moments where a firm realizes that it can't solve something internally and picks up the phone. From there, we get into data, why data strategy has moved from a back-office task to the center of decision-making. We get tactical on building a tech stack for today and tomorrow, the common challenges, the tradeoff between bespoke builds and single platform solutions, and the ongoing tension between incumbents and the nascent players trying to unseat them.

We also talk about how the role of talent is shifting as technology takes on more of the workflow. For anyone building or scaling operations, this is a conversation about what changes when data, technology, and talent start pulling in the same direction.

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Andrew Dorle is the Director of Investment Operations and Analytics at GHR Foundation.  Based out of Minneapolis, GHR’s mission is to is to be of service to people and their limitless potential for good.
Andrew takes us through his migration from the investment side into operations — the unexpected lessons that carried over and why that dual perspective has become a competitive advantage. We dig into how GHR moved analytics from a secondary focus into the core of decision-making.From there we discuss how communication works between teams, why data integrity is the non-negotiable first principle, and what a lean, all-director team can do faster when they’re aligned on the fundamentals.
We get tactical on technology and vendor strategy - their philosophy on best-in-breed versus all-in-one platforms, how they evaluate new entrants and where AI can realistically help a small, nimble foundation move the needle on workflows. For anyone building or scaling operations at a foundation or multi-family office — this is a conversation on what foundation operations can look like when operational discipline and analytical rigor are aligned.
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Mike DeAddio is the Chief Operating Officer of Paloma Partners, the multi-manager platform founded by Donald Sussman in 1981 — one of the original seeders of firms like D.E. Shaw, Elliott, Canyon, and Caxton.

Mike takes us through a technical career that spans across Bell Labs, JPMorgan, Citadel and, Silver Point before bringing that entire playbook to Paloma.

We dig into what it takes to build institutional-grade hedge fund infrastructure today versus a decade ago and how Paloma completed a full technology refresh. All while keeping the plane in the air.

From there, we get into the model that makes Paloma different: flexible operational infrastructure and tailored to each manager’s style and goals — minimizing operational burden so they can focus on alpha generation — and a commitment to their long-term success, whether that means growing within the platform or eventually going out on their own.

For anyone running or building operations at a hedge fund or multi-manager platform — this one’s a masterclass on the operational lift when trying to launch a hedge fund today. 

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Glen Shields is the Founder and CEO of GP Fund Solutions., an independent fund administrator for private fund managers who want institutional-grade back-office operations without sacrificing the trust and partnership of a boutique firm.
In today’s conversation, Glen takes us through 25 years in fund administration — from his early days at PwC and AYCO through the Goldman acquisition and spin-out, leading to the launch of GPFS from scratch with a one-page contract and a single relationship built on trust.
We dig into how GPFS has grown to over $125 billion in assets under administration and what staying independent means in a consolidating industry.
From there, we get into the data question that sits at the center of everything Glen is building — why shadow books signal a trust gap, how GPFS is moving from deliverable-driven fund admin to data-enabled partnership, and what good data design actually looks like when your clients have complex waterfall structures, hybrid fund vehicles, and investors who want information at speed.
For anyone running or building operations at a private fund, this is a grounded conversation on what a fund admin relationship can and should look like when trust, data, and culture are all working together.
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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠)

Adam Ciborowski, Principal – RCP Advisors (EP.77)
Intro Copy: Adam Ciborowski is the head of Research, Portfolio Monitoring, and Data Management at RCP Advisors, an investment firm focused on investing in private equity funds in the lower middle market.
In today’s conversation, we get into how RCP has built its data infrastructure in the fund of funds world across its central operating system, accounting, document collection, portal management, and collaborating with its fund administrator across a growing roster funds.
Adam shares how selection of certain tech eliminated what used to be a dedicated full-time role — pulling documents, labeling them, routing them to auditors and administrators — and now turns that around in hours instead of weeks.
We also dig into RCP’s AI journey — why they passed on the turnkey vendor solutions, why data control and competitive differentiation drove that decision more than cost, and what they are actually building now: an agent that sits in their inbox, identifies incoming documents, scrapes defined attributes, and routes them for analyst review before uploading into their CRM.
Adam’s view is simple — AI is only as good as the data underneath it, and having 15 years of data with a robust infrastructure is exactly what makes that possible at RCP.
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Cesar Estrada is the Head of Private Markets at Arcesium, the data and operations platform built to help private market firms scale their reporting, analytics, and oversight at an enterprise level.
In today’s conversation, Cesar walks us through Arcesium’s role in private markets from its beginnings as a company spun out of DE Shaw. We discuss why “unifying the data” is front and center today and how Arcesium helps its clients with reconciliation to centralizing NAV oversight across internal teams and fund admins.
From there, we turn to all things AI — how Arcesium launched a Copilot feature, what it means to move from natural language queries toward full agents, and who Cesar thinks wins and loses as AI reshapes investment operations software.
For anyone building or running operations at a private markets firm, this is a sharp conversation on where the data problem really lives — and what solving it actually looks like in practice.
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Matt Shaia is a Managing Director and the Director of Investment Operations at Brockenbrough, a Richmond-based wealth management and OCIO firm serving both institutional clients and ultra-high-net-worth families.
One of the more interesting structural questions in investment management today is how a firm serves two very different client types – institutions that demand performance transparency and risk analytics, and families that want holistic, trust-based relationships, without building two separate businesses.
Brockenbrough has found a way to do exactly that, and Matt has been at the center of building the operational infrastructure that makes it work.
We cover how Matt evolved from research analyst to firm-wide operations leader, how Brockenbrough runs a shared investment engine across its OCIO and private wealth platforms, and the technology and data philosophy they’re using as AI tools proliferate. We also get into what it actually takes to differentiate in the private wealth market when everyone is chasing the same technology stack.
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Sloane Payne and Dave Joerger are the COO and CCO respectively at WCM Investment Management, an independent investment firm managing $120 billion in assets. 

WCM has built something unique – a firm culture that actually gets stronger as it grows. 

Sloane and Dave share the team’s simple, trust-first approach to building organizations. They’ve stripped away unnecessary layers to create a repeatable process for scaling culture. 

In our conversation, we unpack the lessons from the founder’s past that shaped WCM’s philosophy of hiring for character over credentials. They share what it really takes to lead through growth without losing the essence of what made the firm special. 

We then turn to the mechanics – how modeling behavior, candid feedback, “honoring the absent in a meeting” and accountability have made WCM what it is today and how that mindset influences the leadership’s approach to compensation, ownership, and succession. 

Finally, Sloane and Dave explain how WCM’s anti-corporate ethos guides everything from product design to talent decisions – and what that means in an industry drifting toward more systematized management cultures. 

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Henry Ward is the CEO and co-founder of Carta, the platform that began as a cap table tool and has since evolved into what Henry describes as the ERP for private markets.

His path to building private market infrastructure is a masterclass in knowing when to pivot and when to double down.

Given his product-led approach, I had to dig into Carta’s distinct chapters. Henry shares how he thinks about recognizing inflection points, the aha moment behind the ERP thesis, and what it actually takes to lead a company through multiple reinventions without losing steam. 

From there, we turn to Carta’s three-layer network spanning companies, funds, and allocators, the thinking behind its latest acquisitions and how Henry balances build versus buy in a market that is accelerating. 

He also shares how AI is reshaping product development at Carta and who he thinks wins and loses in the AI-driven SaaS disruption ahead.

For operators and allocators alike, Henry offers a sharp perspective on where private market tech is maturing, where the real disruption is still to come, and how leadership style shapes hiring, culture, and outcomes at scale.

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Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠)