The Legal Catbird Seat: How Data and AI Are Reshaping Private Credit and Fund Finance - Matt Schwartz - Global Finance Group Leader & Co-Head of Private Credit - DLA Piper

The Legal Catbird Seat: How Data and AI Are Reshaping Private Credit and Fund Finance - Matt Schwartz - Global Finance Group Leader & Co-Head of Private Credit - DLA Piper

Brandon Sedloff and Matt Schwartz explore the evolution of fund finance and private credit on The Distribution. Matt shares insights from his two decades in legal finance, including his journey from representing venture debt transactions to overseeing one of the world's largest law firm finance practices. The conversation examines how the financing landscape has fundamentally shifted over the past decade, with private credit funds taking on more complex transactions while banks have moved into back-leverage arrangements. Matt emphasizes the critical role of data strategy and AI adoption in modern fund operations, noting how GPs are using technology to improve underwriting and portfolio management. They discuss: - Why traditional underwriting standards are returning and how data analytics are improving investment decisions - How banks and private credit funds are increasingly collaborating rather than competing on deals - The role of insurance capital and hybrid structures in expanding fund finance options - Whether retail investors can successfully participate in illiquid private credit markets as valuation tools improve - Why technology and life sciences remain strong despite headlines suggesting otherwise This episode offers fund managers and private market professionals a clear-eyed view of where capital is flowing and how operational improvements can create competitive advantages. Topics: (00:00:00) - Intro (00:00:53) - Welcome and guest introduction (00:03:17) - Matt's journey into law (00:07:15) - Landing in San Diego and building a practice (00:10:00) - Leading DLA Piper's finance practice (00:16:40) - Data and operational alpha for GPs (00:25:00) - AI adoption and compliance (00:27:40) - Fund finance and private credit landscape (00:38:30) - AI's impact on vertical SaaS companies (00:41:36) - Underwriting discipline and data usage (00:47:30) - The next cycle in private credit (00:51:00) - Retail capital and LP allocation shifts (00:54:00) - Closing Links: Matt on LinkedIn - https://www.linkedin.com/in/matt-schwartz-15576617/ [https://www.linkedin.com/in/matt-schwartz-15576617/] DLA Piper -  https://www.dlapiper.com/en/ [https://www.dlapiper.com/en/] Juniper Square - https://www.junipersquare.com/ [https://www.junipersquare.com/] Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/ [https://www.linkedin.com/in/bsedloff/]

A Contrarian's Vindication: Why Grocery-Anchored Retail Is Entering a 7-Year Rental Growth Super Cycle - Brian Kosoy - Managing Principal and CEO of Sterling Organization

Brandon Sedloff and Brian Kosoy explore the transformation of retail real estate from distressed contrarian bet to institutional favorite. Kosoy, CEO of Sterling Organization, explains how his firm built a $4 billion vertically integrated shopping center platform by staying committed to retail through 15 years of headwinds—from the financial crisis through the retail apocalypse and COVID-19. He shares his unconventional path from failing out of Canadian schools to practicing real estate law in New York, then launching Sterling Organization in the summer of 2007, just as credit markets froze. They discuss: - Why vertical integration creates competitive advantages in tenant relationships and lease structuring that third-party management cannot replicate - The structural supply-demand imbalance driving a potential seven-year rent growth supercycle in grocery-anchored shopping centers - How being pigeonholed as "the shopping center guys" during a 15-year downturn created a durable moat as institutional capital returns to the sector - Why the average shopping center deal size makes it nearly impossible for large allocators to deploy $500 million quickly with quality managers - The difference between generating alpha in negative beta environments versus riding positive beta waves This episode examines how conviction through market cycles builds institutional platforms that can't be replicated by trend-followers or capital chasers. Links: Sterling Organization - https://www.sterlingorganization.com/about/ [https://www.sterlingorganization.com/about/] Juniper Square - https://www.junipersquare.com/ [https://www.junipersquare.com/] Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ [https://www.linkedin.com/in/brandonsedloff/] Topics: (00:00:00) - Intro (00:02:01) - Brian’s background and career (00:16:08) - Building Sterling Organization (00:25:48) - Key stats for Sterling Organization (00:30:16) - Building conviction in the shopping center business (00:33:54) - Structural changes and themes for the industry in the future (00:40:23) - Vertical Integration (00:43:49) - Institutional Capital (00:46:20) - Common misconceptions about retail (00:50:19) - Things to keep an eye on

Why Market Returns Require More Than Market Risk: An 80-Year Diversification Playbook - Michael Levy - CEO @ Crow Holdings

Michael Levy joins Brandon Sedloff for a wide-ranging conversation on leadership, institutional evolution, and the long arc of building durable businesses. Michael reflects on his unconventional path from studying fine arts and attending law school at night to becoming a senior leader at Morgan Stanley and eventually CEO of Crow Holdings. He shares lessons from navigating the 2008 financial crisis, why listening and trust-building matter more than quick action when leading organizations, and how Crow Holdings has evolved from a legendary real estate company into a diversified investment platform spanning energy, renewables, and national security. We discuss: • Michael’s unconventional path from fine arts student to Wall Street real estate executive • What Morgan Stanley taught him about mentorship, optionality, and leadership under pressure • The inside story of Crow Holdings’ evolution across three generations of leadership • Why the firm shifted from pure real estate into energy, renewables, and national security businesses • How Michael approaches leadership, decision-making, and building trust inside long-term organizations This episode is a deep look at institutional leadership, business evolution, and the mindset required to build resilient organizations across decades. Links: Michael on LinkedIn - https://www.linkedin.com/in/michael-levy-57033012/ [https://www.linkedin.com/in/michael-levy-57033012/] Crow Holdings - https://www.crowholdings.com/ [https://www.crowholdings.com/] Juniper Square - ⁠https://www.junipersquare.com/⁠ [https://www.junipersquare.com/] Brandon on LinkedIn - ⁠https://www.linkedin.com/in/brandonsedloff/⁠ [https://www.linkedin.com/in/brandonsedloff/] Topics: (00:00:00) - Intro (00:01:44) - Michael’s background and career (00:15:02) - Strategic leadership (00:20:56) - Becoming involved with Crow (00:25:26) - Michael’s mandate when coming into Crow (00:30:18) - The evolution of Crow (00:37:07) - The influence of Harlan Crow (00:41:17) - The size and scale of Crow Holdings (00:45:01) - Trends to look for in the future (00:53:34) - Leadership philosophies

Finding Alpha in Middle Market Real Estate - Collin Laffey - Managing Director @ LFPI

Brandon Sedloff sits down with Collin Laffey, who leads U.S. real estate efforts at LFPI, to unpack how one of the most active allocators in private markets evaluates managers, structures long-duration capital, and identifies opportunity across real estate funds and co-investments. Collin explains why LFPI has intentionally focused on sub-$1 billion managers, how the firm’s 30-year flagship vehicle changes the way they invest, and why transparency and alignment matter more than polished fundraising narratives. The conversation also dives into the realities of institutional capital formation, what differentiates the best operators from the crowd, and how LPs actually evaluate deals behind the scenes. They also explore where Collin sees the most compelling opportunities emerging across today’s real estate landscape, from senior housing to industrial outdoor storage. They discuss: • Why LFPI believes the real alpha opportunity exists in sub-$1 billion specialist managers • How a 30-year evergreen-aligned fund structure creates flexibility across cycles and capital stacks • The role co-investments and continuation vehicles are playing in today’s fundraising environment • What institutional LPs actually look for when evaluating managers, deals, and team dynamics • How GPs can cut through the noise and build long-term relationships with allocators This episode is a valuable listen for anyone interested in private markets, real estate capital formation, LP-GP dynamics, and the evolving structure of institutional investing. Links: LFPI - https://www.lfpi.fr/en/home/ [https://www.lfpi.fr/en/home/] Collin on LinkedIn - https://www.linkedin.com/in/collinlaffey/ [https://www.linkedin.com/in/collinlaffey/] Juniper Square - https://www.junipersquare.com/ [https://www.junipersquare.com/] Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ [https://www.linkedin.com/in/brandonsedloff/] Topics: (00:00:00) - Intro (00:01:58) - Collin’s career and background (00:05:28) - LFPI and their investment thesis (00:11:24) - Unpacking LFPI’s Fund mechanics (00:17:05) - LFPI’s focus on the sub-$1billion of raised equity segment (00:20:26) - More on investment theses (00:23:32) - Identifying a good deal (00:27:51) - Patterns seen across the best managers (00:31:22) - LFPI’s buy box (00:34:26) - What cuts through the noise in outreach (00:38:26) - Collin’s Co-invest philosophy (00:42:02) - Where do you see the most opportunity?

Why Private Capital Is Waking Up to Net Lease - Jonathan Pong - EVP, CFO & Treasurer - Realty Income

Jonathan Pong joins Brandon Sedloff to discuss the evolution of Realty Income from one of the original net lease REITs into a global real estate platform spanning public and private capital markets. Jonathan shares how Realty Income scaled from a roughly $15 billion enterprise value company into a global platform with more than 15,500 properties across the U.S. and Europe, while maintaining its identity as “The Monthly Dividend Company.” The conversation explores the growing institutional appetite for net lease real estate, why private capital is increasingly allocating toward durable income-oriented strategies, and how Realty Income is positioning itself through open-end funds and large-scale joint ventures with firms like GIC, Apollo, and Blackstone. They also discuss Jonathan’s personal journey from growing up in a real estate family in Honolulu to becoming CFO of one of the largest REITs in the world. Along the way, Jonathan explains how Realty Income thinks about risk management, data advantages, tenant diversification, and the role AI could eventually play inside large real estate organizations. Brandon and Jonathan unpack why “boring” cash flows are becoming increasingly attractive in today’s market environment and what institutional investors still misunderstand about the net lease sector. They discuss: • How Realty Income scaled into a $90 billion enterprise value platform with over 15,500 properties globally • Why institutional investors are increasing allocations toward net lease and income-oriented strategies • The launch of Realty Income’s private capital business, including open-end funds and strategic JVs with GIC and Apollo • The misconceptions investors have about tenant credit risk and portfolio diversification in net lease • How Realty Income uses proprietary data and predictive analytics to drive underwriting and asset management decisions • Why build-to-suit industrial and selective data center investments are major areas of focus going forward • Jonathan’s path from Hawaii to USC, Deloitte, Cornell, equity research, and ultimately becoming CFO of Realty Income • How large-scale relationships and repeatable execution create a competitive advantage in modern real estate markets This episode is a deep dive into how one of the world’s largest net lease platforms is adapting to the convergence of public markets, private capital, and long-duration real estate investing. Links: Jonathan on LinkedIn - https://www.linkedin.com/in/jonathanpong/ [https://www.linkedin.com/in/jonathanpong/] Realty Income Corp. - https://www.realtyincome.com/ [https://www.realtyincome.com/] Juniper Square - https://www.junipersquare.com/ [https://www.junipersquare.com/] Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ [https://www.linkedin.com/in/brandonsedloff/] Topics: (00:00:00) - Intro (00:01:35) - Jonathan’s background and career (00:16:28) - The state of Realty Income today (00:22:00) - The experience of Raising Private Capital (00:24:27) - Net Leases 101 (00:32:42) - The evolution toward private capital at Realty Income (00:35:59) - Competitive advantages (00:38:35) - How teams evolve as the market evolves (00:41:15) - The Realty Income portfolio (00:44:41) - How Realty’s model differs from other competitors (00:47:08) - Greatest opportunities looking forward (00:50:36) - Themes Jonathan is seeing in the market