The Distribution by Juniper Square

Juniper Square
  • 5.0 (1)
  • Investing
  • Updated Biweekly

The Distribution by Juniper Square sits you down with industry experts, thought leaders, and some of the biggest names in commercial real estate, venture capital, and private equity, for open and honest conversations about what’s happening in the private markets.

  1. 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

    2d ago

    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/ DLA Piper -  https://www.dlapiper.com/en/ Juniper Square - https://www.junipersquare.com/ Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

    57 min
  2. 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

    Jun 2

    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/ Juniper Square - https://www.junipersquare.com/ Brandon on LinkedIn - 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

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

    May 26

    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/ Crow Holdings - https://www.crowholdings.com/ Juniper Square - ⁠https://www.junipersquare.com/⁠ Brandon on LinkedIn - ⁠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

    1 hr
  4. Finding Alpha in Middle Market Real Estate - Collin Laffey - Managing Director @ LFPI

    May 19

    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/ Collin on LinkedIn - https://www.linkedin.com/in/collinlaffey/ Juniper Square - https://www.junipersquare.com/ Brandon on LinkedIn - 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?

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

    May 12

    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/ Realty Income Corp. - https://www.realtyincome.com/ Juniper Square - https://www.junipersquare.com/ Brandon on LinkedIn - 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

    55 min
  6. Global Real Estate Investing Through Uncertainty - INREV 2026 Barcelona

    May 5

    Global Real Estate Investing Through Uncertainty - INREV 2026 Barcelona

    Brandon Sedloff hosts a special live panel recorded at the INREV annual conference in Barcelona, where he was invited to moderate an exclusive Investor Day session featuring some of the world’s leading institutional allocators. In front of an audience of global pension funds, insurance companies, family offices, and sovereign wealth funds, he sits down with Lucy Fletcher, Marieke van Kamp, and Martin Lemke to unpack how sophisticated investors are thinking about real estate today. The conversation explores how the asset class is evolving within private market portfolios, how global capital is being allocated across regions and sectors, and why fundamentals, data, and operational execution are becoming more critical than ever. Drawing from perspectives across global funds, European insurance portfolios, and family office capital, the panel offers a rare look into how top allocators are positioning for the next cycle. They discuss: How institutional allocators view real estate’s role as a long term, income generating and stabilizing asset within private markets The tradeoffs between global diversification and regional focus, including why some investors remain concentrated in Europe The growing importance of data, transparency, and AI in shaping investment decisions and industry evolution Where investors are finding opportunity today, including living sectors, essential services, and value in retrofitting existing assets What defines a strong operating partner, from alignment and governance to transparency and active portfolio management Links: Lucy on LinkedIn - https://www.linkedin.com/in/lucyjfletcher/ Marieke on Linkedin - https://www.linkedin.com/in/marieke-van-kamp-25794b2/ Martin on LinkedIn - https://www.linkedin.com/in/martin-lemke-germany/ Juniper Square - https://www.junipersquare.com/ Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ Topics: (00:00:00) - Intro (00:04:27) - Introducing the panel (00:06:59) - Reflections as chairpersons of INREV (00:14:50) - What is the role of RE in a portfolio today? (00:21:43) - The role of Real Assets in CBREIM (00:24:14) - Global vs. local investing (00:26:38) - Europe as a capital safe haven (00:28:37) - Geographic diversification opportunities (00:32:34) - Areas of opportunity over the next 12-24 months (00:39:41) - What to look for in partners

    45 min
  7. From Real Estate to Healthcare: Building Enduring Businesses - Fernando De Leon - Founder & CEO - Leon Capital Group

    Apr 28

    From Real Estate to Healthcare: Building Enduring Businesses - Fernando De Leon - Founder & CEO - Leon Capital Group

    Brandon Sedloff sits down with Fernando De Leon to unpack the evolution of Leon Capital Group and the lessons learned from building and operating businesses across healthcare, insurance, financial services, and real estate. Fernando shares how his upbringing between Mexico and Texas shaped his understanding of human behavior and incentives, which later became foundational to how he builds organizations. The conversation spans his early entrepreneurial experiences, navigating the global financial crisis, and the strategic pivots that transformed his firm into a diversified holding company. Throughout, Fernando emphasizes the importance of adaptation, disciplined capital allocation, and aligning incentives to drive long-term success. They discuss: How early exposure to different economic systems shaped his approach to investing and leadership Why concentrated bets and embracing mistakes have driven outsized returns The role of incentives and human behavior in building and scaling organizations How opportunistic investing during the financial crisis created long-term advantages Why AI and automation are now central to improving efficiency and protecting margins across businesses Links: Leon Capital Group - https://www.leoncapitalgroup.com/ Fernando on LinkedIn - https://www.linkedin.com/in/fernando-de-leon/ Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/bsedloff/⁠⁠ Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠ Topics: (00:00:00) - Intro (00:01:40) - Fernando’s background and career (00:24:54) - Leon Capital Group (00:29:46) - Taking Stakes in Investors (00:31:35) - The opportunity created by the GFC (00:36:11) - Fernando’s approach to RE development (00:38:30) - Taking on 3rd party capital (00:42:40) - Biggest learning lessons (00:45:35) - Fernando’s favorite business (00:47:43) - The evolution of the human brain (00:49:28) - Predictions for the next 18 months (00:52:39) - What business would you like to be in that you currently aren’t?

    58 min
  8. How GPs Should Approach AI Right Now - Brandon Rembe - Chief Solutions Officer - Juniper Square

    Apr 24

    How GPs Should Approach AI Right Now - Brandon Rembe - Chief Solutions Officer - Juniper Square

    Brandon Sedloff sits down with Brandon Rembe in Nashville following Juniper Square’s sales kickoff to unpack how AI is reshaping private markets from the inside out. Rembe shares how rapidly advancing technology is forcing firms to rethink not just their tools, but how they operate, make decisions, and deliver results to LPs. The conversation explores why private markets are at a structural inflection point and how firms can stay focused on outcomes while navigating constant change. Rembe also breaks down the evolving role of data, trust, and human expertise in an AI-driven world. They discuss: Why private markets are entering a structural inflection point driven by AI and rapid technological change How GPs should focus on outcomes and outsource complexity instead of chasing specific AI tools or models The importance of clean, structured data as the foundation for any successful AI strategy How AI will shift roles toward “experts in the loop” rather than manual, repetitive work Why trust, transparency, and auditability are critical for adopting AI in financial workflows Links: Brandon Rembe on LinkedIn - https://www.linkedin.com/in/brandon-rembe/ Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/bsedloff/⁠⁠ Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠ Topics: (00:00:00) - Intro (00:02:05) - Brandon’s message to the sales team as Juniper Square focuses in on AI (00:02:48) - How private markets have evolved (00:03:58) - AI private markets (00:05:32) - What is the role of a GP 5 years from now? (00:07:31) - How Brandon advises companies on AI (00:09:12) - How to get started in the AI journey (00:11:23) - Why people should come work at Juniper Square

    17 min
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The Distribution by Juniper Square sits you down with industry experts, thought leaders, and some of the biggest names in commercial real estate, venture capital, and private equity, for open and honest conversations about what’s happening in the private markets.

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