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

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

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/ [https://www.linkedin.com/in/lucyjfletcher/] Marieke on Linkedin - https://www.linkedin.com/in/marieke-van-kamp-25794b2/ [https://www.linkedin.com/in/marieke-van-kamp-25794b2/] Martin on LinkedIn - https://www.linkedin.com/in/martin-lemke-germany/ [https://www.linkedin.com/in/martin-lemke-germany/] 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 (00:04:27) - 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

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/ [https://www.leoncapitalgroup.com/] Fernando on LinkedIn - https://www.linkedin.com/in/fernando-de-leon/ [https://www.linkedin.com/in/fernando-de-leon/] Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/bsedloff/⁠⁠ [https://www.linkedin.com/in/bsedloff/%E2%81%A0%E2%81%A0] Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠ [https://www.junipersquare.com/%E2%81%A0%E2%81%A0] 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?