The Distribution by Juniper Square

Juniper Square
  • 4.8 (61)
  • 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. Picking Winners Late in the Race: Why Venture Secondaries Are a Decade-Long Opportunity

    1d ago

    Picking Winners Late in the Race: Why Venture Secondaries Are a Decade-Long Opportunity

    Brandon Sedloff sits down with Mike Boggs of Revelation Partners and Justin Burden of Industry Ventures at the Venture Secondaries Summit to explore how venture secondaries have evolved from a tool for distressed sellers into an institutional liquidity engine for private markets. The conversation examines the specialist approach required to succeed in this opaque, relationship-driven market where transactions happen by appointment rather than on open exchanges. They discuss: - Why venture secondaries function as a third liquidity option beyond IPOs and M&A, particularly in healthcare where billion-dollar outcomes are considered large - How secondary buyers navigate competition from insider investors by serving as arm's-length pricing partners for founder share sales - The structural liquidity problem created by over $800 billion in unrealized healthcare value and trillions locked in tech, with secondary funds positioned to address this overhang - Why specialization in specific sectors or deal types is becoming essential as commoditization pressures generalist secondary funds - How the flight to quality means focusing capital on late-stage, proven companies rather than indexing across venture portfolios This episode offers private markets investors and operators a practical view of how venture secondaries create value in an environment where companies stay private longer and traditional exit paths remain constrained. Topics: (00:00:00) - Intro (00:00:29) - Guest introductions and firm backgrounds (00:04:47) - Evolution of venture secondaries as liquidity (00:07:20) - What happens if IPOs and M&A return (00:11:28) - Specialists versus generalists in secondaries (00:13:04) - Secondaries as asset class or strategy (00:17:07) - Overcoming discount buyer perceptions (00:19:47) - Building conviction and underwriting (00:22:58) - Navigating competition from top VCs (00:25:32) - Educating the market on secondary options (00:29:52) - Liquidity challenges for the messy middle (00:33:17) - Transfer rights and insider preferences (00:38:22) - LP secondaries market maturation concerns (00:40:15) - Outlooks on the next 5 to 10 years (00:44:04) - What could stop the growth trajectory (00:47:42) - Competition and differentiation challenges (00:50:49) - Closing Links: Mike Boggs on LinkedIn - https://www.linkedin.com/in/michael-boggs-7921343/ Justin Burden on LinkedIn - https://www.linkedin.com/in/justin-burden-46120a/ Brandon Sedloff on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ Revelation Partners - https://revelation-partners.com/ Industry Ventures - https://www.industryventures.com/ Juniper Square - https://www.junipersquare.com/

    53 min
  2. The Overcaution Discount: How Tightening Supply Makes Today's Commercial Real Estate Undervalued - Hessam Nadji - CEO of Marcus & Millichap

    4d ago

    The Overcaution Discount: How Tightening Supply Makes Today's Commercial Real Estate Undervalued - Hessam Nadji - CEO of Marcus & Millichap

    Hessam Nadji, President and CEO of Marcus & Millichap, joins Brandon Sedloff to share his remarkable journey from immigrating to the United States from Iran to leading one of the largest commercial real estate brokerage firms in the country. Hessam reflects on the formative experiences that shaped his career, how an entry-level data entry role at Grubb & Ellis sparked a lifelong passion for research and analytics, and why he believed early on that commercial real estate would evolve from a relationship-driven business into a consultative, data-informed profession. The conversation explores Marcus & Millichap’s growth, the firm's enduring focus on serving private clients, and how technology, AI, and changing market dynamics are reshaping the future of commercial real estate. They discuss: • Hessam’s immigration story, family entrepreneurship roots, and unconventional path into commercial real estate • How research, analytics, and consultative selling transformed brokerage and created new opportunities for advisors • The evolution of Marcus & Millichap’s private client and institutional businesses, including the creation of Institutional Property Advisors (IPA) • How AI is changing brokerage, data analysis, client service, and the future role of commercial real estate professionals • Why current market uncertainty may be creating attractive opportunities across commercial real estate asset classes • The long-term outlook for supply, capital allocation, and wealth creation through commercial real estate investing Topics: (00:00:00) - Intro (00:02:19) - Hessam’s background and career (00:22:01) - The journey to becoming CEO of Marcus & Millichap (00:36:38) - The state of the firm in 2026 (00:47:05) - The structural changes happening in the market (00:52:28) - Shallow buyer supply (00:54:18) - Most misunderstood concepts about CRE as an asset class Links: Hessam on LinkedIn - https://www.linkedin.com/in/hessam-nadji/ Marcus & Millichap - https://www.marcusmillichap.com/ Juniper Square - ⁠https://www.junipersquare.com/⁠ Brandon on LinkedIn - ⁠https://www.linkedin.com/in/brandonsedloff/⁠

    59 min
  3. Demographics as Destiny: Building a $21B Platform on Mission-Critical Real Estate - Al Rabil - CEO of Kayne Anderson

    Jun 16

    Demographics as Destiny: Building a $21B Platform on Mission-Critical Real Estate - Al Rabil - CEO of Kayne Anderson

    Brandon Sedloff and Al Rabil discuss navigating real estate cycles, building investment platforms, and identifying mission-critical assets with decades of demand ahead. Rabil shares how an unconventional path—from philosophy major to commercial real estate workouts during the RTC crisis to running UBS Real Estate Investment Banking—shaped his approach to disciplined capital allocation. He explains why Kayne Anderson focuses on fragmented, operationally intensive sectors like medical office, seniors housing, student housing, and light industrial, and how the firm partners with best-in-class operators rather than building everything in-house. They discuss: - Why listening is the most underrated skill in finance and how it opened doors early in Rabil's career - How Kayne Anderson identifies asymmetric return opportunities by finding demand and letting it run you over - Why the firm is selling seniors housing today and what that signals about pricing and cycle positioning - The difference between asymmetric return-risk dynamics and asymmetric risk-return dynamics - How vertically integrated platforms create alpha in operationally complex real estate This episode offers insight for investors, operators, and allocators interested in real estate fundamentals, disciplined underwriting, and building durable platforms across market cycles. Links: Kayne Anderson - https://kayneanderson.com/ Al on LinkedIn - https://www.linkedin.com/in/al-rabil-3a7163b0/ Juniper Square - https://www.junipersquare.com/ Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ Topics: (00:00:00) - Intro (00:02:41) - Growing up everywhere: A nomadic childhood (00:12:46) - Philosophy major without a plan (00:16:14) - The power of listening in finance (00:19:23) - Learning from the RTC crisis (00:22:49) - Career advice that changed everything (00:29:21) - Leaving Wall Street for entrepreneurship (00:32:50) - Joining Kayne Anderson in 2007 (00:42:31) - Alternative asset classes with decades of demand (00:45:17) - The vertically integrated operator model (00:47:26) - Platform overview: Real estate, credit, and energy (00:51:34) - Disciplined investing across market cycles (00:56:38) - Where the opportunity is today (00:58:48) - Selling senior housing at peak pricing (01:01:38) - Advice for operators seeking capital partners

    1h 9m
  4. 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

    Jun 9

    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
  5. 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
  6. 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
  7. 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
  8. 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
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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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