The Distribution by Juniper Square

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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.

  1. Credit, Secondaries, and 30 Years of Relationship-Driven Alpha - Aaron Gershenberg - CEO @ Pinegrove Venture Partners

    6 dage siden

    Credit, Secondaries, and 30 Years of Relationship-Driven Alpha - Aaron Gershenberg - CEO @ Pinegrove Venture Partners

    Brandon Sedloff and Aaron Gershenberg sit down in California's wine country to explore three decades of venture capital evolution. Aaron, CEO and managing partner at Pinegrove Venture Partners, shares his unconventional path from economic development work and real estate consulting to building SVB Capital into a $10 billion platform, then relaunching after the bank's collapse as Pinegrove, backed by Sequoia Heritage and Brookfield. They discuss: - How Aaron used Monte Carlo analysis to project fund performance and justify additional capital during the dot-com crash - Why he structured distribution-only fee models for anchor LPs instead of traditional management fees and carry - The mechanics of becoming a FOIA blocker to attract pension fund capital - How Pinegrove positions across seed, Series A, Series B, credit, and secondaries to capture alpha at different stages - Why the 2024–2026 vintage may deliver the fastest value creation Aaron has seen in his career This episode offers a roadmap for institutional investors navigating venture exposure, LP sentiment shifts, and the structural innovations that have reshaped fund economics over the past 25 years. Topics: (00:00:00) - Intro (00:03:20) - Growing up between Uganda, Kenya and New Jersey (00:10:50) - Africa's influence and giving back (00:15:40) - Question authority and the unstructured path (00:18:30) - Real estate consulting and the sales pivot (00:21:10) - Breaking into venture in the mid-'90s (00:32:00) - Joining Silicon Valley Bank (00:33:30) - Building community through cycling and kiteboarding (00:37:00) - Launching SVB Capital (00:40:15) - Innovative fund structures and FOIA blockers (00:44:20) - Scaling through three eras: 2000–2023 (00:49:00) - SVB's collapse and rebuilding as Pine Grove (00:50:20) - Partnering with Sequoia Heritage and Brookfield (00:56:30) - Pine Grove's platform and strategies today (01:02:30) - AI conviction and the 2024–2026 vintage (01:09:10) - What keeps you up at night Links: Aaron on LinkedIn - https://www.linkedin.com/in/aaron-gershenberg-7361b23/ Pinegrove Venture Partners - https://pinegrove.vc/ Brandon on LinkedIn - https://www.linkedin.com/in/brandonsedloff/ Juniper Square - https://www.junipersquare.com/

    1 t. 13 min.
  2. Picking Winners Late in the Race: Why Venture Secondaries Are a Decade-Long Opportunity

    26. jun.

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

    23. jun.

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

    16. jun.

    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

    1 t. 9 min.
  5. 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

    9. jun.

    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.
  6. 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

    2. jun.

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

    26. maj

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

    19. maj

    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.
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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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