The Distribution by Juniper Square

Brandon Sedloff and Jamie Montgomery explore the power of compounding across networks, knowledge, and capital in this episode of The Distribution. Montgomery, founder and managing partner at March Capital, shares insights from a forty-year career spanning aerospace consulting, merchant banking, and venture investing. The conversation traces his path from caddying for stockbrokers in 1960s Seattle to building an early growth fund that has deployed close to $2.5 billion, with a decade-long focus on AI before it became mainstream.

They discuss:

- Why compounding your network and knowledge matters as much as compounding capital

- How becoming an AI-first company must be led by the CEO, not delegated

- The role of market size as the critical test in early growth investing

- What it takes to reposition existing portfolio companies for an agentic AI world

- Why the Montgomery Summit creates organic community rather than controlling outcomes

This episode offers a grounded perspective on building meaningful companies, the velocity of capital, and navigating cycles without losing sight of long-term opportunity.

Topics:

(00:00:00) - Intro

(00:02:37) - Getting into finance and investing

(00:08:47) - From UCSD to the Pentagon

(00:12:18) - Connecting the dots on a winding career path

(00:23:14) - March Capital's focus and approach

(00:28:10) - Repositioning portfolio companies for AI

(00:35:04) - What to look for in early growth investing

(00:38:10) - The Montgomery Summit and building community

(00:44:34) - What's top of mind right now

(00:48:56) - AI's impact on the economy

Links:

Jamie on LinkedIn - https://www.linkedin.com/in/jamiemontgomery/

March Capital - https://marchcp.com/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff and Matt Adler explore the world of small bay industrial real estate and the path from family business to independent fund manager. Adler, founder and managing partner of Adler Real Estate Partners, shares how he spun out of a third-generation family operation to build a specialized platform focused exclusively on multi-tenant light industrial properties across the Sun Belt. The conversation on The Distribution reveals why this once under-the-radar asset class has become one of real estate's most sought-after sectors and how focused operators compete when larger managers enter the space.

They discuss:

- Why spinning out of a family business required balancing independence with preserving relationships

- How small bay industrial became a "HALO" asset class, hard assets with low obsolescence, resistant to AI disruption

- What institutional investors misunderstand about office build-outs in industrial properties

- How a disciplined operator grows NOI even when interest rates move against them

- Why staying focused on one property type in mid-sized deals creates competitive advantage against mega managers

This episode offers practical insight for anyone interested in niche real estate strategies, the transition from operating partner to fund manager, or how specialist platforms win by executing better than diversified competitors.

Topics:

(00:00:00) - Intro

(00:02:57) - Matt's family real estate background

(00:09:49) - Early career and deciding to leave the family business

(00:11:19) - Working with Apollo and the GFC

(00:14:18) - Starting the fund business

(00:16:29) - Spinning out from the family business

(00:21:25) - Adler Real Estate Partners today

(00:23:59) - Small bay industrial explained

(00:28:09) - Why small bay industrial is hot right now

(00:31:36) - HALO and the AI advantage

(00:32:47) - Competition and differentiation

(00:38:01) - The office buildout misconception

(00:42:36) - Competing with mega managers

(00:46:34) - Headwinds and opportunities ahead

(00:50:53) - Closing thoughts

Links:

Matthew on LinkedIn - https://www.linkedin.com/in/mladler/

Adler Partners - https://adler-partners.com/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff and Russ Flicker explore the institutional hotel business and the journey from practicing real estate law to building a vertically integrated hospitality firm. Flicker shares how AWH Partners emerged from a borrowed desk during the Great Recession and what shaped his approach to investing through work at the Trump Organization and Blackstone. The conversation covers how AWH differentiates itself through in-house management and development capabilities, and why Flicker believes middle-market hotel assets present compelling opportunities today.

They discuss:

- Why Flicker left Blackstone to start AWH despite limited visibility on deal flow or capital

- How starting with no formal office taught essential lessons about investor expectations and capital raising

- Why seller-prepared hotels often hide operational risks that integrated teams can identify during underwriting

- How vertical integration across acquisition, management, and renovation creates accountability advantages

- Why hotels reprice daily in inflationary environments while other real estate takes years to adjust

This episode offers perspective for investors evaluating hotel allocations, operators building differentiated platforms, or anyone navigating the transition from institutional roles to entrepreneurship during market downturns.

Topics:

(00:00:00) - Intro

(00:00:57) - Introducing Russ Flicker and AWH Partners

(00:02:42) - From engineer's son to real estate lawyer

(00:08:38) - The dotcom startup and meeting his wife

(00:11:52) - Landing at the Trump Organization

(00:20:47) - Why Russ left Trump for Blackstone

(00:23:33) - Working at institutional scale versus entrepreneurial scale

(00:26:58) - The Ian Schrager disaster and the taxi accident

(00:32:24) - Founding AWH from a borrowed desk in 2008

(00:40:27) - Building AWH into a vertically integrated platform

(00:46:00) - Why hospitality gets misunderstood as high risk

(00:49:58) - Opportunity in the next 24 to 36 months

Links:

Russ on LinkedIn - https://www.linkedin.com/in/russell-flicker-67821712/

AWH Partners - https://www.awhpartners.com/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff and Susan Long McAndrews explore the evolving landscape of private markets distribution on The Distribution. Susan brings over two decades of experience from Pantheon, where she led both GP allocation and built the firm's wealth channel from the ground up. Now advising private equity firms on wealth and 401(k) strategies, she offers insight into what works, what doesn't, and where the market is headed.

They discuss:

- Why evergreen funds were never primarily about liquidity and what the recent gating headlines missed

- How single GP evergreen funds are reshaping access for both wealth clients and small institutions

- Why private equity belongs in 401(k) plans and what it will take to get there at scale

- The sales misalignment behind recent evergreen fund gates and how to properly position these products

- What mid-market firms should consider before launching a wealth channel strategy

This episode clarifies the real value proposition of evergreen structures and identifies which private markets firms are positioned to succeed in wealth distribution.

Topics:

(00:00:00) - Intro

(00:03:15) - Early influences on investing

(00:06:45) - Career path from Morgan Stanley to Russell

(00:08:53) - Pentagon and China policy work

(00:13:00) - Journey to Pantheon

(00:15:09) - Allocating capital and manager selection

(00:17:18) - What made a great manager

(00:19:39) - Building the wealth channel

(00:23:12) - Scaling evergreen funds

(00:26:39) - Market evolution from 2020 to 2025

(00:28:50) - Gating headlines and evergreen misunderstandings

(00:29:30) - Why evergreen funds work

(00:36:16) - Advising wealth advisors today

(00:38:56) - Single GP evergreen solutions

(00:41:32) - Advisory work after Pantheon

(00:44:46) - Should mid-market firms enter wealth

(00:49:07) - Looking ahead at private markets

(00:50:03) - The case for private equity in 401(k)s

(00:52:05) - Transparency and technology in evergreens

(00:54:45) - Realizations and market health

Links:

Susan on LinkedIn - https://www.linkedin.com/in/susan-long-mcandrews/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff and Melvin Hibberd explore the evolution of GP solutions and what it takes to build durable enterprise value in private markets. Hibberd, chief investment officer at Hunter Point Capital, shares his path from engineering in northern England to leading investments across a $10 billion platform. The conversation examines how GP solutions expanded from simple minority stakes into a full menu of capital options, and why that shift reflects the maturation of asset management as a business, not just an investing activity.

They discuss:

- Why succession planning will drive transaction volume for the next decade, despite only 38% of GPs having a plan while 96% of LPs say it matters

- How managers' capital needs have evolved beyond permanent equity into preferred capital, NAV lending, and commitment financing

- What defines a persistent right to win in a market where every firm claims proprietary deal flow and differentiated sourcing

- Why bilateral partnerships often create more value than broad auctions when aligning on growth, governance, and long-term strategy

This episode offers practical perspective for founders and leaders navigating strategic capital decisions in an increasingly complex market.

Topics:

(00:00:00) - Intro

(00:02:41) - Introducing Melvin

(00:04:14) - Growing up in northern England

(00:06:52) - Engineering at Cambridge and summers in Japan

(00:08:57) - Starting at a family office

(00:10:35) - Business school and the intentional career path

(00:15:00) - Building a GP stakes platform at Blackstone

(00:19:10) - Why leave Blackstone for Hunter Point

(00:26:04) - The evolution of GP solutions products

(00:30:17) - Building enterprise value in investment firms

(00:32:25) - Succession as a deal driver

(00:35:45) - What makes a persistent right to win

(00:47:53) - Advice for founders seeking capital partners

(00:50:40) - Where Hunter Point is investing today

(00:53:40) - Closing

Links:

Hunter Point Capital - https://www.hunterpointcapital.com/

Melvin on LinkedIn - https://www.linkedin.com/in/melvin-hibberd-bab4b018b/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff and Alex Robinson explore the accelerating intersection of artificial intelligence and private markets operations. Robinson, co-founder and CEO of Juniper Square, explains why investment managers must reimagine their businesses around AI rather than treating it as a simple productivity tool. The conversation balances technical strategy with practical leadership advice for non-technical founders navigating rapid transformation.

They discuss:

- Why making your company "AI legible" requires recording meetings, writing down processes, and controlling your data layer

- How Robinson runs Juniper Square through ORCA, a synchronous operating system designed for AI-native decision-making

- The difference between technology companies building AI applications and service providers arranging human capital

- Why the industry will bifurcate between "sharpshooters" with distinctive strategies and scale players with compute budgets

- How to evaluate partners in a noisy market where every vendor claims to be AI-first

This episode from The Distribution offers a roadmap for investment managers seeking to apply AI thoughtfully without becoming technologists themselves.

Topics:

(00:00:00) - Intro

(00:02:41) - The functional singularity moment

(00:06:00) - Why AI deployment is a CEO's job

(00:07:46) - Becoming an on the record company

(00:11:22) - Running a company with ORCA

(00:14:57) - Practical advice for non-technical leaders

(00:16:11) - Just start writing it down

(00:17:22) - The Aunt Millie problem and AI legibility

(00:22:18) - Cutting through vendor noise

(00:25:21) - What won't change in partnerships

(00:26:12) - Trust and comprehensive platforms matter

(00:29:01) - Protecting your data moat from labs

(00:31:06) - Understanding the applied AI layer

(00:35:00) - How Juniper Square is deploying AI

(00:35:22) - Three transformation domains

(00:42:12) - Tech companies versus human capital shops

(00:45:36) - The future of investment management

(00:46:11) - Sharpshooters and scale players

(00:49:32) - Does data scale matter for GPs?

(00:52:05) - Most excited about AI in medicine

(00:53:23) - Closing thoughts on hackathons

Links:

Alex on LinkedIn - https://www.linkedin.com/in/alexrob22/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff sits down with Dan Carr and Peter Weiss, co-founders of Alpaca Real Estate, for a live conversation recorded at their annual Aspen Real Estate Summit. The two met as analysts at JP Morgan in 2011 and spent a decade building expertise at major institutions before launching their own opportunistic real estate private equity fund in late 2022. What sets Alpaca apart is their commitment to building a technology-first culture from inception, treating their data infrastructure and tech stack as foundational to the investment process rather than an afterthought.

They discuss:

- Why timing mattered when they saw the Fed's rate increases creating a repricing moment in commercial real estate

- How they built a seven-stage deal pipeline with 1,000 transactions cataloged in a proprietary data lake before deploying agentic AI

- Their focus on tailwind asset classes like build-to-rent townhomes and infill industrial, where structural demand drives conviction

- The cultural challenge of technology adoption and why organic buy-in matters more than mandates

- Forward purchase structures that shift construction risk to homebuilders while controlling land upfront

This episode offers a practical look at what it takes to launch and scale an investment platform built on data discipline and institutional-grade operations in a shifting market.

Topics:

(00:00:00) - Intro

(00:01:00) - Recording live at Alpaca's Aspen summit

(00:05:20) - Getting into real estate investing

(00:10:23) - Meeting at JP Morgan in 2011

(00:11:35) - Building the REPEN networking group

(00:12:34) - Post-JP Morgan career paths

(00:15:27) - The 2022 wake-up call from Dan

(00:17:49) - Capitalizing a first-time fund

(00:18:35) - Building technology into the DNA

(00:22:56) - Creating clean data infrastructure

(00:26:55) - Cultural adoption of technology

(00:31:42) - Alpaca's investment focus today

(00:33:45) - Residential and industrial strategies

(00:36:04) - Operating with partners versus direct

(00:38:38) - Closing thoughts for investors

Links:

Dan on LinkedIn - https://www.linkedin.com/in/daniel-carr-98a0a91b/

Peter on LinkedIn - https://www.linkedin.com/in/peter-weiss-86675635/

Alpaca Real Estate - https://alpacarealestate.com/

Brandon on LinkedIn - https://www.linkedin.com/in/bsedloff/

Juniper Square - https://www.junipersquare.com/

Brandon Sedloff and Bill McMorrow trace the evolution of Kennedy Wilson from a $57,000 real estate auction company in 1988 to a global investment firm managing nearly $38 billion in assets. McMorrow shares how a series of pivotal relationships, from early banking mentors to partnerships with George Graziadio and Fairfax Financial's Prem Watsa, shaped the firm's trajectory across four decades of real estate cycles. The conversation on The Distribution reveals how McMorrow identified opportunities in Japan during the 1990s, Ireland and the UK following the Great Recession, and multifamily housing markets when regional banks retreated in 2023.

They discuss:

- Why McMorrow focuses exclusively on housing across the US, Ireland, and the UK after owning every asset type

- How a half-hour conversation at a Berkshire Hathaway meeting led to $20 billion in joint ventures over sixteen years

- The discipline of saying yes to start the journey, even when the path forward isn't clear

- Why narrowing focus and tuning out noise matters more than ever in today's information-saturated environment

- What McMorrow learned from working on commercial fishing boats, in a slaughterhouse, and growing up in a family of nine kids

This episode offers insight for investors navigating uncertainty, building long-term institutional relationships, and recognizing contrarian opportunities when markets feel murky.

Topics:

(00:00:00) - Intro

(00:02:43) - Bill McMorrow's early life and formative years

(00:05:31) - Banking career and move to Philadelphia

(00:08:43) - Acquiring Kennedy Wilson in 1988

(00:10:51) - Expanding to Japan in the 1990s

(00:12:14) - The Great Recession and meeting Prem Watsa

(00:15:06) - Kennedy Wilson's culture and growth to $38 billion

(00:16:36) - Growing up in a family of nine

(00:22:25) - Building relationships with foreign investors

(00:24:25) - The Ireland opportunity and Bank of Ireland deal

(00:30:55) - Kennedy Wilson's business model today

(00:31:24) - Focus on housing and recent acquisitions

(00:39:11) - Staying focused and tuning out the noise

(00:44:22) - The importance of starting the journey

(00:45:39) - Taking chances and betting against the crowd

(00:47:45) - Looking ahead: opportunities and strategy

(00:54:34) - Closing thoughts

Links:

Kennedy Wilson - https://www.kennedywilson.com/

Juniper Square - ⁠⁠https://www.junipersquare.com/⁠⁠

Brandon on LinkedIn - ⁠⁠https://www.linkedin.com/in/brandonsedloff/⁠

Brandon Sedloff and John Bowman explore the future of private markets through the lens of CAIA Association's recent research report, "The World Rewired." Bowman, CEO of CAIA Association, shares insights from eight global roundtables with over 120 C-suite executives across major financial centers. The conversation examines how geopolitical shifts, evolving product structures, and talent needs are reshaping portfolio construction and investment strategy. Bowman argues that the post-World War II regime of low rates, stable globalization, and minimal inflation has ended—requiring allocators to fundamentally rethink how they build portfolios.

They discuss:

- Why geopolitics may replace asset allocation as the primary framework for portfolio construction

- How tokenization could solve liquidity challenges better than traditional gate structures

- The shift from hiring job-ready specialists to recruiting systems thinkers with interdisciplinary judgment

- Why the Gulf region has become a serious contender as the capital of private capital

This episode offers a strategic roadmap for institutional investors, asset managers, and private markets professionals navigating a regime change in global markets.

Topics:

(00:00:00) - Intro

(00:01:28) - Introducing John Bowman and CAIA

(00:02:59) - Early career and path to finance

(00:07:58) - Transition from asset management to CFA Institute

(00:11:49) - Journey through CFA Institute

(00:17:00) - Leading CAIA and building community

(00:29:11) - The World Rewired research report

(00:34:25) - Product innovation and the retail push

(00:44:06) - Geopolitics as portfolio framework

(00:49:01) - Middle East sovereign wealth dynamics

(00:52:19) - Talent and systems thinking

(00:56:47) - Where to learn more

Speaker Profiles:

  Brandon Sedloff

    LinkedIn — https://www.linkedin.com/in/bsedloff/

    Website — https://brandonsedloff.substack.com/

  John Bowman

    LinkedIn — https://www.linkedin.com/in/johnlbowmancfa/

Organizations:

  CAIA Association — https://caia.org/

  Juniper Square - https://www.junipersquare.com/

On this episode of The Distribution, Brandon Sedloff and Raphi Schorr explore what makes inefficient markets the last bastion of alpha in private investing. Schorr, Deputy Chief Investment Officer and Partner at HighVista Strategies, explains how his firm deploys $14 billion across overlooked corners of the market, from lower middle market private equity to venture capital, private credit, and public biotech, where large addressable markets, poor information, and limited competition still reward patient capital and deep networks.

They discuss:

- Why lower middle market private equity operates beneath the radar of most institutional investors

- How backing fund one managers in venture capital creates decades of compounding access

- Why 50% of the S&P 500 is venture-backed and what that means for where value is created today

- The rise of GP-led secondaries in the lower middle market as sponsors seek to hold their crown jewels longer

- How pattern recognition built over 20 years helps identify winning managers and companies in fragmented markets

This episode offers a clear view into how experienced allocators find alpha in markets most investors never see.

Topics:

(00:00:00) - Intro

(00:01:05) - Meeting Raphi Schorr and HighVista Strategies

(00:02:32) - Mathematics and early investing exposure

(00:06:40) - From physics to operations research

(00:09:27) - Joining HighVista and the shift to private markets

(00:12:10) - Building the firm from day one

(00:16:28) - What HighVista does today

(00:20:18) - Inefficient markets and where alpha lives

(00:24:54) - Pattern recognition in lower middle market PE

(00:28:00) - Balancing analytics with relationships

(00:31:10) - Access and the venture capital power law

(00:34:44) - Backing fund one managers

(00:42:29) - Creating optionality through early partnerships

(00:48:22) - Structural themes for the next 36 months

(00:52:41) - What keeps Raphi up at night

(00:54:54) - Closing thoughts on talent and opportunity

Speaker Profiles:

  Brandon Sedloff

    LinkedIn — https://www.linkedin.com/in/bsedloff/

    Website — https://brandonsedloff.substack.com/

  Raphi Schorr

    Linkedin - https://www.linkedin.com/in/raphaelschorr/

Companies:

  Juniper Square — https://www.junipersquare.com/

  HighVista Strategies — https://www.highvistastrategies.com/