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Why Most Capital Raisers Fail (And How to Succeed)

The Real Estate Market Watch - current events through a real estate lens.

Release Date: 04/20/2025

The Crash You Won’t See Coming — Because It’s Already Started show art The Crash You Won’t See Coming — Because It’s Already Started

The Real Estate Market Watch - current events through a real estate lens.

The Real Estate Cycle: A Warning for 2026   Insights from Phil Anderson on the Coming Real Estate Market Crash In my conversation with renowned economist Phil Anderson, you will gain unprecedented insight into the mechanics of real estate cycles and why we are right on the precipice of the next major real estate market crash.   Anderson, author of "The Secret Life of Real Estate and Banking," presents a compelling case that combines economic theory with historical precedent to paint a picture of where we stand today – and where we’re headed tomorrow.   The...

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Real Estate's Margin for Error is Gone show art Real Estate's Margin for Error is Gone

The Real Estate Market Watch - current events through a real estate lens.

The Margin of Error Has Vanished: What CRE Investors Should Be Watching Now Commentary on a conversation with John Chang, Senior Vice President and National Director, Research and Advisory Services, Marcus & Millichap   The New CRE Investment Mandate: Survive First, Then Thrive “The margin of error has narrowed to virtually zero.” This was John Chang’s stark assessment of today’s commercial real estate environment – an era marked by fragile capital markets, rising Treasury yields, policy instability, and speculative hangovers from a decade of cheap money. According to...

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Real Estate's #1 Rule: Don't Lose Money! show art Real Estate's #1 Rule: Don't Lose Money!

The Real Estate Market Watch - current events through a real estate lens.

Leyla Kunimoto brings a rare and unfiltered perspective to today’s commercial real estate conversation: that of a full-time individual LP who writes publicly about her investment decisions. She’s not a sponsor, a capital raiser, or a fund manager; she’s an investor allocating her own capital and speaking candidly about what she sees in the market.   Through her newsletter Accredited Investor Insights, Leyla connects with hundreds of other LPs and GPs, giving her a uniquely well-informed view of how sentiment is shifting, how sponsors are adapting (or not), and why many individual...

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How to Survive the Coming Real Estate Storm show art How to Survive the Coming Real Estate Storm

The Real Estate Market Watch - current events through a real estate lens.

How to Survive the Coming Real Estate Storm – What Sean Kelly-Rand Learned at Lehman   For the experienced real estate investor or sponsor, this is a masterclass in what really matters.   When Lehman Brothers unraveled in 2008, it exposed a truth that many in the real estate world still prefer to ignore: even the most sophisticated capital structures can implode when the cost of capital and access to liquidity are misunderstood – or worse, taken for granted. My podcast/YouTube show guest today, Sean Kelly-Rand, didn’t just watch that collapse unfold; he lived through it...

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Navigating Multifamily CRE in a Volatile Environment show art Navigating Multifamily CRE in a Volatile Environment

The Real Estate Market Watch - current events through a real estate lens.

Navigating Multifamily CRE in a Volatile Environment Insights from Paul Fiorilla, Director of U.S. Research at Yardi Matrix   Paul Fiorilla offers a data-driven view of today’s commercial real estate (CRE) landscape using the vast resources he has at his disposal at Yardi.   While market sentiment may be growing more optimistic, Fiorilla acknowledges investors should separate short-term mood from long-term fundamentals. His perspective, rooted in close analysis of multifamily data and macro conditions, is both pragmatic and cautionary: yes, there’s capital on the sidelines...

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The Real Risk to Real Estate Today show art The Real Risk to Real Estate Today

The Real Estate Market Watch - current events through a real estate lens.

The Dollar Standard, Global Liquidity, and the Coming Economic Reckoning In my expansive and highly accessible conversation with renowned economist Richard Duncan, we discuss the logic behind his long-running critique of the international monetary system, a system Richard calls the Dollar Standard where he explains why current U.S. policy moves, the system could come crashing down.   The Origins of the Dollar Standard and America’s “Exorbitant Privilege” The Dollar Standard, Duncan explains, evolved out of the collapse of the Bretton Woods system (implemented after WWII) in...

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Where Are We in the Real Estate Cycle? show art Where Are We in the Real Estate Cycle?

The Real Estate Market Watch - current events through a real estate lens.

When it comes to understanding real estate cycles, few voices carry as much weight as Prof. Glenn Mueller, of Denver University. With over 40 years in the real estate industry and more than three decades of publishing the Market Cycle Monitor – used by institutional investors, developers, and academics alike – his data-driven framework is one of the most respected in commercial real estate.   In my conversation with Prof. Mueller, he shared where each property type stands today, what signals matter most, and how CRE professionals should be thinking about the road ahead.   ...

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The Illusion of Diversification show art The Illusion of Diversification

The Real Estate Market Watch - current events through a real estate lens.

Unlocking Private Market Potential: Key Insights from Jim Dowd of North Capital   Jim Dowd, CEO of North Capital, brings four decades of experience across the sell-side and buy-side to my discussion with him on a topic top of mind for commercial real estate sponsors and investors: how to navigate a rapidly shifting capital landscape where regulation, liquidity, investor behavior, and macro volatility collide.   Here are the key insights from our conversation – designed specifically to you make better, more informed investment decisions in today’s market.   1. Private...

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What the Debt Markets are Telling Us Now show art What the Debt Markets are Telling Us Now

The Real Estate Market Watch - current events through a real estate lens.

The Pulse of the Debt Markets — with Orest Mandzy, CRE Direct Capital market confidence is cautiously returning, but undercurrents of risk remain. In my wide-ranging conversation with Orest Mandzy, Managing Editor of Commercial Real Estate Direct, we discuss what recent CMBS issuance tells us about liquidity, why delinquency headlines may be misleading, and how sponsors can position themselves amid policy shocks and structural market shifts.   Liquidity Is Back — But Driven by Giants CMBS issuance jumped 110% in Q1 2025, totaling nearly $37 billion. While that headline suggests a...

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Rates, Risk, and the Return of Discipline show art Rates, Risk, and the Return of Discipline

The Real Estate Market Watch - current events through a real estate lens.

What the Debt Markets Are Telling Us — and Why Sponsors Should Listen Insights from Lisa Pendergast, Executive Director, CREFC   In today’s capital markets, where debt is more expensive, less available, and slower to move, understanding how credit flows work has become just as important as understanding your deal. That’s why I sat down with Lisa Pendergast, Executive Director of the Commercial Real Estate Finance Council (CREFC) – a central figure in the $5 trillion CRE debt markets – to ask what the institutions upstream are seeing, and what that means for those of us...

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More Episodes
Meet capital allocator, Flint Jamison, Vestus Capital, who took an unconventional route into real estate transitioning from aerospace engineering to structuring multimillion-dollar investment funds. After spending years modifying aircraft, he turned his analytical mind toward real estate, quickly carving out a niche as a capital allocator and fund-of-funds manager.
 
Through Vestus Capital, Flint has raised millions in investor capital, deploying it across diversified real estate assets, including multifamily, medical office buildings, and specialized fund structures. He’s helped investors access opportunities while working to ensure compliance with SEC regulations, something often misunderstood by others.
 
Decoding the Fund of Funds Model
Flint explains how he structures his fund-of-funds investments, allowing his investors to access preferential terms. With a $30M portfolio that spans multiple markets, he’s seen firsthand how to negotiate with operators, structure fee agreements, and optimize capital allocation to maximize returns.
 
Navigating a Shifting Market
Raising capital today isn’t the same as it was a few years ago. Flint is forthright about the hardest lessons learned, including why “if you build it, they won’t necessarily come.” We talk about how his deals have performed in the face of rising interest rates and market fluctuations, as well as the creative financing strategies he’s deploying to future-proof investments.
 
How to Stand Out in a Crowded Investor Market
With countless syndicators and allocators chasing the same investors, how do you differentiate yourself? Flint shares why most capital raisers fail, the biggest mistakes they make, and the LinkedIn strategy that’s been his most powerful tool for attracting accredited investors. Spoiler: It’s not about templates or AI-generated pitches; it’s about speaking the right language to the right audience.
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Flint’s insights are a must-hear for anyone navigating the complex world of real estate capital allocation. If you want to crack the fund of funds model or scale your capital-raising game, this episode is packed with real-world lessons, actionable strategies, and no-BS advice you won’t hear anywhere else. You're going to rethink everything you know about raising capital!
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Explore the world of real estate capital allocators—a fresh approach to financing that’s reshaping the industry.
 
In this series, I talk with allocators, investors, sponsors, and service providers to give you an inside look at this fast-growing space.
 
PLUS, subscribe to my free newsletter for real estate investors and gain access to:
* Introductions to sponsors, allocators, and investment opportunities.
* Insights drawn from my 30+ years of experience in real estate investing.
* Hacks and tactics for raising capital to help you scale your real estate portfolio.
 
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