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The Illusion of Diversification

AI for Real Estate

Release Date: 05/16/2025

The Data Layer Reshaping Real Estate Decisions show art The Data Layer Reshaping Real Estate Decisions

AI for Real Estate

Most CRE firms do not know how their data is performing. They know the assets. They do not know whether the numbers coming out of their ERP, their property management system, and their third-party data feeds are consistent, auditable, or actually connected.   When AI gets layered on top of that mess, it produces confident-sounding outputs nobody can verify.   LD Salmanson, co-founder and CEO of Cherre, has spent seven years building the infrastructure layer that sits underneath the AI. The alternative is manual - and it breaks. Teams of consultants collect, distill, and...

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AI for Real Estate

My podcast/YouTube show guest today, Cameron Steele has spent the last several years tackling a problem most commercial real estate firms don’t realize they have.   As the co-founder and CEO of Prophia, his focus is simple: turn the most important documents in CRE - leases - into usable intelligence.   The issue is that much of the economic blueprint of commercial real estate still lives inside legal documents. And most firms are still extracting that information manually.   In our latest conversation, Cameron walks through how AI is beginning to change that.   ...

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Most multifamily asset managers are still assembling reports.   Colin Green built software to eliminate that step entirely.   Colin is the founder of BubbleGum BI, a business intelligence platform designed specifically for multifamily asset managers. Before launching it, he built the tool for himself - nights and weekends - to solve the frustration of pulling rent rolls, cleaning spreadsheets, and waiting on Monday Morning Reports.   The result is a real-time operating layer.   In our conversation, Colin answers five important questions for serious CRE operators: ...

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The firms that win with AI in this cycle won't be the ones with the best models. They'll be the ones with the best data.   My Demo Day podcast/YouTube guest today is Michael Mandel, co-founder and CEO of CompStak.   Key takeaway: clean data is the moat - AI is the multiplier.   CompStak spent 14 years crowdsourcing lease and sales comps from nearly 50,000 brokers and research professionals. That foundation is what makes their AI tools actually useful rather than just impressive.   The practical applications worth knowing about: natural language search across 1.3...

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Most pitch decks are failing because PDFs no longer match how investors actually consume information, especially on mobile.   That is the problem Avi Solomon and his team at Pulse are solving with AI.   In brief: • Interactive decks increase conversions • AI now makes advanced pitch decks economically viable • Investors increasingly expect interactive, mobile-native formats   Pulse feels like a category shift because the decks behave like interactive web pages not documents where on-screen motion captures attention, information is layered so investors can skim or...

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Hotels are not underperforming because demand is weak, they are underperforming because the economics of the guest relationship are still being managed manually.   That is the central takeaway from my recent Demo Day conversation with Luca Zambello, Founder, and Jason Lopez, VP of Revenue at Jurny.   [Full disclosure: I am an early investor in Jurny]   In brief: Hotels are leaving meaningful NOI on the table by treating guest experience as a cost center rather than an operating system.   What stands out Personalization at scale is an operational advantage that...

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Want to screen (waay) more deal flow for your acquisition pipeline than you do currently? Here is exactly how to do that with AI (and I'm NOT talking about some clever new way to use ChatGPT).   𝘐𝘯 𝘣𝘳𝘪𝘦𝘧: 𝘛𝘩𝘦 𝘢𝘣𝘪𝘭𝘪𝘵𝘺 𝘵𝘰 𝘶𝘯𝘥𝘦𝘳𝘸𝘳𝘪𝘵𝘦 𝘮𝘰𝘳𝘦 𝘥𝘦𝘢𝘭𝘴 𝘢𝘤𝘤𝘶𝘳𝘢𝘵𝘦𝘭𝘺 𝘸𝘪𝘵𝘩𝘰𝘶𝘵 𝘣𝘳𝘦𝘢𝘬𝘪𝘯𝘨 𝘺𝘰𝘶𝘳 𝘦𝘹𝘪𝘴𝘵𝘪𝘯𝘨 𝘱𝘳𝘰𝘤𝘦𝘴𝘴 𝘪𝘴 𝘢...

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AI in commercial real estate is usually framed around predictions and pricing.   In brief: Underwriting delays come from manual data extraction, not Excel. Institutional CRE teams automate the data layer, not the model. Parsing rent rolls and T12s is now a scale problem, not a staffing one. AI underwriting is being adopted first by lenders and servicers. Speed and consistency are emerging as underwriting risk controls. This Demo Day conversation with Parag Goswami, CEO of Clik.ai, focuses on something more fundamental: how underwriting actually gets done.  ...

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Most CRE teams are not losing deals because of capital, talent, or market access.   They are losing because they move too slowly because initial underwriting and deal marketing are still painfully manual across much of the industry.   Spreadsheets. Templates. Design tools. Email chains. Outsourced vendors.   All stitched together by habit.   That friction costs time, and time costs deals.   In my latest AI/CRE Demo Day show Anton Zajac, CEO of IntellCRE, demonstrates (onscreen) what happens when those bottlenecks disappear.   What stood out...

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Introducing the Demo Day YouTube/Podcast   Demo Day is a new series focused on one simple idea: showing, not telling, where AI is actually revolutionizing commercial real estate.   No theory. No slide decks. Not a clever ChatGPT prompt.   Just live, on-screen demonstrations of AI tools you can use today to get a significant edge against your competitors.   If you think ChatGPT is all AI has to offer, this episode will reset your mental model fast. In this Demo Day, I reveal the extraordinary AI platform, TestFit, a platform that applies AI directly to land...

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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 Markets Are Growing — But Liquidity is the Blind Spot
Jim sees a long-term, secular shift from public to private markets. This trend has been driven by:
  • Rising regulatory costs of public capital raises
  • Falling costs and barriers to entry in private placements
  • Broader investor access due to reduced minimums (from $250K+ to $10K–$20K)
But here’s the warning: private securities still lack liquidity. Investors participating in these syndicated deals should recognize that they are locked in, sometimes for years, with no clear exit.
 
“It’s like three guys trying to run through a door at the same time – when everyone wants out, they can’t.”
 
Solution: Jim’s firm has built an Alternative Trading System (ATS) to create secondary markets for private securities, a concept CRE sponsors might want to look at. While not yet equivalent to public exchanges, these platforms offer an emerging way to address investor liquidity concerns and could give forward-thinking sponsors a competitive edge.
 
2. Don’t Be Fooled by the Illusion of Diversification
Many sponsors pitch private equity real estate as an uncorrelated asset class, perfect for diversifying out of stocks and bonds. Dowd challenges this narrative.
 
“In a crisis, all risk assets tend to correlate. The illusion of diversification is mostly due to slow re-pricing in private markets.”
 
Takeaway: Sponsors should be transparent with LPs. While real estate is a solid long-term asset, it’s not immune to systemic shocks. Treating it as a diversification tool must come with proper liquidity and risk disclosures.
 
3. Risk Has Moved From Banks to Private Markets
Jim argues that the risk which once destabilized the banking sector during the GFC has now migrated to private markets. The positive spin: these markets are mostly backed by equity, not federally insured deposits, reducing systemic risk.
 
Investors (LPs) should understand that the margin for error in private real estate has shrunk. Mispricing risk in this environment is more likely to catch up with you, especially in a rising rate context.
 
4. The 10-Year Treasury: The Most Important Metric in CRE
Jim highlights the 10-year Treasury yield as the single most important signal CRE sponsors should track.
 
Why?
 
“A 6% cap rate in a 2% Treasury environment is fundamentally different than the same cap rate in a 4.5% Treasury world. That delta blows up every underwriting model.”
 
Cap rate spreads are compressing. And yet, many sponsors haven’t recalibrated assumptions.
 
Jim’s advice: treat macro indicators like interest rates and liquidity conditions as core components of your investment thesis, not just afterthoughts.
 
5. Investor Behavior Has Changed: Active Risk is Now in Private Markets
Jim sees a structural shift in how investors approach risk:
  • Liquid portfolios (ETFs, mutual funds) are increasingly passive and macro-driven.
  • Private investments, including real estate, are now where most investors take active risk.
  • For sponsors, this has profound implications:
  • Investor trust and manager selection matter more than ever. Sponsors must demonstrate operational excellence and a clear, differentiated strategy.
  • Geographic proximity still matters. Many large managers raise capital locally. Relationships built within a 100-mile radius still drive much of the private capital flow.
6. On Crypto and Tokenization: Don’t Confuse the Two
North Capital does not allocate to crypto but Jim is bullish on blockchain infrastructure for private markets, especially tokenization.
 
“Blockchain could enable scalable, transparent, and low-cost transactions for private securities – if regulators allow it.”
 
Tokenization may hold long-term promise for CRE sponsors looking to expand liquidity, access global investors, and reduce friction. But the infrastructure and regulatory frameworks are still evolving.
 
7. Investor Advice: Time in the Market Beats Timing the Market
Jim’s advice to investors (including his own son) is simple: don’t try to time the market. Instead:
  • Keep short-term money in treasuries or cash equivalents
  • Deploy long-term capital systematically over a 3–12 month window
  • Accept volatility as the price of long-term outperformance

For sponsors, this means messaging matters. Emphasize long-term fundamentals over short-term fear. Help investors contextualize volatility and maintain confidence in your strategy.

8. Watch for These Signals: What Could Change the Outlook
Jim tracks two key macro indicators to signal inflection points:
  1. The 10-Year Treasury yield (as mentioned above)
  2. Capital flows in public markets – a pullback here could foreshadow slower fundraising in private markets.
Beyond markets, two external shocks could force sponsors to reevaluate assumptions:
  1. A geopolitical crisis (India–Pakistan tensions, Middle East escalation, Ukraine/Russia fallout)
  2. A surprise inflation spike, particularly driven by tariffs, energy, or trade policy shocks
Investors need to ask: “Can my portfolio withstand a 30–40% drawdown without breaking my long term plans?”  If the answer is no, you have too much exposure to risk and should dial back.
 
Final Takeaway for CRE Sponsors
Jim Dowd’s insights are a timely reminder that capital formation in private real estate markets is entering a new phase – defined by rising macro uncertainty, evolving liquidity expectations, and heightened investor scrutiny.
 
Sponsors who embrace transparency, align offerings with institutional risk frameworks, and prepare for greater regulatory and market sophistication will be best positioned to lead, and raise, in this new environment.
 
***
In this series, I cut through the noise to examine how shifting macroeconomic forces and rising geopolitical risk are reshaping real estate investing.
 
With insights from economists, academics, and seasoned professionals, this show helps investors respond to market uncertainty with clarity, discipline, and a focus on downside protection. 
 
Subscribe to my free newsletter for timely updates, insights, and tools to help you navigate today’s volatile real estate landscape. You’ll get:
  • Straight talk on what happens when confidence meets correction - no hype, no spin, no fluff.
  • Real implications of macro trends for investors and sponsors with actionable guidance.
  • Insights from real estate professionals who’ve been through it all before.

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Email: adam@gowercrowd.com
Call: 213-761-1000