You CAN time the market


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October 29, 2025 | Read Online

Morning,

You can time the market.

Yes, you heard that right. The prevailing orthodoxy insists you can’t. The practice of “buy and hold through thick and thin” dominates. But what if the smarter play is acknowledging that yes, you can time markets, provided you recognize where valuations are extreme, where they are depressed, and act accordingly?

The folly and the possibility

Most investment counsel treats market timing as a fool’s errand. Why? Because predicting exact highs or bottoms is impossible in real time. Because momentum often carries prices further than fundamentals justify. And because human behavior, both fear and greed, intervenes.

All true.

But timing is not about pinpointing the next two days; it’s about recognizing asset-classes where the risk/reward has meaningfully shifted. If one asset class is trading at historic excess and another is trading at a discount, then moving capital is not reckless timing, it is intentional repositioning.

When stocks and gold hit historic highs

Consider the state of public markets today. The S&P 500 CAPE (cyclically-adjusted price-to-earnings ratio) is around 40-41: nearly three times its long-term median of around 16. Decades of data show that when CAPE is this elevated, forward returns for equities are muted and downside risk increases. It isn’t prophecy, it’s statistical probability.

Meanwhile gold, traditionally un-correlated or inversely correlated with equities, is also at record highs. In 2025 spot gold reached above $4,000/oz and is hovering around that level still.

Why the twin peaks? A mix of factors: inflation hedge demand, central-bank purchases, geopolitical tension and US dollar weakness. The fact that stocks and gold are rallying together is itself notable because it implies investors are both chasing growth (via equities) and seeking insurance (via gold).

That often signals a reckoning ahead.

Why commercial real estate appears to be bottoming

To the seasoned real estate professional, this may feel intuitive – asset values in commercial real estate (CRE) have been under pressure.

According to the Green Street Commercial Property Price Index, pricing across all-property in US CRE is flat to modestly positive in 2025, after a prior decline. Further, the Federal Reserve’s index of commercial real estate prices shows year-on-year declines of around 3–7 % for recent quarters.

Recent data from Invesco indicate that property-level values are poised to rise heading into 2026, a sign that pricing may have already found its floor. Add to that the tailwind of forthcoming banking deregulation, which is set to release new liquidity into commercial lending, and a monetary policy environment tilting toward lower rates, and the conditions are forming for a rebound in transaction volume and asset values.

At the same time, many CRE borrowers face loan maturities that will force recapitalizations and attract sidelined equity back into the market as debt financing becomes more available. Layer onto this the extended and expanded tax incentives for real estate investors contained in the recent OBBB legislation – measures designed to spur investment and development – and the backdrop for commercial real estate strengthens further.

Together, these factors suggest that the asset class is already trading below its long-term equilibrium while equities and gold hover near historic highs, making a rotation into discounted CRE not just rational, but timely.

A rotation at scale: sell high, buy low

Here is the investor playbook:

  • Sell into excess.
    If equities carry valuations that foreshadow weaker returns, and gold is priced more for speculation than margin of safety, there is merit in reducing exposures at the top of this cycle.
  • Deploy into discount.
    CRE offers yield, structural advantages (inflation de-factoring rents, capital from institutional investors), and a valuation reset that many other asset categories simply don’t.
  • Scale the strategy.
    This isn’t about one deal. It’s about structuring disciplined access to private-equity real-estate syndications and allocating in a cohort of sponsors anchored in underwriting for cycles. The time to act is when pricing is attractive and the forward risk/reward tilts in your favor.

You’re not timing a stock or predicting a gold blip. You’re re-allocating at a strategic juncture: off the froth (public equities, gold) and into the reset (private real estate). That is how you can time the market. The ideal scenario: you sell high, you buy low, and you lock in optionality for the phase of market rotation.

It’s not bold-bravado. It’s simple mathematics rooted in valuation and capital-markets behavior. Every cycle has its vantage point.

This one offers an unusually clear one.

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I wrote a shorter version of this newsletter on LinkedIn this ayem. If you have an opinion on this, share them in the comments - I'd be happy to respond.

Check out the post here.

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If you are a sponsor with a good pipeline and you think the same way as I do about the opportunities we are likely to see in the coming months and you want more equity, let me know.

I might be able to help you raise all the capital you're going to need.

Best,
Adam

This week's Podcast/YouTube show

Guest: Norman Radow, CEO, The RADCO Companies

The Workout Mindset Returns

Norman Radow built RADCO by doing what most sponsors avoid: taking control in chaos, fixing broken assets, and exiting when others are still modeling miracles.

His career was forged in complex restructurings, first as Lehman’s off-balance-sheet “workout company,” and then, after Lehman’s collapse in 2008, unwinding vast, litigation-heavy portfolios. That perspective colors his view of today’s market: price, not platitudes, is what matters – and business plans must adapt as conditions change.


2021’s Hangover Isn’t Done

Radow’s core diagnosis is blunt. Late-2021 buyers paid sub-3.5% caps for 1970s–80s assets, often on pro forma annualized 15% rent growth. Then two things hit at once: rent momentum stalled and rates surged.

Add insurance spikes and heavier OpEx and they were wiped out. He’s seeing many of those deals not merely eviscerate equity but pierce into the risk tranches of debt. In his management book, roughly half of legacy assets are underwater at a magnitude that makes mark-to-market painful – hence lender reluctance to trigger a “transaction event” that would force write-downs.


Lenders: Avoiding Moss (and Marks)

Call it “extend and pretend,” or as Radow prefers, “a rolling loan gathers no loss.”

The point: many credit teams are structuring time-buys, extensions, modifications, A/Bs – anything to avoid headline losses. In one case, RADCO bid roughly 25% below the outstanding loan on a failing 1980s property; the lender instead gave the (out-of-money) sponsor a free extension on similar terms RADCO had proposed for a recap, purely to dodge recognition.

It isn’t a mark-to-market regime, and until price discovery clears that backlog, volume will dribble.


The Liquidity Illusion

Yes, liquidity is back but it’s behaving like early-cycle equity in public markets: it concentrates first in core, large-cap equivalents. In multifamily, that means stabilized, Class-A, institutionally managed properties, some trading at low-4 caps, financed with fixed-rate agency debt around the mid-5s.

That’s negative arbitrage from day one. Buyers are underwriting “make-it-up-in-the-out-years”: below-replacement entry plus rent growth in 3–4 years as supply fades. Radow concedes the logic but treats it as a bet, not a base case. He’d rather start at neutral or positive carry and let upside be gravy.


Supply Clears, But Affordability Decides

The pipeline will thin dramatically. Radow cites research suggesting 2026 multifamily deliveries could look like those in 2012, the post-GFC trough, implying a multi-year window for rent growth as absorption catches up. Yet the constraint won’t only be supply; it will be paychecks. Affordability, after 2021’s spike, caps what tenants can absorb. That steers him toward older assets with room for operational upgrades and selective, ROI-tested renovations, product that can clear at rents middle-market tenants can pay.What CRE Professionals Should Do Now

1) Stop fighting the last war – price today’s risk.
If you’re still “waiting on rates” to save the capital stack, you’re underwriting hope. Many lenders won’t transact because they fear marks; focus on situations where you can solve a problem (delinquency, deferred maintenance, mispriced renewals) and get paid for doing so. Expect bespoke structures – A/B notes, cash-flow mods, short-fuse covenants – to become the norm in the distressed CRE world.

2) Avoid the core crowd unless your capital is competitively priced.
Negative arbitration (buying at cap-rates below cost of capital) is a tax on patience and a subsidy to your pro forma. If you’re playing there, you must have a clear replacement-cost edge, real operating leverage, and confidence you can push loss-to-lease without breaking affordability. Otherwise, let institutions warehouse that duration risk.

3) Hunt “operational distress,” not just financial distress.
RADCO’s edge is systematic triage: cure delinquency, restore an efficient rhythm in how vacant units are turned over and re-leased, normalize renewals, and stage capex based on real leasing signals – not a one-size-fits-all “pallet.” Phasing matters: test, learn, scale. The 2000s thousand plus unit condo-conversion tale he recounts, emptying everything at once and standardizing finishes, was a masterclass in what not to do.

4) Underwrite fraud and insurance like first-order inputs.
Organized application fraud rose with pandemic-era churn; screening systems get gamed. Insurance, especially in coastal and storm-exposed metros, has jumped multiples and capitalizes straight into value. Treat these as base-case assumptions, not tail risks.

5) Syndicators: don’t compete head-on with Blackstone.
Radow’s guidance to accredited capital is consistent across cycles: swim where mega-private equity shops don’t. The crowd will migrate later if returns show up, just as they did when value-add B-class compressed from ~9 caps into the 3s over the last cycle. Your advantage is speed, focus, and a tighter feedback loop between leasing data and project scope.


The 2025–2027 Playbook

The near-term is a stalemate: lenders slow-walk, sellers seek yesterday’s price, and only hairier deals clear. That’s precisely where skilled operators can earn real equity. The medium-term is more attractive: as starts collapse and demand normalizes, the rent curve should steepen, especially for well-located, non-luxury stock improved with ROI-tested upgrades.

If you can buy below replacement, stabilize operations, and finance without relying on heroics, you’ll be positioned to harvest when the market finally re-prices risk.Radow’s parting counsel is deceptively simple: embrace the workout mindset.

In a market built on 2021’s optimistic spreadsheets, the sponsor who solves prosaic problems – collections, maintenance, renewals – will out-earn the sponsor who waits for macro to bail them out.


Watch/listen to full episode here.

Please join the conversation on LinkedIn, here.

Or feel free to reply to this email with any thoughts or comments.


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Please note that I am not an investment advisor or attorney and do not make investment recommendations of any kind. Please seek advice from your financial advisor, accountant, attorney, and any other professional in assessing the risks associated with any investment opportunity, as every opportunity has risks that could result in a substantial loss.

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The GowerCrowd Newsletter

Real estate markets move in cycles, and understanding history is the key to navigating today’s opportunities. As a seasoned investor with 30+ years in the industry, I take a historically informed, risk-averse approach—where capital preservation is the priority. You'll get market insights and investment strategies tailored to both passive investors and capital raisers, with a particular focus on raising private capital. Occasionally, I also share best practices in digital lead generation on LinkedIn and using AI to optimize lead generation. I also introduce my latest podcast and YouTube series, where you'll hear from capital allocators, unpacking trends, strategies, and the future of real estate capital formation. For those looking to invest smarter, raise capital more effectively, and stay ahead of market shifts, The GowerCrowd Newsletter offers a concise yet detailed perspective on the forces shaping our industry.

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