Lakeside HoldingsLAKESIDE HOLDINGS
Insights

Written from the models.

Technical essays on underwriting mechanics, waterfall structure and the errors that survive review. No market takes, no filler.

Waterfalls · 6 min · July 2026

The silent waterfall error.

The most expensive mistake in JV modeling is not a broken formula. It is a waterfall that calculates cleanly and allocates wrongly.

Underwriting · 5 min · July 2026

Downside first: a working definition.

Every investor says they underwrite the downside. Here is what that means when it has to be a procedure instead of a sentence.

Model audit · 7 min · July 2026

Five formulas that quietly cost basis points.

The errors that survive review are not dramatic. They are small, structural and directionally biased. These are the five we look for first.

Model audit · 8 min · July 2026

How to Audit a Commercial Real Estate Underwriting Model.

The eight checks we run when we rebuild a sponsor's underwriting model in a second engine, and the specific error that each one is built to catch first.

AI · 7 min · July 2026

Can AI Underwrite Real Estate Deals?.

AI can draft an underwriting and it cannot decide one. The difference between those two verbs is the whole answer, and it decides where to start.

Debt · 4 min · July 2026

How to size a construction loan before the term sheet does it for you.

A construction loan is sized three times: by your model, by the lender's screen and by reality during the draw. How to make all three agree first.

Debt · 7 min · July 2026

Three Constraints Walk Into a Term Sheet.

Every term sheet quotes three constraints. Your proceeds are set by whichever one binds, and you do not know which one binds until you run all three.

Rent roll · 6 min · July 2026

Full Building, Empty Bank Account: Economic Occupancy.

A building can be 95 percent full and 86 percent paid. Both numbers get called occupancy in the deal package, and only one of them pays the mortgage.

Waterfalls · 7 min · July 2026

The Waterfall Must Allocate Exactly 100 Percent.

A waterfall that allocates 99 percent of a dollar is broken and one that allocates 101 percent is worse. What to trace before you sign the agreement.

Underwriting · 6 min · July 2026

The Exit Cap Does Most of the Work in Your IRR.

The assumption doing the most work in your model is usually the one with the least underneath it. What the exit cap is really worth, priced in dollars.

Screening · 6 min · July 2026

Five Minutes Before You Fall in Love With a Deal.

Every deal deserves five minutes and few deserve a week. One deal walked through our free screener, assumptions stated, with the verdict included.

Rent roll · 5 min · July 2026

Loss to Lease: the Number the Seller Typed Himself.

In place rents are 100 dollars under market, which is upside. The first half of that sentence is usually true. The second half is a claim to check.

Underwriting · 6 min · July 2026

The NOI Bridge, Recomputed Line by Line.

How to calculate NOI in real estate line by line on a 100 unit building, from gross potential rent to 676,242, and the 25,000 error worth 385K of price.

Waterfalls · 5 min · July 2026

Pref, Catch-Up, Promote: Order of Operations.

Two partners can agree on the pref, the split and the promote, sign the same document and still argue at exit. The order of operations is the machine.

Rent roll · 3 min · July 2026

The rent roll is lying to you, politely.

Same building, same tenants, five different truths depending on which report you were handed. The five polite lies, and how to force one honest format.

AI · 3 min · July 2026

What AI should never touch in your underwriting.

Every month another shop announces it is AI powered, and every month another investor asks us to audit a model nobody in the building can explain.

Library · 6 min · July 2026

Why We Publish the Models We Run.

The spreadsheet that decides whether millions of dollars move is a trade secret. The deal it evaluates gets a glossy memorandum. That is backwards.

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