Real Estate Deal Structuring
Master institutional real estate mechanics from capital stack design to complex syndication waterfalls. Stress-test underwriting, negotiate intercreditor agreements, and execute advanced tax and workout strategies.
Like Duolingo, but for Real Estate Deal Structuring. Tomo turns the whole topic into a game you play five minutes a day, until it actually sticks.
22 levels across 3 sections, about 44 minutes end to end, roughly 9 days at five minutes a day. It moves through Underwriting Beyond the Pro Forma, Capital Stack Engineering, and Value Creation and Distressed Execution.
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Key ideas in Real Estate Deal Structuring
- Terminal cap rates should anchor to normalized risk-free yields plus historical risk premiums rather than trough-of-cycle spreads
- Broker models frequently understate terminal expansion by anchoring to prevailing transaction comps during low-rate regimes
- A historical spread of 250 bps over a normalized 4.0% Treasury yields a 6.5% stressed exit cap rate, exposing exit value overstatement
- Annual turnover carpet/paint replacements and standard appliance refreshes recur cyclically and drain cash, unlike true asset-repositioning capital
- Ongoing leasing commissions and standard tenant improvement allowances are essential operational costs to sustain occupancy across lease rollovers
- Discretionary amenity additions and structural roof rebuilds represent genuine one-off capitalized expansions that legitimately sit below the line
- General submarket rent growth reflects broader macroeconomic inflation rather than sponsor capability
- Loss-to-lease realization is bounded by lease expiration schedules and tenant retention elasticity
- Value-add premiums require explicit per-unit capital investment payback math to be credible
- Conflating macro market tide with operational renovation lift conceals underperforming unit economics
- Physical occupancy measures leases signed and doors occupied, ignoring whether cash is actually remitted to the landlord
- Economic occupancy tracks collected gross potential rent minus concessions, credit loss, and uncollectible tenant accounts
- Testing simultaneous negative shifts in exit yield and revenue growth prevents false confidence derived from single-variable isolated stresses
- A dual-variable matrix isolates the combined compounding impact of operational stagnation and valuation multiple contraction
- An equity multiple hovering just above 1.0x with a positive single-digit IRR signals that exit cap rate widening has essentially consumed all equity upside, leaving zero margin of safety against debt amortization or CapEx overruns
- Debt yield (NOI / Loan Amount) measures the lender's cash-on-cash return if they foreclose, completely independent of market cap rates
You've tried the other tabs
Thirty open tabs. Four facts you actually kept.
You watched. You nodded. By Sunday it was gone.
One answer, then back to scrolling.
Eight weeks. You meant to finish. You didn't.
Tomo gives Real Estate Deal Structuring the Duolingo treatment: levels, streaks, and quick quizzes that test what you just learned. That game loop is what the tabs above never had, so it's the one you actually finish.
Here's what playing it feels like
A real question from this course. Take your best guess.
Why do broker pro formas so frequently understate terminal cap rate expansion during low-interest periods?
Get it right to open this lesson and 21 more in the app.
Where Real Estate Deal Structuring takes you
- 1
Underwriting Beyond the Pro Forma
- Stress-Testing Sponsor Assumptions
- Debt Sizing and Covenant Structuring
- 2
Capital Stack Engineering
- Equity Waterfalls and Promote Mechanics
- Subordinated Debt and Preferred Equity
- Tax Optimization and Basis Engineering
- 3
Value Creation and Distressed Execution
- Land Entitlement and Use Arbitrage
- Distressed Workouts and Note Acquisitions
3 sections · 7 units · 22 levels. Built to play, not to enroll.
You pick the voice
Real Estate Deal Structuring is taught in the The Professor style: clear, structured, thorough. Want a different feel? In the app you can spin up the same topic in any of Tomo's teaching styles. Same facts, totally different vibe.
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