25
Nov
Published in Sustainable Investing Digest | In Collaboration with Skyline Property Experts
“Risk comes from not knowing what you’re doing. But even more risk comes from knowing what you’re doing—and measuring the wrong things.” — Adapted from Warren Buffett
You’ve spent years mastering financial modeling. Your DCF models are bulletproof. You understand levered vs. unlevered returns, can calculate XIRR in your sleep, and know the difference between cash-on-cash and equity multiple.
But here’s what keeps institutional allocators awake at night:
Your model shows an 18.3% IRR. So does your competitor’s. Yet one gets funded at 5.2% preferred, the other can’t close at 12% hard money.
What’s the difference?
Modern institutional investors (family offices managing >$500M, PE funds, pension allocators) don’t reject deals based on IRR alone. They reject deals that fail risk-adjusted return thresholds most operators have never calculated.
Real data from our Q4 2024 capital raise:
Same IRR range (16.9%-18.7%). Radically different risk profiles.
Formula:
Sharpe Ratio = (Expected Return - Risk-Free Rate) / Standard Deviation of Returns
What it measures: Return per unit of total volatility.
Why it matters: A 20% IRR with massive volatility (Sharpe 0.6) is institutionally inferior to a 16% IRR with low volatility (Sharpe 1.8).
Real Example:
Deal A: Central Florida expansion
Deal B: Distressed Jacksonville turnaround
Verdict: Deal A delivers 147% better risk-adjusted returns despite lower absolute IRR.
Formula:
Sortino Ratio = (Expected Return - Target Return) / Downside Deviation
What it measures: Return per unit of downside volatility only (ignoring upside volatility).
Why it matters: Sharpe penalizes upside volatility. Sortino focuses exclusively on downside risk—what actually keeps you awake.
Imagine two deals with identical 18% IRRs:
Deal X:
Deal Y:
Institutional verdict: Deal X is superior. Sortino reveals that Deal Y has unacceptable downside exposure masked by moderate overall volatility.
Formula:
Calmar Ratio = Annualized Return / Maximum Drawdown
What it measures: Return per unit of worst-case loss.
Why it matters: IRR and Sharpe don’t tell you the peak-to-trough capital destruction scenario. Calmar does.
“If this deal goes sideways in Year 2, what’s the maximum capital I could lose before recovery?”
Real scenario: $9.5M Tampa expansion
Monte Carlo reveals:
Investor psychology: You’re asking LPs to stomach a potential $1.9M loss (20% drawdown) for a 17.8% return.
Institutional threshold: Calmar >1.2 for value-add deals.
Action taken: Deal restructured with 18-month interest reserve ($280K) to eliminate drawdown scenario.
New Calmar: 17.2 / 8.7 = 1.98 Result: Funded in 11 days.
What it is: Visual ranking of which input variables create the most IRR variance.
Why it matters: Not all assumptions are created equal. Tornado analysis reveals which 3-5 variables will make or break your deal.
Step 1: Identify your 10-15 key variables
Step 2: Flex each variable +/- 20% while holding others constant
Step 3: Calculate resulting IRR range for each variable
Step 4: Rank by IRR impact (widest swing = top of tornado)
Capped at 100% occupancy in practice
What this reveals:
Before Tornado Analysis: Investor spent 40 hours negotiating GC bids to save $180K (4.7% construction cost reduction).
After Tornado Analysis: Same investor spent 12 hours structuring REIT purchase option (locking 5.8% exit cap vs. 6.2% modeled), creating $1.4M in additional value — 7.8× better ROI on time invested.
You need probabilistic outputs (Monte Carlo simulation results) to calculate these ratios properly. Single-point estimates won’t work.
Required data:
Step 1: Run Monte Carlo, export IRR results (10,000 outcomes)
Step 2: Calculate expected return (mean IRR)
Expected Return = AVERAGE(IRR outcomes) = 17.8%
Step 3: Identify risk-free rate
Risk-Free Rate = Current 10-Year Treasury = 4.5%
Step 4: Calculate standard deviation
Std Deviation = STDEV.P(IRR outcomes) = 8.2%
Step 5: Calculate Sharpe
Sharpe = (17.8 - 4.5) / 8.2 = 1.62
Step 1: Define target return (typically your hurdle rate)
Target Return = 15.0%
Step 2: Isolate below-target returns
Filter IRR outcomes < 15.0%
Create array of (Target - Actual) for each below-target outcome
Step 3: Calculate downside deviation
Downside Deviation = SQRT(AVERAGE(squared deviations below target))
= 4.7%
Step 4: Calculate Sortino
Sortino = (17.8 - 15.0) / 4.7 = 0.60
Note: This example shows weak Sortino despite acceptable Sharpe—revealing significant downside tail risk.
Step 1: Calculate annual returns for each simulation path
Step 2: For each path, calculate cumulative equity value over time
Step 3: Identify maximum drawdown per path
Max Drawdown = Peak Equity Value - Trough Equity Value (before recovery)
Step 4: Average maximum drawdowns across all paths
Average Max Drawdown = 18.3%
Step 5: Calculate Calmar
Calmar = Annualized Return / Max Drawdown %
= 17.8 / 18.3 = 0.97
Step 1: Create sensitivity table
Step 2: Sort by range (descending)
Step 3: Create horizontal bar chart with:
Let’s analyze an actual deal through all four lenses.
Traditional verdict: Strong deal, proceed to closing.
Variable distributions:
Results (10,000 iterations):
Sharpe Ratio:
(17.3 - 4.5) / 7.8 = 1.64
Assessment: ✅ Strong (>1.4 threshold for value-add)
Sortino Ratio:
(17.3 - 15.0) / 5.2 = 0.44
Assessment: ⚠️ WEAK (<1.0 threshold)
Calmar Ratio:
17.3 / 16.7 = 1.04
Assessment: ⚠️ MARGINAL (<1.3 threshold)
Traditional Analysis: “Great deal, 18.1% IRR, let’s close.”
Advanced Analysis: “Acceptable IRR, but concerning risk profile:”
Original Structure:
Revised Structure:
Trade-off: Sacrificed 50 bps of IRR to improve risk-adjusted returns by 85-234%.
Institutional response:
Net result: Lower IRR, but 3.5% lower cost of capital = superior risk-adjusted economics.
Based on 47 institutional capital raises (2022-2024), here are the observed acceptance thresholds:
Notes:
Notes:
Notes:
The error: Calculating Sharpe using standard deviation of historical returns.
Why it’s wrong: Self-storage is in a supply-constrained environment (2024-2026) unlike 2018-2020. Historical volatility doesn’t reflect current market structure.
The fix: Use Monte Carlo forward-looking volatility based on variable distributions.
The error: Treating each year’s occupancy as independent.
Why it’s wrong: Year 2 occupancy is highly correlated with Year 1 (ρ ≈ 0.78 in self-storage).
The impact: Independent assumptions understate compounding risk.
The fix: Model with correlation matrices:
The error: Using 10-year Treasury (4.5%) for 3-year hold period.
Why it’s wrong: Duration mismatch.
The fix: Match risk-free rate duration to project duration:
Impact: Using wrong duration can inflate/deflate Sharpe by 0.15-0.30.
The error: Using 0% as target return (minimum acceptable return).
Why it’s wrong: 0% isn’t your actual hurdle. You need >15% to justify risk.
The fix: Set target return = your opportunity cost (typically hurdle rate or WACC).
The error: Testing +/-20% on ALL variables (including those with natural caps).
Why it’s wrong: Occupancy can’t exceed 100%. Testing 110.4% occupancy is nonsensical.
The fix:
I’ll walk through building a self-storage risk ratio calculator.
Sheet 1: Inputs & Assumptions
Sheet 2: Monte Carlo Engine
Sheet 3: Risk Metrics
Sheet 4: Tornado Analysis
excel
=IRR(CashFlowArray_1:CashFlowArray_5)
Copy across 10,000 columns.
excel
=(AVERAGE(IRR_Array) - RiskFreeRate) / STDEV.P(IRR_Array)
excel
=(AVERAGE(IRR_Array) - TargetReturn) / DownsideDeviation
Where DownsideDeviation =
SQRT(AVERAGE(IF(IRR_Array<TargetReturn, (TargetReturn-IRR_Array)^2, 0)))
excel
=AnnualizedReturn / MaxDrawdownPercent
Where MaxDrawdownPercent =
(PEAK_EquityValue - TROUGH_EquityValue) / PEAK_EquityValue
excel
=IRR(CashFlowArray with Variable X at -20%)
=IRR(CashFlowArray with Variable X at +20%)
=ABS(IRR_High - IRR_Low)
Rank by range, largest to smallest.
Property: 78,000 SF Orlando suburban facility Purchase Price: $12.8M Pro Forma IRR: 19.3%
Traditional metrics: ✅ All green lights
Risk analysis:
Tornado revealed: 82% of return variance driven by single variable (rent growth in Years 1-2).
Problem: Underwriting assumed 7.5% rent growth. Market comps showed 3.8-4.2%.
Outcome:
Lesson: Risk ratios revealed fragility hidden by single-point IRR.
Property: 52,000 SF Lakeland value-add Purchase Price: $6.2M Pro Forma IRR: 16.1%
Traditional metrics: ⚠️ Below 17% target, almost passed
Risk analysis:
Tornado revealed: Return drivers highly diversified. No single variable >15% impact.
Outcome:
Lesson: Superior risk-adjusted profile = superior execution probability.
Slide 5: Financial Returns
Decision: Approve / Deny based on IRR vs. hurdle
Slide 5: Financial Returns (Risk-Adjusted)
Tornado Top 3:
Risk mitigation:
Decision: Approve with confidence in risk-adjusted economics.
Measures duration and depth of drawdowns (more sophisticated than Calmar).
Formula:
Ulcer Index = SQRT(Average of Squared Drawdowns over Time)
When to use: Long-hold assets (>7 years) where drawdown persistence matters.
Compares excess returns to tracking error vs. a benchmark.
Formula:
Information Ratio = (Portfolio Return - Benchmark Return) / Tracking Error
When to use: Portfolio-level analysis, comparing your self-storage returns vs. REIT indices.
Probability-weighted ratio of gains vs. losses.
Formula:
Omega = Area of Returns Above Threshold / Area of Returns Below Threshold
When to use: When return distributions are non-normal (common in development deals with binary outcomes).
The power emerges when you combine yesterday’s Monte Carlo framework with today’s risk ratios.
Step 1: Build deterministic model (traditional DCF)
Step 2: Identify 10-15 key variables
Step 3: Assign probability distributions to each variable
Step 4: Run 10,000-iteration Monte Carlo
Step 5: Calculate risk ratios from Monte Carlo outputs:
Step 6: Build Tornado from sensitivity analysis
Step 7: Identify top 3 risk variables
Step 8: Restructure deal to mitigate top risks
Step 9: Re-run Monte Carlo with risk mitigation
Step 10: Compare risk ratios pre/post mitigation
Tornado Top 3:
Mitigations applied:
Results:
Cost: $225K (2.4% of equity)
Benefit:
ROI on risk mitigation: 730% ($1.87M / $225K)
Day 1 (2 hours):
Day 2 (1 hour):
Day 3 (3 hours):
Day 4 (2 hours):
Day 5 (1 hour):
Week 1: Calculate risk ratios for your last 5 closed deals
Week 2: Create benchmark database
Week 3: Integrate into underwriting process
Week 4: Implement in portfolio management
A: Yes. Risk ratios are scale-invariant—they measure risk-adjusted returns as percentages, not absolute dollars.
However: Larger deals often have institutional advantages (better pricing, more resources for due diligence, professional management) that reduce volatility.
You may see Sharpe ratios 0.2-0.4 higher on >$25M deals vs. <$10M deals—not because larger deals are inherently better, but because they access better execution.
Best practice: Segment your benchmarks by deal size:
A: Three common approaches:
Our recommendation: Use hurdle rate. It reflects your actual return requirement and makes Sortino comparable to Sharpe (both measured against a meaningful threshold).
A: Bimodal distributions occur when you have a binary risk (e.g., entitlement approval/denial, anchor tenant signs/doesn’t sign).
The challenge: Standard deviation (used in Sharpe/Sortino) assumes normal distribution. Bimodal violates this.
Solutions:
A: This reveals asymmetric risk—your upside is volatile (creating high total volatility) but your downside is catastrophic (creating concentrated downside deviation).
Translation: You have lottery ticket risk profile—small probability of big win, larger probability of significant loss.
Institutional view: Unacceptable. Most LPs prefer the inverse (weak Sharpe, strong Sortino) if forced to choose.
Fix: Identify and eliminate downside tail risks (often: exit cap protection, lease-up guarantees, construction cost caps).
Short answer: Yes, but you’ll get caught.
How people try:
Why you’ll get caught: Institutional investors run their own Monte Carlo on your assumptions. When their risk ratios don’t match yours, they:
Our observation: We’ve seen 12 deals rejected in 2023-2024 specifically because operator-provided risk ratios didn’t match institutional re-underwriting—and the discrepancies indicated assumption manipulation.
Based on our analysis of 89 self-storage acquisitions (2021-2024):
Insight: Newer facilities have 46% better risk-adjusted returns (Sharpe) despite similar absolute IRRs.
Every experienced operator already thinks about risk-adjusted returns intuitively:
What you say: “I like the Tampa deal better than the Orlando deal.”
What you mean: “Tampa has similar returns with less downside risk.”
What risk ratios do: Quantify that intuition with institutional precision.
Before risk ratios:
After risk ratios:
Existing policy: “All deals must exceed 16% IRR hurdle”
Enhanced policy: “All deals must meet minimum return thresholds AND risk-adjusted return standards:
Tier 1 (preferred allocation):
Tier 2 (standard allocation):
Tier 3 (requires special approval):
Rejected:
We’ve built a comprehensive Excel template that includes:
Access: Contact Skyline Property Experts for complimentary template
python
import numpy as np
from scipy import stats
def calculate_sharpe(returns, risk_free_rate):
excess_returns = returns - risk_free_rate
return np.mean(excess_returns) / np.std(returns)
def calculate_sortino(returns, target_return):
excess = returns - target_return
downside = excess[excess < 0]
downside_dev = np.sqrt(np.mean(downside**2))
return np.mean(excess) / downside_dev
def calculate_calmar(returns, equity_curve):
annual_return = np.mean(returns)
running_max = np.maximum.accumulate(equity_curve)
drawdown = (equity_curve - running_max) / running_max
max_dd = abs(np.min(drawdown))
return annual_return / max_dd
# Monte Carlo runner
def run_monte_carlo(base_case, distributions, n_sims=10000):
results = []
for i in range(n_sims):
scenario = sample_distributions(distributions)
irr = calculate_irr(scenario)
results.append(irr)
return np.array(results)
Academic:
Practitioner:
June 2024: Two Florida self-storage opportunities hit our desk same week:
Deal Alpha (Jacksonville):
Deal Beta (Orlando):
Traditional analysis: Both exceed 16% hurdle, both approvable, tie goes to… whichever we see first?
Monte Carlo results:
Tornado top 3:
Assessment: ✅✅✅ Exceptional risk-adjusted profile
Monte Carlo results:
Tornado top 3:
Assessment: ⚠️⚠️⚠️ Weak risk-adjusted profile, high execution risk
Equity available: $7.2M (enough for one deal)
Traditional logic: Beta is cheaper, similar IRR, higher value-add upside → Pick Beta
Risk-adjusted logic: Alpha delivers 106% better Sharpe, 219% better Sortino, 162% better Calmar → Pick Alpha
We chose: Alpha
Deal Alpha (we purchased):
Deal Beta (we passed):
Value of risk ratio analysis: $3.2M
Calculation: ($7.2M equity × 19.7% actual) – ($7.2M equity × 11.2% competitor actual) = $612K annual difference × 5-year hold = $3.06M NPV
Deal Beta’s hidden risks:
Deal Alpha’s hidden strengths:
The lesson: IRR told us returns. Risk ratios told us probability of achieving those returns.
Every Friday at 4 PM (15 minutes):
Track in simple dashboard:
Action triggers:
First Monday of each month (60 minutes):
Goal: Continuously improve portfolio-level risk-adjusted returns
In 2024-2025, self-storage deal competition is intense:
How do you compete?
Wrong answer: Pay more (destroys returns)
Right answer: Underwrite faster and better
Operator A (traditional underwriting):
Operator B (risk ratio underwriting):
Result: Operator B wins despite offering same price—seller values certainty of 2-day approval over 5-day competitor.
Traditional IC conversation:
Risk-ratio IC conversation:
Result: Faster IC approvals, larger check sizes, more aggressive pursuit of best deals.
2024 capital raising reality:
Fund Manager A (traditional pitch):
Fund Manager B (risk ratio pitch):
Capital raised:
Cost of capital:
Monday: Read this article, highlight key sections
Tuesday: Download Excel template, familiarize with structure
Wednesday: Run risk ratios on your last closed deal (benchmark)
Thursday: Run risk ratios on current live deal
Friday: Present findings to team, discuss implementation
Week 1: Train team on Monte Carlo + risk ratios
Week 2: Integrate into acquisition model template
Week 3: Update IC memo format to include risk ratios
Week 4: Calculate risk ratios for entire portfolio
Month 1: Build risk ratio tracking database
Month 2: Establish institutional benchmarks by deal type
Month 3: Implement automated weekly risk reviews
IRR tells you the destination.
Risk ratios tell you the probability of arrival—and the cost if you get lost along the way.
For 30 years, institutional investors have known this. Now you do too.
🏢 Skyline Property Experts Commercial Real Estate Brokerage 📞 786-676-4937 📧 scott@skylinepropertyexperts.com
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The most insightful response gets a free comprehensive risk ratio audit of their current deal pipeline.
“The goal of investing is not to eliminate risk—it’s to take intelligent risks that are properly compensated. Risk ratios help you distinguish between the two.”
— Modern Portfolio Theory, applied to self-storage
Let’s finish this week strong. 💪
Calculate your risk ratios today. Underwrite like an institution tomorrow.
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