Winthorpe & Valentine
Global Wealth & Legacy Command Center
Net Worth
Investment Performance
Real Estate & 1031
Liquidity & Cash Flow
Tax Position
Family Governance
Operational Health
LIVE MULTI-ENTITY CONFIDENTIAL
Period
Full Year
YTD
Q1
As Of
2022
2023
2024
2025
Entity
All Entities
Winthorpe III FO
Valentine Foundation
Total AUM & Wealth Overview Winthorpe III Family Office · All Entities Consolidated · April 29, 2025
CONSOLIDATED
Total AUM
$487.3M
▲ $65.5M (+15.5%) vs 2024
LIQUID
Liquid Assets
$89.2M
18.3% of total AUM
ILLIQUID
Illiquid Assets
$398.1M
81.7% of total AUM
After-Tax ROI (2025)
12.3%
▲ vs 8.7% benchmark
Capital Preservation Rate
98.7%
↑ 0.4pp YoY · target ≥95%
Wealth Velocity
+$5.5M
avg monthly AUM growth
Net Worth Trend — 2020 to 2025
Total AUM vs Liquid assets · annual snapshot
6-Year View
Total AUM
Liquid Assets
AUM Target ($500M)
Asset Allocation
By asset class · current period
Concentration
Liquid vs Illiquid Breakdown
Detailed asset classification
Asset ClassValue ($M)% AUMLiquidity
Public Equities$127.4M26.1%Liquid
Money Market / Cash$42.8M8.8%Liquid
Hedge Funds$34.6M7.1%Semi-Liquid
Private Equity$168.4M34.6%Illiquid
Real Estate$112.8M23.2%Illiquid
Venture Capital$30.2M6.2%Illiquid
Total AUM$487.3M100%
Concentration Risk
Single-entity exposure limits · Family Office policy
Risk Monitor
Investment Performance — IRR / MOIC Analysis Private Equity · Venture Capital · Public Markets · Foundation Endowment
Total Invested (Committed)
$205.0M
across 8 active funds
Portfolio Avg IRR
18.7%
▲ vs 15% target hurdle
Weighted Avg MOIC
2.4×
above 2.0× benchmark
Best Performer
3.4×
a16z Fund V · IRR 32.1%
Valentine Fdn Endowment
$28.5M
8.2% return · above 5% rule
Private Equity & Venture Capital Holdings
IRR / MOIC / NAV by fund · as of Q1 2025
8 Active Positions
Fund NameTypeVintageCommittedNAVIRRMOICCapital CallStatus
IRR vs Benchmark — By Fund
Red dashed = 15% target hurdle rate
Relative Performance
Billy Ray Valentine Foundation
501(c)(3) Endowment · 5% Annual Distribution Rule
$28.5M Endowment
Real Estate Portfolio & 1031 Exchange Tracker 1031 ID Deadline: Apr 14, 2025 — 16 Days Remaining
TOTAL RE
Total RE Portfolio Value
$112.8M
4 properties · 2 structures
Aggregate Cost Basis
$62.5M
blended avg 8.3 years hold
Unrealized Gain (Total)
$50.3M
80.5% appreciation
DEFERRED
1031 Deferred Tax Liability
$24.7M
Glen Cove + NNN planned
Property Holdings — 1 Mansion Drive & Portfolio
FMV · Cost Basis · Gain · Tax Strategy
4 Properties
PropertyTypeFMVCost BasisUnrealized GainHold (Yrs)Monthly IncomeStrategy
1031 Exchange & DST Tracker
IRS §1031 Tax-Deferred Exchange Timelines · 45-day ID & 180-day Replacement Rules
2 Active Exchanges
RE Value by Property
FMV vs Cost Basis comparison
FMV
Cost Basis
Unrealized Gain
DST Portfolio Holdings
Delaware Statutory Trust positions
Replacement Properties
Liquidity Forecast & Capital Event Scheduler 12-Month Rolling Forecast · Capital Calls · Distributions
AVAILABLE
Available Liquidity
$89.2M
cash + public mkts
Monthly Burn (Estate)
$485K
1 Mansion Dr + staff + ops
90 DAYS
Capital Calls Due
$2.4M
3 funds · 90-day window
INCOMING
Expected Distributions
$8.7M
3 events · 90-day window
Net Liquidity Runway
14.3 mo
at current burn rate
12-Month Cash Flow Forecast — May 2025 to Apr 2026
Green = net positive month · Red = net outflow · Line = cumulative position
Scenario: Base
Net Positive Month
Net Outflow Month
Cumulative Net Position
Upcoming Capital Calls
Committed capital draw notices — next 90 days
$2.4M Total
Pending Distributions
Expected proceeds from private investments
$8.7M Expected
Tax Position & Planning — 2025 Fiscal Year K-1 Status: 12 of 20 received · Filing Extensions Pending
EST.
Est. Federal Tax Liability
$18.2M
effective rate ~37.2%
NY State + City
$5.2M
$3.8M state + $1.4M city
1031 Deferred Gains
$24.7M
contingent tax liability
OPPORTUNITY
TLH Opportunity
$2.8M
3 positions · harvest now
2025 Tax Liability Breakdown
Federal, State, City, Deferred · Est. components
$23.4M Total
K-1 Receipt Tracker
Schedule K-1 status by entity · 2024 tax year
20 Entities
RECEIVED
12
OUTSTANDING
8
TOTAL
20
Tax-Loss Harvesting Opportunities
Public equity positions with unrealized losses · act before year-end
$2.8M Available
Filing Deadlines & M-1/M-2 Status
Entity returns · individual · foundation · extensions
Calendar 2025
Family Governance & Lifestyle Operations 1 Mansion Drive, Glen Cove NY · Billy Ray Valentine Foundation · Estate Management
YTD Estate Spend
$3.27M
vs $3.51M full-year budget
Budget Variance
-$62K
T&E 13.8% over — watch
Foundation Grants YTD
$987K
69.3% of $1.425M target
Household Staff
14
FTE · Glen Cove estate
Budget vs Actuals — Estate & Lifestyle
1 Mansion Drive, Glen Cove · All categories YTD
2025 Budget
Budget
Actual
Over Budget
Billy Ray Valentine Foundation
Annual grant activity · 5% distribution compliance
$28.5M Endowment
Governance Calendar & Family Events
Investment committee · family council · foundation board · key deadlines
Next 12 Months
Operational Health — Vendors · Projects · Compliance Legal · Tax · Property Mgmt · Advisory · Custody · Risk
Avg Vendor Score
92.0
6 vendors · target ≥90
Open Projects
6
2 critical · 2 high priority
Pending Items (Vendors)
15
legal & tax backlog
Next Governance Event
16 days
1031 ID Deadline — Apr 14
Vendor & Advisor Performance Scorecard
Quarterly review · SLA compliance · open item count
6 Relationships
Open Projects & Action Items
By priority · owner · due date
6 Open
Compliance & Regulatory Calendar
Filing deadlines · reporting obligations · governance events
2025 Schedule
⚡ Decision Desk
Live Alerts · Action Required
AUM Snapshot
Total AUM$487.3M
Liquid$89.2M
After-Tax ROI12.3%
Cap. Preservation98.7%
Upcoming Events
1031 ID Deadline16 days
Capital Call (BX)10 days
KKR DistributionJun 15
Family CouncilJun 15
Foundation Status
Endowment$28.5M
YTD Distrib.$987K
5% Rule %69.3%
Grants Awarded12
Tax Watch
Est. Federal$18.2M
K-1 Received12 / 20
TLH Avail.$2.8M
Deferred (1031)$24.7M