Chapter III

Proven execution across
secondary markets.

Anchored by a representative direct transaction on a top crypto exchange — entry below $4B implied valuation, partial exit at 2.2× cash-on-cash, capital fully returned with a significant remaining position.

Direct Cap Table · December 2024 Crypto Exchange · Top 5
Entry $5M · $19.5 PPS ~$4B valuation
Partial Exit $5M · $43 PPS ~2.2× cash-on-cash · capital returned
Remaining ~$6M held IPO scenario ~5× vs. entry · ~$20B potential
0
Private Ventures IRR · 2023
4.0× MOIC
0
Private Ventures IRR · 2024
2.4× MOIC
0
Total Realized MOIC
CoinList portfolio · 6.1×
0
Investments · Seed → Series B
DPI 1.0× · capital fully returned
III.II Augmented Screening

From universe to high-conviction candidates.

AI-augmented screening and human judgment narrow the late-stage crypto universe into a focused investment pipeline. Four selection criteria, four diligence pillars, one investment decision.

10,000+
Startups Screened
Global late-stage universe
1,400+
Unicorns Identified
$1B+ valuation filter
15
Crypto Unicorns
Infrastructure category
2
Candidates Selected
Diligence-stage pipeline

Liquidity Pathway

Visible potential for IPO, M&A, token event, or future secondary exit.

Category Leadership

Clear position in a core crypto infrastructure vertical.

Valuation Discipline

Attractive entry relative to last round, fundamentals, and expected liquidity path.

Downside Protection

Security type, structure, rights, or pricing create a margin of safety.

Deep diligence turns access into disciplined entry.

a.

Valuation Velocity Audit

Isolate exceptional growth from temporary momentum.

  • Revenue by stream, geography, product line
  • Customer usage, churn, segmentation, pricing elasticity
  • Cohort behavior, monetization, CAC compression
b.

Liquidation Stack Analysis

Understand real ownership and downside exposure.

  • Rights across common, preferred, SAFEs, convertibles
  • Liquidation preferences and participation rights
  • Dilution from RSUs, options, notes, side letters
c.

Price Settings

Convert diligence into disciplined entry pricing.

  • Secondary trades, fund marks, broker quotes, comparable markdowns
  • Seller profiles, block sizes, lock-ups, liquidity constraints
  • MoM targets, downside scenarios, walk-away thresholds
III.III Sourcing Advantage

Proprietary access creates repeatable deal flow.

As more category leaders remain private for longer, secondary supply becomes larger, more fragmented, and harder to access.

Global Unicorns
201339
×40
20251,563
Decacorns
20133
×31
20259437 exited · 57 private
i.

Cap Table Access

Fund and investor relationships reveal potential seller supply.

ii.

Founder & Employee Supply

Direct networks surface fragmented early-stakeholder liquidity.

iii.

Advisor Network

Operators help identify non-brokered positions and larger blocks.

iv.

Closed Ecosystem Access

Private events build direct access to founders and investors.

III.IV Execution Capability

Keystone makes secondaries executable.

Transfer, carry, and allocation barriers are solved through sourcing, settlement, and aggregation. Specialized capability converts deal-level friction into pricing power.

Barrier

Transfer Execution Gates

SHA & Articles · Board consent · ROFR / ROFO · Co-sale rights. Structural limits can make a transaction non-executable.

Solution

Early Transfer-Path Coordination

Identifies executable supply and coordinates transfer approvals early. Seller / cap-table access · consent / ROFR coordination · alternative structures.

Barrier

Allocation Size

Average secondary platform transaction ~$400K. Supply is episodic and sourced from employees or early investors — typically below institutional check sizes.

Solution

Proactive Common-Stock Aggregation

Aggregates smaller blocks into institutionally relevant exposure through broker, marketplace, and direct channels — target position building.

Barrier

Carry Net-Off

GP carry creates a pricing gap between buyer entry and seller proceeds. Appreciated positions often require gross-up or structural adjustment.

Solution

Structured Carry Settlement

Aligns buyer entry price, seller proceeds, and carry economics via gross-up / true-up structures preserving target returns.

III.V Preliminary Deal Flow

Category leaders, identified
early.

Three live opportunities representative of the Keystone mandate: regulated infrastructure, stablecoin liquidity, and category-leading prediction networks.

Kalshi

Regulated Prediction Infrastructure

Fast-growing volume, strong take-rate potential, and clear relevance for event-driven institutional trading.

Dec '25 Monthly Volume
$6.5B
YoY Volume Growth
29×
Series E Valuation
$11B
Q4 '25 Gross Margin
90%+
Expected Net Income
$100M+
Annualized Revenue
$1B+
Annualized Rev. Multiple
10–12×
2025 Take Rate
~1%

Tether

Global Stablecoin Liquidity Layer

Massive adoption, treasury-scale reserves, and high-margin financial infrastructure with deep regulatory relevance.

Users
500M+
Issuances Since Inception
$2T
Stablecoin Market Share
~61%
Excess Reserves · Sep '25
~$6.7B
Weekly Active Users
65%
USDT as Savings Alt.
37%
Investment Portfolio
~$20B+
U.S. Treasuries Rank
18th

Polymarket

Category-leading Prediction Network

Strong engagement, strategic exchange backing from ICE/NYSE owner, and clear monetization upside through hybrid on-chain settlement.

Current Valuation
$11.6B
2025 Trading Volume
$22B
Prediction Market Share
42–47%
DAU All-Time High
151K
1-Month Retention
50.2%
2026E Revenue
$50–100M
Strategic Investment
$2B · ICE
Settlement Model
Hybrid CLOB