Confidential · LPs only

Earl Grey Fund II

NAV Build

Active Securities

$9.08M

Unrealized + retained securities + escrow

Cash on Hand

$255K

Gross bank balance

Fund NAV

$9.34M

Clean, no double-counting

Distributed to LPs

$951K

Layer2 cash + May Ripple secondary

Total Fund Value

$10.28M

$10.28M / $5.72M = 1.80x

Complete Portfolio - Schedule of Investments

Active Exited Write-off

Company	Round	Date	Invested	Total Value	MOIC
CrewAI	Pre-Seed	Feb 2024	$275,000	$2,435,985	8.86x
CrewAI	Seed Pro-Rata	Aug 2024	$83,349	$276,872	3.32x
CrewAI	Series B Pro-Rata	Mar 2026	$332,000	$332,000	1.00x
Layer2 Financial (Rail) ▸	Seed	Aug 2022	$300,000	Exited $626,100 Ripple retained	5.16x
Acquired by Ripple (Q3/Q4 2025). 5.16x exit MOIC. $939K cash distributed to LPs. Retained Ripple Class A common stock currently marked at $626K (illiquid, $50B tender reference price).
Layer2 Financial (Rail) ▸	Series A Pro-Rata	Mar 2024	$100,000	Exited	2.09x
Acquired by Ripple (Q3/Q4 2025). Cash + escrow only, no stock consideration on the Series A pro-rata.
Rubie	Pre-Seed	Jun 2024	$300,000	$1,066,666	3.55x
Archetype AI	Seed	Dec 2023	$150,000	$444,005	2.96x
Archetype AI	Series A Pro-Rata	Sep 2025	$349,998	$349,999	1.00x
The Clearing Co. ▸	Pre-Seed	Jun 2025	$500,496	Exited $364,760 COIN retained	2.34x
Acquired by Coinbase (Jan 2026). 2.34x exit MOIC. $475K cash recycled into Andromeda Surgical (Section 1045 QSBS rollover). 2,089 shares of locked COIN stock currently marked at $365K (Q1 close). COIN lockup expires January 2027. $162K cash escrow held back.
Zeer.ai	Pre-Seed	Mar 2025	$500,000	$500,000	1.00x
DoubleFifth	Seed	Jun 2025	$375,000	$375,000	1.00x
AI Assessment Co	Pre-Seed	Nov 2025	$500,015	$500,015	1.00x
DataChain	Pre-Seed	Nov 2025	$250,000	$250,000	1.00x
Sava	Seed	Dec 2025	$500,000	$500,000	1.00x
Dreambase	Seed	Dec 2025	$300,000	$300,000	1.00x
Andromeda Surgical	Series A-1	Mar 2026	$475,000	$475,000	1.00x
TakeShape	Seed	Sep 2022	$300,000	$0	Write-off
Cash on Hand			$254,568
Total · 16 positions + cash (excludes exited Layer2 Series A)			$5,490,858	$9,050,970

Click an exited position to expand details

CrewAI · Top Performing Position (On-Paper)

Total Invested

$690K

Current Value

$3.04M

Blended MOIC (ex-Series B)

7.57x

% of Active Portfolio

34%

Pre-Seed

8.86x

$275K @ $15M SAFE

Seed

3.32x

$83K @ $40M SAFE

Series B

1.00x

$332K @ $185M post

Q2 2026

· Rubie Series A closed at $60M post (Outsiders-led). Position marked at 3.55x.
· Fund Net TVPI reaches 1.80x. Net IRR ~33.5%.
· Capital call imminent for continued deployment.

Q1 2026

· Clearing Company acquired by Coinbase (Jan 2). Second exit, 2.34x return.
· $475K of Clearing Co proceeds recycled into Andromeda Surgical via QSBS 1045 rollover.
· CrewAI Series B: $20M at $185M post. Pre-seed markup reaches 8.86x.
· CrewAI pro-rata executed ($332K) to maintain 1.644% ownership.
· New investment: Andromeda Surgical (surgical robotics, Series A-1, Standard Capital led).
· AI Assessment Co (Legend) raised ~$4M SAFE at $35M cap. Bloomberg Beta led.

Q4 2025

· New investment: AI Assessment Co (edtech/AI). Co-founded by Matt Sornson and MasterClass co-founder.
· New investment: DataChain (AI data infra). Founded by creator of DVC. True Ventures led.
· New investment: Sava (fintech/trusts).
· New investment: Dreambase (analytics/Postgres). Felicis-led seed.
· TakeShape written off ($300K).

Q3 2025

· Rail acquired by Ripple for $200M+. First exit, 5.16x on seed.
· First LP distributions: ~$938K returned. Fund DPI reaches 0.16x.
· Archetype AI Series A: $35M at $145M post. Co-led by IAG and Hitachi. Jeff Bezos participated.
· Archetype pro-rata executed ($350K).
· Clearing Company came out of stealth (USV/Haun co-led round).
· CrewAI: first seven-figure deal. Blowout revenue quarter.

Q2 2025

· New investment: Clearing Company ($500K at $60M post). Largest non-lead position behind USV, Haun, Variant.
· New investment: DoubleFifth ($375K at $15M post).
· CrewAI reaches $1M revenue quarter. Doubled Q1.
· Rubie approaching $200K ARR.
· Capital call #2. Fund reaches 45% called.

Q1 2025

· Zeer.ai incubation formed. Amit co-founding, Santosh Sharan as CEO.
· New investment: Zeer.ai ($500K pre-seed, ~10% ownership at formation).
· Amit met President Donald Trump and spoke at Mar-a-Lago on behalf of Earl Grey.

Q4 2024

· CrewAI enterprise launch. First paid product live.
· CrewAI on track for $1M+ ARR in first months of monetization.
· Archetype: enterprise pilots with Kajima, Volkswagen, Diageo.
· Rail surpasses $10M ARR.
· Fund final close completed. Fund size ~$13M.

Q3 2024

· CrewAI seed pro-rata: $83K at $40M (Boldstart led, Craft, Andrew Ng, Dharmesh, Jack Altman).
· New investment: Rubie ($300K at $13.5M cap, pre-seed). Afore led.

Q2 2024

· Jeff Bezos invests in Archetype at $80M SAFE.
· CrewAI: 5K daily OSS downloads, 500+ enterprise inbound requests.
· Archetype publicly launches (Wired feature). Enterprise pilots initiated.

Q1 2024

· New investment: CrewAI ($275K at $15M pre-seed). First check in.
· Rail closes Series A at $65M post (Galaxy Digital led). First fund markup.
· Rail pro-rata: $100K at $65M.
· Principal Forrest Hardy joins the team.

Q4 2023

· Clearbit acquisition by HubSpot closes (Dec 1). Nine-figure exit.
· New investment: Archetype AI ($150K at $30M, seed). Venrock, Amazon, Hitachi in round.
· Rail hits $3.3M ARR, up from near-zero eight months prior.

Q3 2023

· Fund I close. First capital call (20%).
· New investment: TakeShape ($300K, seed).
· New investment: Rail / Layer2 Financial ($300K at $30M, seed). First check written in Fund II.

Earl Grey Investment Fund II, LP · Confidential · May 2026 · v27 amit@earlgrey.capital

Earl Grey Fund II

Earl Grey Fund II

Key Metrics

Performance Charts

NAV Build

Complete Portfolio - Schedule of Investments

CrewAI · Top Performing Position (On-Paper)