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Khosla Ventures AI Portfolio: OpenAI, Glean, Replit & Sakana AI

TL;DR

An in-depth analysis of Khosla Ventures's AI investment portfolio, strategy, co-investors, and sector focus across 26 tracked deals as of November 2026.

Key Takeaways

  • As of November 2026, Khosla Ventures had participated in 26 tracked AI funding rounds across 23 companies, totaling $12.2B in aggregate round sizes.
  • As of November 2026, Khosla Ventures had led 15 AI funding rounds (58% of its tracked deals).
  • Largest tracked round: OpenAI's Series D at $6.6B (Oct 2, 2024).
  • Most active sector: AI Robotics with 7 deals, across 11 AI sectors in total.
  • As of November 2026, Khosla Ventures had co-invested alongside 88 other investors; the most frequent is Sequoia Capital (6 deals together).

Investor Overview

Khosla Ventures is a venture capital firm founded in 2004 by Vinod Khosla, co-founder of Sun Microsystems. The firm invests across clean energy, AI, healthcare, and frontier technology with over $15 billion in assets under management. Khosla Ventures led Glean's Series E and has backed Replit, reflecting the firm's deep conviction in AI's transformative potential for enterprise productivity and software development. Vinod Khosla is known for his bold, thesis-driven investing style and willingness to fund ambitious moonshots. The firm invests from seed through growth stage and maintains a highly concentrated portfolio approach.

Detail Value
Name Khosla Ventures
Type VC
Website https://khoslaventures.com
Tracked AI Deals 26
Unique Portfolio Companies 23
Total Capital in Tracked Rounds $12.2B
Lead Investments 15

The AI funding landscape continues to evolve rapidly, with significant capital flowing into companies pushing the boundaries of artificial intelligence. This period's activity reflects both growing investor confidence and the increasing maturity of the ecosystem. Deal sizes and valuations continue to climb as AI transitions from experimental technology to core enterprise infrastructure.

Portfolio Summary

As of November 2026, Khosla Ventures had participated in 26 tracked AI funding round(s) across 23 companyies. Below is a complete breakdown.

Company Sector Round Amount Valuation Date Role
Sakana AI Foundation Models & AGI Seed $30M N/A Jan 15, 2024 Participant
Collaborative Robotics AI Robotics Series B $100M N/A Apr 10, 2024 Participant
Ramp AI Fintech Series D Extension $150M N/A Apr 17, 2024 Lead
Glean Enterprise AI Series D $200M N/A Aug 12, 2024 Lead
OpenAI Foundation Models & AGI Series D $6.6B $157.0B Oct 2, 2024 Participant
Physical Intelligence AI Robotics Series A $400M $2.4B Nov 4, 2024 Participant
Genesis AI AI Robotics Seed $105M N/A Jul 1, 2025 Participant
Field AI AI Robotics Series B $405M $2.0B Aug 20, 2025 Lead
Sakana AI Foundation Models & AGI Series B $300M N/A Nov 20, 2025 Lead
Replit AI Developer Tools Series C $200M N/A Jan 5, 2026 Participant
Waabi AI Robotics Series C $750M $3.0B Jan 28, 2026 Lead
Glean Enterprise AI Series E $260M $4.6B Feb 10, 2026 Lead
Rhoda AI Robotics Series A $450M N/A Mar 11, 2026 Lead
Glydways AI Robotics Undisclosed $170M N/A Apr 15, 2026 Lead
Factory Enterprise AI Undisclosed $150M $1.5B Apr 16, 2026 Lead
Rogo AI Fintech Series D $160M N/A Apr 29, 2026 Participant
Parallel Web Systems AI Infrastructure Series B $100M N/A Apr 29, 2026 Participant
Synthetic Enterprise AI Seed $10M N/A May 14, 2026 Lead
Phia Consumer AI Series A $36M N/A Jun 2, 2026 Lead
Ramp AI Fintech Series F $750M N/A Jun 5, 2026 Participant
Mach Industries AI Defense Series C $300M $1.8B Jun 5, 2026 Participant
Pramaana Labs AI Security Seed $27M N/A Jun 17, 2026 Lead
Clair Health AI Healthcare Seed $12M N/A Jun 17, 2026 Lead
General Intuition Foundation Models & AGI Undisclosed $300M $2.3B Jun 25, 2026 Participant
Twenty AI Defense Undisclosed $30M N/A Jul 20, 2026 Lead
Arda Defense AI Series A $160M $1.5B Oct 20, 2026 Lead

Total Capital Deployed in AI

Across all tracked rounds, Khosla Ventures has participated in deals totaling $12.2B in aggregate round sizes. Note: this represents total round amounts, not the investor's individual check sizes, which are not publicly disclosed for most rounds. Amounts are stated in the currency each round was reported in; no conversion is applied.

By Company

Company Rounds Participated Total Round Value Latest Round
Sakana AI 2 $330M Series B (Nov 20, 2025)
Collaborative Robotics 1 $100M Series B (Apr 10, 2024)
Ramp 2 $900M Series F (Jun 5, 2026)
Glean 2 $460M Series E (Feb 10, 2026)
OpenAI 1 $6.6B Series D (Oct 2, 2024)
Physical Intelligence 1 $400M Series A (Nov 4, 2024)
Genesis AI 1 $105M Seed (Jul 1, 2025)
Field AI 1 $405M Series B (Aug 20, 2025)
Replit 1 $200M Series C (Jan 5, 2026)
Waabi 1 $750M Series C (Jan 28, 2026)
Rhoda 1 $450M Series A (Mar 11, 2026)
Glydways 1 $170M Undisclosed (Apr 15, 2026)
Factory 1 $150M Undisclosed (Apr 16, 2026)
Rogo 1 $160M Series D (Apr 29, 2026)
Parallel Web Systems 1 $100M Series B (Apr 29, 2026)
Synthetic 1 $10M Seed (May 14, 2026)
Phia 1 $36M Series A (Jun 2, 2026)
Mach Industries 1 $300M Series C (Jun 5, 2026)
Pramaana Labs 1 $27M Seed (Jun 17, 2026)
Clair Health 1 $12M Seed (Jun 17, 2026)
General Intuition 1 $300M Undisclosed (Jun 25, 2026)
Twenty 1 $30M Undisclosed (Jul 20, 2026)
Arda 1 $160M Series A (Oct 20, 2026)

This area of the AI market continues to attract significant investor attention, reflecting the sector's rapid growth and substantial long-term potential.

Sector Breakdown

Khosla Ventures's AI investments span 11 sector(s). Here is how their deal activity breaks down by sector.

Sector Number of Deals % of Portfolio
AI Robotics 7 27%
Foundation Models & AGI 4 15%
Enterprise AI 4 15%
AI Fintech 3 12%
AI Defense 2 8%
AI Developer Tools 1 4%
AI Infrastructure 1 4%
Consumer AI 1 4%
AI Security 1 4%
AI Healthcare 1 4%
Defense AI 1 4%

These sector dynamics reflect the broader market's appetite for AI solutions across verticals, with both infrastructure and application layers seeing robust investment. The concentration of capital in leading sectors signals where investors see the highest near-term returns.

Co-Investor Analysis

As of November 2026, Khosla Ventures had co-invested alongside 88 other investor(s) in tracked AI rounds. The most frequent co-investors are:

Co-Investor Deals Together Relationship
Sequoia Capital 6 Frequent co-investor
Lux Capital 4 Frequent co-investor
Thrive Capital 4 Frequent co-investor
General Catalyst 3 Frequent co-investor
Lightspeed Venture Partners 3 Frequent co-investor
NVIDIA 3 Frequent co-investor
Kleiner Perkins 3 Frequent co-investor
Founders Fund 2 Repeat co-investor
Bezos Expeditions 2 Repeat co-investor
Eric Schmidt 2 Repeat co-investor
Insight Partners 2 Repeat co-investor
Microsoft Ventures 1 Single co-investment
SoftBank Vision Fund 1 Single co-investment
OpenAI Startup Fund 1 Single co-investment
Bond 1 Single co-investment
Eclipse 1 Single co-investment
Bpifrance 1 Single co-investment
HongShan 1 Single co-investment
Intel Capital 1 Single co-investment
Temasek 1 Single co-investment
Andreessen Horowitz 1 Single co-investment
G2 Venture Partners 1 Single co-investment
Uber 1 Single co-investment
BlackRock 1 Single co-investment
Radical Ventures 1 Single co-investment
HarbourVest Partners 1 Single co-investment
Suzuki Motor Corporation 1 Single co-investment
ACS Group 1 Single co-investment
Mitsui Chemicals 1 Single co-investment
Gates Frontier 1 Single co-investment
Obayashi Corporation 1 Single co-investment
Blackstone 1 Single co-investment
J.P. Morgan Growth Equity Partners 1 Single co-investment
BoxGroup 1 Single co-investment
Mantis VC 1 Single co-investment
Jack Altman 1 Single co-investment
Evantic 1 Single co-investment
Positive Sum 1 Single co-investment
Index Ventures 1 Single co-investment
First Round Capital 1 Single co-investment
Spark Capital 1 Single co-investment
Terrain Capital 1 Single co-investment
Basis Set Ventures 1 Single co-investment
Tobias Lütke 1 Single co-investment
Notable Capital 1 Single co-investment
Sydney Sweeney 1 Single co-investment
Paris Hilton 1 Single co-investment
Priyanka Chopra Jonas 1 Single co-investment
Khloé Kardashian 1 Single co-investment
Jessica Alba 1 Single co-investment
Mindy Kaling 1 Single co-investment
Alix Earle 1 Single co-investment
Karlie Kloss 1 Single co-investment
Alexandre Arnault 1 Single co-investment
Halsey 1 Single co-investment
Ice Spice 1 Single co-investment
Ashley Graham 1 Single co-investment
Bobbi Brown 1 Single co-investment
Rachel Zoe 1 Single co-investment
Leila Hormozi 1 Single co-investment
Winnie Harlow 1 Single co-investment
Vlad Tenev 1 Single co-investment
Naomi Gleit 1 Single co-investment
Mellody Hobson 1 Single co-investment
Charles Porch 1 Single co-investment
Mati Staniszewski 1 Single co-investment
ICONIQ 1 Single co-investment
GIC 1 Single co-investment
Ontario Teachers’ Pension Plan 1 Single co-investment
Goldman Sachs Alternatives 1 Single co-investment
D.E. Shaw 1 Single co-investment
Morgan Stanley Investment Management 1 Single co-investment
Generation Investment Management 1 Single co-investment
BroadLight Capital 1 Single co-investment
D1 Capital Partners 1 Single co-investment
T. Rowe Price 1 Single co-investment
137 Ventures 1 Single co-investment
Coatue Management 1 Single co-investment
Infinite Capital 1 Single co-investment
Ribbit Capital 1 Single co-investment
Bedrock Capital 1 Single co-investment
Jeff Bezos 1 Single co-investment
Altimeter Capital 1 Single co-investment
Accel 1 Single co-investment
XYZ Venture Capital 1 Single co-investment
8VC 1 Single co-investment
SV Angel 1 Single co-investment
Felicis Ventures 1 Single co-investment

Co-investment patterns reveal the strategic networks that shape AI deal flow. Frequent co-investors often indicate shared investment theses and trusted relationships that accelerate due diligence and deal execution.

Deal Timeline

A chronological view of Khosla Ventures's tracked AI investments:

  • Jan 15, 2024 — Seed in Sakana AI: $30M (Participant)
  • Apr 10, 2024 — Series B in Collaborative Robotics: $100M (Participant)
  • Apr 17, 2024 — Series D Extension in Ramp: $150M (Lead)
  • Aug 12, 2024 — Series D in Glean: $200M (Lead)
  • Oct 2, 2024 — Series D in OpenAI: $6.6B at $157.0B valuation (Participant)
  • Nov 4, 2024 — Series A in Physical Intelligence: $400M at $2.4B valuation (Participant)
  • Jul 1, 2025 — Seed in Genesis AI: $105M (Participant)
  • Aug 20, 2025 — Series B in Field AI: $405M at $2.0B valuation (Lead)
  • Nov 20, 2025 — Series B in Sakana AI: $300M (Lead)
  • Jan 5, 2026 — Series C in Replit: $200M (Participant)
  • Jan 28, 2026 — Series C in Waabi: $750M at $3.0B valuation (Lead)
  • Feb 10, 2026 — Series E in Glean: $260M at $4.6B valuation (Lead)
  • Mar 11, 2026 — Series A in Rhoda: $450M (Lead)
  • Apr 15, 2026 — Undisclosed in Glydways: $170M (Lead)
  • Apr 16, 2026 — Undisclosed in Factory: $150M at $1.5B valuation (Lead)
  • Apr 29, 2026 — Series D in Rogo: $160M (Participant)
  • Apr 29, 2026 — Series B in Parallel Web Systems: $100M (Participant)
  • May 14, 2026 — Seed in Synthetic: $10M (Lead)
  • Jun 2, 2026 — Series A in Phia: $36M (Lead)
  • Jun 5, 2026 — Series F in Ramp: $750M (Participant)
  • Jun 5, 2026 — Series C in Mach Industries: $300M at $1.8B valuation (Participant)
  • Jun 17, 2026 — Seed in Pramaana Labs: $27M (Lead)
  • Jun 17, 2026 — Seed in Clair Health: $12M (Lead)
  • Jun 25, 2026 — Undisclosed in General Intuition: $300M at $2.3B valuation (Participant)
  • Jul 20, 2026 — Undisclosed in Twenty: $30M (Lead)
  • Oct 20, 2026 — Series A in Arda: $160M at $1.5B valuation (Lead)

Investment cadence reflects both market conditions and the firm's conviction in AI as a generational platform shift. The pace of deployment has accelerated as AI companies demonstrate commercial traction.

Lead vs Participation Analysis

As of November 2026, of Khosla Ventures's 26 tracked AI deals:

  • Lead Investor: 15 deal(s) (58%)
  • Participant: 11 deal(s) (42%)

Deals Where Khosla Ventures Led

  • Ramp Series D Extension: $150M (Apr 17, 2024)
  • Glean Series D: $200M (Aug 12, 2024)
  • Field AI Series B: $405M (Aug 20, 2025)
  • Sakana AI Series B: $300M (Nov 20, 2025)
  • Waabi Series C: $750M (Jan 28, 2026)
  • Glean Series E: $260M (Feb 10, 2026)
  • Rhoda Series A: $450M (Mar 11, 2026)
  • Glydways Undisclosed: $170M (Apr 15, 2026)
  • Factory Undisclosed: $150M (Apr 16, 2026)
  • Synthetic Seed: $10M (May 14, 2026)
  • Phia Series A: $36M (Jun 2, 2026)
  • Pramaana Labs Seed: $27M (Jun 17, 2026)
  • Clair Health Seed: $12M (Jun 17, 2026)
  • Twenty Undisclosed: $30M (Jul 20, 2026)
  • Arda Series A: $160M (Oct 20, 2026)

Deals Where Khosla Ventures Participated

  • Sakana AI Seed: $30M (Jan 15, 2024)
  • Collaborative Robotics Series B: $100M (Apr 10, 2024)
  • OpenAI Series D: $6.6B (Oct 2, 2024)
  • Physical Intelligence Series A: $400M (Nov 4, 2024)
  • Genesis AI Seed: $105M (Jul 1, 2025)
  • Replit Series C: $200M (Jan 5, 2026)
  • Rogo Series D: $160M (Apr 29, 2026)
  • Parallel Web Systems Series B: $100M (Apr 29, 2026)
  • Ramp Series F: $750M (Jun 5, 2026)
  • Mach Industries Series C: $300M (Jun 5, 2026)
  • General Intuition Undisclosed: $300M (Jun 25, 2026)

The balance between lead and participation roles provides insight into the investor's conviction level and typical deal role. Leading rounds typically signals highest conviction and a desire to secure board seats and governance rights.

Notable Deals

The largest rounds that Khosla Ventures participated in:

1. OpenAI — Series D ($6.6B)

  • Date: Oct 2, 2024
  • Valuation: $157.0B
  • Role: Participant
  • Sector: Foundation Models & AGI
  • Details: Record-breaking round led by Thrive Capital at $157B valuation, with participation from Microsoft, NVIDIA, and SoftBank.

2. Waabi — Series C ($750M)

  • Date: Jan 28, 2026
  • Valuation: $3.0B
  • Role: Lead Investor
  • Sector: AI Robotics
  • Details: Khosla leads $750M (plus a $250M Uber milestone commitment) as Waabi expands from driverless trucks into Uber robotaxis.

3. Ramp — Series F ($750M)

  • Date: Jun 5, 2026
  • Role: Participant
  • Sector: AI Fintech
  • Details: Ramp raises $750M at $44B as Harvard classmates turn a corporate card into America’s fastest-growing finance platform

4. Rhoda — Series A ($450M)

  • Date: Mar 11, 2026
  • Role: Lead Investor
  • Sector: AI Robotics
  • Details: Rhoda raised $450M in a Series A round.

5. Field AI — Series B ($405M)

  • Date: Aug 20, 2025
  • Valuation: $2.0B
  • Role: Lead Investor
  • Sector: AI Robotics
  • Details: Two consecutive rounds totaling $405M back hardware-agnostic field autonomy for construction, mining, energy, and defense.

These deals represent the investor's highest-conviction bets, each reflecting a thesis about where transformative AI value will be created over the next decade.

Frequently Asked Questions

How many AI companies has Khosla Ventures invested in?

As of November 2026, Khosla Ventures had invested in 23 AI companyies tracked by AI Funding: Sakana AI, Collaborative Robotics, Ramp, Glean, OpenAI, Physical Intelligence, Genesis AI, Field AI, Replit, Waabi, Rhoda, Glydways, Factory, Rogo, Parallel Web Systems, Synthetic, Phia, Mach Industries, Pramaana Labs, Clair Health, General Intuition, Twenty, Arda.

What sectors does Khosla Ventures focus on in AI?

Khosla Ventures's most active AI sector is AI Robotics with 7 deal(s). They invest across 11 AI sector(s) in total.

Who does Khosla Ventures co-invest with most often?

Khosla Ventures's most frequent co-investor is Sequoia Capital, having co-invested in 6 deal(s) together.

Has Khosla Ventures led any AI funding rounds?

Yes, as of November 2026, Khosla Ventures had led 15 AI funding round(s), including Ramp's Series D Extension, Glean's Series D, Field AI's Series B, Sakana AI's Series B, Waabi's Series C, Glean's Series E, Rhoda's Series A, Glydways's Undisclosed, Factory's Undisclosed, Synthetic's Seed, Phia's Series A, Pramaana Labs's Seed, Clair Health's Seed, Twenty's Undisclosed, Arda's Series A.

What is the largest AI deal Khosla Ventures has participated in?

The largest tracked round is OpenAI's Series D at $6.6B (Oct 2, 2024).

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