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Pioneer Square Labs

North America, Washington, United States, Seattle

Description

Pioneer Square Labs (PSL) is a distinctive venture studio based in Seattle, Washington, known for its innovative approach to company creation. Unlike traditional venture capital firms that primarily invest in existing startups, PSL operates as an incubator that ideates, builds, and launches new technology companies from scratch. This unique model involves an internal team developing promising concepts, providing initial capital and operational support, and then recruiting experienced CEOs to lead the newly formed ventures. PSL's focus is on de-risking early-stage concepts before they seek external funding, positioning them as a foundational partner for their portfolio companies.

Since its inception, PSL has demonstrated a strong track record of securing capital to fuel its studio model. The firm has successfully raised four dedicated funds, accumulating over $270 million in committed capital. This includes a $12.5 million inaugural fund in 2015, followed by two $80 million funds in 2018 and 2021, respectively. Most recently, PSL closed its fourth fund at $100 million in 2024, signaling continued investor confidence in their venture studio strategy and capacity for growth. These funds are primarily deployed to support the creation and initial development of the companies spun out of the studio.

When PSL launches a new company, it typically provides the initial seed capital to get the venture off the ground. This initial investment, often referred to as the "first check" in the context of their studio model, generally ranges from $1 million to $2 million. This capital is crucial for building the initial product, assembling a core team, and establishing market fit. Following this initial internal funding, PSL actively assists its portfolio companies in raising subsequent rounds of financing from a broader network of venture capital firms, leveraging its expertise and connections to facilitate growth. Their comprehensive support system aims to significantly increase the likelihood of success for the startups they create.

Investor Profile

Pioneer Square Labs has backed more than 25 startups, with 5 new investments in the last 12 months alone. The firm has led 4 rounds, about 16% of its total and boasts 1 exits across its portfolio.

Investment Focus Highlights

  • Concentrates on Seed, Pre Seed, Series A rounds (top funding stages).
  • Majority of deals are located in United States, Mexico.
  • Strong thematic focus on Software, Artificial Intelligence (AI), Information Technology.
  • Led 1 rounds in the past year.
  • Typical check size: $1M – $2M.

Stage Focus

  • Seed (52%)
  • Pre Seed (20%)
  • Series A (16%)
  • Series B (8%)
  • Series Unknown (4%)

Country Focus

  • United States (88%)
  • Mexico (12%)

Industry Focus

  • Software
  • Artificial Intelligence (Ai)
  • Information Technology
  • E-commerce
  • Customer Service
  • Document Management
  • Document Preparation
  • Legal
  • Financial Services
  • Fintech
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FAQ

Frequently Asked Questions

Learn who this investor regularly partners with—both firms and angels—and explore their latest activity.

Who does Pioneer Square Labs frequently co-invest with?

Two Sigma Ventures
North America, New York, United States, New York
Co-Investments: 2
IV
North America, California, United States, San Francisco
Co-Investments: 2
Trilogy Equity Partners
North America, Washington, United States, Bellevue
Co-Investments: 8
Y Combinator
North America, California, United States, Mountain View
Co-Investments: 2
Flying Fish Partners
North America, Washington, United States, Seattle
Co-Investments: 2
Foundry Group
North America, Colorado, United States, Boulder
Co-Investments: 4
Shasta Ventures
North America, California, United States, Portola Valley
Co-Investments: 2
PSL Ventures
North America, Washington, United States, Seattle
Co-Investments: 2
Alumni Ventures
North America, New Hampshire, United States, Manchester
Co-Investments: 2
Forefront Venture Partners
North America, Florida, United States, Boca Raton
Co-Investments: 2

Which angels does Pioneer Square Labs often collaborate with?

KM
North America, California, United States, San Francisco
Shared Deals: 1
JR
North America, Washington, United States, Seattle
Shared Deals: 1
AW
North America, California, United States, Los Angeles
Shared Deals: 1
AP
North America, New York, United States, New York
Shared Deals: 1
JH
North America, United States
Shared Deals: 1
David Shim
North America, Washington, United States, Seattle
Shared Deals: 2
Federico Ranero
North America, Distrito Federal, Mexico, Mexico City
Shared Deals: 2

What are some of recent deals done by Pioneer Square Labs?

Dropzone AI

Seattle, Washington, United States

Dropzone AI delivers pre-trained autonomous AI security agents that work alongside human analysts on security operations teams

Artificial Intelligence (AI)Cyber SecuritySaaS
Series BJul 17, 2025
Amount Raised: $37,000,000
Gumshoe AI

Seattle, Washington, United States

Gumshoe AI is revolutionizing how companies use AI-powered search.

Artificial Intelligence (AI)Generative AIInformation Technology
Pre SeedApr 29, 2025
Amount Raised: $2,000,000
SingleFile Technologies

Seattle, Washington, United States

SingleFile Technologies is a companies and law firms fill out reports, manage filings, maintain internal records and remain in good standing

Information TechnologyLegal TechSoftware
Series AFeb 19, 2025
Amount Raised: $9,000,000
KamiwazaAI

Silverthorne, Colorado, United States

KamiwazaAI offers scalable AI solutions for cloud, core, and edge environments.

Artificial Intelligence (AI)Data ManagementInformation TechnologyMachine Learning
SeedJan 9, 2025
Amount Raised: $8,500,000
Potato AI

Issaquah, Washington, United States

AI research assistant for biology.

Artificial Intelligence (AI)BiotechnologyInfrastructure
Pre SeedOct 28, 2024
Amount Raised: $1,000,000
Mudstack

Roswell, Georgia, United States

Mudstack is an asset management platform for game studios and artists.

Digital EntertainmentDigital MediaEnterprise SoftwareGamingSoftware
SeedAug 19, 2024
Amount Raised: $4,000,000
Overland AI

Seattle, Washington, United States

Overland AI is a manufacturer and developer of autonomous navigation for off-road autonomous vehicles.

Artificial Intelligence (AI)Autonomous VehiclesMachine LearningSoftware
SeedMay 20, 2024
Amount Raised: $10,000,000
Enzzo

Seattle, Washington, United States

Enzzo is an AI-powered platform that aims to expedite and streamline the creation of innovative hardware products.

Artificial Intelligence (AI)ElectronicsHardware
SeedMar 5, 2024
Amount Raised: $3,000,000
Recurrent

Seattle, Washington, United States

The best way to buy and sell used electric vehicles.

AutomotiveElectric VehicleSoftware
Series AJan 8, 2024
Amount Raised: $16,000,000
Maximal Learning

Bellevue, Washington, United States

Maximum Education utilizing AI to help each student reach their full potential.

Artificial Intelligence (AI)EdTechEducation
SeedMay 31, 2023
Amount Raised: $5,700,000