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Geoff Entress

North America, Pennsylvania, United States, Pittsburgh

Description

Geoff Entress is a highly respected and influential figure in the Pacific Northwest's venture capital and startup ecosystem, currently serving as a Managing Director and Co-Founder of Pioneer Square Labs (PSL). His career spans decades, marked by a deep involvement in company building, early-stage investing, and strategic guidance. Prior to co-founding PSL, Entress held significant roles as a venture partner with prominent firms such as Voyager Capital and Madrona Venture Group, where he gained extensive experience in identifying and nurturing high-growth technology companies. His unique blend of operational insight and investment acumen has made him a sought-after advisor and investor.

PSL operates as a distinctive startup studio, a model that differentiates it from traditional venture capital firms. Instead of merely investing in external companies, PSL actively conceives, validates, and builds new ventures from the ground up, providing them with initial capital, strategic direction, and operational support. This hands-on approach is central to Entress's current work, where he plays a pivotal role in the ideation and incubation phases. PSL announced a $100 million fund (PSL Fund III) in 2021, underscoring its capacity to provide substantial initial funding to its incubated companies, typically ranging from $500,000 to $1,500,000 as the initial seed capital before subsequent external rounds.

Beyond his institutional roles, Entress is renowned for his prolific angel investing career. He has personally invested in over 100 companies, primarily focusing on early-stage technology startups across various sectors, including B2B SaaS, artificial intelligence, and deep tech. This extensive portfolio highlights his commitment to fostering innovation and supporting founders from the earliest stages. His investment philosophy often emphasizes strong founding teams, disruptive technologies, and scalable business models, with a particular affinity for companies rooted in the Pacific Northwest.

Entress's impact extends beyond capital deployment; he is known for providing valuable mentorship and leveraging his vast network to support portfolio companies. His operational background, including roles at companies like McCaw Cellular Communications, further enriches his ability to guide entrepreneurs through the challenges of scaling a business. His contributions have significantly shaped the regional tech landscape, solidifying his reputation as a founder-friendly investor dedicated to long-term success.

Investor Profile

Geoff Entress has backed more than 33 startups, with 1 new investments in the last 12 months alone. The firm has led 0 rounds, about 0% of its total and boasts 14 exits across its portfolio.

Investment Focus Highlights

  • Concentrates on Seed, Angel, Series Unknown rounds (top funding stages).
  • Majority of deals are located in United States, Canada.
  • Strong thematic focus on Software, E-Commerce, Internet.
  • Typical check size: $500K – $1.5M.

Stage Focus

  • Seed (70%)
  • Angel (15%)
  • Series Unknown (6%)
  • Series A (6%)
  • Pre Seed (3%)

Country Focus

  • United States (94%)
  • Canada (6%)

Industry Focus

  • Software
  • E-commerce
  • Internet
  • Saas
  • Mobile
  • Enterprise Software
  • Apps
  • Advertising Platforms
  • B2b
  • Android
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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 Geoff Entress frequently co-invest with?

Founders' Co-op
North America, Washington, United States, Seattle
Co-Investments: 5
Summit Capital
North America, Washington, United States, Seattle
Co-Investments: 2
Techstars
North America, Colorado, United States, Boulder
Co-Investments: 4
Trilogy Equity Partners
North America, Washington, United States, Bellevue
Co-Investments: 3
500 Global
North America, California, United States, San Francisco
Co-Investments: 2
Geekdom Fund
North America, Texas, United States, San Antonio
Co-Investments: 2
Voyager Capital
North America, Washington, United States, Seattle
Co-Investments: 4
Elementum Ventures
North America, California, United States, Menlo Park
Co-Investments: 2
Alliance of Angels
North America, Washington, United States, Seattle
Co-Investments: 8
Wisemont Capital
North America, Washington, United States, Seattle
Co-Investments: 2

Which angels does Geoff Entress often collaborate with?

SP
North America, Washington, United States, Seattle
Shared Deals: 3
RG
North America, Washington, United States, Seattle
Shared Deals: 5
MG
North America, Washington, United States, Seattle
Shared Deals: 3
Ryan Holmes
North America, British Columbia, Canada, Vancouver
Shared Deals: 3
Dan Shapiro
North America, Washington, United States, Seattle
Shared Deals: 3
JW
North America, Washington, United States, Seattle
Shared Deals: 3
AW
North America, Washington, United States, Redmond
Shared Deals: 4
AA
Europe, England, United Kingdom, London
Shared Deals: 3
T. Trent Gegax
North America, Georgia, United States, Atlanta
Shared Deals: 2
AL
North America, Washington, United States
Shared Deals: 4

What are some of recent deals done by Geoff Entress?

Potato AI

Issaquah, Washington, United States

AI research assistant for biology.

Artificial Intelligence (AI)BiotechnologyInfrastructure
SeedApr 8, 2025
Amount Raised: $4,500,000
Trainiac

Seattle, Washington, United States

Trainiac provides a fitness application intended to offer personalized workout videos.

AppsFitnessTrainingWellness
SeedDec 31, 2019
Amount Raised: $2,200,000
Lockstep

Seattle, Washington, United States

Lockstep connects accounting teams to help them work better together.

AccountingFinTechInformation ServicesSoftware
SeedMay 1, 2019
Faira

Kirkland, Washington, United States

Faira is a real estate technology platform that is revolutionizing the way people buy and sell homes.

E-CommerceInternetPropTechReal EstateResidentialService Industry
SeedJun 13, 2018
Amount Raised: $2,500,000
Hack Capital Ventures

Vancouver, British Columbia, Canada

Hack Capital is a software company that helps digital companies hire, train, retain, and motivate employees.

Enterprise SoftwareSoftwareVenture Capital
SeedFeb 13, 2018
Amount Raised: $750,000
Blok24

Bellevue, Washington, United States

Blok24 is building a spontaneity marketplace, connecting people with local businesses for activities happening now

MarketplaceMobile Apps
AngelMay 12, 2017
Amount Raised: $450,000
Helm

Bellevue, Washington, United States

Helm is a consumer privacy and security company helping people take back ownership of their data.

Network SecurityPrivacySecurity
SeedFeb 24, 2017
Amount Raised: $4,000,000
Ampd

Seattle, Washington, United States

Ampd is the fastest, easiest and simplest way to drive external search traffic to your Amazon marketplace store.

Advertising PlatformsE-CommerceInformation TechnologySoftware
Pre SeedJan 1, 2016
Amount Raised: $1,400,000
Metricstory

Seattle, Washington, United States

The ad automation toolkit that amplifies efforts and ad dollars.

AdvertisingAnalyticsArtificial Intelligence (AI)B2BMachine Learning
SeedDec 9, 2015
Amount Raised: $1,450,000
Allay

San Francisco, California, United States

Allay is the operating system for benefits brokerage firms to easily create, underwrite, and recommend self insured health plans.

Human ResourcesInsurance
SeedOct 22, 2015
Amount Raised: $3,400,000