Geoff Entress
Geoff Entress is an Executive Committee Member at Alliance of Angels, Board Member at Bonanza, Copper Banking, and Enzzo, and Manager at Goat Peak Ventures. He co-founded Pioneer Square Labs, a startup studio and venture firm, where he is still active, and has expertise in angel investing and information technologies.
Author Departs Pioneer Square Labs After 7+ Years and 40+ Companies, Reflects on Career Highlights and Team Bonds
The author marks their last day at Pioneer Square Labs after over seven years and involvement with more than 40 companies, reflecting on memorable experiences and expressing gratitude for colleagues and mentors. They highlighted unique moments like pitching their AI-powered dating app 'Jail Date' and emphasized the lasting relationships formed during their tenure.
Seattle Startup Desk Raises $800,000 to Automate Real Estate Contract Work with AI
Seattle startup Desk has raised $800,000 to use AI for automating real estate contract administration, helping over 500 agents streamline paperwork with high accuracy. The company leverages recent AI advancements to offer 'better-than-human' contract processing, accelerating agent workflows without replacing them.
The Agentic Entrepreneur: How the next wave of AI is changing the startup playbook
This week on the GeekWire Podcast: How artificial intelligence is changing the way companies are created, built, and operated. We're on location at Pioneer Square Labs in Seattle with investor and entrepreneur T.A. McCann, a managing director at the startup studio and venture capital firm. He explains how AI agents are automating complex functions, letting small teams do the work that once required large groups of people. As AI makes product development easier, he says, the key strategic moat for many startups is now shifting to distribution and data. Other topics include: The wearable AI recorder that captures everything he…
Organizations
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Pioneer Square Labs Co-founder and Venture Partner 2026–present, Managing Director 2015–2026 · current
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Zucca Board Member 2025–present · current
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Enzzo Board Member 2023–present · current
Education
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University of Michigan Law School JD, Law · 1995–1998
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Carnegie Mellon University - Tepper School of Business MSIA, Business Administration · 1986–1988
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University of Notre Dame BA, English · 1982–1986
