Greg Gottesman

Greg Gottesman is a Managing Director and Co-Founder of Pioneer Square Labs, the Seattle venture studio he launched in 2015 alongside Geoff Entress, Mike Galgon, and Ben Gilbert. PSL builds companies from scratch by running structured experiments — intentionally testing and killing most ideas before committing capital — and its affiliated fund, PSL Ventures, backs both studio spinouts and independent Pacific Northwest startups. Gottesman describes his philosophy simply: "Venture is about finding truly great entrepreneurs and supporting their efforts in every way possible. The rest is noise."

Before PSL, Gottesman spent roughly 20 years at Madrona Venture Group, where he was one of the firm's three initial Managing Directors. He joined Madrona in 1997 (after working as an associate at The Boston Consulting Group) and became a Managing Director in 1999. At Madrona he led investments in companies including Dantz Development (acquired by EMC), Rendition Networks (acquired by Opsware), Singingfish.com (acquired by Thomson), LiveBid.com (acquired by Amazon), and AdRelevance (acquired by Media Metrix). He also founded and led Madrona Venture Labs, an early precursor to the studio model he later scaled at PSL.

Gottesman is best known as the co-founder, former CEO, and longtime board member of Rover (NASDAQ: ROVR), the pet-sitting and dog-walking marketplace, which went public and was ultimately acquired by Blackstone for roughly $2.3 billion. That founder-then-investor arc is central to his identity in the Seattle ecosystem.

Academically, Gottesman graduated Phi Beta Kappa with honors and distinction from Stanford University, earned an MBA with honors and distinction from Harvard Business School, and a JD with honors from Harvard Law School, where he was an editor of the Harvard Law Review. He has taught entrepreneurship for roughly 25 years as an adjunct faculty member at the University of Washington's Paul G. Allen School of Computer Science & Engineering and the Foster School of Business, and has authored several books.

• Stage & checks: Concentrates on pre-seed and seed rounds; individual investment range roughly $500K–$3.0M, with a sweet spot around $1.5M.
• Studio + fund model: Co-created the venture-studio model at PSL — "running experiments that intentionally kill ideas before funding" — then invests in the survivors, plus makes independent seed investments across the Pacific Northwest.
• Founder-first: His stated north star: "Venture is about finding truly great entrepreneurs and supporting their efforts in every way possible. The rest is noise."
• Marketplace expertise: Deep, hands-on interest in marketplace dynamics and how to connect buyers and sellers — informed directly by building and scaling Rover.
• Mission-driven bets: Appreciation for companies tackling large global problems, notably climate/environmental technology (e.g., Ever.green) and services that navigate complex systems such as immigration (e.g., Boundless).
• Sectors: AI, SaaS, consumer tech, fintech, and proptech feature prominently in his and PSL's activity.