Greg Gottesman

Greg Gottesman

Board Member at Gumshoe AI
Greater Seattle Area

Greg Gottesman is a board member at Boundless Immigration, Ever.green, Gumshoe AI, and Joon Care, and serves as a board observer at Shipium. He co-founded Pioneer Square Labs, which is still running, and previously co-founded Rover.com.

News 40 Podcasts 6 Videos 6
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Pioneer Square Labs’ Greg Gottesman Discusses Building Marketplaces, Rover, and 'Killing Great Ideas' on Podcast Episode #75

This podcast episode features Greg Gottesman, co-founder and managing director of Pioneer Square Labs and co-founder of Rover, discussing his entrepreneurial journey, marketplace-building strategies, and lessons like obsessing over marketplace dynamics and 'killing great ideas.' The conversation targets digital marketplace founders, COOs, and CEOs and covers topics such as Pioneer Square Labs’ genesis, marketing funnels, and the concept of 'starting with 1.'

Taylor Soper / GeekWire

Seattle startups raise record $3.1B in H1 2021, producing 12 local unicorns as Auth0 exits for $6.5B

Seattle-area startups raised a record $3.1 billion across 205 deals in H1 2021, driven by mega-rounds that produced at least 12 local unicorns and broader Pacific Northwest tech funding topping $5 billion. National VC activity and IPO/M&A dollar volumes are also surpassing prior records, with major exits like Auth0’s $6.5 billion acquisition by Okta highlighting regional maturation.

Taylor Soper / GeekWire

Pioneer Square Labs raises $100M Fund II to back 30+ Pacific Northwest startups with $1–3M initial checks

Seattle-based Pioneer Square Labs raised $100 million for its second venture fund, exceeding its $80 million target due to strong institutional demand, and will invest across more than 30 early-stage Pacific Northwest companies with initial checks of $1–3 million. The firm operates a startup studio (raised $29 million) and a venture fund model that splits capital roughly half to studio spinouts and half to external startups.

John Cook / GeekWire

SPACs Let Founders Reach Public Markets Faster and Keep Larger Equity Stakes, Say Startup Observers

The article explains how SPACs (special purpose acquisition companies) let founders and early employees reach liquidity faster and often retain larger ownership stakes than through later-stage VC or private equity rounds. Using examples like Sana Biotechnology and Seattle entrepreneur Sujal Patel, it argues SPACs can preserve founders' equity by bypassing dilutive funding rounds.

Taylor Soper / GeekWire

Madrona Venture Group Raises $345M for 8th Fund and $161M for 2nd Later-Stage Fund in Largest Ever $500M Capital Raise

Madrona Venture Group raised over $500 million for its largest fundraise ever, including $345 million for an eighth early-stage fund targeting 35-40 Pacific Northwest startups and $161 million for a second later-stage Acceleration Fund. The firm continues to focus on supporting the Pacific Northwest tech ecosystem while also backing later-stage companies across North America.

Taylor Soper / GeekWire

Pioneer Square Labs and Fortive launch joint innovation studio to build spinout companies, starting with a COVID-19 workplace-safety concept

Seattle startup studio Pioneer Square Labs (PSL) has partnered with publicly traded industrial company Fortive to form a joint innovation studio that will build and spin out new companies and products, starting with a confidential workplace-safety concept prompted by COVID-19. PSL will apply its in-house startup studio model to create standalone venture-backed businesses or concepts Fortive may acquire, while Fortive aims to accelerate innovation and cultural change.

Clare McGrane / GeekWire

Pioneer Square Labs names Peter Denton marketing lead; Museum of Flight promotes Matt Hayes to EVP

Pioneer Square Labs hired Peter Denton, formerly VP of marketing at Stellar and ex-Cheezburger product manager, as its marketing lead to oversee digital marketing, product–market fit, and customer acquisition and to advise studio spinouts. Seattle’s Museum of Flight promoted long-time staffer Matt Hayes to its first executive vice president, moving him from CFO to run day-to-day operations.

John Cook / GeekWire

Startup Weekend names new board including Greg Gottesman, Brad Feld, Carl Schramm and Steve Blank

Startup Weekend, a Seattle nonprofit running 54-hour startup marathons worldwide, has formed a new board including venture capitalists and entrepreneurship leaders such as Carl Schramm, Steve Blank, Greg Gottesman, Brad Feld, Laura McKnight and Nick Seguin. The organization, which has hosted 295 events creating over 2,450 startups, also detailed the Startup Foundation supported by the Kauffman Foundation to research and map startup ecosystems.

Organizations

See all 10
  • Gumshoe AI Board Member 2025–present · current
  • Shipium logo
    Shipium Board Observer 2025–present · current
  • SingleFile Board Member 2024–present · current

Education

  • Harvard Business School MBA, with Honors and Distinction · 1995–1998
  • Harvard Law School JD, with Honors; Editor, Harvard Law Review · 1994–1998
  • Stanford University Bachelor of Arts (A.B.), Phi Beta Kappa, with Honors and Distinction, Political Science and Government · 1988–1992

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