Greg Gottesman
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.
Founding Rover and the business model behind Pioneer Square Labs, a conversation with Greg Gottesman
New episode location: https://www.youtube.com/watch?v=x0gjMWcuEmA&list=PLqH2XogpwLRmYvCCxOj-W-eOAlCrhrk7i&index=2 Brought to you by TiE Seattle Hosts: Shirish Nadkarni and Gowri Shankar Guest: Greg Gottesman Producers: Minee Verma and Eesha Jain Learn about the founding of Rover and how it scaled its service to form the largest pet sitting service in the country, Explore the business model behind Pioneer Square Labs and how they incubate new companies. Greg Gottesman is a Managing Director and Co-Founder of PSL. Prior to PSL, Greg served as one of the three initial Managing Directors of Madrona Venture Group, where he worked for almost 20 years. He also co-founded and led…
The founding of Rover and the business model behind Pioneer Square Labs, a conversation with Greg Gottesman
Send us Fan Mail In 2011, Greg Gottesman had a bad experience leaving his dog for the weekend at a local Kennel. That experience led him to pitch the idea for Rover at a Startup Weekend which he won. That led to the formation of Rover and the rest is history. In our second podcast episode, Gowri Shankar and I explore the foundation of Rover as well as the business model behind Pioneer Square Labs. Greg Gottesman is a Managing Director and Co-Founder of PSL. Prior to PSL, Greg served as one of the three initial Managing Directors of Madrona…
Seattle’s Pioneer Square Labs Raises $20M Third Fund to Accelerate Generative AI Startup Studio
Seattle startup studio Pioneer Square Labs raised $20 million for its third fund to invest in generative AI, building multiple AI-driven apps in finance and healthcare. Founded in 2015, PSL has 33 startups with most securing follow-on investments but no unicorn exits yet.
Seattle Startup Ever.green Secures $6.1M Seed Funding to Accelerate 20 GW/Yr Clean Energy Marketplace
Ever.green, a Seattle startup, raised $6.1 million in seed funding to expand its marketplace that connects corporations funding clean energy with developers building renewable projects, aiming to accelerate solar and wind power deployment. The platform also leverages investment tax credits from the Inflation Reduction Act to help scale renewable energy infrastructure rapidly.
Seattle’s Felix&Fido Raises $4M Pre-Seed Led by PSL Ventures and Rover to Launch Subscription Veterinary Care
Seattle startup Felix&Fido announced a $4 million pre-seed funding round led by PSL Ventures and Rover to launch subscription-based veterinary care combining telemedicine, in-clinic, and at-home services. Founded by former Army captain and Expedia executive Gavin Woody, the company aims to tackle the veterinary shortage with an innovative membership model.
Madrona Venture Group Raises $690M Across Two Funds to Support Startups in Seattle and Nationwide
Madrona Venture Group has raised $690 million across two funds, marking its largest ever, to back startups primarily in the Pacific Northwest and nationwide. The firm plans about 40 venture investments with increased capital per company amid a strong U.S. venture market.
Tom Alberg, Amazon Early Investor and Madrona Co-Founder, Dies at 82 After Shaping Seattle Tech
Tom Alberg, co-founder of Madrona Venture Group and early investor in Amazon, is remembered for his significant yet understated contributions to Seattle's tech industry, including his mentorship and 23 years on Amazon's board. He died at 82, leaving a lasting legacy both publicly and through his personal impact on colleagues and entrepreneurs.
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.'
Ignite's Meet the Investor with Greg Gottesman of Pioneer Square Labs
Catch the replay of the October 2021 edition of Ignite's Meet the Investor program featuring Greg Gottesman, Co-Founder and Managing Director of Pioneer Square Labs and Co-Founder of Rover.com. Meet the Investor is sponsored by Witherspoon Kelley.
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.
Pioneer Square Labs
This week our partners chat with Greg Gottesman, Managing Director & Co-Founder at Pioneer Square Labs, a startup studio and venture capital fund based in Seattle, WA.
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.
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.
Pioneer Square Labs spins out 25 startups in five years; six launched during pandemic surge
Seattle startup studio Pioneer Square Labs (PSL) spun out 25 startups in five years — six during a six-month pandemic stretch — by rapidly testing ideas, though it has yet to produce a breakout unicorn and faces criticism over founder dilution.
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.
Madrona leads $2.6M seed round for OthersideAI to build GPT-3–powered automated email composer
OthersideAI, founded months ago by Matt Shumer, Miles Feldstein and Jason Kuperberg, raised a $2.6M seed round led by Madrona to build a GPT-3–powered tool that automatically composes email drafts; the company is testing a Chrome extension with ~100 early users and a ~10,000-person waitlist.
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.
GeekWire Awards Winners Revealed
The strength and success of the people and companies across the Pacific Northwest tech ecosystem was on full display Thursday night at the GeekWire Awards. GeekWire's Jonathan Sposato, John Cook and Todd Bishop share highlights and clips from the night on this episode of the GeekWire Podcast. More highlights here. See omnystudio.com/listener for privacy information.
Greg Gottesman
Greg Gottesman, a major influencer in the Seattle startup community, sits down and shares his knowledge about entrepreneurship, his passion for the early stage of building companies, and the story behind what sparked the idea for Rover, where Greg is a co-founder. Greg serves as a Managing Director and co-founder of Pioneer Square Labs, both its studio and fund. He was a partner of Madrona Venture Group for 20 years and founder of Madrona Venture Labs. In this episode, he also discusses the entrepreneurship class he teaches at the University of Washington, what he looks for in entrepreneurs’ pitches, and…
Never Stop Being Curious | Greg Gottesman
We're kicking off 2019 Creator Institute podcast with a longtime friend of mine Greg Gottesman - a managing director and co-founder of Pioneer Square Labs. Prior to PSL, Greg served as one of the three initial Managing Directors of Madrona Ventures Group, where he worked for almost 20 years. Check it out! #EricKoester #CreatorInstitute #Podcast FOLLOW ERIC KOESTER FACEBOOK: http://bit.ly/2ONpDSk LINKEDIN: http://bit.ly/2BurtG1 INSTAGRAM: http://bit.ly/2PrQhBk TWITTER: http://bit.ly/2OT77In FOLLOW CREATOR INSTITUTE FACEBOOK: http://bit.ly/2N5upua LINKEDIN: http://bit.ly/2nWGOpk TWITTER: http://bit.ly/2nTNVi7
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.
Pioneer Square Labs Raises $12.5M from Foundry Group, Bezos Expeditions and 50 Angels to Build Start-Ups
Pioneer Square Labs, a Seattle "start-up studio," raised $12.5 million from over a dozen VC firms and 50 angel investors to build companies from in-house ideas. Backers include Bezos Expeditions, Rich Barton, and lead investor Foundry Group among others.
Pioneer Square Labs raises $12.5M from 13 VCs and 50+ angels; Foundry Group led, Brad Feld joins board
Pioneer Square Labs, a new Seattle startup studio co-founded by Geoff Entress, Greg Gottesman, Mike Galgon and Ben Gilbert, raised $12.5 million from 13 VC firms and over 50 angels. Foundry Group led the round and Brad Feld will join PSL's board.
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.
Seattle 2.0 Names Finalists From Nearly 7,000 Nominations; Public Voting Open Through May 11 — Winners Revealed May 19
Seattle 2.0 announced finalists for its annual Seattle tech startup awards after nearly 7,000 nominations across 11 categories, opening public voting through May 11 and scheduling the awards event for May 19 with keynote Jonathan Sposato.
Organizations
See all 10-
Gumshoe AI Board Member 2025–present · current
-
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
