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.
Yifan Zhang announces AI House Demo Day: 25 teams pitched in Seattle with 42 investors attending
AI House held its first AI House Demo Day in Seattle where 25 teams (half portfolio companies) presented to an audience that included 42 investors; founders, investors, and organizers connected through pitches, meetings, and events around the day.
Lev names startup veteran Jay Bartot as CTO to build its ‘AI co-founder’ and productize PSL playbook
Lev, a Pioneer Square Labs spinout building an 'AI co-founder' for entrepreneurs, named veteran startup builder Jay Bartot as CTO to help productize the venture-studio playbook and launched Lev Learn, a free guide to startup terminology.
Former Redfin CEO Glenn Kelman Joins Greylock as Executive in Residence Following $1.75B Acquisition
Glenn Kelman, former CEO of Redfin who left after its $1.75 billion acquisition by Rocket Companies, has joined venture firm Greylock as an executive in residence to advise founders while exploring new mission-driven ventures. Kelman plans to remain in Seattle and use this role to support his creative process without becoming a venture capitalist himself.
Robbie Cape Launches The Instrument to Disrupt Trillion-Dollar Insurance Industry with Pioneer Square Labs Backing
Seattle entrepreneur Robbie Cape is launching The Instrument, a new startup backed by Pioneer Square Labs, to disrupt the trillion-dollar insurance industry. After a nine-month job search and drawn by the sector's complexity and financial potential, Cape aims to build generational wealth unlike his previous mission-driven ventures.
Tin Can CEO Chet Kittleson and Founders Share Key Startup Lessons at Seattle Flow Day on May 15
At Seattle Flow Startup Day, experienced founders including Tin Can CEO Chet Kittleson shared lessons from their hardships, emphasizing building passionate companies, maintaining emotional stability, hiring capable people, disciplined fundraising, questioning the need for venture capital, and considering acquisition early. Kittleson recounted surviving a disastrous network outage that nearly ended his startup, highlighting resilience and customer-driven growth.
T.A. McCann Becomes CEO of Lev, AI-Powered Startup Spun Out From Pioneer Square Labs with $1M Investment
T.A. McCann, after eight years as managing director at Pioneer Square Labs, is now CEO of Lev, an AI-powered co-founder platform designed to help early-stage entrepreneurs by automating guidance and validation. Lev, spun out from PSL and backed with over $1 million in investment, aims to scale founder support using AI tools for ideation, validation, and company formation.
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.
UW Students Pitch AI Startup Ideas to Seattle Venture Capitalists After 10-Week Program at Pioneer Square Labs
University of Washington students from seven teams pitched AI-driven startup ideas to influential Seattle investors at Pioneer Square Labs, concluding a 10-week entrepreneurship program led by venture capitalist Greg Gottesman and UW professor Ed Lazowska. The event featured realistic pitch rounds, attracting prominent tech leaders as guests throughout the course.
Seattle Startup Tin Can Raises $3.5M to Scale Screen-Free WiFi Landline Phones for Kids
Seattle startup Tin Can has raised $3.5 million from venture investors to scale its WiFi-enabled landline phones for kids, designed to limit screen exposure. The $75 phones connect children through approved contacts only, addressing parental concerns about smartphone and social media impacts on children's mental health and social development.
Seattle Startup Founders Highlight Focused Community and Talent Amid Risk-Aversion Concerns
Seattle startup founders praise the city's focused, welcoming community, strong technical talent, and unique advantages like proximity to Joint Base Lewis-McCord. However, concerns remain about the region's risk-averse culture, limited local capital, and government policies.
Seattle VCs Greg Gottesman and Matt McIlwain Urge Startups to Rethink Defensibility Amid Rapid AI Advancements
Seattle venture capitalists Greg Gottesman and Matt McIlwain emphasized at Seattle Venture Day that startups must develop new defensibility strategies, like 'reasoning flywheels,' to survive rapid scaling and vulnerability in the AI era. They advise founders to move beyond traditional intellectual property moats and focus on unique data, engagement, and workflows.
Seattle Investors and Founders See AI Boom as Key Startup Opportunity Amid Cultural and Capital Challenges
Seattle's startup ecosystem is poised for significant growth amid the AI boom, thanks to a strong talent pool and tech presence, according to over 20 investors and founders. However, concerns about a risk-averse culture, limited local capital, and government policies could hinder the city's ability to fully capitalize on this opportunity.
University of Washington Students Pitch AI and Tech Startups After 10-Week Entrepreneurship Course Led by Greg Gottesman
The University of Washington offers a popular 10-week entrepreneurship class led by venture capitalist Greg Gottesman, culminating in student pitches of tech startups at Pioneer Square Labs. The course attracted strong demand, featured high-profile guest speakers like Amazon CEO Andy Jassy, and highlighted trends such as AI and computer vision.
Pioneer Square Labs’ Julie Sandler to become venture partner next year, stepping down as managing director
Julie Sandler will move from managing director to venture partner at Seattle startup studio Pioneer Square Labs next year, continuing to help founders, seek investments and serve on boards. The change will occur before PSL Ventures raises its next fund, and Sandler will also chair the Washington Roundtable in the coming year.
Julie Sandler to Shift from Managing Director to Venture Partner at Pioneer Square Labs in Late 2024
Julie Sandler, managing director at Pioneer Square Labs since 2017, will transition to a venture partner role in late 2024 while continuing to engage with the firm and its portfolio. She will also chair the Washington Roundtable next year, reflecting her ongoing influence in the Pacific Northwest tech and business communities.
Pioneer Square Labs' Greg Gottesman Forecasts Generative AI Will Transform Venture Capital Operations by 2033
Greg Gottesman of Pioneer Square Labs predicts venture capital will fundamentally change in the next 5-10 years, increasingly leveraging generative AI to provide startups with more than just funding, including operational and coding support. Sheila Gulati of Tola Capital adds that early-stage investing is becoming more democratized, with a broader investor pool amid the recent AI-driven revival in venture capital.
Pioneer Square Labs Assembles Expert Technical Advisory Board Featuring Seattle Tech Leaders to Support Early-Stage Startups
Pioneer Square Labs has formed a new Technical Advisory Board comprising leading technology researchers, executives, and startup veterans to support its early-stage startups, with a focus on AI and technology innovation. The board includes prominent figures from the University of Washington, Microsoft, Google, and other notable tech companies.
Vivek Ladsariya Joins Pioneer Square Labs as Managing Director, Moves from Bay Area to Seattle
Vivek Ladsariya, a veteran Bay Area investor with experience in enterprise technology startups, has moved to Seattle to become managing director at Pioneer Square Labs, playing a key role in their Ventures arm and Studio. He aims to focus on technically driven enterprise software infrastructure startups, especially those delivering real automation, enhancing Seattle's venture capital ecosystem.
Gaurav Oberoi’s Lexion Acquired by DocuSign for $165 Million, Marking Third Successful Exit for the Entrepreneur
Serial entrepreneur Gaurav Oberoi, co-founder of AI-based legal tech startup Lexion, will exit successfully as Lexion is acquired by DocuSign for $165 million. Oberoi, known for his customer-centric approach and expertise, has now had three startups acquired, earning strong respect in Seattle’s tech community.
Pioneer Square Labs and Mayfield Partner to Co-Invest $1.5M Minimum in AI Startups
Seattle's Pioneer Square Labs and Silicon Valley venture capital firm Mayfield have formed a partnership to co-invest at least $1.5 million in AI-focused startups spun out from PSL. This collaboration combines PSL's startup incubation with Mayfield's venture funding strength to accelerate AI technology ventures.
Ben Gilbert Transitions to Venture Partner at Pioneer Square Labs to Focus on Top-Ranking 'Acquired' Podcast
Ben Gilbert, co-founder of Pioneer Square Labs, is shifting from managing director and general partner to venture partner to focus on the popular 'Acquired' podcast, which now has over 450,000 monthly listeners and is the top tech podcast on Apple and Spotify. The podcast's in-depth episodes require extensive research and production time, leading Gilbert to prioritize it over his previous dual roles.
Boundless CEO Xiao Wang Uses Personal Immigration Experience to Revolutionize U.S. Green Card Process
Boundless co-founder and CEO Xiao Wang, an immigrant himself, launched the company to simplify the complex U.S. immigration process after witnessing his parents' struggles. Leveraging his tech background and extensive research, Wang aims to address systemic pain points and help families navigate immigration more efficiently.
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.
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
