Kirby Winfield
Kirby Winfield manages this profileKirby Winfield is the Founding General Partner at Ascend, a pre-seed venture capital fund focused on enterprise AI and deeptech. He is a first check investor in Endurance Energy and Overland AI, and serves as Investor in Residence at AI House. He co-founded and led Dwellable as CEO. His previous roles include President and CEO at AdXpose, Senior Vice President at comScore, and founding team positions at Marchex and Go2Net.
EP12: Kirby Winfield - Founders first VC
## Key Points ### Keywords venture capital, investment strategies, AI technology, founder insights, decision-making frameworks, early stage investing, capital allocation, startup funding, Overland AI, Kirby Winfield ### Summary In this conversation, Martin Tobias interviews Kirby Winfield, a seasoned venture capitalist and founder, discussing his journey in venture capital, particularly focusing on his investment in Overland AI. Kirby shares insights into his decision-making frameworks, the importance of founder evaluation, and the evolution of his investment strategies over the years. He emphasizes the need for confidence in capital allocation and highlights common pitfalls that investors face in early-stage ventures. The discussion culminates…
Seattle Tech Week 2026 Draws ~250 Events Over Five Days, Showcasing City’s Tech Talent and Innovation
Seattle Tech Week 2026 ran five days with roughly 250 events across diverse venues, celebrating Seattle’s dense tech talent and community connections while highlighting themes from founders, investors, and academics. Organizers view the event as a community-led showcase that reinforced Seattle’s historic and ongoing contributions to cloud, AI, and other innovations.
Elizabeth Liu celebrates an electric SeattleTechWeek, spotlights Crowd Cow customer Randa Minkarah and event highlights
Elizabeth Liu celebrates SeattleTechWeek, praising the region's fast-moving startup ecosystem, sharing event highlights (Madrona/J.P. Morgan pickleball, AI House BBQ, rave) and a chance meeting with early Crowd Cow customer Randa Minkarah.
By Kirby
Kirby Winfield announces Overland AI launches Ibex autonomous resupply vehicle — 2,000-lb payload, 35+ mph, 250-mile range, $24.5M+ orders
Kirby Winfield highlights Overland AI’s debut of Ibex, an autonomous ground vehicle that can carry 2,000 pounds, travel up to 250 miles, and reach 35+ mph while operating off-road for Marine Corps, Army, and Special Operations. The Seattle startup has two prototypes in daily testing, more than a dozen AGVs ordered under roughly $24.5 million in contracts, and production planned later this year.
Former GeekWire Writer Nathan Bek Named First Associate at Ascend.vc to Drive Deal Sourcing and Content Creation
Ascend.vc has hired former GeekWire writer Nathan Bek as its first Associate to source deals, conduct diligence, create content, and support portfolio companies. Bek joins a notable group of reporters-turned-VCs and will focus on Seattle startups alongside Jen Haller.
Survey of 70 Seattle Founders: Local Angels Are Risk-Averse, Hidden and Losing Deals to Seed Funds
A February survey of 70 Seattle-area tech founders found widespread frustration with local angel investors, who are described as risk-averse, conservative, hidden, and out of touch; founders say angels must be more visible, faster, and willing to take bigger risks to compete with active local and Bay Area seed funds.
Organizations
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Endurance Energy First Check 2025–present · current
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Overland AI First Check 2023–present · current
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Ascend Founding General Partner 2019–present, Founder and Founding General Partner · current
Education
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Seattle University School of Law Coursework towards JD · 2002–2003
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Middlebury College BA, English · 1992–1996
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Seattle Preparatory School 1988–1992
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Assumption School 1986–1988
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Seattle Country Day School 1980–1986
