Kirby Winfield
Kirby Winfield is Investor in Residence at AI2 Incubator and the Founder and Founding General Partner at Ascend. He founded Ascend and Ascend.vc, both funds, and remains active in both.
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…
Kirby Winfield | Ascend
Winfield is a four-time operator (two IPOs, two acquisitions) who spent two years as investor-in-residence at the Allen Institute for AI before launching Ascend in 2019. That background drives a blunt thesis most polished VCs won't say out loud: pre-seed money from finance-trained "quants" is dangerous, because the people writing first checks need to understand the zero-to-one journey, not underwrite growth. He frames his own value as narrow and purpose-built for the first check, and tells founders that if they don't want to take his call again after the first meeting, they shouldn't take his money....
Kirby Winfield: Founding GP@Ascend on Enterprise AI & Defense Tech
Kirby Winfield is the founding GP of Ascend, a pre-seed VC fund focused on enterprise AI. The fund's flagship investment is Overland AI, which powers autonomous ground navigation for the US Defense ecosystem. Prior to Ascend, Kirby's career as a tech founder included two IPOs and two venture backed exits.Topics: Enterprise AI Investment Thesis:Defense Tech InnovationBuilding Defensible AI Startups#AIStartups #TechExits #VentureCapital #AIInvestment
Humanizing Your Brand with Kirby Winfield
What does it take for a venture capitalist to build a successful brand strategy that resonates with founders and investors alike? In this episode, host Lindsay Pedersen sits down with Kirby Winfield, the founding general partner at Ascend, to explore the importance of defining and embodying a brand identity in the world of venture capital. Kirby shares insights on the value of authenticity, problem-driven processes, and the power of being intentional in shaping a brand that stands out in a competitive market. Define Your Brand Early: It's crucial to define your brand early on to...
8 tips for how to pick great Pre-Seed Founders by Kirby Winfield from Ascend.vc
Kirby's original post https://www.linkedin.com/posts/winfield_preseed-investing-is-easy-a-dont-activity-7186077270862659584-J1J4/?utm_source=share&utm_medium=member_desktop
What's happening at the seed stage? Featuring Jenny Fielding, Kirby Winfield, and Nate Williams
Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.This week we're doing another special roundtable discussion with a focus on the seed stage market. Joining us are Jenny Fielding of Everywhere Ventures, Kirby Winfield of Ascend, and Nate Williams of UNION Labs.This whole conversation was focused on seed stage investing. We spent most of our time discussing how the market reset affects seed-stage decision-making, fund sizing, and reserve strategies. We also touched on what they are seeing and hearing from LPs...
Ignite VC: Shaping the Future of Startups and Venture Capital with Kirby Winfield of Ascend VC | Ep41
In this episode of the Ignite podcast, Kirby Winfield, founding general partner of Ascend VC, shares his journey from a marketing executive in early internet startups to a seasoned venture capitalist. Kirby's narrative begins with his roots in Seattle, detailing his initial foray into the startup world with GoToNet and his subsequent ventures, including Marchex and Dwellable, highlighting the lessons learned from each. He candidly discusses the challenges and personal sacrifices involved in the startup ecosystem, such as the impact on his health and family life, which led to a significant personal and professional recalibration. Kirby's transition to venture...
AI Investing in Seattle with Ascend.vc General Partner Kirby Winfield
In this episode of Shift AI, Kirby Winfield General Partner at Ascend.vc shares his journey from founding multiple successful startups to becoming a leading AI investor and outlines lessons learned, insights on the Seattle startup ecosystem, and his optimistic yet pragmatic views on generative AI and the future of work. Summary of topics covered: Background and early career: Kirby gained experience as an entrepreneur early in his career through founding multiple companies. Transition to Venture capital: Looking for a new challenge, Kirby leveraged his experience operating startups to co-found Ascend and advise other founders. Investment thesis and framework for evaluating…
Kirby Winfield, Founding GP at Ascend VC
In today's episode of Category Visionaries, we speak with Kirby Winfield, Founding GP at Ascend VC, about his love for angel investing and the passion he feels in providing founder-friendly venture capital with genuine value to add to their partners’ offerings. By leaning into projects they have a genuine love for and interest in, Ascend gives so much more than just capital, forging a unique identity among a crowded field of VC firms through real commitment and support to turn business aspirations into commercial reality. We also speak about Kirby’s background in the startup space and taki...
SVB aftermath; remote work 'affliction'; and Microsoft puts AI to work
This week on the GeekWire Podcast ... We catch up on the latest on the Silicon Valley Bank collapse, and consider the long-term implications of the meltdown on the startup ecosystem and the U.S. financial system. Then, a point-counterpoint on the issue of the return to office, as Downtown Seattle Association President Jon Scholes laments the "affliction" of remote work, and Zillow Group CEO Rich Barton says the ways we work (and the places we work) have changed forever. And finally, we catch up on the latest in the world of generative artificial intelligence, listening to Microsoft CEO Satya Nadella's…
What's next in the Silicon Valley Bank saga
Startups and investors cheered the U.S. government's promise this weekend to fully protect deposits after the Silicon Valley Bank collapse. But the move left many unresolved questions and challenges for the U.S. financial system and the tech industry. Our guests on this episode of the GeekWire Podcast discuss their recent experiences and offer their informed opinions on what could come next. Speaking with GeekWire co-founder John Cook are: Kirby Winfield, founding general partner of Seattle venture capital firm Ascend; and Aviel Ginzburg, general partner at Seattle VC firm Founders’ Co-op. They both reflect on what happened last week, explaining how…
Building Startup ecosystems, the solo GP life, and lessons from the dotcom bubble with Kirby Winfield of Ascend.Vc
The road of a solo GP is full of highs and lows, and today’s guest Kirby Winfield has been through all of it. After working in the 90s tech and startup scene in Seattle, Kirby went on to found Ascend VC as a solo GP. We talk about his biggest lessons, the best advice he’s gotten, and dig into some of the stories from the trenches as an emerging manager.About Kirby Winfield:Kirby Winfield is currently the Founding General Partner at Ascend.vc, a pre-seed stage venture fund investing in marketplace, e-commerce/DTC, and B2B...
GeekWire's Elevator Pitch: Analyzing the four winning pitches in advance of the upcoming live finale
This week on the GeekWire Podcast, we hear the pitches made by four startup CEOs in the 32 seconds it takes to get to the top of Seattle's historic Smith Tower, on their way to winning their respective episodes on this season of GeekWire's Elevator Pitch series. It's a preview of the upcoming season finale, in which each of the four will make a final pitch at the GeekWire Summit next week, live on stage. Episode 1 winner: Amina Moreau, CEO of Radious, an online marketplace that turns houses, apartments and other residential properties into workspaces, rentable by the day…
#27 Geoff Harris: Managing Partner Flying Fish VC
In this episode of Startup Project we spoke to Geoff Harris, Managing Partner Flying Fish VC. Flying Fish is a thesis driven fund focused on Al/ML. Geoff Harris spent 15 years at Microsoft in engineering leadership and executive leadership positions. His career at Microsoft began in digital media where he ran the Windows Media Player team. Full conversation includes: Developing Natural language processing at Microsoft Angel investing to raising a fund Core insight behind Flying Fish AI Use cases for future Web3 & Venture ----- Past guests of Startup Project podcast include Ali Moiz (stonks.com), Kirby Winfield (Ascend.vc), Eric Bahn…
730 - Kirby Winfield, Founding Partner at Ascend.vc
Kirby Winfield is a seasoned startup operator and investor, and is currently the Founding General Partner at Ascend.vc, a pre-seed stage venture fund investing in marketplace, e-commerce/DTC, and B2B software startups in the Pacific Northwest. ★ Support this podcast ★
018 - Kirby Winfield, Founding Partner at Ascend.vc
About KirbyKirby Winfield is a seasoned startup operator and investor, and is currently the Founding General Partner at Ascend.vc, a pre-seed stage venture fund investing in marketplace, e-commerce/DTC, and B2B software startups in the Pacific Northwest. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit words.seedscout.com
018 - Kirby Winfield, Founding Partner at Ascend.vc
About KirbyKirby Winfield is a seasoned startup operator and investor, and is currently the Founding General Partner at Ascend.vc, a pre-seed stage venture fund investing in marketplace, e-commerce/DTC, and B2B software startups in the Pacific Northwest.
Kirby Winfield
Kirby is a seasoned startup operator and angel investor. He is currently the Founding General Partner at Ascend.vc, a pre-seed stage venture fund investing in marketplace, e-commerce/DTC, and B2B software startups in the Pacific Northwest. He is also a Techstars mentor, passionate Board member, and Board Chair-elect at Special Olympics of Washington, where he helped bring the 2018 Special Olympics USA Games to Seattle. See omnystudio.com/listener for privacy information.
Kirby Winfield (Ascend VC) on shifting mindset, investing in founders, and finding love in the game
Kirby Winfield is a 3x founder with 3x exits who turned VC. But his journey was not all unicorns and rainbows even after his repeated success. He goes behind the scenes on his path to finding love in the game, what he looks for in startups, and his unique approach to investing in founders at Ascend.vc.
Secret Startup Ingredient: Microsoft
Would you have guessed that nearly 25 percent of the Seattle region's top tech startups are led by CEOs with backgrounds at Microsoft? That was the surprising result of our analysis of the GeekWire 200, our index of the top privately held tech companies in the Pacific Northwest. And fundings for the region's startups bucked the national trend, as reflected in data from our new startup deal tracker. Nintendo unveiled a new iteration of its Switch game console; former Microsoft CEO Steve Ballmer pulled off what might be his greatest deal ever; and an Amazon employee showed the potential of…
Organizations
See all 14-
Endurance Energy First Check 2025–present · current
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Overland AI First Check 2023–present · current
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Ascend Founder and Founding General Partner 2019–present · 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
