AI House
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. His sharpest point is…
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....
YEPS 2025 (Seattle Tech Week) - The Investor-Founder Playbook: Building Unbreakable Alignment
YEPS 2025 (Seattle Tech Week) - The Investor-Founder Playbook: Building Unbreakable Alignment - Bill McAleer, Co-Founder & Managing Director @ Voyager, Firm has $550 million under management and he has experience on 28 public and private boards, with 18 exits for over $5 billion - Kirby Winfield, Founder and General Partner @ Ascend (Emerging fund) - Susanna Niu, CEO of Meeboss (2nd-time founder, 1 exit) Matt McKinney, Head of Growth @ ArcBlock - Susan Paley, Parnter @ Conduit Venture Lab (Emerging fund) Young Entrepreneurs & Professionals Summit (YEPS) 2025 Wednesday, July 30 2025 9:00 AM - 6:00 PM Microsoft Reactor…
Amazon's big bet, a 'MySpace for bots', and a conversation with AI veteran Oren Etzioni
Upcoming GeekWire Podcast Live Event: Join us from 4 p.m. to 6 p.m. Thursday, Feb 12 at Fremont Brewing for a live recording of the GeekWire Podcast with Todd Bishop and John Cook. Free for Fremont Chamber members, $15 otherwise. Register here. This week on the show: Andy Jassy tells Wall Street that Amazon is planning $200 billion in capital expenses this year, mostly to build out AI infrastructure, and investors give it a thumbs down. Microsoft's financial results beat expectations but the company loses $357 billion in market value in a single day after investors learn the extent of…
Building Category-Defining AI Startups with Yifan Zhang (AI2 Incubator)
We’re excited to feature Yifan Zhang, Managing Director at AI2 Incubator, one of the most successful AI incubators in the world, born out of the Allen Institute for AI and backed by a newly announced $80M Fund III. Yifan is a 2x founder and CEO, Entrepreneur “50 Most Daring Entrepreneurs” honoree, and Forbes 30 Under 30 alum. Her journey spans building and exiting venture-backed startups, navigating extreme founder adversity, and now helping the next generation of AI founders go from idea to impact. In this episode of From Startup to Exit, Yifan shares: * How AI2 Incubator works differently from…
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
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 Innovation - Building Defensible AI Startups #AIStartups #TechExits #VentureCapital #AIInvestment
Oren Etzioni - Founder of TrueMedia.org
Dr. Oren Etzioni is the founder of TrueMedia.org, a free-use product that allows critical election audiences from around the world to quickly and effectively detect deepfakes. He was the Founding Chief Executive Officer at the Allen Institute for AI (AI2), having served as CEO from its inception in 2013 until late 2022. He is Professor Emeritus at the University of Washington where he helped to pioneer meta-search, online comparison shopping, machine reading, and open information extraction. He has also authored several award-winning technical papers, and founded and sold many companies. In addition to his role at TrueMedia.org, he is currently…
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...
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 capital…
Point72 Ventures, Managing Partner - Sri Chandrasekar
🌟 Sri Chandrasekar, Managing Partner of Point72 Ventures and who leads the Deep Tech investment team and co-leads the Consumer investment team, joins Thomas Joshi for a groundbreaking episode on AI's Future and Entrepreneurial Wisdom! 🚀 In this must-listen episode, dive deep into the world of AI with Sri, a visionary in the tech investment landscape. Here's what's in store: 🔍 AI Revolution: Discover Sri's perspective on AI's potential to spark a new Industrial Revolution, transforming the knowledge work sector akin to the impact of steam engines on factory work. 🤖 Human-Centric AI Paradigm Shift: Explore Sri's innovative framework where…
Kirby Winfield on Growth of Seattle's Venture Ecosystem
Kirby Winfield speaks about his experience being an operator in Seattle over the past 30 years, how the venture ecosystem has evolved throughout the years and some similarities and differences between the venture landscape in the 90s/early 2000s and today. Kirby Winfield is a Seattle-based founder, operator and now investor. From 1996-2015, Kirby led 4 startups, either as a co-founder and/or executive from start to exit (2 IPOs and 2 acquisitions). He then began angel investing and in 2019 he launched Ascend VC, which is now the most active pre-seed VC firm in the Pacific Northwest investing out of their…
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...
EP 38: AI, Content & ChatGPT w/ Stew Fortier of type.ai and Kirby Winfield of Ascend.VC
We have two fantastic guests joining us today. First up, Kirby Winfield, an investor in AI-based companies. He has his own fund and a residency at the Allen Institute for AI in Seattle. Our second guest is Stew Fortier, an entrepreneur who has focused on content-related businesses, such as Foster and Well Said Labs. Currently, he is the co-founder and CEO of type.ai. Together, we explore the potential of AI-generated content, its implications for businesses, and how it can enhance customer experience. Kirby and Stew share their expertise and insights on the evolution of AI chat and its impact on…
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...
#17 Founding Partner of Ascend.vc: Kirby Winfield on all things Venture | Startup Project by Nataraj
In this Episode of Startup project (https://thestartupproject.io/) , Nataraj talked to Kirby Winfield, Founding GP of Ascend.vc (pre-seed fund based in Seattle). Prior to founding Ascend.vc, Kirby was part of founding teams at Go2Net (GNET), Marchex (MCHX), Dwellable (Acquired by Home Away (AWAY)) & AdXpose (Acquired by comScore (SCOR)). Full conversation includes: - Through line of a successful career - How can companies strategize for an exit? - The why behind starting a pre-seed fund? - Helping startups from zero to one - Price discovery of startups in current private markets Follow Kirby on LinkedIn at https://www.linkedin.com/in/winfield/. Checkout Ascend.vc for…
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.
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