Fri. Jul 19th, 2024

Nobody cares about your AI…customers don’t care about your AI. They care about the problem that you’re solving and that you’re doing it 10 times better or 10 times more efficiently…An AI just enables a new set of challenges and tasks to be tackled organically in a way that maybe wasn’t before.

That’s one of the insights from Kirby Winfield, founding general partner at, on this episode of Shift AI, a show that explores what it takes to thrive and adapt to the changing workplace in the digital age of remote work and AI.

We discuss Winfield’s experience as a serial entrepreneur and his transition to a Seattle venture capitalist investing in some of the most innovative new AI companies in the Pacific Northwest. 

Listen below, and continue reading for highlights from his comments, edited for context and clarity. Subscribe to Shift AI and hear more episodes at

The early years and first job: My first job was hocking strawberry shortcakes at summer festivals. It was my first sales job and you can’t have a whole lot of shame if you’re selling shortcakes. I quickly realized I wasn’t comfortable with outbound sales, but the initial thing that helped me was thinking about the value that I was providing to people. It’s a lot easier to sell shortcake at a summer festival than it is to sell software as a service to a midsize enterprise. It’s all about time to value and the time to value for shortcake is very short. 

Investing thesis on AI at Ascend: We like to say we’re the most prolific pre-seed investor in the Pacific Northwest.  We invest in software and B2B and a vast majority touches in some way on artificial intelligence, machine learning, data, or vertical software. I think applied AI is basically vertical software 3.0. It’s software as a service (SaaS)…it’s just a better technology to do SaaS. 

Framework for evaluating AI opportunities: I think our framework really forces you to ask a couple basic questions about artificial intelligence as an investor. Is it an applied AI opportunity or is it a structural AI opportunity? If it’s applying a new technique, or novel technology approach to an existing workflow or problem, then you have to think really hard about how it differentiates and how it maintains an advantage over time. The question just becomes how can you differentiate and solve the problem better than others, what data advantage do you have, what feedback loop and fine tuning advantage do you have and what brand and user experience advantage do you have?

Portfolio companies: Overland AI is trying to tackle the autonomous software stack for off-road vehicles. Specifically, the go-to-market is in defense and robotic control vehicles. We’ve had drones in the air for a long time, but you haven’t had autonomous movers of material supporting troops on the ground. We are excited about that opportunity and we are seeing a lot of traction.

Clarity, another one of our portfolio companies, is a team of incredible software engineers and cyber warriors out of the 8200 Division of the IDF who are creating cutting-edge technology to identify and prevent the proliferation of deepfakes. It’s hard to imagine a world where deepfakes are not an immense problem and so it’s exciting to be a small part of trying to solve it, or at least prevent harm.

Incumbent tech companies and AI: If you think about what’s happening at the enterprise today, companies are changing the way they’re behaving and new companies are being built with entirely different fabric and structure with regards to how code is written, how goals are managed and how communications happen internally. Anyone who is active in investing in artificial intelligence would tell you that an enterprise operating today is going to look entirely different 20 years from now. It will be unrecognizable. And so the question is how can you create a solution today that’s impactful enough, and durable enough to grow with those enterprises as they become this next generation of technology company.

Seattle’s potential as a tech hub: I think the opportunity has never been brighter. Seattle has more AI software engineers than anyone else in the U.S. outside of the Bay Area and our talent pool is extremely deep. We have centers for excellence, like the Allen Institute forArtificial Intelligence (AI2) and we have a top research university in the University of Washington. This point in time is an inflection point for Seattle as a startup ecosystem.  We now have the ingredients we had lacked for decades that kept our big outcomes sort of sporadic. 

Mentors and influences:  My father-in-law was my first big influence. He grew up in Kansas, his parents owned a grocery store, he worked there since he was a kid and he went on to start a title insurance company that’s now the largest privately held title company west of the Mississippi. He was the one to teach me that you have to ask the question that no one else is asking. 

John Keister is probably the most powerful mentor I’ve ever had. During the time I worked for him at Go2Net he tirelessly redlined my work, walked me through it, let me go rebuild it, redlined it again, and walked me through it again. He took me into meetings I had no right to be in, gave me responsibility that I probably hadn’t earned and cared for me as a friend, first and foremost.

Future of work and AI: I think that we have infinite potential for freeing ourselves from a lot of the shackles of the work that we are doing today. Things are going to get incredibly more efficient and as a society we will be able to do higher order work that will yield things that we can’t understand because they don’t exist yet. We’re living in the future right now…we just don’t see it because the future happens slowly, but in retrospect, very, very quickly. I think it’s an incredible time to be alive and investing in this technology.

Listen to the full episode of Shift AI with Kirby Winfield here.

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