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CG: My path into design is really similar to John’s. I also started with Legos, but when Legos became too expensive, I switched over to Minecraft. In high school, I spent my nights and weekends working as a professional Minecraft builder designing 3D worlds in the game by re-creating existing buildings and imagining new ones in collaboration with Microsoft and various museums/historic sites. Naturally, I was always fascinated with architecture, but I also started getting really into photography and web design, and that’s how I eventually fell in love with product design. As I learned more about what it meant to design effective software, I realized that I had already been practicing a lot of the skills required to craft user-centered experiences when I was designing worlds in Minecraft. The thinking required to build successful gameplay environments, like considering lines of sight and discoverability, turned out to be perfectly applicable to helping guide users through an interface. I’ve always been interested in exploring the intersection of technology, visual design, and human psychology, so to me, software design feels like the best encapsulation of the three.

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MK: You’re starting a new design event here in NYC, Double Diamond. What sparked the idea to create this series, and why now?

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JF: The idea came from attending what felt like every design event in New York City. I met Chase at one of the first design events I went to after moving here in February. We connected because we were both designing at early-stage startups, which is honestly pretty uncommon to find at the bigger industry events. We became good friends and started going to events together, anywhere from two to three on any given week for about six straight months.

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Having seen all the different types of events out there, we consistently found ourselves wanting to go deeper with the conversations we were hearing. A lot of these events had fantastic speakers, but we'd get the most value by going up to them afterward and asking questions. That became kind of a natural habit for us. Around summer, we started talking about creating our own event series based on an interview format that would give us (and hopefully others) the kind of depth we were looking for.

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Why now. We got really lucky because two things coincided at the exact same time. First, we were connected with the team at Framer, who had launched an initiative to support community builders working in design here in New York City. I give Framer a lot of credit here because all we had was an idea, and they were willing to sponsor us based on that concept alone. Second, when me and my other partner Alex Herschmann met Alex Pavlou at one of his events, he had been actively looking for design community events to help sponsor and enable, and was also a really early supporter of the Double Diamond concept. He's been a fantastic partner in enabling us to take this from idea to reality, both in terms of helping us host the events and also positioning us to create content around them.

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CG: Echoing what John said, it really was the perfect storm of meeting the right collaborators at the right time—we absolutely couldn't have brought our brand/event to life without them! A few other factors worked in our favor. There's been intense discussion around how AI is reshaping software, with one of the main questions being: "what will the UI for AI look like?" or if there will even be any UI at all. At the same time, there has been a lot of discourse across LinkedIn and Twitter about the value of design in the age of AI, how design roles are evolving, and whether or not design and taste will be differentiators for companies. With all this brewing, we wanted to build a space where the leading designers actively answering these questions could have candid discussions with each other.

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MK: The event is designed as a longer, more intimate setting. What do you hope that format makes possible for the conversations and connections that happen there?

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JF: The long-form conversational format and intimate setting are really intentional. Going back to me and Chase attending all those design events, we found ourselves wanting something different than the typical panel format. We'd sit in on some of these panels and the conversation would never quite have the flow we were hoping for. It felt a bit disjointed in a way that's hard to articulate.

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Chase and I both found tons of value in the times we've had personal long-form conversations with other people working in design. We also get some of these conversations by consuming all the content available to us online, including podcasts like Dive Club. We believe the long-form conversational format allows the people we're interviewing to really get into the depths of why they think certain things. Questions like "How are you thinking about building an AI product and bringing it to market?" are genuinely hard to answer. You just can't answer them in the minute and a half you get on a panel.

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Similarly, a lot of these events have massive audiences, which maybe we'll do one day, but we believe you want a speaker to feel comfortable. If they're going to be up there for a long period of time, you want them in a small enough room to just feel comfortable being themselves and not feel like they're on stage performing or having to act a certain way. If you have a small, curated room of the right people, that can go a long way.

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CG: Like John mentioned, it’s hard for events that present a panel of speakers to go deep into one subject because you want to give every guest a chance to speak, but some of the guests might differer widely in their opinions. This can force the conversation to stay at a high level and can make it difficult to come away from the event with deep learnings or actionable insights. What really excites us about the format of our Double Diamond events is that we have the opportunity to really explore our guests’ deep knowledge of designing and building successful products by giving them a platform to express their ideas at length. We also feel that the easiest way to digest ideas is through examples, so we encourage our speakers to show demos of the projects they’re working on as a way to illustrate how they follow their design philosophy in practice. I think the other component here is that with so much uncertainty around the future of software and how the tech industry will look in even the next 5 years, people crave in-person events where they can meet other designers and product thinkers who are solving the same problems they are. John and I both also deeply believe in the value of community, so we intentionally keep our events on the smaller side and really focus on curating the attendee list to encourage our guests to have these candid conversations we think are so valuable.

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MK: New tech brings exciting moments to define software design for potentially years to come, what surface areas in AI do you guys find most exciting?

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JF: This is such a great question, and there's so many answers I could give. I think the most exciting surface area that I think about is, broadly speaking, how non-determinism as a design principle will change what we can make and change the products we use. Non-determinism really in two parts.

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First, in terms of outputs. When you're working with a model or some kind of system where you prompt a model to do something and that model provides an output in return, the different ways that we can figure out how to output the right thing to either answer the user's question or solve the user's problem. I think there's so much left to be built there.

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Which kind of leads me to the broader thing about non-determinism that excites me: I really see a future where UI as we know it is not deterministic either. Right now, the outputs of prompt boxes are the non-deterministic surfaces we're seeing. But ultimately, we've been designing software based on pattern recognition that, at scale, solves a lot of problems for different people. The actual correct thing to do would be to give the user the UI that solves all of their problems specifically. You just want to give people the thing that solves their problem. We haven't been able to do that because everybody has slightly different problems in slightly different use cases, but non-determinism as a UI principle allows you to say, "Actually, no, we're going to enable the user to create or configure this UI to solve exactly their problems." You could potentially have a world where people are creating their own custom UI elements, their own custom workflows and applications, which is a very exciting thought.

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CG: To give a different answer, while I agree that fully deterministic interfaces will definitely become more prominent in the future, the success of general-purpose AI platforms like ChatGPT and Claude have established chat dialogs as the de-facto paradigm for interacting with AI for the time being, and I don’t see that going away anytime soon. I think there are two aspects of interface design within a chat that excite me here though. For one, I think having specific chat inputs that can trigger bespoke UI elements with specific interactions based on your prompt, like ChatGPT’s “canvas” mode for drafting emails, or Claude’s “artifact” viewer for code prototypes, is where the future of chat-based interactions are headed. In this world, there’s still a fixed set of UI elements with specific affordances that you can access, but instead of navigating to different parts of your product through a left-hand sidebar, you access can them dynamically based on the context of your prompts to the chat. Additionally, I’m excited by the challenge of representing agents visually in a UI. Right now, AI agents largely do the same work that humans do (clicking on buttons, navigating between screens, reading through documents, etc.) but we may be moving towards a world where we build and design software specifically for agents as the primary user rather than humans. In this case, I think there’s still a lot of open questions around how we should communicate what agents are, what actions they’re taking, and how and when we should expose controls to keep humans in the loop.

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MK: For design teams who are shaping AI products today, what resources, frameworks, or references would you recommend?

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JF: This is kind of a non-answer, but I think the best resource is just trying things. I make an effort to try new tools, to use new things, and that has been probably the best source of learning in and of itself. You try things and in the process of trying things, you look up resources for how to do things better and you begin to create this picture in your head of what's possible.

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Also, specifically in the context of building AI products, just move fast. I guess that's always been the case, but what do you do if you're trying to shape a product? How do you know if you're doing the right thing? You build, you ship, you learn, you iterate. Just do that.

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To be more specific, if you want to learn how to build websites with AI, try Framer. If you want to learn how to build an application with AI, try Lovable or v0. If you want to learn how to automate a lot of the work you do on a day-to-day basis using an agent, try Notion's agent. Just try these things, and get used to using ChatGPT, Claude. Make an effort to try to do these things and spend time learning how to get better at using them.

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CG: Totally agreed with John here. For me, I try and use as many different AI-native tools as I can on a daily basis to get a sense of how they work functionally, but also to see how other designers are approaching the problems that all AI software runs into. I’m usually most interested in seeing how other tools approach visualizing the size of context windows, what items (documents, images, files, etc.) might be in vs. out of a chat’s context, and the ways that these tools allow you to add or remove items from context. Right now, I think Cursor has some of the best solutions to these problems that I’ve seen, so I’d definitely recommend trying it out.

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MK: What's a dream guest you'd like to have speak at a Double Diamond Event?

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CG: For me it would probably have to be Carl Rivera, the Chief Design Officer at Shopify. He’s super active on Twitter and openly shares his perspectives on how he’s building a world-class design team and how he’s preparing them for a future where design roles are ever-evolving. I feel like Shopify has been one of the most design-forward companies recently— between their acquisition of the highly regarded product design studio Molly, to Carl’s emphasis on craft and taste as the ultimate differentiators, to their recently announced design apprenticeship program for juniors that addresses the design industry’s tendency to prioritize senior talent. I’ve been really impressed with how he’s been approaching building out a design org and with how candid he’s been online about his process, so I would love to learn more about where he sees the future of design heading.

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JF: I have an absolutely massive list of people. It's hard to pick just one. But if you forced me to choose one that I think would be difficult for geographic reasons, I would say Ryo Lu from Cursor. I follow Ryo on Twitter, and the way that he's bridging the design and engineering gap and getting designers into code and production is just so incredible and inspiring. That's the kind of work that I think really does materially influence the entire practice of product building, which is really hard to do, and I think he is doing exactly that right now. I think he's honestly just got one of the coolest jobs in the world and has such a unique way of thinking about product that he's very public about, which I also really appreciate. So Ryo Lu easily.