Brett Westervelt: Measure Twice, Cut Once

Sana Rao is a contemporary expressionist artist based in London. Her work is a personal meditation and a weapon to guard against the numbness brought on by an entirely mechanised existence. Sana’s artwork draws from the expressionist tradition and depicts the vision of a playful yet symbiotic future. Before returning to art, Sana spent nearly two decades in the world of design and tech working in companies like Twitter, Deliveroo, Apple and Peanut across three continents.

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Brett Westervelt is currently the Head of Design at Instagram. We spoke about his life and career, from growing up in Oklahoma, tinkering with his grandfather, to taking a course at Stanford, experiencing startup life, and growing as a leader. This episode has tons of nuggets about how he thinks of building strong teams to create great software, how he thinks about design at scale, and how to keep craft at a high bar.

Andy is a creative director, designer, and event producer. He is most well known for XOXO and Build Conference. He also recently started a non-alcoholic craft brewery called Heck. We spoke about the events that he's created, and how he went from event production to non-alcoholic beverages. Most notably, Andy's career has run parallel to the evolution of the tech industry in the last 15 years, and he shares some of his perspectives on this.

Gabriel Valdivia is a product designer, and currently an independent fractional design leader. He partners with founders as their design leadership counterpart while embedding with engineering teams to execute and iterate towards product/market fit. We talked about the rise of the model of fractional design leadership, the current issues tech teams are facing after bloating their organizations these last few years, and many other takes of various temperatures.

Cat Noone is a product designer turned founder, and now CEO of Stark, a startup streamlining accessibility compliance for software teams. We talked about her path from designer to business leader, the mistakes made along the way, and how she keeps a high bar for craft of the product and of decision making.

In the inaugural episode of 2024, Aaron and I explore three compelling topics. First, we discuss the qualities of our most effective cross-functional partners and partnerships. Then, we delve into the significance of designers considering their work in the context it lives in, and focusing on the impact it can have. And finally, we share insights on the most impactful feedback we've received.

Majd and Jasper are the co-founders of Darkroom, a photo and video editor for iPhone, iPad and Mac. In this episode we go through the whole history of Darkroom, how they think about the product in the context of the competitive landscape, and how they look at evolving the product going forward.

Brian Lovin and Ryan Nystrom are the co-founders of Campsite, a tool for product teams to communicate with increased signal, rich institutional knowledge, and reduced noise. We talked about the lessons they have learned from starting the company, but also about their past lessons and experiences that inform the way they approach building Campsite. We covered a lot of topics that continuously roam around in my mind as I think of how to support my teams in the best way.