Diego and his small team at Family Office articulate company-changing strategies and design resulting brand identities, user interfaces, spaces, packaging, and more. The firm's previous clients have described the work as “stronger and more business-savvy than any brand strategy work we have seen before.” He co-founded Terms-Eccles to host conversations at the intersection of finance and culture. Previous guests include legendary financial writer James Grant, co-founder of Union Square Ventures Brad Burnham, bestselling financial memoirist Carrie Sun, infamous it-girl Cat Marnell, the podcast duo behind The Ion Pack, senior director of social media at GQ Sasha Mutchnik, lifelong financial journalist and author David Carey, and MorningBrew video star Macy Gilliam. The most recent event took place on April 15, 2025, for a crowd of 200+. Previously, he co-founded a company called Nation. Backed by Placeholder, M13, Slow, Circle, and Tribe Ventures, the company went on to build a handful of software products, in the end resulting in Vellum before the team disbanded. Before Nation, he was a Senior Designer at Waybridge (acq. Minehub).

He began his career as the youngest designer ever hired at the prolific brand transformation agency, COLLINS. He is the author of a 2018 book, The Dropout Manifesto.

He is @messybirkin on Instagram and X, and is reachable via email.