Diego Family Office Letters

The Other Shore

Essay —

I’ve had a year I would describe as quiet. No major tumult, a full year of running Family Office, a routine that has remained approximately the same. But it’s a sort of quiet “that felt like a sound, rumbling inside my head1.” This has been a good year; I will not see it repeated.

That isn’t for greed, but for fear of stagnation. Some may say that a truly content person would not be ambitious and would not go on wandering, but I don’t think it’s so simple. My favorite parable is that of Budai Shai, or Master Cloth Bag, described as “rather plump, with a wrinkled forehead and a big belly […] he would lie down to sleep just where he happened to be, carried a cloth bag on the end of his staff in which he hoarded all bits and pieces offered to him.”

One day a monk approached the master and asks:

“What is the main thrust of the Buddha-dharma?”
The master put down his cloth bag and placed his palms together in reverence.
The Record of the Transmission of the Lamp. 27.10 Ven. Mingzhou Fenghua Xian Budai (Hotei)

That was all for a moment: just putting down his burden.

“Is it only this or is there something higher still?”
The master took up his burden and left.
The Record of the Transmission of the Lamp. 27.10 Ven. Mingzhou Fenghua Xian Budai (Hotei)

Took up his burden and left. As in: kept on carrying it. You can renounce your ambition and experience peace. Or, you can do good with what good you have, “wholly engrossed in the due fulfillment of the task” in front of you, “without [attached] desire for the result.” For the love of self-actualizing, unbothered by the results, you continue the walk.

And so, I stand here in good position, good health, and with clear sight towards a future that does not look like running a design studio for the next five years, nor like the expected logical progression of my career thus far. I see the metaphorical “far shore”2 away from where my career has so far landed me. But:

Few are those who reach the other shore; most people keep running up and down this shore.
Dhammapada 85, 86.

I hope not to follow. But in the meantime, let’s start where we are.

Family Office

Since I last wrote, we’ve added one member to the team, Roan Collom, an uncannily talented illustrator-designer with excellent taste. He rounds out a six-person team, which conveniently is the exact number of people I think we can fit in this office without sacrificing the wall of bookshelves.

Among the projects we’re able to talk about this year:

In favor of brevity, I’ll spare mention of every project—especially those who have not yet launched—but needless to say, we’ve been hard at work.

I am most proud of how, with an exceptionally young team, every designer has stepped up to the plate to own a project that has ended up being a showcase piece for us. Laia, David, Jesse, and Roan are all immense talents.

2025 rounds out to in revenue on expenses of resulting in EBITDA of . All in all, that’s an interesting lesson in the business of services: managing a larger team and taking on significantly more work, I’ve made within of what I earned in 2024 when I was overworking myself as a freelancer with contractors. (My first hires were made late in the year in September of 2024.) The team is in strong shape and we’re doing our best work. As of January 1, we have nine months left on our small corner unit at 401 Broadway. Looking out on the coming year, we’re going to continue to do the best possible work we can do to grow as a design studio. However, there’s another part of the business, beyond just agency work, that we’re working towards. It will take time, but it is the ultimate goal for us to go from vendors to stakeholders.

Yves

Yves3 is a buyout fund aiming to purchase control equity stakes to transform companies with product and narrative design. That is to say: what Family Office does as an agency, we will instead do as owners of businesses. That means: longer-term buy-in, clear incentives to see a transformation through to the end, and the upside that comes with it.

It is a partnership between myself and a financier friend fueled by the belief that today’s firms misunderstand what it is to be a good stewards of capital. In particular, private equity firms have long refined the only art they know: that of buying a company, saddling it with debt, and making it “more efficient” by slashing costs as opposed to stronger by growing sales. As Lauren Sherman wrote about LVMH in contrast to American fashion conglomerates:

When LVMH buys a brand, the thought is: ‘If we get our hands on it, we can market and merchandise the hell out of it to make it bigger.’ When American fashion companies consolidate, they think, ‘We can save money this way.’4

Yves aims to be a venn diagram of artistic power, commercial instincts, and financial stewardship. Those with the strong concepts and lucid articulations of the future will rule, and in doing so we hope to achieve greater returns than our cost-cutting, company starving private equity competitors.

Great ideas are nothing without power. Control is wasted on those with no ideas.

Yves will be the firm with both.

Joining the ADC Board

Founded in 1920, The Art Director’s Club has been dignifying and celebrating the commercial arts of advertising and design with 100+ years of exhibitions, award shows, and annual publications. During my first winter in New York in 2019, I watched my then-colleague Leo Porto win Young Guns, the ADC’s annual international award for a small handful of the world’s most talented art directors under the age of 30. I tagged along for the awards ceremony at Sony Hall that winter and met so many of the designers whose work I thought to be the absolute best (and who were winning the awards to prove it). Chloe Scheffe, Gabriela Namie, Heejae Kim, Erik Berger Vaage, and Danaé Gosset were all winners that year, and I had the pleasure of meeting many of them.

This July, I hopped in a cab uptown to The One Club’s offices for my first meeting as a member of the ADC’s newly assembled board. To be in conversation about the design industry with the likes of Alan Dye, Gail Bichler, John Maeda, Steven Heller, and Debbie Millman among others is a great honor. Especially at this moment for the creative industry.

And returning to the event that solidified my adoration for the design work that has come to shape my career, I’m working alongside the team at the ADC to make the upcoming Young Guns party on January 28, 2026 an excellent event. You are, of course, invited.

ruks.org

Clients and friends ask all the time for freelance design help and/or to be pointed in the direction of great creatives who may be willing to join a new company. And of course, running a design studio, we come across literal thousands of portfolios of graphic, motion, 3D, and product designers constantly, not to mention the art directors, illustrators, and photographers we bookmark on a regular basis.

Ruks.org is a collection of links to over 1,400 individuals (and studios) as of this writing, sortable by category, location, and attributes. Each listing shows a small thumbnail and links to the person’s portfolio and other links (Instagram, Are.na, and Linkedin among the most common.)

It’s all available at ruks.org, and by creating an account you have access to the full database. Email admin@ruks.org for any and all feedback.

The team behind this deserves many thanks: Franco Guevarra who has been developing ruks.org days, nights, and holidays, Annie Swanson here at Family Office who has wrangled the massive database, and Ethan and Jasmine, our young assistants on the project who worked on various portions of data entry and validation.

Extracurriculars

We co-hosted Office Party with Nikole Naloy, a downtown extraordinaire and a part of the team at WSA, and Michael Montella on December 5th. The event far exceeded capacity and unfortunately we had to turn down many of the 650 people who RSVP’ed, but the party itself I could not be more pleased with.

Isabelle Basha, Katil1yn, and Cami Árboles performed, Crowdsurfers and Rex Detiger DJed, and Matthew Yoscary took photos while Nikole presided over the event like the room-ruler she is, and I bumbled into conversations with anyone and everyone for the entire event. I was asked about my social battery at some point during the night; the true bottleneck was whether I could keep from losing my voice. (I held on.)

Thank you to everyone who showed up. And I am very sorry to those of you who got stuck waiting on Water Street at the door.

In November, I was asked to come speak to a small class at Parsons, my first fielding of such a request, and now that I think of it, it was my first time ever stepping foot into any sort of college classroom. Paul, a part-time lecturer at the school admitted he had no clue who I was, but that some of the students put down my name as someone they’d like to hear from for their class on Creative Entrepreneurship, and so there I was in a quiet, windowless classroom and a room of students who are no more than 36 months younger than me, wondering what possible answers about the topic I could provide.

I probed their current knowledge and tried to fill in the gaps, explaining to them what exactly it is that investment bankers do, where the VC money comes from, and deciphered a few headlines about private equity taking over the world. Of course, one cannot in 45 minutes outline a full view of the business world. My aim was to, by speaking about finance plainly, make it clear that by reading and paying attention, the topic is nothing to be afraid of.

I hope it was useful. Thanks for listening. Especially the young man in the front row who walked in mid-nap and woke up during the first ten minutes.

In partnership with the Art Director’s Club, we’ll be hosting a some Family Office Business School sessions in the New Year, which will be short lectures and Q&A with financial minds for creative people to learn about the driving forces of the businesses we work for and with as designers. If you’re interested in joining those sessions, email Annie.

In other news

I moved once again and this time, didn’t bring a single item of furniture with me. Just clothes, books, and some frames.

For my 25th birhday I threw a party in the lounge in my building and blew out the candles on cupcakes held by I’ve never thrown a birthday party in the city before, and nearly every photo of me throughout the night was with her.

I thought of not writing about this at all, matching silence with some detachment of my own,

I read 52 books this year. The ones worth mentioning:

Two football games, a trip to Paris, a trip to Texas, many events, and many more friends made later, I look back on my calendar and rest easy knowing I packed as much as I could into this year.

Footnotes

1 From Silence by Erling Kagge.

2 I’ve encountered the metaphor of the “near shore” and the “far” or “other shore” in the Dhammapada, the near shore representing the worlds of samsara which I’ll describe as worldly attachments for the sake of simplicity, and nirvana, when one breaks free from the dualities of good or bad. One is “the way that leads back into the world, to the round of becoming, and [the other] the way out of the world, to nirvana.” See this commentary.

3In October of 1957, the most influential fashion designer of his time died and the House that sported his name was nearly shut down. The weight of the company fell on one 22-year-old designer’s shoulders: the young Yves Saint Laurent. In January of 1958, he presented his first collection and became a hero not only to the licensees of Dior who desperately wanted the label to continue to flourish, but also the French fashion industry at large. 50% of export volume was owed to the House of Dior.

4 Lauren Sherman in “Coach & Kors’ Marriage of Convenience”, August 14, 2023.

5 Dhammapada 145. Translated by Eknath Easwaran.

6 The books, in order as mentioned: Empire of the Elite by Michael Grynbaum, The Millionaire’s Factory by Chris Wright and Joyce Moullakis, The Nvidia Way by Tae Kim, The Iron Triangle by Dan Briody, They All Came to Barneys by Gene Pressman, The Partnership by Charles D. Ellis, eBoys by Randall E. Stross, House of Huawei by Eva Dou, and The House of Nomura by Albert J. Alletzhauser.