Last Friday I attended the second SEED conference in Chicago. The “One-Day Conference on Design, Entrepreneurship & Inspiration” is put on by 37signals’ Jason Fried, famed Chicago designer Carlos Segura, and Jim Coudal of Coudal Partners, The Deck, and other endeavors. We’ve been fans of 37signals long before they became a product firm, when their website looked like this, and of course are ever fans of t.26 and other Segura efforts.

The day was a bit scattered. Each of the sponsors presented separately about individual key learnings and the overlap occurred in periodic Q&A. These three clearly have some common ground: Segura was one of the 37signals original partners, and Fried and Coudal share an office space in Chicago. But they come from different places and have separate pursuits, which became evident as they presented. When asked, I found myself at a loss for words when describing the conference I was attending. Their description is fitting. It’s a day of three accomplished individuals — designers — talking about their entrepreneurial efforts and what inspires them. Not a bad way to spend the day.

The common theme was about taking risks to persue personal/business ventures beyond client work. The goals were varied, but they included developing alternate forms of income, and/or as a way to generate interest in the firm. For 37signals, the new channel led to a change from a design services to a product firm, whereas Coudal and Segura have sideline moneymaking ventures which serve as “internal” clients and lessen their reliance on consulting work.

There was a part of me that didn’t like some of their motives — several came to these ends out of frustrations doing client work. As Yang pointed out upon my return, there is a little part of this that is like giving up. That we, a professional designers, should be able to overcome challenging client situations without becoming our own clients. Surely that can’t always be the answer.

Still, there were several good nuggets which made me glad that I went.

Segura is a real designers’ designer who creates beautiful work and reminds us that you have to work to be fresh. That designers advocate for the users, the market, and that they should seek the truth and be brutally honest with clients. That it’s easy to be cool, but better to be smart. Amen. Of course I wonder if this technique can work for all designers… Segura has achieved a higher order of cool than most of us will, which begs the question whether he’s the norm or the anomaly.

Fried is a designer of sorts, but is becoming more a productivity guru with a machine-like focus on dissecting business norms. He appears to live by his own “cookbook”, Getting Real, advocating that “Meetings are toxic”, “interruption does not equal collaboration”, and that one should always strive to make small, incremental decisions. Small decisions are progress and when you make them, you can’t make big mistakes. Truly a proponent of agile development. While I find many of these ideas compelling, I struggle to find their place in more formalized settings, corporate environments, or consulting engagements. Still, I took the most notes here.

Coudal lives to prove the theory that following your passion — commercial or non-commercial — will lead to success. Try anything, stay curious, be willing to fail. He made the same connection I made recently about how a design firm is like — our perhaps should be like — a Montessori school. I’ve been exposed to a bit of this method through my son’s school and feel like I could lift all this language and put it directly into our HR manual. Coudal’s criteria for work are: Can we make money? Can we do work we’re proud of? Can we learn something new along the way? Otherwise, all bets are off.

Here are few quotes I picked up that bear repeating:

“Communication usually fails, except by accident.”
— Osmo Wiio, communications theorist

“You can either outspend or out-teach your competitors.”
— Kathy Sierra, Creating Passionate Users

All three share have become serial entrepreneurs, by design or default. Each advocates being very honest, starting with yourself, and the value of giving away information — sharing what you know. I admire each of them on different levels, and we can learn from their examples.

A footnote to those who may want to attend SEED 3, if there is one: The conference was held at IIT in the new campus center by Rem Koolhaus, a fantastic building worth a trip to the south side of Chicago to experience. Further, the day included a lunchtime presentation about the new building and the adjacent Mies Van Der Rohe’s Crown Hall — the “Parthenon of our era” according to presenter and NPR personality Edward Lifson. Koolhaus was told that he should not put his new building so close to the Mies masterwork, out of respect, to which Koolhaus responded: “I don’t respect Mies. I love Mies.”

This alone made the trip worth it.