Jay O’Callahan – Storyteller
Storyteller Jay O’Callahan held the 99U audience in the palm of his hand as he moved through a dramatic recount of NASA’s first moon landing. Using the classic “show, don’t tell” technique, Jay wove some golden threads of wisdom about the art of storytelling and the art of giving feedback into his tale:
- Stories are people, place, and trouble. These are the core ingredients in any good story. Stories, and the people in them, are what unlocks our imagination and allow us to transport ourselves into a situation.
- You must have listeners. A story isn’t a story without an audience of listeners who are participating in the imaginative experience. To give our work value and evolve it, we must share it with an audience when it’s ready.
- “Appreciations” are crucial to nurturing stories and art. As Jay put it, “Leave it to the ignorant to just point out the faults.” More important than nitpicking in the early stages of creation is gathering appreciations. Ask your listeners what’s alive in your story, or in your work. That’s what you should emphasize.
Masamichi Udagawa & Sigi Moeslinger – Partners, Antenna Design
The husband-and-wife design team of Antenna Design, who have masterminded such huge projects as designing the new NYC subway cars and ticket vending machines, sat down with host Josh Rubin and Behance’s Scott Belsky for an in-depth conversation about creative partnerships. Some of the tips and insights shared, included:
- Test-drive the partnership. Do a trial project with a potential partner to test the viability of the relationship before getting in too deep.
- Be ready to share ownership of ideas. A successful partnership requires a willingness to share ideas and credit.
- Don’t be afraid to disagree. If you aren’t disagreeing, then something is missing. The disagreement generated in partnerships is “productive friction.”
- A good partnership is more than the sum of its parts. Partnerships should be based on aligning complementary traits and skill sets, so that together you can accomplish more than you could alone.
- Friendship is not a partnership. Don’t confuse a good friendship with someone who can be a good fit as a partner. Successful partnerships are ones that help you make ideas happen (i.e. produce a result), and create and enjoyable working environment.
Martin Ping – Executive Director, Hawthorne Valley Association
Decades ahead of the now-booming organic/sustainability movement, Martin Ping has been cultivating a holistic vision in New York’s Hudson Valley for more than 20 years. With a 400-acre biodynamic farm as his centerpiece, Martin heads up the Hawthorne Valley Association, a nonprofit promoting social and cultural renewal through the integration of education, agriculture, and the arts.
For Martin, making ideas happen is all about aligning your inner vision with your outer work:
- Transforming society begins with transforming yourself. To manifest change outside of ourselves, we must start by creating an authentic inner picture of (and belief in) what we want to manifest.
- The capacity to pause and reflect is what it means to be human. We are losing what distinguishes us if we fail to periodically take a step back and contemplate the meaning of our work in the world.
- Set aside time to focus your attention on your intention. In the hustle of the everyday, it’s easy to lose sight of our true goals as we react to the people that surround us. Take time to break from your normal routine and make sure your actions are aligned with what you want to achieve.
Frans Johansson – Author & CEO, The Medici Group
An extremely energetic and kinetic speaker, Frans Johansson took the stage and jolted the audience to attention like an electric shock. After a breathless 75-second personal history to introduce himself, Frans talked about the importance of risk-taking and trial-and-error in pushing innovative ideas forward.
- The purpose of a strategy is not to come up with the right answers. It’s to enable you to act. Or, as former Southwest Airlines CEO Herb Kelleher put it, “We have a strategic plan; it’s called doing things.” Frans talked about the development of Sweden’s no. 1 tourist attraction: the ice hotel. The strategy? To “sell” winter.
- Groundbreaking innovators generate and execute far more ideas. After a series of small-scale failed executions (e.g. an ice exhibition, an ice gallery, an artic hall), the creator of the hotel finally hit on the idea that worked, the one that people wanted – an ice hotel. (In one of the earlier ice project iterations, he realized people loved laying on ice beds for some reason!)
- What is the smallest executable step that you can take to develop your idea? Define it. Don’t blow your wad on the first execution. The only reason the ice hotel idea was ultimately realized was because the creator first pursued his intial ideas using minimal resources. Then, by the time he hit on the right idea, he still had the means to execute it.
John Maeda – President, Rhode Island School of Design
Designer, computer whiz, and now university president John Maeda closed out the day with a discussion of a little-touched-on topic: The awkwardness of the creative enterprise, and the challenges of having leadership thrust upon you. Presenting from his fascinating pictorial cue cards, Maeda delivered a deeply thoughtful talk, blending pragmatic advice and koan-like insights:
- Make money. Artists and creatives need to understand money as a medium. John recounted his Yoda moment with idol Paul Rand (“the Michael Jordan of graphic design”). Much to his surprise, Rand told him to make lots of money. Why? Making a decent living will allow you to create what you want.
- Don’t get angry, it’s not useful. In discussing the wonderful awkwardness of creative leadership, John talked about how he gets to “field lots of anger” as a college administrator, but he doesn’t get to “feel lots of anger.” Also, getting angry only makes you look silly.
- All artists yearn to struggle, when they struggle they know they’re alive. So what happens when you become a leader, and you’re no longer struggling? Or you’re not allowed to show that struggle? How do you lead creative people? The answer to this question is something we need to contemplate as we will be leading more creative teams in the future.
- We all have the ability to live with ambiguity, and live with mistakes. (Everything is going to be okay.) Creative people love making mistakes and learning from them, and we don’t mind hanging out in the realm of uncertainty. It’s these qualities that define us, occasionally drive us crazy (or make us feel awkward), and that will ultimately see us through.
Cool Hunting Videos
A huge part of what makes 99U so distinctive as a conference are the amazing stories that our partner Cool Hunting’s original videos bring to the table. This year, we premiered new CH video profiles of Swedish bed-making company Hastens, food revolutionary Jamie Oliver, bean-to-bar chocolate makers the Mast Brothers, and Nike CEO Mark Parker. You can watch the new Hastens video right here. We’ll link to the rest of the videos as Cool Hunting rolls them out online.
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If you missed our first 99U Conference recap, you can read Part 1 here.





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