Director of Brand Strategy , Twitter Japan and Asia Pacific
“Whenever I see an opportunity, I go for it. I am comfortable with a high degree of uncertainty -- constantly reminding myself "what’s the worst that can happen?” It's common for us to overestimate the downside and underestimate the upside.
What is the most surprising thing about you that most people don’t know?
Left high school early and was a volunteer firefighter until going to University. My goal was to go to the army, but unfortunately I didn’t listen to myself - it was the last time that happened.
What are the most important decisions you made in your career?
There’s really only one decision, and that was to always ask for more than anyone (including myself) thought I could handle in terms of workload, responsibility.
When I worked as a production assistant in the film business, I was “a helping hand”. I drove trucks, paint sets, move things around. Having known the streets of NYC like the back of my hand, I saw an opportunity in location scouting. So I went out, took some pics and next time a producer was asking about locations, I showed my pics with some suggestions. Then next day I was scouting locations and organizing film permits. I didn’t know how to do it, but I knew I could figure it out.
Since then, I’ve had three different careers, and expect to have a few more before my flame burns out. I first worked at HBO, a pay-TV network that didn’t have commercials; from there I moved into digital advertising making ads at an agency; today I work at Twitter as a brand and social media expert.
Whenever I see an opportunity, I go for it. I’m comfortable with a high degree of uncertainty -- constantly reminding myself “what’s the worst that can happen?” It’s common for us to overestimate the downside and underestimate the upside.
What will be the most valuable skill for your profession in the next 3 years ?
As someone in the marketing & advertising space, from a skills perspective I don’t see big changes over the next three years. People get too caught up with the technical aspects of “digital” broadly speaking. The truth is that the methods of persuasion used in advertising haven’t changed much over the last few thousand years of recorded history. It’s rooted in human truths exposed in great storytelling. I’m constantly exploring what that is, and how to use interesting tools to tell interesting stories.
Being a great storyteller is a hard skill to master. It’s a skill that you typically hone throughout your life. The Economist recently published an article “Why so many artists do their most interesting work in their final years” highlighting artists like Van Gogh, Beethoven and others who did their best work towards the end of their life.
The tools available to us will continuously evolve - a process which is non-linear. There’s no doubt we need to know when to retire old tools and adopt new ones. This is especially true for technicians, for whom new tools are always being invented. Surgeons for example, may spend 10+ years in school, yet when a new tool is invented to improve outcomes in surgery, they need to go back and learn how to use this new tool. They are never done learning.
Of course, there are outliers. Woody Allen has used the same typewriter for over 50 years, writing every film script he’s made on it! There’s something beautiful about his process which works for him, and results in films I continue to enjoy.
As it applies to digital media: when I was in film school in the late 90’s we learned how to use film cameras; video cameras were a novelty. In 20+ years the industry has completely changed. And change is coming again. I was recently giving a talk about VR and 360 live video broadcasts. In the transition from film to video, the canvas remained a 16×9 rectangle. With the introduction of 360, the canvas is now the inside of a sphere -- and it can be live! The new ways you can tell a story and deliver an experience are incredible, but first, how does one begin to think about that canvas? For sure, this is exciting and an area for storytellers to explore.
But the story is the story. You can get very stuck with a tool and lose the story.
What’s your worst mistake and how did you overcome it?
My biggest personal mistake was when I decided not to go to the army. And that came from not listening to myself. I wanted to be a battlefield medic. I knew I was good in high pressure situations.
To prepare myself for the army, I joined the fire corp while still in high school. But there was a lot of pressure for me to go to the university. So I applied to only one university, hoping I would not get accepted. I got accepted and it was Film Production at New York University, which was really hard to get into. To this day, I think I should have deferred University and gone to the army first.
On a professional level, when I first came to Singapore, someone told me: “get the culture right and everything else will work itself out”. I heard those words, but looking back I didn’t really understand. I understood what it meant, but putting it into practice was harder than I ever imagined.
In Singapore the diversity is more pronounced than anywhere I’ve lived or worked. It’s an amazing facet of this city, but also a big hurdle to overcome. We have people from all over the world, coming with a wide range of communication styles and expectations on how things are done.
At first, I was very focused on operations, bringing revenue in and I assumed everything else will come together. And there I learnt in a strong way what a leadership means. Spending most of your time getting the best out of the people. Now every day I make sure I do something to bring my team together.
What’s your biggest ambition now?
I am a strong believer in lifelong learning. If I could focus on anything today is to drive an environment of lifelong learning.
What is the most interesting book you have read and why did it impress you?
Very hard… not sure I have the most interesting book. I read a ton. Two books I think about a lot, and which I gave to my team over the last two years are:
Setting the Table Broadly because I love the restaurant business, and he breaks down so nicely what it means to work on a team, have a customer-first attitude rooted in service, and how to draw on your passions to achieve things no one, including you thought you could do.Zen and the Art of Motorcycle Maintenance This book asks a remarkable question “can you define quality?” In a creative industry such as mine, this question strikes at the core of what we do. The book explores “romantic” views and “classical” views on how to determine what is “good” — in my industry this is a classic dichotomy. Is something good because it works well? or because it is built beautifully. You can argue that Apple has balanced this out better than most companies, which is why they’re so unique.
I’m currently reading Bruce Lee, Artist of Life. It’s a collection of his essays. The man was simply amazing and we’re lucky to be able to learn from him. I’ve been exploring philosophy lately, specifically stoic philosophy, so I’m seeing it everywhere I look.
What talks (such as TED) or podcasts do you listen to?
Exponent hosted by Ben Thompson and James Allworth – a must if you want to understand what’s going on in technology today.
The Knowledge Project by Shane Parrish. I love how humbly inquisitive he is. He conducts great interviews.
Invest Like the Best by Patrick O’Shaughnessy. While it is generally about investing, I find Patrick to be a really smart guy who gets amazing people on his show. His interviews with Morgan Housel, Eric Maddox, and Brian Koppelman (just to name a few) barely touched on investing money, but were more about how to invest your time. Amazing people with amazing stories to tell. Patrick is also a really well-read person who manages the discussions remarkably.
This American Life – easily the best storytellers around.
Song Exploder – wonderful bits of music by a great selection of artists, who tell the story of how they created a song.
What industry websites, blogs or influencers should we bookmark right now?
This is a hard one as my bookmarks list is as long as my arm. I love Farnam Street and Brain Pickings. Honestly, a well-curated Twitter feed is the single most important tool if your goal is to know what’s happening in your industry (and I’m not saying that as a company man). This is true if you’re a biologist (@annewhilborn is amazing - there’s an Atlantic article about her), or if you’re in the digital space @eskimon, @ejacqui, @karaswisher, @jonrussell, @newley are all great.
What are you going to learn in the year ahead?
I’m going to delve into a lot of philosophy this year. I’ve been devouring courses on Coursera, and reading some of the classics like Meditations, which I never read before.
I’m also hoping to find time to re-watch and re-read some of the books that had an amazing impression on me years ago, such as several of Eli Wiesel’s books, Shantaram, among others. Might also be a good time to re-read Ayn Rand.
Follow Steve Kalifowitz on Twitter @skalifowitz
“Whenever I see an opportunity, I go for it. I accepted to be comfortable with a high degree of uncertainty and always remembering what’s the worst thing that can happen.”
Twitter. Twitter has 328 million monthly active users globally; over 35 offices around the world and employs 3,860 people worldwide.
Explore the career journeys and resources that shaped the Great Owls
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“You’ve got to learn how to un-learn and re-learn again. Things are changing very fast, you can choose to complain about it or you find a way how to get involved.”
“Whenever I see an opportunity, I go for it. I’m comfortable with a high degree of uncertainty — constantly reminding myself “what’s the worst that can happen?”