Jack Cheng is a writer and designer living in Brooklyn, NY. He co-founded Disrupto, an interactive design studio, started Steepster, an online community of tea lovers, and created Memberly, a slick subscription service. Jack keeps himself quite busy, but still managed to find some time to chat with me about working from the road, lo-fi tools, work/life balance, starting your own thing, and living a well-lived life.
Justin Kropp: Jack, can you give us a bit of background about yourself?
Jack Cheng: My family moved to Detroit from Shanghai when I was five. I grew up in Troy, Michigan, whose claim to fame is being the hometown of the fictitious band Stillwater in the movie Almost Famous.
I went to school in Ann Arbor and majored in Communication Studies and minored in Econ. Summer of my junior year, I did an advertising internship that put me in New York along with sixty other interns. We were all from different parts of the country, all working at different agencies, and all living in student housing outside Columbia. It was a defining summer. You tend to rebel against what you grew up with, and for me I was ready to trade in oceanic parking lots, run-down strip malls and well-proportioned town houses for squealing subways, cloud-piercing skyscrapers and cramped apartments.
When I graduated the following year, I moved out to New York without a job and landed my first advertising gig by basically showing up there unprompted and working without pay for a month (they never asked me to leave). After three years in advertising as first an art director and then a copywriter, I quit my job, did freelance web design for a few months and then started Disrupto.
JK: More designers, and professionals in general, are embracing an exploration of different business models and founding their own startups. You did just that by founding Disrupto, Steepster, and now Memberly. What lead up to your decision to leave a full-time job and start your own?
JC: I realized I was too comfortable. I went to the park one day and wrote down all the various goals I had, then went back and circled the ones I thought I could accomplish in one, five and ten years. I don’t have the list anymore, but I remember writing that I wanted to start and run my own company. I saw that I wasn’t getting any closer to that goal by staying in advertising, and the hunger inside me was getting its edges sanded down by the act of coming up with a bunch of ideas to sell products, but rarely getting to affect the experience of the products themselves.
I wanted the lack of employment and stable income to motivate me to do something. I wanted credit card companies pounding at my door about unpaid debts, because it would only be a greater incentive to get out there and hustle. I left my job in fall of 2008, right when the big investment banks were on the verge of collapse. I remember going to our office near Wall Street on my last days of work and walking past news vans parked outside Lehman Brothers.
A new friend recently called me a chaos junkie, and I can see how it might appear that way from the outside. But to me it was a decision between staying put doing something I knew wouldn’t satiate me, or taking a chance and discovering what else was out there. It was an easy call to make.
M&Co’s 10-1-4 Watch serves as a daily reminder for Jack.
JK: There has been quite a bit of noise recently concerning the decision to move away from client services and start a product company. You have set up camp on both sides of that line. How do you balance your roles in both?
JC: Balance is a tricky word, because I think most people see it as this moment frozen in time, when the two sides of the scale are in equilibrium. To me, balance implies movement. A more appropriate instrument would be a pendulum—constantly swinging back and forth. With a scale, stasis is desirable, but with a pendulum, stasis is death.
Disrupto began as a product company when we built Steepster. When others saw the experience we’d created around it, they came to us asking for design and product strategy work. Our client services business took off, allowed us to build an amazing team, and when that was happening, we used whatever downtime we had to work on our own ideas. Now we’re swinging back over to building products with the launch of Memberly and easing up on the number of client commitments. Our product work feeds into our client work, which feeds back into our product work. One creates momentum for the other.
But I want to be clear—swinging back and forth between the two isn’t necessarily any better of a strategy than doing solely one or the other if you’re not primed for it. There’s this innate human tendency to want to have your cake and eat it too. We want both the control that product work affords us and the variety that comes with client work, but there are always tradeoffs. Trying to do both at once and with full force only leads to burnout. It starts with understanding what those tradeoffs are, and whether they fit with what you’re looking for as an individual or a company.
JK: Did your personal philosophy behind running Steepster influence your actions at Disrupto and vice versa?
JC: We bring our personal philosophies, consciously or not, to everything we do. The collection of philosophies, the way they overlap and rub against each other, makes up a company’s culture. We currently have seven people on staff and a full-time contractor, and every additional person has changed our culture in a significant way. You notice it when someone is out sick or working from home—the entire office has a different vibe, turning more serious or more whimsical depending on who’s there and who’s not. It’s a tremendous learning experience being around people with shared interests and varied viewpoints. We’re not going to agree on everything, but many times we come away with new frames for thinking about our life and work.
JK: Before starting Steepster, did you have any idea that it would become a success or that it would generate such a passionate online community, or did that even matter to you at the time?
JC: Steepster was born out of a personal need—I had stopped drinking coffee and was getting more into tea, and wanted a way to keep track of the teas I was drinking. At the time, the goal was to just get Steepster out there, to see if anyone else found it useful. And by that definition, we were successful. Once we hit that goal, our definition of success changed, and we set out to grow our community and improve the quality of information on the site. We did that in a bunch of ways, which again changed our definitions of success. Emerson uses the metaphor of a set of concentric circles—as soon as we find the edges of one, we push past it, discovering another one encompassing it, and then we expand past that into another. Circles upon circles, ever-widening, out to infinity.
JK: Can you talk about your year of travel for a moment? Did that experience influence your desire to author your own projects and start your own company?
JC: The year of travel happened after I had already launched the first version of Steepster, and was working remotely with my two co-founders. I spent time in Michigan and New York, out on the West Coast and in China and Japan. I get emails sometimes asking how I found the experience of working and traveling simultaneously, and I tell people that it was stressful at times, but I ended up learning a lot about myself.
I found that when I was in a familiar place—like Michigan or New York, or even my parents’ apartment in Shanghai, I was able to enjoy myself and still get a lot of work done. But when I tried that in a new place, it quickly got overwhelming. Whenever you go somewhere new, you’re burning through a lot of energy because you’re paying more attention, noticing more things, creating maps in your head that didn’t exist before. If you tack onto that the additional burden of dealing with deadlines and client obligations, you can see how it quickly gets to be too much.
We have a limited supply of attention every day and thus a sweet spot for novel experiences. Too little novelty and you’re bored. Too much and you’re overwhelmed. But with the right amount, you’re learning and growing. It’s the client/product pendulum all over again.
JK: On the topic of starting a company, does living in NYC present an entrepreneur certain opportunities that might not otherwise be found in another location?
JC: Opportunities can be found anywhere if you pay enough attention, though I do think that the sheer density of bodies and the friction they create here improves your chances.
But what I really love about New York is that it is absolutely humbling. You meet all these people at bars and parties, on trains and in grocery stores, and they’re all doing so many different things, in so many different industries. When you’ve been working in one area for a while and are getting good at it, there’s a tendency to feel like you’ve conquered the place. But New York has a way of swiftly knocking you off your pedestal. You meet someone who’s mastered an entirely different field and you realize that you’re a just tiny speck in the world. There’s always someone better, smarter, more accomplished, right across the room.
JK: From your experience in building businesses, what are some important initial steps and things to consider for the fledgling entrepreneur? Would you have done anything differently?
JC: Know yourself. Understand your feelings and desires, work to figure out what you really want. Read more. Especially fiction. Accept yourself for all your talents and flaws. Remind yourself why you’re doing this, that an entrepreneur in the purest sense is a person who takes responsibility for himself. A person who takes his life into his own hands. Let go of how you expect things to happen and pay attention to the miracle of the world unfolding in front of you.
I would’ve done all these things more, because they’re things you can never do too much of.
JK: For this same fledgling entrepreneur — whether they are in the design industry or not — how important is design in the success of that product, service, or community?
JC: I taught a class with David Cole recently, and the way we defined design in that class was “the act of making and breaking patterns to achieve a specific outcome.” I think this definition is broad enough that it can apply to anything. We synthesize our experiences into patterns and then consciously act to bring new ones into the world. When our early ancestors tied a sharp rock to a tree branch, they designed a hatchet. It one of the hallmarks of our humanity.
As a result, design can never be too important to a product, service or community because it is inseparable from these things. The patterns exist, whether you realize it or not, whether you act on them or not. You can always improve your understanding of the patterns that impact what you’re working on and develop more appropriate ones for the task.
JK: How important is building the right team and what advice would you give the young entrepreneur looking to build that team? Where should she look to begin making the right connections?
JC: We wouldn’t be discussing this if I didn’t have amazing colleagues and co-founders. The right team to me consists of a group of people who are simultaneously mentor and mentee, skilled at certain things and eager to learn about others. Honest communication is vital to how this knowledge and experience are exchanged, so it helps if you get along. To the young entrepreneur, I’d suggest starting with friends and people you’ve worked with in the past, particularly ones with complementary skill sets.
You also have to put yourself out there, let people know you’re looking. I met my co-founders Mike Potter and Jason Roos because one of them saw my blog post about leaving my advertising job and sent me an email. I met David Cole when I was in San Francisco last year and we hired him and Tag Savage for a project before they joined our team full-time. Our developer Ricky Cheng showed up to a Steepster meetup, and our other designer Matt Quintanilla knew Mike and Jason from their last job. We’ll usually start working with someone on a freelance or contract basis to see if we get along. And if the feeling’s mutual, then we’ll talk about a longer commitment. It’s like dating. If you’re not a good fit, then no harm done. But you have to first put yourself out there.
By the way, we’re looking for a lead Rails developer :)
JK: You are a proponent of utilizing lo-fi tools and processes to accomplish certain tasks and protect us from being overwhelmed by technology and distraction. Can this strategy extend into redesigning our everyday activities to live a more fulfilling and productive life?
JC: I like lo-fi tools because they tend to enforce modal constraints. When you’re reviewing a printed sheet of paper with a pen in your hand, you’re more or less locked into an editing mindset. Whereas if you’re staring at that same document on your computer screen, it’s easier to find yourself jumping back and forth between a creation mindset and an editing one, never giving the latter enough time to sit with the work.
But at the end of the day, I think lo-fi tools and processes are a false idol, because in a way, you’re shirking the responsibility and putting it on the tool. True progress is made through developing the internal constraints—namely your self-discipline and willpower. I remember reading that Thoreau himself said any idiot can go off into the woods and find peace and solitude (I’m paraphrasing here), but it takes an uncommon individual to maintain it amid the hustle and bustle of modern civilization.
True fulfillment and productivity come from applying your tools with intent. The tools can be lo-fi or hi-fi, analog or digital, but the intent stems first and foremost from a mastery over self. Your tools will not save you.
JK: How has your life changed since leaving your job and founding Disrupto, Steepster, and now Memberly?
JC: It’s been absolutely incredible. I’ve grown tremendously in the past three years. I’m more relaxed, confident, and aware of my thoughts and feelings. I love going to work. I love learning new things, and I’m continually improving myself. I feel like I’m experiencing the world closer to the way I did when I was a kid, the result of unlearning some of the biases and tendencies I’ve picked up over the years. I have a more accurate picture of reality, and that’s been liberating in a lot of ways.
I did an exercise around this time last year where I pretended I had six months to live. At the end of it, on the night before my “last day,” I wrote out a sort of will, a final letter in my notebook before I went to bed. I read the letter every few months, and in it I wrote that “I may not have accomplished everything I dreamed of accomplishing, but here, today, I’m at the best I have ever been.” The very last words in the letter were simply, “I am profoundly happy.”
JK: I believe it is important to achieve a healthy work/life balance. For many, though, there is no stability. No downtime. How important is this separation and how do you work towards maintaining this parity?
JC: Life is what shapes us and work is how we take that and affect change on the world. We’re back to the pendulum again. Just like traveling and freelancing, just like serving clients and building products, it’s ultimately about the way the two flow into each other, the back-and-forth motion. Life and work are never strictly separate, not masses on opposite ends of a scale. They’re two states of the same thing. And you’re the clockmaker, fine-tuning the motion between those states. It’s up to you to keep the clock regular.
I’m a big proponent of journaling, because it builds self-awareness, which is always the first step to improvement. I’ve been journaling almost daily for two and a half years now, and it helps me recognize the irregularities. I believe we all have a natural understanding of the appropriate timing for ourselves but the problem for most of us is that it’s buried under layers of false expectations and misplaced obligations. Honest journaling helps you face your own fear and neglect.
These days I journal in a new blank text document on my laptop every day, but when that’s not accessible I’ll use pen and paper. Buster Benson’s 750words.com is a great way to start out if you’re looking to build a journaling habit.
JK: Lastly, where are you going next in life—literally or metaphorically?
JC: I don’t have any other major trips planned outside visiting family in Asia for the holidays. My friend James wrote a phenomenal photo memoir called The Road to Somewhere, about him renting a car whenever he had free time and driving out into America to see what he’d find. It’s inspired me to take more smaller trips here and there. I’m also trying to reserve time on the weekends to wander the city without an agenda. I did it when I first came to New York, I do it when I travel, and I realized that even after living here for 6 years, there’s always more to discover, and the place you call home tends to be the one you take most for granted.
Aside from that, Disrupto, dating and spending time with friends, there are one or two side projects I’ve been working on that I’m not ready to talk about yet. Those words I wrote in my 6-month letter are still true today and I live and work every day to make sure they stay true.