20 Questions

This Entrepreneur Shares the One Word You Need to Build a Culture That Lasts

Asana co-founder Justin Rosenstein explains why teamwork is everything.
This Entrepreneur Shares the One Word You Need to Build a Culture That Lasts
Image credit: Courtesy of Justin Rosenstein
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
12 min read

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

Justin Rosenstein began his career at Google and Facebook, but working in product and engineering management, he quickly found that as much forward movement as there was in those kinds of innovative tech environments, so much progress was stymied because of the time spent coordinating logistics around something as simple as booking a meeting.

With his co-founder Dustin Moskovitz, with whom he worked closely at Facebook, the pair decided that they wanted to make it easier for anyone to stay on top of their goals. So in 2008 they founded Asana to better help teams keep track of their work and manage their tasks and milestones.

“McKinsey has a study that over 60 percent of people's time is spent on [doing] work about work, which is wild,” Rosenstein told Entrepreneur. “And so we [thought] if we can improve that even just a little, if we can make it even a little bit easier for people to collaborate then we can unlock so much human potential.”

This emphasis on clarity, communication and collaboration has paid off. Today, Rosenstein says Asana is used by over 35,000 paying customers, including organizations like IBM, Lyft, Spotify, NASA, General Electric, Teach for America and the city of Providence, Rhode Island.

The company has raised more than $163 million in funding and its annual revenue has grown by over 80 percent per year since its launch. The platform is used in 192 countries.

We caught up with Rosenstein to ask him 20 Questions and find out what makes him tick.  

This interview has been edited for clarity and brevity.

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1. How do you start your day?
I do some combination of meditation, running or yoga in the morning. Meditation is really valuable for getting centered and being able to get into the the mindset required to be present for the rest of the day. And for me, there is no substitute for cardio and exercise to get into an energized place for the rest of the day. Then I do at least five minutes of journaling on three things I'm grateful for, along with three intentions I have for the day and what will make it a great day.

2. How do you end your day?
Mostly by not using technology and actually taking the time to sit quietly and meditate again or do slower yoga. I'll also do some journaling to reflect on what things went well and what I could have done better that day. Sometimes it's the same thing that I've said many days in a row. By reflecting on it, I'll eventually get through it and be able to make that thing better.

If you become 1 percent more efficient every day, then you're able to get 15 times more efficient every year. It's often tempting to look for a silver bullet in life when it's just the hard work, day in day out.

3. What’s a book that changed your mind and why?
The 15 Commitments of Conscious Leadership by Jim Dethmer, Diana Chapman and Kaley Klemp. It is about shifting from a way of being rooted in fear, drama, and scarcity to one born from curiosity, honesty, and win-win possibilities.It changed my mind in the literal sense; it changed the structure of my mind.

I approach problems in a different way after having gone through that training program. I'm much more able to notice when I am making myself a victim in a situation. I'm able to zoom out and take a much more creative, playful perspective and see how you always have options, and a lot of things that were constraining me were just stories in my own head. It’s provided a lot of cognitive freedom with which to approach problems in both work and life.

4. What’s a book you always recommend and why?
The Untethered Soul by Michael Singer, is a great secular introduction to many of the insights that underlie the great spiritual/wisdom traditions. In my experience, wisdom traditions have so much to offer us in cultivating our ways of being and working, yet their insights are often shrouded in jargon. The Untethered Soul covers important topics like questioning your thoughts, letting go, non-duality, and the nature of the Self with enjoyable, accessible, non-dogmatic writing.

Related: Use This Successful Entrepreneur's Scheduling Secret to Have Your Most Productive Day

5. What’s a strategy you use to stay focused?
I try to queue up a task list in the way you might queue up a playlist. You make a playlist once, hit play, and you can listen to all the songs in the order you cue them up in.

I try to do that with my task list. It's my one prioritization and triage process.  I go through the list. During that time, I put my phone on an airplane mode, close the applications that could distract me and irrelevant browser tabs. The temptations of multitasking are great since it makes you feel more productive, but research is clear that interruption is a huge productivity drain. I am not always successful by a long shot, but that is my strategy.

6. When you were a kid what did you want to be when you grew up?
At age 12, I wanted to be some sort of hybrid of a monk and a creator of software that helped people work together. I'm not totally sure about why it's of interest to me at age 12 but sure enough, that's what I did.

7. What did you learn from the worst boss you ever had?
Humility. I think it's important to listen to people that you work with, even if you have higher status than them. When you're a leader, maybe you have more context, but the people who are on the ground doing the work, often have a lot more information about that specific area. So, I try to defer when possible. I try as much as possible to let them be the decision maker, and we've incorporated that pretty deeply into the way Asana works. We have this distributed responsibility model.

8. Who has influenced you most when it comes to how you approach your work?
A friend of mine, the performance artist Amanda Gregory, talks about erotic productivity. It is not about sexuality, but it's kind of like finding the juiciness in whatever you're working on. It's like instead of letting work be a slog, how can you stay connected to the part of those tasks at hand that you find attractive and make it more playful.

9. What’s a trip that changed you and why?
A few years back, I went to the Amazon in Peru. I also visited rural Kenya and spent time with people who were living very different lives than me. Those trips made me feel more connected to humanity. Seeing the ways people live very different lives, yet a lot of the things we enjoy and struggle with are fundamentally similar.

Related: Shark Tank's Barbara Corcoran Explains Why You Must Make Time in Your Schedule For Fun

10. What inspires you?
I'm really inspired by what people can accomplish working together. I look at all of the challenges that we face as humanity, and it feels like they come down to insufficient collaboration. We have enough food to feed everyone; we're just not distributing it well. It is certainly within our grasp to develop technology for sustainable energy. Asana is a manifestation of that -- trying to solve software that enables teams to work together more easily but that extends all the way to the global level of what is going to take for us as a species to collaborate effectively as one.

11. What was your first business idea and what did you do with it?
As a teenager I built one of the first discussion forums on the internet. It was called The Road Less Traveled. It was kind of like a proto Facebook group specifically for discussing philosophy.

12. What was an early job that taught you something important or useful?
My first job out of college working was working at Google. Google is an amazing company and gets a lot done, but nonetheless, going from being a solo programmer to then working on teams I was so frustrated and disappointed. Once you start working on a team, let alone at a big company, you end up spending very little of your time actually making stuff. You spend the vast majority of your time talking about making stuff and not doing work, but doing work about work -- just coordinating between people. At first I thought I was doing something wrong, and then realized actually, no this is just what work is like and what people do every day. This led to starting Asana as a solution to our problems and making it easier for teams of people to work together.

13. What’s the best advice you ever took?
A mentor at Google once gave me this advice: Use “we” instead of “I.”

When I was young and foolish, I found it tempting to talk about my product or my plan. This was really demotivating to the team, and it was inaccurate. It's much more honest and inspiring when you change your language from me to we. That wasn't just a language change, but the beginning of a whole change in my attitude and a much greater emphasis on teamwork.

14. What's the worst piece of advice you ever got?
When I was an undergrad in college there was the normal computer science track you're supposed to go through. You take prerequisites and more and more advanced classes. I had grown up programming and knew some things but had gaps in my knowledge in other places. I started taking classes that were meant for Ph.D. students, and I hadn't taken the prerequisites. The professor took me aside and said you may be getting by now in this class, but at some point it's going to bite you. At first I took him pretty seriously, but eventually, I realized that actually going in someone else's sequence is too constrained a way to live. I thought about the people I admire; they made up their own path.

Related: This Entrepreneur Shares Why an Ability to Change Course Is What Will Set You Up for Success

15. What’s a productivity tip you swear by?
One thing comes to mind is overcoming procrastination. I struggle with this quite a bit, and the solution I've found that works is to identify the source of discomfort and face it. The reason I'm procrastinating is there is something about the task that I'm supposed to do that makes me just slightly uncomfortable. I'm going to have to disappoint someone, or think about a hard problem that I don't know the answer to yet. So, I just need to be real about it, and breath into it. And then suddenly it's not such a big deal. I can handle that.

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I recommend everyone have a single place to keep every detail of what you're working on in your life. I have a project for each part of my life. The calm that comes from not having to keep a running list in my head of all these things I need to do, knowing that list is waiting for me and that everything is in one place organized is critical.

17. What does work-life balance mean to you?
When people think about work-life balance, they think about the compromise they are going to make between maximizing output and maximizing enjoyment in life. I think that's a false trade-off . For me, work-life balance is actually work-life maximization. It's finding that sweet spot where I'm both maximizing my work output and maximizing my ability to nourish myself.

18. How do you prevent burnout?
Staying inspired by the mission. I think some people have the attitude of you found your calling once work is fun, and not what the world needs from you. I never bought that. There's a lot of things the world needs that are not fun and that are important to do. If you believe in the mission and the higher purpose of what you're doing, even on those days when it gets really hard, you can come back to that mission and remind yourself this is important and why it matters. That's what keeps me going.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
Walk away. Go for a run. Visit nature or meditate. Sometimes it's hard to meditate, because you feel like you’re procrastinating, but I know well enough now, that it's not. Another strategy is jamming with a buddy. If I'm stuck in my own head, and I can't figure this out, finding someone else who is also passionate about the problem and bouncing ideas back and forth is helpful.

20. What are you learning now?
Equanimity. When you're doing something you're passionate about and working hard, it is natural to become stressed about it.  All the time you spend being stressed and worrying is time and energy that would be better spent on just thinking about the problem. The attitude of the emotional state of worry has never been as helpful to me as the emotional state of curiosity and of playfulness.

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