Arash Ferdowsi is co-founder of Dropbox, which first partnered with Sequoia in 2007 as a pre-product-release seed startup with a headcount of two—and is now a multi-billion dollar public company. Arash is also the proud owner of three cats—Gucci, Priscilla and Collette—who have their own Instagram account.
A few years ago I was introduced to a personality typing system called the Enneagram. It’s different from something like Myers-Briggs, which feels overly scientific to me because it’s sort of a set of on-and-off switches—you’re either an introvert or an extrovert; a thinker or a feeler—when actually, you can move between those states. In the Enneagram, there are nine core personality types, and the idea is that everyone embodies all nine, but we each have one type that’s dominant and represents our intrinsic temperament. For example, my dominant type is individualist. I tend to value authenticity and doing things differently.
The Enneagram has helped me understand not only my strengths and weaknesses, but also my gaps in self-awareness, and it’s made me better at empathizing with people who are wired differently than me. Often it can help you figure out what’s at the root of conflict, where one person really cares about something that the other doesn’t value as much. We’ve done a bunch of Enneagram workshops at Dropbox, and there’s actually a spot in our company directory where you can add your type if you want to. When you’re growing as quickly as we are, it gets both more difficult and more important to collaborate effectively, and I think a culture of self-awareness and empathy is key.
Much of what is special about Dropbox can be traced to some of our earliest hires. At that stage, you have to find people you’ll trust to make the right decisions, because if you micromanage great people, they’re not going to want to work for you for long. Part of it is just hiring brilliant people, but it’s also about hiring people who have experience and truly know their craft. We had some key early hires at the senior level who Drew and I fully trusted and who were great cultural fits, like Sujay Jaswa on the business side, who eventually became our CFO. Aditya Agarwal was also transformative. He joined as our VP of Engineering at a time when we had a lot of people who were right out of school. None of us had actually managed anyone before, but he had that experience from Facebook and knew how to scale. It’s critical to not only land really great people, but to also give them the space to lead.
Meditation. It’s so easy to get distracted by the unrelenting stream of text messages and Gchats and emails. We context switch constantly these days, which makes it hard to focus and be present in the moment.
I started about three years ago, at a time when I was feeling pretty burnt out. I took a little break to work on getting healthier—I started eating better and exercising, as well as meditating. I’m up to about 20 minutes of meditation a day now, and it definitely helps me to be more measured and less emotionally reactive.
When it comes to building products, people say something needs to be 10 times better than the alternative before someone will switch to it, but I wish there were a way to be more scientific about that. How do you truly know when a product is sufficiently better? That would help us figure out when we have a product issue versus a growth or marketing issue.
On the sillier side, I also always wonder what my cats are thinking. What makes them tick? Do they really care about me? Sometimes I think they do and sometimes I don’t—there’s certainly attachment there, but it could just be because I’m the person who gives them food and belly rubs. Either way, their psychology and motivations are fascinating to me.
Right now I have Play Bigger, which Bryan Schreier recommended. I haven’t started it yet, but it’s about company-level positioning and category creation, which is important for us at Dropbox. It’s essentially what we did with version 1—elegantly solve several common problems around files with a simple interface—and now we’re trying to do it again with content, by tying together the collaborative universe. We need to not only get the narrative right, but also get the whole company behind it.
Another book that I read a while ago and liked is Creativity, Inc. I think it’s important to understand how fragile innovation is. It’s especially tough at scale—as a public company, there’s a lot of focus on things like quarterly earnings—but we need to be mindful of protecting teams from dynamics that can starve innovation. Especially when an idea is in its earliest stages, you need to give people room to explore without too much fear of failure. If you’re reporting on it to the entire company from the beginning, for example, that’s a recipe for disaster. There are too many eyes on it, and people will feel like they have to rigorously prove that the path they’re pursuing is going to work. But in reality, there’s always going to be a lot of failing and learning before you get to the right answer.
When we were starting out, I think Drew and I struggled with people who were more direct and confrontational. Certain personality types intrinsically have more trouble with other personality types, and that direct type—in the Enneagram, they’d be an 8, or Challenger—was a hard one for us. We were too sensitive to confrontation. But we’ve learned to be more conscious of our biases and to understand that when someone’s direct, that doesn’t mean they’re upset or a mean person. Now nearly half of our management team are Challengers, which never would have been possible before Drew and I recognized our own issues. And we gain so much from having those people on the team. You need people who aren’t afraid to speak up when something’s not working. Without them, we probably wouldn’t have some tough, important conversations.
I’m pretty introverted, so recharge time feels particularly valuable to me. There are lots of different charge cycles—a year is one, because we tend to have that natural reset at the end, where you can go home and spend time with family and step away a little bit. You’re naturally less reactive and more reflective. I think a day is a cycle, too. If you’re fried and stuck at the end, a good night’s sleep can make a big difference.
And recharge time doesn’t necessarily have to be downtime. One thing I like to do is have a full day where I focus on something I’m passionate about. Right now, it’s the design of our new HQ; I’m spending most Thursdays in design sessions or visiting the construction site to see the progress. Anything that energizes you can be a chance to recharge.
- Protect innovation
- Recognize your biases
- Empathy is key