How I Email: Sam Rosen, Co-Founder and CEO, DeskPass
Email is a non-negotiable part of everyday life. For some, it’s an unruly time suck, but enlightened email users have systems to ensure they’re not a slave to the inbox. We’re asking smart thinkers to give us a peek inside their inboxes, share tips, ideas, gripes, and everything in between.
Coworking pioneer Sam Rosen says his dynamic inbox is a “source of great joy and anxiety.” That duality is easy to comprehend considering how much Sam is juggling — he’s the CEO of DeskPass, a monthly coworking subscription service available in six U.S. cities, and is also a founding partner of the digital design agency One Design. In the interview, he discusses chasing Inbox Zero, what drives him nuts about communication in 2017, and how being a designer affects his inbox preferences.
This interview has been edited for length and clarity.
What’s your system for managing your inbox?
Typically I try to review each email quickly and read it so it’s read. I used to use a tool called SaneBox when I just used Gmail’s interface. SaneBox is awesome just because it’s machine learning and it gets good at taking the not-important crap out of your inbox.
Now I use a tool called Newton, which is like a local email client that I use on my computer and my phone. After you send an email, Newton allows you to have it come back up in your inbox on a certain date if it hasn’t been replied to. I rely on that heavily.
I always have this thing between my to-do list and my inbox, and oftentimes there are things in my inbox I send to my to-do list, and things on my to-do list I send to my inbox. But I try to have things only live in one place. I use Todoist, which plugs into Newton. I can press a button and turn it into a to-do, but Todoist will keep the nested email information in it.
There are two other features that I like. Undo, so I can press command+Z if I realize I’ve fucked something up or I want to rethink my email before I really send it. So you can unsend emails for about 10 seconds. Then it has receipts to see if people open the email. I used to find that kind of creepy, but I adore it now. I’m fundraising and dealing with a lot of investors and people who I have to get a hold of, and being able to go back to that original email and know no one opened it versus this person has opened it four times, just gives me a little more context to work on my next email and how I address it.
I am strict and obsessed with my inbox. It’’s a source of great joy and anxiety in my life, and I feel like I am always chasing the elusive Inbox Zero. But I am not someone who has given up yet. I think oftentimes my anxiety correlates to my unread inbox count.
What made you decide to use Newton rather than just the Gmail desktop interface?
I’d always used Mac Mail since I’ve had an email address. But Mac Mail has turned out to be so shitty — it’s hard to search, and it crashes a lot. It just wasn’t working for me anymore. I’m sure there are ways to get around this but I have about five Gmail accounts because I use Google Small Business and I have a different Gmail account for each company. So Newton has a unified inbox so I can see all the emails at one time. And I like the way they just kind of keep things organized in one central inbox in place.
And then the other thing is that I’m a designer and I’m kind of a snob. Newton is minimal and very clean. When you’re writing, it doesn’t feel cluttered or messy, it just feels like a blank canvas. Having it on my phone, having it on my computer — it just works well. But I’m always in constant pursuit of a new email solution. I never really got deeply into Gmail. I love Google’s mail service, I think it’s great, but I like having a native Mac client.
A lot of entrepreneurs and founders seem to mingle their personal and business email accounts. Where do you fall on that?
I like keeping the correspondence separate. Even if somebody emails on the “wrong” email, I’ll reply from the right email address.
I get a few hundred emails every day. I don’t have a deep folder systems or nested tags or anything like that. So just being able to approximately know which account this is in and who it’s from is kind of an easy way for me to parse through stuff.
What’s one of your biggest frustrations with email?
One thing that just drives me crazy that I wish was a problem that was solved — I’m getting emails, text messages, I get encrypted text messages through Signal, I get messages through Twitter, and Facebook, and LinkedIn, and Instagram. And one of the biggest problems I have is: I know I got a message from you, but I have no freaking clue where it is. That drives me nuts!
Someone like me who’s an entrepreneur, has multiple business, I’m getting hundreds of emails a day — and it’s almost always someone who wants something from me or wants me to do something for them. It’s really noisy.
I know from my email communication and through the people who communicate to me, I really value people who can break the monotony of the normal fucking email. When I write emails and the emails that I respond to the most are emails that feel like they came from a real human with a real personality that are sometimes kind of goofy.