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Why the CEO of Caraway Sends Himself 20+ Emails a Day

We sat down (over Zoom) with Jordan Nathan, the CEO of Caraway, to talk working from home, productivity, and scaling his rapidly growing DTC brand during a pandemic.

Home Work Issue No. 1: Jordan Nathan, Founder & CEO of Caraway

Jordan Nathan is the founder and CEO of Caraway, a direct-to-consumer cookware brand that features safe, non-toxic materials and colorful designs. Describing himself as “disorganized-organized”, Jordan’s unusual productivity system has helped him guide his team through both a $5.3 million seed round and a global pandemic.

Tell us about your home office or wherever you’re getting most of your work done these days.

I don’t have a home office—I live in a very small apartment in New York with my fiancée, so we both have to make that work. We’ve been bouncing around quite a bit, from New York to Connecticut to Maine. Right now, I'm with my fiancée at my parents’ house by the beach. I actually work in bed pretty often, although we just got a new dining room table in my NYC apartment which has been a great addition. I like to move between my bed, couch, and dining room table.
Since I don’t have a monitor or fancy keyboard, I’ve gotten used to just plugging in my laptop and headphones and working from anywhere. Even back in college and high school, I always worked in my room and on my bed—luckily I’m one of the few who can do that without getting distracted or falling asleep.
What’s one aspect of your home office that influences your productivity?
Something as simple as opening up my curtains and getting more light in my room can make a big difference. I also have a wooden lap desk that I’ve used since high school—it’s great because it lets me work from anywhere. Once the lap desk comes out, it’s game time.
How do you deal with distractions?
My schedule has become more flexible—I’ve been starting my days earlier, which can help. It’s nice when you’re at the office because there’s always people to talk to, and you can leave to grab lunch or go for a stroll. At home, I’ve learned to be more flexible with my days. There are times when I just don’t feel like working—I’ll hit a wall and can’t sit down anymore. In general, I’ve become more comfortable pushing meetings and shifting my schedule around.
When it comes to distractions, I live by the High Line, so I’ll go for a walk while I take calls. It’s a good way to get in a better headspace and focus on work. I know some people take a break by going on their phone or watching TV, but I spend too much time staring at a screen. If I need a break I’ll go outside for a walk or run my apartment’s stairs which has become my new exercise routine.

I’d imagine you’re spending more time in the kitchen these days. How has this change influenced the way you think about your products, and has it inspired any new ideas?

I wouldn’t say products, necessarily, but we have definitely become much more active with social and content. We launched a blog a few weeks ago, we’ve built out our marketing team, and we’re constantly evolving our strategy. I think we’ve created an active space where customers can reach out for tips and advice. Being able to spend time in the kitchen has helped me and my teammates get into our consumer’s mindset, which lets us become more of a resource for our customers.

I'm disorganized-organized and have been since well before COVID.

Tell us how you stay organized and productive. Do you use a physical planner or online tools?

I’m “disorganized-organized”, and have been since well before COVID. I have around five places where I keep notes, and my main method is that I actually send emails to myself for both work and personal tasks. My email inbox is my task list—I’ll use tags to organize different types of tasks, and the body of each email is empty with a one-sentence reminder in the subject line. If an email is unread, it represents a task I still need to do. I’ll send myself at least 20+ emails a day. I’ll also have some Google drafts up and my Mac’s Notes app.
Your email method sounds like a digital version of writing reminders on your hand!
Definitely, only sometimes I accidentally send them to my teammates…they’ll get empty emails with a subject line telling them to do the laundry.
What made you gravitate towards email?
I already spend most of my time in Gmail, and I’ve created an organized system of unread emails, things that needed followup, etc. I want to centralize all my work into one place. We use Asana as a team along with lots of other tools and platforms across the brand. But since I’m typically the one assigning, Asana isn’t super helpful for my own tasks.
So do you always have a really high number of unread emails?
I do my best to keep it pretty low—the only items in my inbox are things that I need to answer within a short timeframe. So, currently 268 emails which is lower than usual. I feel less stressed when that number is lower! It’s actually a pretty good metric to track my mood.

As Caraway grows, how will your productivity system and management style change?

I think it’s too early to know. We launched in November, so we’re a little under a year old. As our team has grown to 11 full time employees and a few part-time as well, I’ve been getting a lot more emails and meetings are filling my day. It’s worked so far, and I think as we continue to grow I would look into either hiring some more help or possibly having two inboxes to separate my work and personal life. I don’t think I’m quite at that point, though.
From a workspace perspective, I think scaling will definitely pose challenges. I have lots of product samples at my home—it’s so important to be able to feel and test out our prototypes. However, they take up a lot of space and there is definitely a point where you can’t do that at home. At some point I’m going to run to my office to grab my monitor and keyboard; I’m sure that will make me more efficient. I didn’t expect COVID to keep up out of the office for that long, so we didn’t really make plans at first to get everyone’s monitors from the office. We’re making plans now to set up everyone better for work from home.
On the topic of getting your team adjusted, how have you changed your approach to hiring and other elements of scaling up?
We’ve actually onboarded about six or seven employees remotely—we have more remote new hires than not! In general, the process definitely takes longer because we have new potential hires speak with more people on our team. We also have every candidate complete a project before they’re hired; it’s a good way to vet but also a chance to see them present and see how they interact with the team. For example, if it’s a growth hire we’d have them look at a dataset and present some recommendations based on their findings. It lets us see how someone works digitally with our team.
Until about two weeks ago we’d been video-off for most calls; we’ve switched to a video-on policy since. This helps everyone feel more engaged, and we’ve made it clear it’s a judgement-free zone (pajamas on a call are totally ok). It’s nice to see peoples’ faces and it makes it easier to feel a sense of normalcy.

Our company will always need some type of physical space to test out new products, but that doesn't necessarily mean an office space.

If you do eventually return to the office, do you think some of these changes will stay for the “new normal”? For example, more breaks to go walk outside, doing calls instead of in-person meetings, and remote hiring?
It’s something I’ve put a lot of thought into, but don’t have a final answer yet. I think through the end of the year we will definitely be out of the office—in the long-term, it’s unlikely that we’ll be fully remote. It’s possible we might have a mostly remote model with occasional in-person meetings. However, for our company, we will always need some type of physical space to be able to try out and test new products, but that doesn’t necessarily mean an office space.

About a month ago, Forbes ran an article detailing your successful $5.3 million seed round—what was it like raising capital in a time of so much uncertainty and volatility?

We were fortunate to have started the process months in advance, so a lot of the COVID impact hit at the end. Our round was mostly filled, but with February’s market crash and then COVID, angel investors became even more cautious. Towards the end of the process, we had a handful of investors drop out, which meant twice the work. We had to just keep pushing and give it our all, and eventually, we were able to recoup it.
Had we started post-pandemic, I think we would have been in a very different position. Even so, as the pandemic hit we saw that lots of the questions changed– investors became concerned with our supply chain being in Asia, or they would be more focused on helping their current portfolio companies vs. investing in new ones. Investors became much more focused on immediate risk as opposed to the companies’ long term potential; as a $400 product manufactured in China, it was tough to address these concerns.
How did you address those concerns? Did you point them towards trends around an increased interest in healthy eating and cooking?
Yes, we ended up making a new short deck to address this. We were only a few months old, but we had enough data to show that our customer base wasn’t going to be too affected by the virus.

Was it weird at all to raise from investors when you’re both at home? Did it feel more casual, or more intense?
When I was raising, people were still adjusting to remote work and we usually just spoke over the phone. It was definitely harder to get a followup call—when things were normal I’d be able to bring investors into our office showroom so they could see for themselves how great our products are. Not being able to do that was tough—even with great photography, it’s not the same thing.

There has never been a better time for content and all the ways you can provide value outside of your physical products.

What do you think are the unique challenges and opportunities that DTC companies such as Caraway are facing in the midst of the pandemic?

Funding can be really difficult in the consumer segment, and it’s probably 10x more difficult because of COVID. Entire categories are struggling– travel, and clothing, for example. On the flip side, when it comes to opportunities there has never been a better time for content and all the ways you can provide value outside of your physical products. We’ve always wanted to become a destination for people interested in cooking and design
I also think that the falling costs of brick and mortar could present an interesting opportunity. In addition, I’m sure people will be making lots of lifestyle changes—they are going to be more comfortable doing a group call with friends instead of going to a bar, for example, and businesses will need to adjust to that.
That’s a great point about providing value outside of the product itself—lots of DTC companies have a goal of becoming a lifestyle brand.
For sure. I’m also expecting that we will see a lot of new ad channels crop up that can reach people in their homes. Facebook and Google rates have been fluctuating for various reasons, and we also have big retailers pumping lots of money into digital ads. It’s too variable to say what to expect, but it’s fair to say that certain existing channels will become much more challenging to sustain, and new channels and growth tactics will arise.

On new furniture, exclusive sales and more.

Thank You!