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As the Editorial Director at Smooch, Dan Levy is the force behind The Message, a fortnightly company newsletter that digs into the way communication technologies (email, messaging, chat, voice) impact the way we connect to each other and how brands connect with customers.

For this issue of the Letterlist interview series, Dan talks about his curation and editing process, his top 5 newsletters, the true value of publishing a company email, and why the traditional values of journalism are critical for the modern web.

Tell me about Dan. Where are you? Where did you grow up?

I was born and raised in Montreal and I’m still here, after stints in Boston, DC and Vancouver. I studied journalism and then slowly found my way into working for startups but I still think of myself less as a marketer than a writer/editor/storyteller whose “beat” is marketing and communications.

What else are you working on? (feel free to introduce Smooch and any other projects)

In my role as Editorial Director at Smooch I oversee the company’s brand and content strategy, a really fun job that includes writing articles, industry reports and (of course) newsletters about conversational technology like messaging apps, voice assistants and chatbots. I also do some consulting work for a variety of interesting companies that are looking to express their values and vision in a compelling, story-driven way. Oh, and I also write songs and record music!

How did The Message come about?

When I joined Smooch at the end of 2017 it quickly became clear to me (as it had to the company’s founders, who brought me on) that the rise of messaging wasn’t just a business or tech story but one that impacted all aspects of society — politics, sex, religion, arts and culture, you name it. I started seeing relevant and fascinating stories about this stuff everywhere but there was no single publication curating them and, more importantly, providing context and insight into why they matter. The Message came about to fill that gap and to help showcase Smooch’s unique vision and expertise along the way.

You obviously think a lot about messaging at Smooch? Where does email fit into the modern communication ecosystem?

It’s funny, because while Smooch is known for messaging, our product also integrates with email. That’s because we believe brands (which doesn’t just mean businesses but also non-profits, government organizations, political campaigns, etc.) should be engaging with their communities wherever they are. Almost everyone uses email and it’s one of the only digital channels that isn’t owned or mediated by a private company. It’s an incredibly powerful (and personal) channel if used responsibly. I myself only let a handful of high-quality newsletters into my inbox and those are the first things I read every morning.

Which ones? … I might add them to Letterlist.

I suspect you’re already familiar with most of them! I like the Quartz Daily Brief for a quick and smart summary of the news. The Hustle does a good job covering the tech industry, though it can be a bit bro-y sometimes. Seth Godin is consistently wise and inspiring and mercifully succinct. I’ve also been digging CB Insights these days. It’s full of original research and analysis and is just a great read.

How many subscribers do you have, right now? What have you done to attract an audience.

We currently have around 2,831 subscribers. We’ve built our audience in two key ways — one is by publishing related content like our annual State of Messaging reports and then giving those readers the opportunity to subscribe to the newsletter. The other is by asking new users of Smooch (through our sign-up flow) if they would like to stay up to date with industry news and trends. I haven’t run the numbers but a significant percentage of people who sign up to use Smooch also opt in to receive The Message, and most of them stick around!

I’m obsessed with other peoples’ process – let’s nerd out a bit on how The Message comes together. What’s your workflow? What tools do you use? Who else is involved?

The Message comes out every other Friday so on the Monday before I spend a chunk of time catching up on unopened newsletters and Google Alerts and relevant links I’ve come across on Slack and Twitter but left sitting in one of the way-too-many tabs I have open. I like doing this at the beginning of the week when Friday is a distant thought and I can let my mind wander without a deadline looming. I use an awesome bookmarking tool called Milanote, which lets me highlight particular quotes and file them under different “boards” I’ve created (think Delicious meets Pinterest).

I start writing on Wednesday, once I’ve collected enough string and the big stories of the week have emerged. On Thursday I update and edit and edit some more and then share my draft with some trusted team members for feedback. Friday morning is when I transfer it from Google Docs to MailChimp, further refining and trimming it as I go. Then I schedule it for 11:45 AM and hold my breath.

Interesting that you’re formally trained in journalism. Now that anyone can (and will) publish anything on the internet, are we overlooking / at risk of losing important aspects of journalism? Discuss.

I think the value journalists bring to the information ecosystem has become abundantly clear since 2016. Fairness. Fact-checking. Attribution. Free speech. Empathy. Truth-seeking. Storytelling.

These aren’t just journalistic values but democratic/humanistic ones and I don’t think you need to write for The New York Times to subscribe to them. I try to uphold these principles in whatever work I do and seek out the work of others who do the same, regardless of where they’re publishing. Are we at risk of losing them? Yes. That’s why we must fight/write back!

What’s the economic model for The Message? Do you quantify where it fits into the business model for Smooch?

The Message serves multiple business objectives for Smooch. We don’t quantify it by any one metric. It helps us build and nurture relationships with our customers and industry peers, demonstrate our expertise and credibility in the space, distribute the content we produce on other channels, and drive demand for business messaging and, by extension, Smooch. Almost every time I talk to one of our customers they tell me they read The Message and recommend it to their own customers and colleagues. So we’re pretty sure it’s working.

Where do you see messaging going over the next decade? What changes? What stays the same?

I think “messaging” will cease to exist as a category on its own and just become the de facto way we communicate. In Asia, for example, the way most people text is to send short audio messages back and forth. It’s both futuristic and a throwback to good old fashioned phone tag! The smart speakers in our kitchens and living rooms (Alexa, Google Home, etc.) will likely become messaging portals. And we’ll be able to do just about anything from within the chat window — order a cab, play a game, watch the Oscars with friends on the other side of the country. The big question mark for me is interoperability — will we all be able to send messages to each other regardless of which phone or app we’re using — as with traditional SMS-based texting — or will Facebook, Google, Apple, Amazon and whoever comes keep us in their own walled gardens?

What big idea would you love to work on if you had unlimited time and money?

I’d like to think that if I had a clear answer to this question I’d already be working on it — because you don’t need unlimited time and money to make an impact. But it would probably have something to do with changing the paradigm around masculinity. And it would definitely involve writing.

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