Writing a Must-Read Newsletter

An Interview with Web Smith

We hopped on Clubhouse with Web Smith, author of the newsletter 2PM, to chat about his writing process, the ins and outs of writing a weekly must-read newsletter, and managing a media business.

For more interviews and insights like this,
subscribe to our weekly newsletter.

How would you describe 2PM and what you do?

is short for “two polymaths." It’s a B2B publication for the e-commerce industry, but it has a deep generalism angle.

I believe you get better at your own vertical by understanding other industries, practices, and educations. The newsletters we write are broad curation, and the essays include ideas that wouldn’t commonly touch each other in a traditional publication. If a publication is about brands, then you're rarely going to hear elements of sociology or history and vice versa.

What is the origin story of how you started to write and publish online?

It was close to the 2016 election. I wanted a place where I could read about my industry without having to read political coverage. Every single publication at that time found ways to talk about the election. I sent the first newsletter to twelve friends and I committed to 180 issues, five days a week. 

When I got to 180 issues, I realized there were people on the email list that would have never talked to me in real life. And I had developed a strong audience, maybe not in number, but in depth. That’s what made me decide to continue and move towards a monetization strategy.

What have been the biggest factors in improving as a writer?

It’s mostly just daily practice. The cadence I committed to early on forced me to write almost every single day. And I was writing and getting feedback from readers so frequently, it impacted my writing. 

Nowadays, one of the biggest factors is my team. The team is now seven people, six are part-time. People like Hilary Milnes who used to work at Digiday and now works at Vogue Business. Their professionalism has elevated 2PM into a much more polished and corporate publication.

Have you dealt with imposter syndrome at all as you’ve grown 2PM?

The short answer is that I still deal with imposter syndrome now. It only gets worse over time because more and more people expect consistency and perfection.

Early on, I treated 2PM as a student. Every single day, I spend hours pouring over data, old essays, and historical context. The problem is I can come off as an expert, even though I don't really consider myself to be one. But I’d venture to guess that I might know my niche a little bit better than most people do because I’ve spent so much time studying it.

Do you have any advice on picking ideas or categories to write about?

For me, the number one thing was to find something I was passionate about changing. I wanted to broaden people's perspectives and provide depth.

The most important thing about 2PM is helping readers understand that e-commerce is infrastructure. It’s no different than the bridges, railroads, telephone lines, power lines, and railroad tracks of the 19th and 20th centuries. If readers begin to see it that way, then it will impact how they operate within their own industries, whether it's traditional retail, healthcare, education, you name it. I'm trying to educate readers so they can anticipate changes and get ahead of the curve.

Can you tell us about your writing and time-management routines and how they have changed over time?

The most important thing I would say is: do not do what I do. I have two daughters and I try to be present for them. That means when they need to go to practice in the evening, I take them to practice. What that means for me is when they're in bed, I'm usually up until 2:00 or 3:00 in the morning. 

Writing this much and having to hit home runs often creates a level of anxiety that I don't think people can truly understand until they do it for themselves. I'm not trying to scare anyone away. There are obviously a lot of gifts that come with this work. But anxiety has developed over the last several years because when you write for the public and you're judged every day, it can be really hard on your psyche. 

I wake up at 7:00 or 7:30 am, so I typically get five hours of sleep at night. Then I work out and I start my day. And that's about six days a week. I'm in the process of operationalizing and removing myself from some parts of the equation, but that's a slow process because it’s hard to duplicate how I think about my writing when using freelance writers.

How important is the frequency or consistency of publishing?

Consistency is really important, especially if people are paying for it. Right now people are paying $200 per year. That's not a small sum of money. Therefore, we have an obligation to produce. Some days are harder than others. Some days there's not enough news and 2PM relies heavily on the news cycle. 

And so I try to honor that commitment because this is my full-time job. My kids think that they have it made, and part of that is because of how much work I do with 2PM and I don't want to jeopardize that.

What are some of the hurdles you’ve overcome as you’ve continued to grow your audience?

The hurdles never leave, they only compound. The difference is, I stopped looking.

For the first three or four years, I looked at the unsubscribe list every single day. I stopped and that alleviated a lot of pressure and daily psychological damage.

A great practice to start early on would be to just continue publishing. Look for feedback, but don't stress over the people that want to leave because the more people that leave, the stronger your niche.

At 2PM you’re writing and running a business at the same time, how do you think about the balance of the two?

The short answer is that I don’t love writing, but I love having written.

This started as a hobby and became my life. I was bored and curious and it snowballed from there. Being a newsletter writer is an exhausting job and it’s not for everyone. And unless the economics are right, you’re not going to continue it.

Foster is a community of writers elevating their craft.
Apply here!

You can follow Web on Twitter here, or subscribe to his newsletter 2PM

Write With Us