Using Commerce to Understand Everything

Welcome to Free Radicals — a collaboration between Everything and Sherrell Dorsey, founder of The Plug. Free Radicals is a limited series celebrating those who embody lleadership in this moment. Each edition features a conversation between Sherrell and a leader in tech, focusing on equity, advancement, and progress. This is the second edition, featuring Web Smith.

To read previous editions, and sign up for future updates, click here.

Enjoy.

“Everything we do revolves around consumption and selling,” says Web Smith, founder of the commerce newsletter and community 2PM. 

“It’s the foremost American expression.” 

This is not a cultural critique as much as a framing for Smith’s insights into how the retail world operates, and why it matters. Commerce is not just about commerce. It’s about race, class, technology, opportunity, family — everything.

At 2PM, Smith doesn’t just dig into the numbers. He looks at what leaders are doing, and what they’re thinking about doing next. And he connects today’s circumstances to the history that led us here.

One of the most compelling aspects of 2PM is the deft way Smith mingles deep data sets with historical narrative context, using thrice-weekly essays to explain not just what Americans are consuming, but how and why. He’s as much a sociologist as a trend forecaster. Smith has a way of moving seamlessly from retail and entrepreneurship, to access to capital and real estate, to the social forces, particularly race, that shape the market. A conversation with him might leap from retail square footage in the U.S. to Brown v. Board of Education to the current pandemic. Makes you understand why he chose the name “2PM”—“to polymaths.” 

Nothing about Smith’s delivery or his approach is dry. “I clearly take the writing aspect of my job very seriously,” he says. “I do want to be taken seriously as someone who is putting in the work journalistically; but I want people to know that when I write something, it’s as an operator, not merely an observer. If I put numbers or a thought on paper, there’s someone behind it, doing that or about doing that—there are no takes or opinions. I’m doing my best to tell you what’s going on behind closed doors, without breaking non-disclosures or breaching trust.” 

In this second edition of Free Radicals, Sherrell Dorsey speaks with Smith about the future of retail, the intersection of race and commerce, why how and where we buy things matters, and what it’s like to be a Black founder on the internet.

You write about trends in commerce and business and the future of employment, sometimes in the context of your experience as a Black person. What is it like talking about race and culture with CEOs and entrepreneurs?

It’s always scary for me because I know that when I ruffle some feathers, it’s likely to have at least some negative outcome. But especially at this juncture in time, I feel I have to do my best to authentically represent what I am. I can’t set aside some parts of me for the sake of economics. 

For example, I wrote a piece about my grandmother and Juneteenth. I realized I had to write it when I was being interviewed by Modern Retail, and they asked me to name folks who are direct-to-consumer founders of color. I couldn’t do it. There’s Tristan Walker, of course, but outside of him it was really difficult to think of names. 

This made me upset. I have to keep in mind that I’m probably the closest that a lot of folks have to that voice, that Black founder voice, in their circles. I’m typically the only one in the room, right? If I don’t say something, then they’re not going to hear it. 

Not long after that piece — which is about Black people waiting to be recognized as humans, as citizens, as entrepreneurs — was published, you tweeted that it had resulted in unsubscribes because members felt it was outside the bounds of 2PM. How do you manage that? Does chip away at you a little bit?

It hurts. It hurts me a lot. I take everything personally and I can get really bent out of shape.

How does that affect the way you show up on social media? How do you balance these kinds of difficult but important conversations with the regular insider, ‘business expert’ tweets most people in tech respond best to? 

I don’t have a strategy on Twitter. What people see on Twitter is that I’m in this all day, every day. I’m thinking through problems, trying to solve issues, obsessing over data, working on new insights seven days a week, 24 hours a day. I sleep maybe five hours, or four-and-a-half a night if I’m having a bad day. And so people recognize that my mind is always there and I’m publishing from a passion perspective and not merely an economic one.

Twitter’s not the best platform to have nuanced dialogue. Where are you having those conversations, where there are maybe opposing viewpoints on difficult questions?

I have a lot of great discussions like that in Polymathic [2PM’s membership community for commerce and media leaders]. It’s a confidential community. I try to invite people that I believe are capable of nuance. We keep it civil, but we have in-depth conversations that can be very complex. I’ve taken pride in the community that I’ve built there, and I hope that I can continue to scale it in that form.