Open Letter: The Downside And The Up

The newsletter began as a hobby and became something greater. I’d do it for free if I could.

My intentional attempts at entrepreneurship were peppered with failure. This one was unintentional – it just sort of happened. For that reason, maybe it would work.

2PM was born out of the desire to understand commerce and how it interacted with other industries and professions. The concept was simple: Understand it well enough to anticipate how it will impact our markets over time. Arguably, there is no greater economic force, art form, or science today than commerce. Our world is being redefined by the intersections of commerce, technology, art, media, and economic policy. NFTs anyone?

Web Smith on Twitter: “Deep generalists are thriving and specialists are working to understand why art, science, media, finance, economic theory, commerce, religion, and software engineering are suddenly converging. / Twitter”

Deep generalists are thriving and specialists are working to understand why art, science, media, finance, economic theory, commerce, religion, and software engineering are suddenly converging.

The goal of the newsletter was to connect ideas and foster new ones. Many readers chime in happy with their heightened ability to replace abstract thoughts with actionable, practical strategy. The niche audience of 2PM is the deep generalist: The type of “beginner mind” who understands the value of finding meaningful connections between unrelated ideas (also called apophenia). At first, I could only find 12 of you who were interested. I sent letter No. 1 to each of them on March 22, 2016.

Today’s essay isn’t about growth hacks, monetization, or the joys of the creator-market fit. Rather, it’s about the mental and emotional cost of doing business as a solo creator.

Nearly two years after I sent the first newsletter in 2016, I still had a day job. I’d just driven my weekly three hours to Pittsburgh for an urgent meeting. My right leg was in a full-length cast following a catastrophic injury and a reconstructive surgery, and had to be propped in the passenger seat for the ride. At the meeting, I was told that my salary would be cut to 50% for the foreseeable future. In an instant, $120,000 became $60,000. The company was struggling and measures needed to be taken. I certainly understood this and I didn’t fight it. The acute problem was that I was on the hook for $37,000 in medical bills.

I was at a turning point. By then, I’d emailed over 200 free issues of 2PM. The writing had improved, the following slowly grew and the production process tightened with repetition. The list was peppered with industry leaders who would have never given me the time of day. Letting 2PM die wasn’t an option. In some ways, it was my best shot at really doing what I wanted: Make an impact on the industry that I love.

I made one call to a former boss of mine named Eric Yang, the founder of Gear Patrol. Over my time there he beat the Japanese concept of kaizen into my consciousness: “continuous improvement.” I knew that he’d have a practical take. His words continue to resonate:

You know that your head is with 2PM. Go all in.

My previous attempt at entrepreneurship had nearly bankrupted me and I had $17,000 in my savings account. While paltry, that figure represented tremendous progress. This made the next decision symbolic in ways. My intentional attempts at entrepreneurship were peppered with failure. This one was unintentional – it just sort of happened. For that reason –  maybe it would work, I thought.

I invested in the technical replatforming of The new stack was hosted by WordPress and I selected Mailchimp for email distribution. (Substack hadn’t yet made the waves that it is known for today.) For nearly 10 days straight, and in my spare time, I transferred 200+ email posts to the new site’s archives. A colleague of mine designed the 2PM mark and assets for $4,000. The rest of the savings went to subscription software, additional build outs, and legal documents. At the end, I had $1,026 remaining. It wouldn’t even cover our mortgage. I incorporated, I recruited the services of Memberful, and then I sent the monetization announcement.

The first issue on Mailchimp (No. 252) featured the original, cookie-cutter artwork. By No. 283, my coworker delivered on the brand standards, and the 2PM that you know today was born. By then, I felt that I’d done enough to prepare for the paid membership announcement. The stakes couldn’t have been higher. At my day job, salary cuts had escalated to company-wide layoffs, and I had about four weeks of runway. As a father of two, with depleted savings, I had a newsletter, a self-designed website, and 18,000 Twitter followers to promote them both. I remember looking at my then 10-year-old daughter and promising her that everything was okay. I was saying it for myself. At the time, it was not okay.

But there’s no way else to say it: 2PM actually saved us.

The first member essay published on February 23, 2018, two years after the initial newsletter reached inboxes. I published a short thesis on an idea that I coined Linear Commerce. Within a few weeks, I was covering costs and reinvesting what I could into further professionalizing the platform. By January 2019, I was able to host dinners and other gatherings. Meeting readers in real life became what drove me forward. And then, just one year later, a considerable part of 2PM’s growth engine, our monthly roundtable dinners, halted with the rest of the world’s meetings in February 2020.

Between February 2020 and today, the entire world changed. Customer acquisition strategies had to evolve with the constraints. Newsletters became an industry of its own thanks to Substack’s genius. Industry leaders The Hustle and Morning Brew exited. And outfits like Every, Not Boring, The Plug, and Trapital became forces in their own rights. The power of amateur-run media gave way to the professionalization of the industry. Readers began to expect perfection and consistency. With every letter, I sought to improve on the last. Today’s depth and quality of newsletter is representative of that commitment. But it comes at a cost.

Six amazing, dedicated, and consistently great part-time contractors assist in the creation of what you see. They are a cohesive unit. We’re honest with one another, and I am proud of the work environment. Each week, I read and curate over 40 articles. I write and publish 3,000 to 4,000 words. We send three letters. We manage a community of deep generalists. And with the help of 2PM’s crack team, we commit to 10-15 hours of weekly industry research that enables us to improve the reliability of our top databases. A DTC database that began with 700 cells is now a ranking system spanning 10,000 cells of constantly updating data.

With every email sent comes greater responsibility and greater feedback. Negative responses, trolls, and bad actors rise with every send. As more subscribers become paid members, the more I work to assure the quality of their monthly or annual investment into 2PM.

There is an unspoken truth. The intensity of five years of treading water, taking flight, and handling setbacks takes a toll on the soul. There is a mental and emotional weathering that begins to impact the people who matter most. If I struggle, the team around me is impacted. Over time, I’ve learned how to compartmentalize for their sake. A number of tough lessons litter that path.

If I had to do it again, I would have prioritized balance and superior communication. I would have spent more energy improving as a leader and less as a creator. I would have operationalized the company much faster. I would have delegated better, freeing myself to give more to the business owners and thinkers who email in with questions or requests.

And I would have found the time to take more breaks, at the cost of disgruntled emails or the loss of the precious momentum.

The creator economy needs a conversation around the pressures associated with the joys of the industry. The 2PM that I want to finish building is one that is even better every day, inside and out. What began as a hobby became my life’s professional pursuit. As more novice creators achieve the same, they will need support and empathy. The work is never as easy as it appears. Our oldest daughter was 10 years old when she nodded and gently replied to my promise that everything would be okay, saying “I know, Dad” as if promises always stick the landing. But for all of the strain that comes with building in public, it’s good to know that – at least for now – she was right.

By Web Smith

A special thank you to: Hilary, Andrew, Alex, Brad, Vincenzo, Joe, Katie, Grace, Meghan, and Tracey for your contributions to this first five years. 

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