Steph Smith: Writing for a 7-figure paid newsletter

What’s your background? Have you always been a writer?

It’s a long story and certainly a non-linear path. Just 5 years ago, I finished my degree in chemical engineering. Throughout university, I worked in laboratories and did multiple academic research projects: one in civil engineering, one in forensic science, one in liquid crystal displays, and another in battery material discovery. I found the analytical work compelling, but unusually slow-moving. So, after university I decided to try out management consulting. There were things I loved about that role as well, but I knew almost immediately that the 2h+ daily commute and the client bureaucracy wasn’t for me. 

I spent almost a year looking for a remote role that would allow me to travel the world, while still advancing my career. I happened to luck out and join Toptal, eventually spending years there -- first as a member of their growth team and then leading their Publications team. After that, I started my own company to work with several companies, including the Hustle. I did a lot of research and writing for Trends for nearly a year, before eventually leading the entire product. During my time at Toptal, I also began to learn how to code, which led me to launch a few products, including my personal blog, which has been read by over 400k people since launching last year. 

It’s been really interesting to see that people now refer to me as a writer. I have always thought of myself as the more technical breed (in the past, I actually really struggled with writing), but it’s been something that I have learned to love. And as part of that journey, I’ve learned to accept that my journey is fluid, so who knows where I’ll be in 5 years. :)

TheHustle is one of the largest and most popular newsletters in the world. How did you get the gig?

Sam found me! I started writing my blog in early 2019 and it quickly took off. Several of my articles went viral. The first one that got really big was You Don't Need to Quit Your Job to Make and the second was How to Be Great? Just Be Good, Repeatably. Both of these (and two more of my articles since), went to the top of Hacker News and ended up being read by over 30k people. 

By the time the second was making its way around the web, Sam had heard of me. But this time, he reached out and wanted to get me involved with Trends. By that time, I had spent 3 years at Toptal and also 3 years as a fan of The Hustle. I wanted a new challenge and Trends sounded like the dream challenge that bridged my love for data, writing, and entrepreneurship. If I could give advice to anyone, whether they are actively looking for jobs or not, it would be to openly create things online when people aren’t watching. Anyone can hype themselves up in an interview, but the best way to find great people or access opportunities that you didn’t even know existed is to show what you can do when “no one is watching”. You can read more about being antifragile with work here.

You can guide someone on how to improve their writing or show them great resources to leverage, but it’s much harder to train someone to determine whether something is interesting.

What does your job look like?

The Trends gang is a surprisingly small team within a relatively small company. I can say with confidence that I have never worked on a team that moves faster. And I wouldn’t have it any other way, since that makes everyday a new learning opportunity. Some days, I’ll be researching new Trends, others I’ll be analyzing our growth data and launching new campaigns, or others I’ll be engaging with the thousands of people within our community.

What is it like to work at Trends? Related: are you involved at all with TheHustle’s free newsletter?

It’s a wonderful job to have. I essentially get paid to do what I enjoy and would likely be doing anyway: following my curiosity. Every day, I get to learn from smart people, research new industries, and dissect innovative business models. I do some work on the daily newsletter, but am mostly focused on Trends

Trends is famous for its in-depth, well-researched content. Can you explain how the process works and how do you decide what trends to cover?

Thank you! Without going into too much detail about the process itself, I think we’re able to create such great content because of the people we’ve hired. Most, if not all of our Trends hires have come from some sort of referral and we have gone through many dozens of other applications along the way. And perhaps what may surprise most people is that we don’t necessarily hire for writing ability or prior business experience. In fact, we have a previous community manager on the team and similarly, a blockchain consultant. 

What we instead vet for is someone’s ability to understand what people find interesting. That might sound vague, but it’s intuition that you cannot teach. You can guide someone on how to improve their writing or show them great resources to leverage, but it’s much harder to train someone to determine whether something is interesting.

Once you have great people like this in place, you also can give them the freedom to explore their curiosities. We don’t have a single person on the team that determines what trends to cover and that’s a great thing. Instead, we hire smart people that consistently identify opportunities on their own and we lean on our community for ideas as well. 

As for determining how deep to go, we’ve trained out analysts to consistently ask themselves the question: “If you showed this to 10 people on the street, how many would be delighted?”, which more actionably means, “How many of these people would not know X or be surprised to learn X?”. If a report isn’t on a topic that is unique enough and/or doesn’t go deep enough, this question can help surface that.

A free newsletter typically serves the function of entertainment. As a paid newsletter, your content must err on the side of truly being a “need to have”.


I’ve read some of your reports and they are quite impressive. What are some writing tips you’ve learned?

As mentioned above, it’s best to follow your curiosity. Make a habit of doing this, meaning that even if you’re not writing a long report about something, start a note on your computer where you log interesting things that you stumble upon. Revisit this document often. Make a habit of hearing a fact and investigating it further. If you hear of an interesting public company, make a habit of diving into their public filings. If you’re looking for more tips relating to the process of getting the words onto paper, I went over my personal process here.

Trends is one of the largest paid newsletters in the world, with revenues already above 7 figures. What are some differences between writing for a “traditional”, free newsletter and writing for a paid newsletter?

The most obvious difference is the level of expectation. A free newsletter typically serves the function of entertainment. With a free newsletter, if you do a good job of providing value to the subscriber on a relatively consistent basis, they will keep you around. But with a paid newsletter, you need to be nearly always excellent and if possible, be solving a real problem for your customers. Now, to be clear, entertainment can be a form of solving a problem for someone, depending what they’re trying to solve. But perhaps a better way to understand the concept is the difference between selling a vitamin versus a painkiller. As a paid newsletter, your content must err on the side of truly being a “need to have”.

The most common mistake that anyone makes when starting a newsletter is investing in writing, but not distribution.

Paid newsletters are all the rage. What are some tips for anyone who has a paid newsletter or is thinking about starting one?

First, understand why paid newsletters are taking off. Since the age of the internet, the barrier for entry to publishing online has slowly been withered away. This is a great thing in many ways: for one, it makes it possible for anyone to participate. But with a lower barrier to entry, it means that many people add to the online library because everyone else is doing it or to make a quick buck. That has made the ratio of good content within the growing sea of content lower over time. In other words, it becomes harder for people to find and access the best stuff. With that, mediocre content has become a commodity. The best way to stand out, whether you’re a paid or free publication is to “trade” on quality. For that very reason, more people are willing to pay for content, if they truly solve a problem for them. Again, make sure that if you’re starting a paid newsletter especially that you are solving some sort of problem for the reader.

Likewise, what do you think are some common mistakes of folks with paid newsletters?

The most common mistake that anyone makes when starting a newsletter is investing in writing, but not distribution. People often spend 90% of their time writing and a fraction of their time in distributing their content. No matter how good content is, if you don’t invest in getting it in front of people, no one will see it. 

The writing: distribution ratio should be more like 50:50. Harry Dry’s Marketing Examples newsletter is a great place to learn more about how to distribute your products.

Trends has a referral program like TheHustle’s. What’s the difference between TheHustle’s referral program and Trends’?

The Hustle has an ambassador program where people get rewarded through things like swag or getting to be part of an exclusive referral community. Trends referral program was recently re-launched, but operates more like a traditional SaaS referral program, where people can give $100 and get $100 in cash.

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