post cover

How Dru Riley of built a six-figure, one-person newsletter

Learn the techniques, mindsets and frameworks Dru used...


Wes Kimbell

Jul 21 2021

10 mins read


Can't think of a business idea? Then you should check out, a service by my friend Jakob Greenfeld. His newsletter makes it easy to learn about profitable opportunities that are outside of your day-to-day worldview. Get a free premium report and two bonus resources straight to your inbox if you subscribe today 👉

We've all dreamed about doing it. Saving up a bit of money, quitting your job, and building a nice business for yourself that frees you from the 9 to 5 corporate life.

And some of us have done it. But the reality is only a handful of people actually take the plunge. Even fewer become successful. Most fail and return to the corporate gig.

After studying Dru Riley of, I believe if more people understood the simple rules that Dru follows, not only would more people quit their jobs and pursue their dream, but more people would become successful at it.

A few examples of Dru's rules for life include: "Life is short. Not fair," and “Perfect is a myth. Make a choice,” and “Set goals. And work backwards.” (See the end of this issue for more of Dru's rules).

Dru Riley has the power of taking enormous tasks (like building his 6-figure newsletter business) and distilling the challenges into simple to execute progress goals. By doing this he's able to make the tasks not only possible, but meaningful.

Every week Dru takes a new industry or new trend that he's interested in and distills it down so people can easily grasp the concepts and how to take advantage of it.

His newsletter currently boasts 36,000+ free subscribers, nearly 1,000 paid members (Trends Pro) with 800 people active in the community. At a price point of about $200 to $300 per year, I estimate he pulls in around $200,000 to $300,000 annually. He recently introduced a $1,000 "Masterminds" product.

[NOTE: These numbers are an estimate based on articles and third-party interviews with Dru. I personally reached out to Dru several times across different platforms for an interview to verify his stats but he did not get back to me at the time of publication 😕. You there, Dru?]

Now he routinely gets investment offers or people wanting to buy his newsletter.

Want to learn how to build your own highly profitable, one-person newsletter? Let's dig a little into his past so we can discover the steps he took to build it.

Dru taught himself Ruby on Rails out of college and worked in Atlanta for five years as a software developer. The skill that transferred from his job to was logic. "If you get something wrong, it's your fault, it's never the computers told it what to do," Dru said. "In a similar way when I'm looking at things like predictions or opportunities I'm just looking at incentives and as long as these incentives stay static," you can predict what might happen in the future. "It's the ruthless logic of not what you want to happen, but what might [actually] happen given current incentives and the current players."

Before starting Trends, Dru saved $250,000 to cover his runway until he found a project that worked. It ended up taking him three years.

"I was reading Tools of Titans...[and something I read] made me put a date on my phone," Dru said of when we was going to quit his 9-5. He always saved money for his planned escape and 250K felt like enough to "build a plane while it's on its way down." He also felt like quitting his stable job was a great motivator to make this new project of his actually work. The positive feeling of him succeeding was stronger than the negative feeling of watching his bank account drain.

Dru knew he had about 37 months of runway to start bringing in income. But in the last six months, after thinking he may have to go back to work, he received a $15 donation for one of his reports.

He decided would be his winning project and never looked back.

But Dru struggled at monetizing his newsletter. He received great feedback on the free reports—people loved them. But they just weren't paying. He tried multiple ways to monetize including selling each report individually and trying to sell every alternate report. But this didn't work.

"It felt bad particularly because a lot of people said 'oh you should charge for this,' it was almost like pulling the market out of me." Dru said in an interview. He was comfortable waiting longer but people were encouraging him to turn on paid. Despite the lack of success initially, Dru knew it was going to work.

He decided to keep each report free, but hide parts of the report behind a paywall. Now when a reader really wanted to dive deeper into one of the weekly issues, they would subscribe to get all the good information on the topic. This monetization strategy works well for him.

He had a major inflection point when he launched his newsletter on Product Hunt. This took his newsletter from around 6,000 subscribers to 25,000. It supports the argument it's better to launch on Product Hunt after you've built your audience to the thousands in order to gain a critical mass needed to succeed on launch day.

I've dissected all of Dru's interviews, dived into his writings, and distilled all the high-value content into the bullet points below to save you time. Read on to learn more about how to build a six-figure newsletter business...

The Techniques

  • On taking the leap into solopreneurship: Dru actually quit three jobs and took off months between them. The third time he calls it a mini-retirement. The main reason he left? "It was comfortable. Too comfortable," Dru told Packy McCormick.
  • On the power of habit (secret to his success!): Dru credits much of his success to the sheer volume of work he produces. He says he is able to do this by making it a habit and using tools like Habit List.
  • On writing: Dru sees stories on one side, and insights on the other. If he's not investing in telling the best story, he will invest in not wasting his readers time. If you are an amazing story teller, there's no need to be precise because the readers are going to "escape into what your writing." But he warns, if you are not an amazing story teller, you're going to have to put in the effort and edit down the piece.
  • On business in general:
    • “The most important part of business is the market. It’s easier to ride a wave than it is to make one.” — A good team won’t survive a bad market. A good product won’t survive a bad market. A bad team with a bad product can survive in a good market. Pick hungry markets. This comes from Marc Andreessen who wrote The Only Thing That Matters.
    • “Copy businesses that are working. These are formulas. Steal and improve them.” — Find a proven market. Study the problem. Be different or better or both.
    • “Play long-term games. Compound returns.” — Focus on the long-term. Most benefits come from later stages of compounding. Pick up habits that you can see yourself sticking with. Jeff Bezos says to focus on what doesn’t change.

The Frameworks

  • On constraints: Dru cuts out 80-90% of his draft before he publishes a report. He has a self-restraint mechanism of only publishing 1,000 words per report. Constraint is the tool that allows him to filter exactly what needs to be removed and what needs to stay in the final report.
  • On productivity:
    • “Perfect is a myth. Make a choice.” — Start and iterate.
    • “Start super simple.” — Make the simplest version first. Don’t complicate things. Build an MVP. Or a concierge MVP.
    • “Get it working by any means.” — Inspired by test-driven development. Improve the solution after the test passes. This applies to more than code.
    • “Set goals. And work backwards.” — Use big goals and small goals. Milestones can expose whether you undershot or overshot.
  • On growth:
    • On his preferred distribution channel: Dru believes twitter is a lesser known and used distribution channel that can really pay off in a big way. Dru built his Twitter following and used it as a funnel to drive traffic to his reports. He would distill his weekly reports into Twitter threads and if it goes viral, it can really pump his subscribers. For instance, one Twitter thread earned him 2000 subscribers. 
    • “Focus on doing the thing, not the outcome.” — Commit to the process, not the outcome. You control whether you do it, not how it turns out.
    • “Continuous improvement requires feedback.” — Feedback is a gift. No feedback. No improvement.
    • “If you decide to only do what works. You’re leaving a lot of opportunity on the table.” — Experiment.
    • “Fear is a good thing. It means you’re close to making a breakthrough.” — Fear can indicate potential growth opportunities.
    • On his secret to "hockey stick" growth: Dru urges anyone starting a product today should focus on building the audience first. Build your audience and solidify trust with them before you go paid.

The Mindsets

  • On 'hard choices easy life, easy choices hard life: Dru said if you don't think about the hard choices now and take action, they will come back to haunt you over time. But if you can make the hard choices now, it'll really help you over time.
  • On the trust treadmill: For every piece of content, you've got to keep the trust of your audience. This responsibility never goes away. 
  • On starting from scratch today: Dru doesn't feel there was significant element of luck involved in his success. He said if he were starting from scratch he would join a community around whatever niche he wants to pursue. If he had access to some capital, he would also pay for a coach who has done what he wants to do. Then it all comes down to "execute, execute, execute." 
  • On 'life is short, not fair': "This attacks idealism," Dru said. "It's a reminder that things don't work that way. You can waste your lifetime, someone elses, and someone elses if your fixated on that, as opposed to trying to understand the dynamics of the game we are actually playing. And saying 'this is the hand i was dealt' this is how im going to play this." "Whatever your dealth, it's best to be realistic about it".
  • On becoming more courageous: Dru treats courage like a muscle. he consistently uses it to make it stronger by putting himself in spots that force him to be courageous, like quitting his job to start Trends and taking on a nomadic life. "That's where the asymmetric rewards come from: I'm gonna reach out to this new person, I'm gonna try this new app, I'm going to visit this new location...any of these could be what gives you more leverage." 
  • On what it will take to succeed: “I just say try to find something that you can stick with for a while. It matters, the market needs to have what you have to offer but I think that version zero never survives and you have to be willing to stick it out through pivots and through iterations. That’s hard to do if you don’t love what you’re working on.”

Read more posts like this in your inbox

Subscribe to the newsletter