Creator Spotlight: Dru Riley's Success on Gumroad

By late April 2020, Dru Riley had gone 37 months without income, experimented with dozens of projects, written 13 Trends Reports, and his latest experiment to make money had just failed. Since then he’s earned more than $100,000 on Gumroad.

There’s the simple version of his journey as a creator, and then there’s the real version, one that involves “easily more than a hundred different projects” over the past ten years. “People say I’ve done a lot of experiments. But there are ten times more experiments I want to do.”

 

Dru is the Founder of Trends.VC, a community and newsletter for founders discovering new markets and ideas. We asked him to reflect on his creative journey, and we learned that his path has been anything but linear.

QUITTING HIS DAY JOB AND EXPLORING WITHOUT INCOME

After college, Dru worked as a software developer, focused on Ruby on Rails, JavaScript, Scala, and Spark. He liked the work but he wanted to control his time.

So, in February 2017, with $250,000 in savings and no plan other than taking a mini-retirement, Dru quit his job. “The decision was hard,” he said, “because I enjoyed the pay, flexibility and coworkers at my last gig. It was comfortable. Too comfortable. That’s why I left.”

It was also a risk he was willing to take. “When you take a leap and tell people what you’re doing, a lot of them say, ‘Oh, I wish I could do that’ or, ‘You’re so brave,’ but I didn’t think of it that way. I knew I could go back to being a developer.”

Dru spent the next two and a half years traveling and learning, practicing Jiu-Jitsu and doing improv comedy. Along the way, he kept a journal that became a source of ideas for future projects. With each passing month, though, Dru’s runway was getting shorter. He was already experimenting with several projects, but as 2019 wore on, he needed one that would allow him to maintain an independent lifestyle.

For Dru, getting serious about building meant an identity shift. “I had to take my developer hat off and put a founder hat on. That’s what opened me up to exploring content, and that’s what allowed me to focus to the point where I was looking for valuable problems to solve.” Dru took inspiration from his “Maker Crew,” friends he’d made in the Indie Hacker community and in the Mastermind group Zero To One Makers.

In early Fall 2019, Dru created the B2B SaaS Marketing Playbook and began sharing it with fellow makers and Indie Hackers one chapter at a time. He also started working on StrongStack, another project focused on SaaS founders and marketers. Both projects grew, but their initial momentum began to stall, and by then end of 2019, Dru had gone 32 months without income. 

PRIORITIZING VALIDATION AND DOING WHAT FELT LIKE PLAY

In January 2020, Dru posted to Indie Hackers that he was “prioritizing validation above all else.” He pivoted StrongStack, which became SaaSReport (a competitive intelligence product for SaaS founders and marketers), and to “release steam” from that work, he started doing something that felt like play. “I was struggling on SaaS Report and I love writing about trends.”

On February 10th, 2020, Dru posted Trends #0001 — Cloud Kitchens, the first-ever Trends Report, crediting his Maker Crew for the encouragement. Thus began Trends.VC, which has become Dru’s breakout success. 

“Up until I started Trends.VC, every project I’d worked on was a training ground for comparative analysis and lateral thinking. The through line was all about trends.”

“If you look at other newsletters and projects I started, it’s always been about lateral thinking. I pull from seemingly unrelated industries to prove a point. Sometimes people get mad. Every week I get email replies about how I’m talking about one vertical and then referencing another one, and people will say these two things aren’t the same. I reply, “I did that to get you out of this box and let you know even though these two things seem unrelated, they’re tied together.”

Starting with the first Trends Report, Dru constrained himself to a short and recognizable format, with sections on the Problem, Players, Predictions, Opportunities, Haters, and Links (later iterations have included sections on the Solution and Key Lessons). The length is capped at 1,000 words. “It was different. The assumption was people appreciate shorter content.”

Each report is the product of more than 50 hours of research, interviews, and writing. “Sometimes people see the links section and say, ‘Oh, this is the research you did.’ It’s like, ‘No, I listened to 100 podcasts, saw countless videos, read countless articles, and you get the top ten links and resources. You get what is, in my opinion, the highest signal stuff.”

“You can read and learn voraciously, but the other half of learning doesn’t come unless you try to teach it to someone. It’s cliché but true: if you can’t explain it simply, then you don’t understand it.”

Dru applies core principles of writing online: write before you're an expert on a subject; write to become an expert on a subject; share the best of what you’re learning. “I cover such a broad range of topics that if we waited for someone to become an expert in every one of these, then no one would do this. That holds a lot of people back from doing a lot of things they want to do. And I’m not just leaning on confidence in myself; I’m leaning on confidence and belief that Zero To One Makers instilled in me that they like what I’m putting out and — before it was even a thing — that I could do it.”

“The first week there were seven or eight subscribers, and the next week there were maybe there were 30 or 40.” Then it was featured by Michael Gill, founder of No Code Coffee and a fellow Maker in Zero To One Makers. “After Michael featured Trends.VC, that’s when I was the most nervous, because it went from 70 to 400 subscribers.”

To grow his audience, Dru focused on creating quality content, and he used Indie Hackers and tweetstorms to spread it. “People don’t realize constraints breed quality, and without constraints you just have a lot of noise. Some weeks I’ll write 13,000 words and I have to distill it down to less than ten percent of that. There's a lot of editorial judgment. Sometimes I miss something or don’t see a company, but 95 percent of the time I see it and don’t include it because the report has to be front loaded. The goal is for the final report to be concise, dense, and readable.”

GOING PAID, FAILING, AND THEN TAKING OFF

In April 2020, Dru started to draft Trends #0011 — Paid Newsletters. “I was writing about so many examples of people monetizing their work, and I decided to give it a shot. I was surrounded by examples of success and that became my reality. I just thought, ‘I can do this.’”

After writing two more reports, Dru announced in Trends #0013 that starting immediately, bi-weekly Trends Pro reports would be available, and reports would alternate between public and private each week, starting with Trends Pro Report #0015. He took pre-orders for that first paid report and received … exactly zero.

“The strategy I used at first, it just failed. I was like, ‘That didn’t work out. No one bought it.’” Despite the setback, Dru was transparent about his process. 

Instead of giving up, Dru changed tactics. “I ended up doing something people close to me told me to do up until that point.” Dru broke the weekly report down and made half of it free and the other half paid. “At first, I didn’t want to do that because the reports were already short. But it ended up working. I ended up doing more research to keep the length the same. That’s when the work expanded, but that’s what allowed it to take off in terms of making money.”

On May 10th, Dru published Trends #0014 — Paid Communities and made $162 on the first day. Over the next ten days, he earned the first annual Trends Pro subscription (May 12th); published an Indie Hackers post, “3 Years. No Income.” (May 13th); earned 14 total Trends Pro subscribers (May 17th); and raised the price of Trend Pro to $12/month and $7/issue (May 20th).

Dru had crossed the Rubicon. “The moment the first person subscribed really made me lock in. I said, ‘Okay, you're doing this for at least a year.’ I repeated that to myself for the first 50 or so annual subscribers. These people believed enough, with little evidence, to stake for a year. That means a lot.”

 

The momentum has only accelerated since then.

  • In May (two days after he first monetized the project), Dru received an outside offer to invest in Trends when it had less than $200 in revenue. He rejected the initial offer, countered at $500k, and the deal fell through. “They were early believers. I just believed more than them.”
  • By June 22nd, Trends Pro crossed 100 subscribers, and a month later someone voluntarily paid $50 for a single Trends Pro report using the Gumroad “pay what you want” feature (Dru gifted the generous patron Trends Pro access for a year); 
  • In August, Dru raised the price of Trends Pro to $149/year, and by the end August, Trends.VC was number one on Product Hunt;
  • In October, Dru stood up Trends Pro community, launched Stand Ups, started a 10-Day Trends Pro Challenge, and the Trends Pro annual price doubled to $297/year. Trends.VC earned $38,000 in October alone. 
  • In November, Dru launched an affiliate-friendly program called Deal of the Week. “Every Deal of the Week,” he said, “has been a Gumroad product because the affiliate program is so easy to figure out.” 

BUILDING TRUST AND VALIDATING THE ANNUAL SUBSCRIPTION MODEL

Dru’s customers — the people who understand the recurring and compounding value of Trends.VC — understand a crucial and counterintuitive truth: Trends.VC isn’t about trends. “Trends isn’t about what’s popular, it’s about what matters that no one’s looking at. It’s about what really matters that no one is paying attention to.”

In Dru’s words:

A lot people think it’s about trends or about venture capital, but the people who are close-to-the-metal – the people who really know what it is – they know it’s evergreen. No matter which report you read, there's something that will be transferable to your business. It goes back to thoughtfulness.”

That's why I was on Trends #0043 and hadn’t yet covered Remote Work, because everybody has been talking about it. It’s just beating a dead horse. If I pick something up, I want to do something with it. I want to say something that hasn’t been said before. And that’s the responsibility I take on: the report has to do a job, it has to achieve that goal.

If you pull up the backlog of reports, there are things in them that are going to be true ten years from now. Some of the opportunities might change, but the principle guiding them is still going to be true. The real value of Trends.VC is drawing lines through seemingly unrelated areas. If people didn’t get it before, I think they’ll get it soon.

Much of Dru’s recent success comes from understanding his customers. “One of my goals in 2020 has been to interview 100 customers. I interviewed 15 customers before I rolled out the Trends Pro community – and it’s a full-time job that I didn’t expect. With the Trends Pro Stand Ups, I know exactly what is going in on other people’s businesses and lives – it’s much richer information than interviews would have yielded.”

“From the first day I started monetizing Trends successfully, I had this feeling things would be okay, no matter what, because I’d found the thing I could do forever. Even with just $100 or $200 in revenue, I felt the model had been proven and revenue would just go up from where it was. There’s no end game; it’s an infinite game. For me it was, ‘What problem do I care enough about that I think I can stick with for a while?’”

Dru originally started making money by selling individual reports. The first breakdown from his first $162 in revenue was split between 32 Trends Pro members and 82 single reports sold.  

Today, 99 percent of Trends.VC revenue is recurring in the form of Annual and Quarterly subscriptions (Dru deprecated monthly subscriptions earlier this year). The single reports were a low-stakes foot in the door offer for people to see what they would get, because it’s hard for people to sample the product.

The pendulum has shifted so far in fact, “The only reason single reports are still around is because I haven't figured out a way to give people a representative sample of what they would get out of the Pro Reports and the community.” Single reports are also a forcing function. “When I have to put up a Gumroad page for a single product, I'm forced to write copy for that page and convey what people will learn from a report. Now, though, I don't even expect to sell singles, I actually expect people to subscribe.”

SHOWING UP FOR A GROWING AUDIENCE, AND CHARTING THE FUTURE

Much of the way Dru has approached building is counter-intuitive: he’s a software engineer who writes reports for a living; he’s left a number of jobs in search of something he can do forever. He’s in the competitive community and newsletter industry and he doesn’t think about competition. He’s free to adopt any content design and he constrains himself to a format.

“Trends.vc solves my own problem. I write about things I’m curious about. I’m one of those people where I need to solve my own problem and it gives me a deeper level of empathy. At this scale, now there's a sense of having to show up for a lot of people.”

When the report hit an inflection point of tens of thousands of people, there was a palpable sense of responsibility. “It’s a trust treadmill: of those tens of thousands of people, there's going to multiple people out there who know more about each one of these topics than I do. So I have to think about how to preserve that trust with them, and how to be intellectually honest about the limits of my understanding each week.”

In the early days, Dru would pace back and forth before he hit send to 20,000 or 30,000 people. “I'm more conditioned to that now. It's still a lot of hard work. I read a report out loud 40 times before I hit publish, because I want it to be butter. I'm very surgical about things.”

At this point in the journey, Dru recognizes the need for balance. “There's a part of me that's low-key ambitious. And there's also a part of me that's trying not to get on a hedonistic treadmill and never be happy. Now I do this dance of remembering I found something I love doing, and all I have to do is keeping doing it. I’ll be provided for and it doesn’t have to get any bigger. The other side of me is we like to see numbers go up and to the right. But I never want to forget that first part and just keep telling myself, ‘It’s just a game. It’s just a game. It’s just a game.’”

Looking to the future, Dru may incorporate investing into his rhythm, turning his reports, as he said, “into skin in the game.” He’s already studied bootstrapped funds and has had a long-term interest in early private equity.

“I just started working with a business coach. We just put a game plan together for delegation a few days ago. I’m writing job descriptions and putting together tests like, ‘I don't care how well you interview, show me what you can do.’ Then I need to build a systems after that.”

CLOSING THOUGHTS, IN DRU’S WORDS

My core skill is probably just being thoughtful. I feel like there's a lot to learn from other areas. Things that are right in front of your face but you don’t see them.
I study Superhuman (the email app) and observe it has elements of Tesla in it and seemingly unconnected things. Trends is about connecting them and putting them together.

A lot of the time, writers aren't willing to do the work. The point of doing the work is to save your audience from having to do the work. It’s not about sounding smart. I break multiple syllable words down to single syllables. The point is to make it readable, easy-to-understand, and concise. Don't waste readers' time. Brevity is hard. But if you do it, hundreds, thousands, or even millions people won't have to.

I know some people who throw work out there and apologize if something goes wrong. Part of me feels like you learn so fast and effectively this way.  But I don’t know if I can take on that mindset without giving up what thoughtfulness has given me.

And therein lies the contradiction at the heart of Dru’s success: running a lot of experiments, thoughtfully. In the end, as Dru’s friend Edmund Amoye from Zero To One Makers once told him, “Your taste is all that matters.”