Happy Sunday, creators. To keep you in the loop, we’re starting a Gumroad newsletter that will be in your inbox every Sunday. Its entire goal is to help you make more money as a creator.

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Creator Spotlights (we may feature you)
How to content (how to build an audience, how to create a high converting sales page)
Weekly updates from our team
What’s happening in the creator economy
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Let’s dive in.

How Dru Riley Went From 37 Months Without An Income to $100K+ on Gumroad

Post-college, Dru worked as a software developer, focused on Ruby on Rails, JavaScript, Scala, and Spark. And in 2017, he made a tough decision. A decision that would give him control over his time.

He quit his six-figure job.

With 250k in his savings, Dru went on a mini-retirement to travel, learn Jiu-Jitsu, and improv comedy. During that time, he worked on side projects. But none ever gained enough traction.

Dru took off his developer hat and put on his founder hat.

Taking off his developer hat meant disconnecting from code and exploring content. His identity shift sent him down an avenue where he was obsessively searching for valuable problems to solve.

He quickly spun up two projects: The B2B SaaS Marketing Playbook and StrongStack. Both gained initial traction but quickly stalled.

By the end of 2019, Dru had gone 32 months without an income.

He pivoted. Again.

Dru went from something that felt like work to something that felt like play.

So, he started writing about Trends.

Something he’s always loved.

On February 10th, 2020, Dru posted Trends #0001 — Cloud Kitchens, the first-ever Trends Report.

A Trends Report broke down into the sections:

Problem
Players
Predictions
Opportunities
Haters
Links

It was a compilation of 50 hours of research and writing ad interviews into a report capped at 1000 words.

It cut through the noise and provided you with valuable high signal trends.

Things finally started to look upward.

His high-quality content caught early traction. He used Indie-Hackers and Tweet Storms to scale.

It was working.

After reading about the success of other creators monetizing their content, Dru decided to monetize his.

In his 13th report, Dru announced Trends Pro where he would alternate between free reports and paid reports.

He launched his pre-order for the first-ever paid report two weeks later.

Dru didn’t generate one sale.

So, he pivoted again.

Not once, but twice.

First, Dru made half of his reports free and the other half paid. His first report in that format brought in $162.

After much advice, he switched from a monthly subscription to an annual subscription.

Here’s the timeline:

By June 22nd, Trends Pro crossed 100 subscribers.
In August, Dru raised the price of Trends Pro to $149/year.
Trends.VC was number one on Product Hunt.
In October, Trends Pro annual price doubled to $297/year. Trends.VC earned $38,000 in October alone.
After 6 months, Dru turned Trends into a product generating $100k+