How Dru Riley went from software developer to Trends Pro community founder

We continue our Rosieland Community Interview series with Dru Riley, Founder of and the Trends Pro Community.  Trends Pro is supporting founders to “leverage our community to build profitable businesses, sharpen our thoughts and learn together.”

This interview dives into how Dru went from a software developer to starting a newsletter and eventually launching a community.  He shares what it takes to run the Trends Pro community and lessons for future community professionals.

What’s your background and how you found yourself in community?

I'm a software developer by trade. After taking a 3-year break, I started as a newsletter. It eventually became a paid newsletter. As I got to know my subscribers through email, I decided to start a community where members could connect with each other.

What would you would do differently if you had to start your community career over?

When I started the community, I didn't spend enough time testing different platforms. If I had to do it again, I would spend more time testing different platforms before making a decision.

Trends Pro's goal is to help solo entrepreneurs who are building internet businesses. Solo entrepreneurs often struggle with getting feedback, staying accountable, and missing certain details about their market or their business strategy. To help with these struggles, we created Trends Pro Reports, Daily Standups, 1:1 Founder Intros and Weekly Masterminds.

What tech stack are you using to run the community?

We mainly use two tools, Circle and Meetsy, but we also use lots of JavaScript and other tech tools to make Circle work better for us.

We're always trying out new ideas for our business model. Right now, we use a subscription model, and we also offer a lifetime membership through a program called MetaTrends. We started as a paid newsletter, so it felt natural to use a subscription model when we started our community.

We've focused on creating high-quality experiences for our members rather than growth. We've done this through programs like Masterminds and 1:1 Founder Intros.

I've written about my experiences building this community in a blog post called "How I Built a Paid Community to 1,000+ Members in 10 Months." In it, I talk about how to use content to attract members, the importance of establishing rituals, and how to create meaningful experiences for members.

What types of community generated content worked well?

Each week, we send an email called "Founder Finds." This email includes members' achievements, the best tools our members have discovered, and a spotlight on one of our members. Sometimes, "Founder Finds" gets more engagement than our original product, Reports.

Tell us about a failure and the lesson it taught you in community building.

One of the biggest things I've learned is the importance of what I call "strategic friction." For example, we once lowered the requirement for joining masterminds from 30 days of standups to just 10 days. But we found that when it was easier to join, members didn't value it as much. So, we're going to bring back the 30-day requirement.

Many of our members have met each other in real life. We're working on ways to make it easier for them to find each other and build stronger relationships. We're also working on improving our Daily Standups, 1:1 Founder Intros, and Trends Pro Masterminds programs.

We hope you enjoyed this interview with Dru Riley and the Trends Pro Community journey.  We’d love to hear your thoughts in the comments!

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