How to Grow a Paid Community [Interview With Anthony Castrio]

Anthony Castrio from Indie Worldwide is showing us how to build a thriving paid community.

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It’s not easy to build a community that people is willing to pay for. It demands consistency, great planning, and most important of all: genuine interest in the problem you’re trying to solve.

That’s how Anthony Castrio is building Indie Worldwide, a private community with over 2000 indie founders that learn together, stay accountable and challenge each other.

We interviewed Anthony to get a closer look on how it’s like to build and manage a paid community that always has something new to offer. Here’s what he shared with us:

How did you come up with the idea of starting Indie Worldwide, and what were your steps in getting the first members?

5 years ago I started traveling the world as a digital nomad. I knew I wanted to become an entrepreneur, but I wasn’t sure what to build yet or how to do it, but I did have some experience organizing events, so that’s what I started to do.

Each city I went to I tried to start an indie hackers meetup: Medellín, Boston, Montreal, Mexico City.

It was a lot of fun! But every time I moved cities I was leaving the community I built behind and starting over. It couldn’t compound.

That’s when I started Indie Worldwide: to create a virtual community I could take with me anywhere. We would be the meetup group for indie hackers who didn’t live in a popular city or for whatever reason couldn’t go to local meetups.

My first members came from the Indie Hackers website, from people I’d met hosting in-person meetups, and from Twitter.

If you had to highlight the top reasons for joining the community, what would they be?

Building a startup is hard, bootstrapping it is even harder, and doing it alone is hardest of all. If you don’t already have a group of founder friends inspiring you and motivating you to keep at it, then your chances of succeeding plummet.

Joining Indie Worldwide gives you that founder peer-group instantly:

  • Meet startup founders from around the world you wouldn’t get access to otherwise.
  • Surround yourself with like-minded people who you can learn from.
  • Get motivated by other founders, get that push to keep going.
  • Quickly unblock yourself on the questions you just can’t google like how to hire, fire, hack your marketing, or whatever other roadblocks you might encounter as a founder.

How do members engage and share knowledge? Which are the most important events or regular activities?

Daily: Conversation in our private Slack group. Share wins, get quick feedback, & boost your product launches.

Weekly: Targetted 1-1 introductions via email to other members in the group. Form deeper relationships and trade insights.

Monthly: Mastermind sessions, expert Q&A’s, and workshops to help you level up.

Semi-monthly: Group growth challenges that push you to improve by orders of magnitude on some metrics like paid users, newsletter subscribers, or SEO traffic through friendly competition.

How did you monetize the community? What motivated your decision of going paid with Indie Worldwide?

We didn’t charge any money for the first year and a half. Once I started doing the targeted 1-1 introductions, multiple members offered to pay a subscription fee. I was hesitant at first, but eventually decided to take the money!

Currently, it costs $490/year to join Indie Worldwide which includes:

  • Access to the Slack
  • Weekly 1-1 introductions to other founders
  • Access to all events and challenges
  • Over $20000 in free resources for your startup

We also have revenue from sponsors who pay for shoutouts in the newsletter.

Year 1: $0

Year 2: $11,209

Year 3: $26,717

Can you tell me about the tools that you use to manage the community daily?

Chat: Slack

Payments/Auth/Support/CRM: Outseta

Newsletter & Email Automations: ConvertKit

Website Hosting: Carrd + Feather

Blog: Feather

Podcast Recording: Riverside

Podcast Hosting: Transistor

Design: TeamTown

Introductions: Intros AI

Video Meetings & Events: Whereby, Butter, Hopin

Event Registration: Luma, Mixily, Hopin

Knowledge Base: Notion

Would you share your tips for effectively managing an online community, specifically for indie founders communities?

Find a pace of content you can keep up with forever. Most communities fizzle out when the founder gets bored. You have to have some way to keep things moving and interesting.

For Indie Worldwide that’s been our monthly events and challenges. There’s always something new and interesting to keep people engaged. We have lulls and peaks, but we keep moving forward.

On the member side of things, you should always be looking for ways to increase the number of 1-1 connections between members in the groups.

Some ways to do that:

  • Every time someone introduces themselves in the group, tag 3-5 other members who you think they should meet based on some relevant criteria.
  • Collect data about your members and then make regular 1-1 introductions between them.
  • Host frequent live events where members get 1-1 time with each other.
  • Interview your members and then feature their story to the rest of the community so that people start to recognize each other.

What’s coming next in Indie Worldwide?

This year we’re doubling down on the number of challenges we’re running.

Last year we ran one group challenge, this year I plan to run at least six (shorter) group sprints.

The first one – Speedrun 1000 – is live now. A group challenge to get 1000 new newsletter subscribers in 30 days or less.

Sofia Terlesky

Sofia Terlesky

I'm an SEO content manager with over five years of experience planning and writing for blogs and social media, helping small and mid-size businesses grow organically. Now, I'm responsible for planning Unita's content calendar—ensuring we are offering valuable content for community builders and founders.