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Side Hustle School

Ep. 3054 - First $1,000: Community Host Boosts Engagement and Retention

Side Hustle School

Chris Guillebeau / Onward Project

Business, Entrepreneurship, Careers

4.83.3K Ratings

🗓️ 12 May 2025

⏱️ 6 minutes

🧾️ Download transcript

Summary

In this week’s First $1,000 story, learn how a personal touch and organized virtual events enabled one community manager to surpass the $1,000 mark while fostering a supportive space for solopreneurs.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

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Transcript

Click on a timestamp to play from that location

0:00.0

Lemonada. A community host boosts engagement and retention. And she also gets paid for it, of course.

0:16.1

Welcome to Side Uswell School. My name's Chris Gillebeau. In this week's first $1,000 story,

0:20.6

you're going to learn how a personal touch with organized virtual events enabled one community manager to surpass this $1,000 mark while fostering a supportive space for solopreneurs. What am I talking about? I'm talking about the story of Ariel. She had an idea, well, she has been hosting online events.

0:39.5

She's all about building community, responding to comments, getting people talking about

0:44.4

different topics and so on. And she turns this into a business. She was an administrative

0:48.7

of assistant. And then she decided to kind of strike out on her own with this side hustle.

0:53.5

And she goes on to earn a lot more than $1,000.

0:55.7

But in this feature, we focus on how someone goes from idea to income, how they in fact get going.

1:01.8

So without further ado, let's let Ariel tell us the story.

1:05.2

I'll come back at the end with a few words of wrap up.

1:23.3

I'm Lena, and my side hustle revolves around hosting an online community for aspiring entrepreneurs.

1:24.6

Before this, I worked as an administrative assistant at a startup accelerator, where I watched

1:29.3

how founders thrived when they had constant peer support. But I also saw how easily they felt

1:35.2

isolated once a program ended. Around that time, a friend asked if I could help manage an online

1:40.6

membership group she was starting for solopreneurs. The pay was low, but I jumped in, excited by the prospect of helping people feel more connected.

1:49.2

I was invited to moderate a Slack community, welcome new members, and handle basic customer

1:54.0

support, like lost passwords or billing questions for the monthly membership.

1:58.8

I also hosted weekly virtual check-ins where folks shared

2:02.1

progress updates and asked for feedback. Since the community had fewer than 30 people at

2:07.1

first, it felt manageable. But soon, more entrepreneurs joined through word of mouth. I quickly

2:13.2

found myself organizing live workshops, coordinating guest speakers, and even mediating occasional

2:19.2

disagreements in the chat. Every time a new member joined, I messaged them personally.

...

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