Many well-known online communities started as side projects. A founder with a job or a degree built a place for people who shared an interest and ran it in spare hours until it could pay its own way. Chess.com and Product Hunt both began like this, and their early years show why communities suit the hours after work.
In this guide
- At a glance
- Why communities grow well as side projects
- The stories in this group
- What these communities have in common
- The hard part: turning members into a business
- If you are building one
- More community stories on the way
- Frequently asked questions
At a glance
| Community | Started | Built alongside | Where it went |
|---|---|---|---|
| Chess.com | 2005, launched 2007 | An MBA at Stanford and a co-founder’s day job | Profitable without investors; more than 150 million members by 2024 |
| Product Hunt | 2013 | A product job at PlayHaven | Acquired by AngelList in 2016, reportedly for about $20 million |
Figures come from the full stories, where each one is sourced.
Why communities grow well as side projects
A community needs time more than money. The first version is often tiny: an email list, a forum, a page where people can post. What makes it grow is the founder showing up, again and again, to welcome people, start conversations and keep the place useful.
That kind of work fits around a job. It can be done for an hour in the evening, and it compounds. Each member who stays makes the place more valuable to the next one, so a community that is looked after steadily for a few years becomes very hard to copy. Competitors can copy features in weeks; they cannot copy the people.
The flip side is that communities are slow to make money. Members come for each other, not for a product, and charging them too early can break what made them come. The stories in this group show founders finding ways around that, and taking very different routes to do it.
The stories in this group
Chess.com. Erik Allebest and Jay Severson met as students at Brigham Young University, where Severson, the stronger player, beat Allebest at chess and then gave him lessons. Allebest built two chess businesses before business school and sold both. In 2005, as he started his MBA at Stanford, he bought the chess.com domain at a bankruptcy auction for $56,000, by his own account.
The two split the work. Allebest handled the front end of the site during business school; Severson built the back end after he finished work at 6 pm. No venture capitalist would invest. Chess.com opened in May 2007, the month Allebest graduated, as a community of profiles and forums without online play. Members quickly asked to play on the site itself, so the founders built that too.
Within about 18 months of launch, paid memberships for learning tools made the business profitable, and it never raised venture money. Then chess itself boomed: between 2020 and 2023, streaming, the pandemic and The Queen’s Gambit brought millions of new players. By 2024 Chess.com had more than 150 million members, and in 2026 Allebest put revenue at more than $200 million. Read the full story: Chess.com: Built at Business School and After a Day Job.
Product Hunt. Ryan Hoover was the first product manager at PlayHaven, a mobile gaming company in San Francisco, and wrote a blog about products and startups on the side. In 2013 he noticed a conversation that kept coming up among his friends: have you seen that new product? There was no single place to find them.
He was not an engineer and did not want to build a site to test the idea. On November 6, 2013, he set up a daily email digest on Linkydink in about twenty minutes and invited a few dozen investors, founders and friends to submit products. In two weeks the list reached about 170 subscribers. The numbers were small; the reaction was not. Over Thanksgiving, Hoover and his friend Nathan Bashaw, a developer, built the first website in about eight days.
Founders soon launched there on purpose. Product Hunt joined Y Combinator in 2014, raised a $1 million seed round and a $6.1 million Series A, and in November 2016 AngelList bought it in a deal Recode reported at about $20 million. It had made almost no revenue; AngelList was buying the community. Read the full story: Product Hunt: The 20-Minute Email List That Sold for $20M.
What these communities have in common
The two stories are very different in scale and speed, but they share three features.
They started smaller than a product. Product Hunt began as an email list on a free tool, not as a website. Chess.com launched without the online games it is now known for. In both cases the founders tested whether people would show up before building anything heavy.
The founder was part of the audience. Hoover followed new products as part of his job and his blog. Allebest had played chess and run chess businesses for years. Running a community you belong to is easier to sustain in spare hours, because the work overlaps with something you would do anyway.
Members did much of the work. On Product Hunt, the community submitted and voted on products. On Chess.com, members played, wrote and taught each other. A side-project founder cannot produce everything alone; a community lets the members produce most of the value.
The hard part: turning members into a business
The two stories show two answers to the money question.
Chess.com chose memberships. Most of the site stayed free, and paying members got more lessons, analysis and features. Because no investor would back them, the business had to pay for itself, and it did so within about 18 months. Years of steady growth meant it was ready when the market suddenly grew.
Product Hunt took the venture route. Instead of charging members, it raised money to grow quickly and was sold within three years of the first email, while earning almost nothing. That path is faster, but the community ends up owned by someone else.
For a founder running a community after work, the lesson is less about which route is better and more about timing. Both founders built the audience first and worked out the business model once people were already there.
If you are building one
These stories suggest a few practical rules for building a community in spare hours.
Test with a tool that already exists. Hoover used an email digest service instead of writing software. A group, a list or a forum on an existing platform is enough to see whether people care.
Measure reaction, not size. Product Hunt’s first list had about 170 subscribers. What convinced Hoover was the unsolicited enthusiasm. In a young community, a few people who care a lot are worth more than many who signed up and forgot.
Give members a job to do. Submitting, voting, playing, answering. The more members contribute, the less the founder has to produce alone, and the faster the place feels alive.
Keep the core free and charge for depth. Chess.com kept the community open and charged for learning tools. It is a model that protects what members came for while still paying the bills.
Be patient. Chess.com grew steadily for more than a decade before its biggest jump. A community built in the evenings rarely explodes; it accumulates.
More community stories on the way
The 5 to 9 is adding community stories every week. Coming next in this group are Craigslist, the email list Craig Newmark ran while keeping his day job; Facebook, started in a Harvard dorm; Twitter, a side project inside Odeo; Flickr, a side project of a company building an online game; IMDb, Col Needham’s hobby project while employed; and Dribbble, the side project of two designers.
All the stories published so far are listed below and on the All stories page.
Frequently asked questions
Which online communities started as side projects?
Among the communities covered here, Chess.com and Product Hunt both began as side projects next to a degree or a job. Craigslist, Facebook, Twitter, Flickr, IMDb and Dribbble also started that way and will be covered in this group.
Why do communities work well as side projects?
They need time more than money, and that time can be spread across evenings. A community also gets more valuable as it grows, so steady work over a few years compounds. The trade-off is that they are usually slow to make money.
How do online communities make money?
In this group, Chess.com charges for optional memberships while keeping most of the site free, and became profitable within about 18 months of launch. Product Hunt raised venture capital and was acquired while earning almost no revenue.
Can a community be valuable without revenue?
Yes. Product Hunt had made almost no money when AngelList bought it for a reported $20 million. The buyer was paying for the audience and its activity, not for profits.