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Side projects, what developer would be without them? They come in all shapes and sizes, from applications that solve minor irritations, to projects much more ambitious in scale. What’s more, they can be pivotal in opening up new opportunities, growing a career, or providing additional income — often neither anticipated or expected.

Developers generally don’t get into side projects because of the benefits they’ll offer. More typically devs become immersed in a side venture purely out of passion, or curiosity, or because they have an itch to scratch. They take on side projects to dig deeper into something they love, to learn something new, to satisfy an urge, to satisfy a siren call. They take on side projects to solve a problem or a mystery no one else has yet solved. Perhaps which no one else has yet identified.

“…[Tumblr] was born out of a perceived problem with an existing project.”

Yet, such side projects can sometimes become wildly successful: they can become keys to accidental success.

To celebrate those who’ve succeeded, and to help those who haven’t (yet) ventured, this post will showcase ten side projects which became runaway successes — successes which the creators and founders, largely, never envisaged happening — and offer practical advice on how you can emulate that success, growing a cherished side project into something more.


Twitter was started in 2006 by a number of people, most notably Noah Glass, Jack Dorsey, and Florian Webb. Today it’s one of the most recognized and most used social media platforms in the world. It has more than 100 million users, who send more than 340 million tweets a day.

It’s available in web format, with apps for every major platform, along with a number of applications which integrate with it, such as the well known HootSuite.

Twitter is particularly well known for being a key, empowering player in several global movements, most memorably, perhaps, the Arab Spring. Here’s a glimpse into what motivated its start:

Williams decided Odeo’s future was not in podcasting, and later that year, he told the company’s employees to start coming up with ideas for a new direction Odeo could go. The company started holding official hackathons where employees would spend a whole day working on projects. They broke off into groups.

That excerpt, from an article by Business Insider, illustrates that Twitter was not intended from the start as a product, but was instead a project endorsed by the management team at the company where all the Twitter founders worked, called Odeo.

Odeo was creating a podcasting platform right around the time that Apple launched iTunes podcasting. Needless to say, going up against Apple, and the largely runaway success that the iTunes podcasting platform became, wasn’t a recipe for success.

The team saw the writing on the wall and decided to look to other ideas, other solutions, one of which eventually became Twitter, originally called Twttr. Quoting the article further:

It was a system where you could send a text to one number and it would be broadcasted out to all of your friends.

So you see, even the original idea for Twitter wasn’t what it ultimately became, though in concept it was pretty close.


GitHub, today valued at over $750 million USD, is self-described as a social coding platform. GitHub was started by Tom Preston-Werner, Chris Wanstrath, and PJ Hyett, with help from Git guru Scott Chacon, in April 2008.

GitHub was started to provide simple social code sharing for the Git version control system. Whilst Git itself has a very steep learning curve, GitHub, whether through the web interface or the range of available native applications, has done a stellar job of removing much of that difficulty. It’s not only made the tool fun, it’s made it a must-have.

Whilst there are other code hosting services, such as BitBucket and Codebase, none of them have either the market share or the developer mind-share that GitHub has.

Here’s a glimpse into how it got started, by one of the co-founders:

[GitHub] was born into a world where there was no existing market for paid Git hosting. We would be creating the market. I vividly remember telling people, “I don’t expect GitHub to succeed right away. Git adoption will take a while, but we’ll be ready when it happens.”

But where did the idea come from? Good question. To quote one of the other co-founders, Chris Wanstrath:

It started more out of necessity than anything else: we both loved Git but there was no acceptable way to share code with others. Tom thought I’d be interested in helping fix the problem, and I was.

It began as a side project, one worked on over weekends, as all three had full-time jobs. Chris and PJ were working at their current startup, and Tom was at Powerset, which was developing a natural language search engine.

By their own admission, it was a side business which became an accidental success. Repositories were initially free, but people were increasingly emailing to ask how they could pay for private repositories. This was the tipping point for them all to take the project seriously, and commit to it full-time.


Dwolla, founded in Des Moines, Iowa, in 2009, by Ben Milne and Shane Neuerburg, is a U.S.-based online and mobile payment network. Dwolla is a cutting-edge alternative both to traditional merchants such as Banks and PayPal and to newer merchants like Square.

One of Dwolla’s core aims is to side-step credit cards and keep costs down, as the company mission attests:

Allow anyone (or anything) connected to the internet to move money quickly, safely, and at the lowest cost possible.

Ben was only 28 when he started Dwolla, mainly out of a sense of frustration with paying fees. Dwolla started out small, moving $50,000 a week, but now it moves between $30 and $50 million a month. Here’s an insight into what motivated him:

Dwolla started out of my old company. I owned a speaker manufacturing company and we sold everything directly through a website. I got really obsessed with interchange fees and how not to pay them. Every time a merchant gets paid with a credit card they have to give up a percentage. In my case, I was losing $55,000 a year to credit card companies. I felt like they were stealing from me — I was getting paid and somebody was taking money out of my pocket.

So you see, he was already running a successful business, but he had an itch to scratch, one which would eventually lead him to creating Dwolla, a business getting rave reviews for the positive disruption it’s causing in the financial space.


Pinterest is one of the most popular photo organizing and sharing websites in the world, largely because of the ability to pin a photo or create pin boards, which organizes content by a topic or theme.

Started by Ben Silbermann, along with Paul Sciarra and Evan Sharp, in March 2010, Pinterest gained 10,000 users within nine months after launching, and now has over 11 million total visits a week.

Here’s a glimpse at what motivated Ben to found Pinterest, compiled from a presentation he gave:

Ben got a job at Google in customer support, “because [he] was more excited than the previous applicant.” Ben got frustrated because Google wouldn’t let him build products. He complained a lot. Finally his girlfriend said: stop complaining and just go do it. Ben says, “If you’re really lucky in life you have someone to call you out on your own bullshit.”

Pinterest is slightly different to the companies we’ve looked at so far. It wasn’t an active side project, but an idea, one which Ben couldn’t let go of, to the point that his girlfriend told him to put up or shut up. From this came the true motivation to start the project.


Before being acquired by Facebook in 2012, Instagram was started by Kevin Systrom and Mike Krieger in 2010. With over 300 million users, Instagram is, like Twitter and Pinterest, one of the most popular social networks around, focused on photo sharing and commenting. Here’s a little insight into what motivated Instagram’s inception:

Systrom and Krieger were unhappy with Burbn. It was “cluttered” and “overrun with features,” Systrom noted on Quora, adding that the photo feature was by far the most popular. So in August, the founders made an incredibly risky, but perhaps prophetic, decision: They’d scrap Burbn almost entirely in order to build an entirely new app from the ground up.

Here’s how they did it:

They began by studying all of the popular photography apps, and they quickly homed in on two main competitors. Hipstamatic was cool and had great filters, but it was hard to share your photos. Facebook was the king of social networking, but its iPhone app didn’t have a great photo-sharing feature. Mike and Kevin saw an opportunity to slip in between Hipstamatic and Facebook, by developing an easy-to-use app that made social photo-sharing simple. They chopped everything out of Burbn except the photo, comment, and like features.

This intense research led to the explosive success which Instagram enjoyed. It had one million users within two months of being launched, 10 million within a year, and 150 million within three.


Mashable, one of the most popular and highly trafficked news websites in the tech space, was founded in 2005 by Pete Cashmore. From humble beginnings, it now has 42 million monthly unique visitors and 21 million social media followers.

If you’re a regular internet user, chances are you’ve read quite a number of posts from Mashable, which covers key themes in social media, tech, business, and entertainment. Here’s a bit of an insight into why it got started:

When I was 13, I had an appendectomy and for whatever reason it didn’t go too well and I didn’t really recover. So I was out for quite a few years trying to like rest up, get better. And I missed school a lot, so I was kind of out of sync with my friends. So I just started going my own way, using computers, trying to learn as much as I could. Blogs were springing up, so I subscribed to as many blogs as I could. Read absolutely everything I could and it kind of became my replacement education in a way.

For Pete Cashmore, Mashable was brought about not intentionally, but almost by accident. When he found himself limited by recovery from an operation, blogging and online news provided a sense of release and fulfillment which was difficult for him to acquire otherwise.

From that time spent came the genesis of the idea — and the desire — to start Mashable, through which he now has an estimated net worth of $95 million USD.


Tumblr, founded by David Karp in 2007, is a microblogging platform and social networking website. Tumblr is different to the more traditional blogging platforms of WordPress, Blogger, and Moveable Type.

In contrast to these platforms, Tumblr is much more free-form, allowing users to add all types of content, and strongly control their blog’s appearance. It was acquired in 2013 by Yahoo! for $1.1 billion USD, in cash.

Here’s a bit of background on what motivated Karp to start Tumblr:

At the time, Karp was running his own consultancy, Davidville, which built business websites, along with a 24-year-old programmer called Marco Arment, who would later found Instapaper. The pair had a steady stream of work, but often infuriated their clients with their lackadaisical approach to admin. . . “They loved what we did, but hated working with us.” At the end of 2006, Karp and Arment had a two-week break between contracts. Karp told Arment, “I’ve got enough of a vision of this thing. Let’s see what we can put together in the two weeks before our next gig.”

So Tumblr wasn’t a side project either in the traditional sense, but it was born out of a perceived problem with an existing project. If the pair had been better organized, Tumblr might never have happened. But that we’ll never know.


Craigslist, created by Craig Newmark, was originally launched in 1995 as an email list for friends to discover social events in the San Francisco area. This is before just about all of the world’s most popular sites, the same year that Internet Explorer, Java, and Intel’s 133 MHz Pentium processor launched.

Within a year, the list had grown and users were calling for a web interface, which was launched in 1996. Craig had been working, successfully, as a Java programmer for IBM, but by 1999 Craigslist was incorporated as a private for-profit company, because it had become so popular.

From pretty humble origins Craigslist, today, has the following statistics:

  • 25% owned by eBay
  • Turnover of about $130 million USD
  • Is in over 700 cities in 70 countries
  • Regularly serves over 50 million queries a day
  • Has one million job postings each month

Once again, Craigslist is a different kind of side project. It was a bit of fun, a helpful way to stay in touch with friends and to know what was going on in the area, and a great way to socialize. It wasn’t started with the intention of growing a career or building net worth, and yet Craig is reported to now have a net worth of over $400 million USD.


Let’s look now at one final example. Shutterfly, started in 1999 by Dan Baum, is one of the largest sites in the world where people can share, organize, and store their photos and create photo books. Whilst there are a number of competitors, such as Mixbook, Snapfish, and Pinhole Press, Shutterfly is one of the oldest and best around. As of 2014, it had 2.6 million customers and 4.2 million orders.

But even it too started as a side project. Well, almost. Given that the idea was generated and fielded whilst the founder was still working at another job, it qualifies to be in this list of ten. Here’s a glimpse into how it started:

During a vacation from work at Silicon Graphics, where he had been an engineer and engineering manager in the late 1980s to 1999, [Baum] began testing photo image enhancement technology with a friend, developing a strategy to form a startup company that would allow people to upload digital images and print from an internet site. “In a rather uncharacteristic move for me, I returned from vacation, quit my job the next day and started the company in our guest bedroom with nothing more than some technology demos and a PowerPoint presentation,” he said.

The referenced article shows that it’s not always easy to build a side project into a viable business, one which lasts over the long term. But it is possible. It also shows that you don’t need to be young, or even under 30, to have what it takes. You can come from a traditional career working for others, yet still have an idea which will turn into a commercial success.


And there’s a showcase of 9 side projects, all of which became great successes. What can you learn from these success stories? A lot. But let’s distill the key elements, so you can begin quickly — today perhaps — to pave your own way to success.

Pivot for Success

In every project there are missteps, no matter how experienced the founders are. But Twitter, Instagram, and Tumblr show that by looking at what’s not going right, as well as what is, there’s often the opportunity to pivot, even completely change direction. Through such nimble tactics, a hidden gem can be uncovered, one which can lead to ultimate success.

Iterate, Iterate, Iterate

As the case of Twitter showed, even the first few attempts, a number of which can seem OK, may not be enough. It may take several iterations, adjustments, even rewrites, to succeed. What’s more, that success may not even be immediately clear to everyone.

It’s not unusual for people to reject what’s new or what doesn’t seem initially to be working, but that doesn’t mean the idea’s not a good one. If you believe in it, have the conviction to persevere. But, conversely, you’ll need to develop the instincts to know when it’s time to let go and move on.

Make the Decision to Start

Starting, simply starting, is critical. The ideas showcased here weren’t run through committees, or analyzed within an inch of their lives: they were started. Too often, the prevailing wisdom is to “make sure you’re ready,” often with extensive spreadsheets and weighty business plans.

“…his girlfriend told him to put up or shut up.”

Whilst it’s great to be prepared, preparing for too long can squelch an idea before it’s begun. Take a leaf from the book of these ten businesses, and if you have an idea, sketch it out in enough detail to get a clear, basic understanding, but then take action. Even if you’re not sure where it will end up.

Don’t Wait for Conditions to Be Right

GitHub is an excellent example of not waiting for the conditions to be exactly right before jumping in. When the founders started out, Git was only just past the ultra-early adopter phase and had only recently become usable by normal people. But despite that, developers were talking about it more and more at meetups and user groups, a testament to the growing reach of the concept.

But still, circumstantially, there didn’t appear to be a patent demand for hosting. Reading between the lines, I don’t think people thought they needed it. Yet the founders started anyway, based on a perceived, and projected future, need. This kind of start can be riskier than others, but there are a number of other examples, such as Apple, which show this can work.

How to Get Exposure

Exposure is something everyone wants, and some companies pay hundreds of thousands, if not millions, for. But if you’re working on a side project, you don’t have a large bank account to spare (or waste). So, how do you get exposure?

There are a number of approaches at work in these ten successful projects, but the one that rises to the top is getting in touch with and becoming an active participant in the communities which do, or would, use your product or service. You can connect online, but connecting in person works so much more effectively. It’s so personal. You can create meaningful, lasting friendships and people have a face to put to the name.

Success comes from turning … passion into something other people will be passionate about too.

However, in-person connecting does have its limitations. You can only be in so many places over the course of a year. Working on a startup or a side project, you have only so much time, so much income, to spare for traveling to and attending events.

But if you’re keen to get involved, in most cities you’ll find a meetup or user group which suits your product or service. If there isn’t one, why not start it up yourself? In addition, there are likely to be one or more conferences which you can speak at. Both of these strategies are great for getting you coverage and exposure.

Why? Because you get to speak to a ready audience, which can help start buzz and extend your reach. And your presentation, either a recording or the slides, will likely be posted online, which means you’ve the chance now of reaching even more people in your target audience. When done right, the audience will learn key details about you, not only your credentials and your vision, but contact info as well — your name, where you work, and your social media handles — right from the start.

But if you’re not quite comfortable yet with speaking, there are a number of ways you can connect with communities online. Here’s a short list of suggestions:

So even if you’re just starting out, there are a wealth of opportunities for you to gain more exposure for your project.

Where to Look for Collaboration

Most of the examples showcased in this post have shown, time and again, that successful projects are a group, not a solo, effort. Whether it’s the three co-founders of GitHub, the multiple founders of Twitter or Instagram, or the fact that others (as in the case of Pinterest and Dwolla) came onto the project in the early days to inject new life into it, what these stories illustrate is that few can create something of true value alone. Everyone needs others around them to complement their own skills and to contribute skills they themselves don’t have. As Richard Branson, founder of the Virgin Group, says:

When it comes to business success, it is all about people, people, people.

But how do you find great talent? Where do you look? Asking those questions is the way to start. There are loads of great resources available, but start with people you know, people in your local user group, and people you meet at conferences.

The last two, especially, are likely to be fantastic resources, as those are the people with similar interests as you. They may even be working on, or considering working on, side projects themselves. The rest comes down to networking and building relationships.

If you don’t already have a large network, start building one — today. Get proper business training, meet people, talk to people, build relationships. In addition to that, if you’re not already using it, starting using that social networking tool that leads the pack — LinkedIn.

Each social network has a raison d’être, or a reason for existing, and LinkedIn’s, with over 300 million active users, is for business and professional networking. People go there looking for work, to find employees, to find freelancers and contractors, in short for business opportunities.

So don’t let this gold mine slip past you. It’s free to sign up with and free to use, though premium accounts are also available, offering more features, should you need them.

How to Assess Project Size

This can be a tough one, as no one has a crystal ball, and 20/20 vision is easy in hindsight. But when a project’s in its infancy, with maybe not even a handful of users, it’s difficult to tell if it’s going to develop into anything, let alone anything worthwhile.

And it’s one thing to take on a project, it’s another to know just how much of a commitment it might end up being. Knowing this is important, because you’ll likely devote a lot of your spare time to it. And if it takes off, you’re going to be devoting the majority of all your time to it.

What’s more, if it takes off, it’ll also be your main source of income. If you’ve no dependents, then maybe this isn’t so important to you. But if you have a family, children, or older family members to care for, it will be.

The final thing you need to do is to be able to make a realistic assessment of whether or not you should undertake the project. Admittedly, this isn’t the easiest thing to do. Likely the best thing you can do is to find others who’ve trodden the same path before — find experienced mentors.

Whilst no one will know your position exactly, and no one except you is in the hot seat with the decisions directly affecting them, mentors enjoy similar experiences to you. They can apply the lessons they’ve learned, and offer advice based on those experiences, offering guidance and counsel.

Note: Likely the worst thing you can do is listen to armchair critics, people who’ve never done what you’re doing, and likely never will. Their advice, whilst no doubt well intentioned, won’t be based in the practical knowledge and experience necessary to help you in any meaningful way.

How to Find A Mentor

Mentors come in all shapes and sizes, and are available both on- and offline. Do you know someone who’s started a side project which turned into a successful business? Does someone you know know someone?

Is there someone in one of your sporting clubs or user groups? Ask around. Oftentimes we form the false impression that people who are successful either are unwilling to share what they know or have no time to do so. From personal experience, I’ve often found this not to be the case. I’ve found that successful people are usually more willing than others to share their experiences.

But whilst offline mentors are perhaps the best, because you’re right there with them, don’t discount online. Online development programs for executives are a great way to gain new skills and knowledge if you don’t know someone who can mentor you in person, the internet is your friend. Nearly everyone has a Twitter, Google+, or other social media account, especially people in business and the public spotlight.

What’s more, some of the best also blog. Take Richard Branson for example. He regularly blogs about a wide range of topics, interests, and events he’s participating in. Make use of these resources to learn all you can, gaining in situ mentors.

But when there’s so much great content, mixed in with a lot of white noise, how do you stay abreast of the best and filter out all the chaff? Depending on the medium you’re using, there are two ways: Social media and blogs.

Social Media

For social media, Lifehacker has four great suggestions, specifically relating to Twitter:

  1. Follow the right people
  2. Utilize lists to manage your feeds
  3. Filter out the junk you don’t want to see
  4. Give up on seeing everything

Twitter is like a veritable fire hose of information. You can’t take in everything, even if you tried. But the same goes, more or less, for other social media platforms such as Google+, LinkedIn, Pinterest, Instagram, and Facebook.

With Google+, instead of lists, you circle the right people and participate in the right communities. On Facebook, you’d like the right pages. You don’t need to be on every social media platform, or, for that matter, even any. But it helps.

If you plan to become involved in social media, start simple and build up slowly, making the best use of each platform as you go along. If you are on multiple platforms, consider using a tool such as HootSuite or TweetDeck to make your time more efficient. With these, you can work with multiple platforms simultaneously, scheduling updates, plus a lot more.


The number of blogs available on the internet is astronomical. So make sure you’re using aggregation tools to manage the available content. Whether you’re using a desktop browser or a mobile device, there are tools to help you out:

The Bottom Line

That’s the tour. Are you inspired enough to want to take on a side project of your own? Have you an idea, or maybe just the inkling of an idea? Do you think it might boost your career, make you rich? It just might, but be sure that at the start you’re pursuing the passion — the problem you see, the curiosity you have, that itch to scratch — and don’t let dreams of success distract you. Work to grow your audience, to expand your reach, to get the ideas out there, but in service of your project, not in anticipation of where that project might take you. Success comes most often in these endeavors out of the right ideas, at the right (or even in advance of the right) time. Success comes from turning that passion into something other people will be passionate about too.

Or perhaps your project is only a hobby, and you’re thinking of keeping it that way. No worries. But if the project blossoms, follow it. Because from the smallest of endeavors, from the most unexpected of corners, can come wildly unexpected success.

Whether you dream large or small, the best side project is the one you can’t imagine not doing. If you can’t imagine not doing it, it might be that others won’t be able to imagine not using it. And however modestly you start, your passion just might lead you to develop the next Pinterest, the next GitHub, or the next Twitter. Your passion just might lead you to excellence.

Matthew Setter
Matthew Setter
Matthew Setter is a software developer and freelance technical writer with over 14 years of professional software development experience gained in Australia, England, and Germany. He is the author of Zend Framework 2 Foundations, writes for a variety of publications including PHP Architect magazine and, and regularly develops with PHP and related technologies.