Slack, Instagram, Twitter: Side Hustles That Became Billion-Dollar Companies

Thirty years ago, when I lived in a very small town, my next-door neighbor, John, would often stand in his backyard, staring off into space, sometimes for hours.

He was a very nice man, but still: I thought it was odd.

Only later did I realize that John, a computer science professor at a nearby university, was working through how to create the systems architecture for one of the first–and for a time, most successful–language-learning software products.

For John and his brother-in-law Allen, Rosetta Stone was just a side hustle.

If you’ve been thinking about starting a business while keeping your full-time job and are searching for a little motivation, here are some successful companies that began as side hustles.


While working at Nextstop, Kevin Systrom decided to create his own location-based iPhone app: one that let users check in at specific locations, make plans for future check-ins, earn points for hanging out with friends…and, since he loved photography and had built a photo-sharing site for fraternity brothers while in college, to post pictures of those meetups.

Since he liked whiskey, he called it Burbn. 

Unfortunately, Burbn was hard to use. Too many features. Too complicated to navigate. Hardly anyone shared their location.

But they shared lots of photos. And they wanted to share great-looking photos, which led Systrom to create filter apps.

So Systrom decided to focus solely on photo sharing–and Burbn became Instagram, a company that, when purchased by Facebook for $1 billion, only had 13 employees.

All because Systrom loved building products–and photography.


In 2006, Adi Tatarko was working at an investment firm. Her husband, Alon Cohen, worked at eBay. They bought an old home in need of renovation and struggled to find the right designers and contractors. 

So they built their own online directory service to try to make the process easy, enlisting parents from their kids’ school and a smattering of local designers and architects to be their first users. 

Today, Houzz has tens of millions of users and has attracted more than $600 million in funding. (And is the first site my wife turns to when she’s looking for design ideas.)

All because Tatarko and Cohen decided to make the process of renovating their home a little easier.


Dharmesh Shah is a serial entrepreneur, so after he sold Pyramid Digital Solutions to SunGard Business Systems, he worked on other opportunities.

One was an idea for an online marketing platform based on pull, not push. But he wasn’t sure the idea would fly–so on the side, he and co-founder Brian Halligan launched the HubSpot blog.

After all, if they couldn’t attract an audience to the blog through content marketing…how would they build a business based on that marketing strategy?

As Shah says, “A tiny blog with no budget generated more traffic than companies with professional marketing teams.”

And HubSpot, a company with a current market cap of over $10 billion, was born.

All because Shah created a side project to validate an idea. 


Stewart Butterfield co-founded a game company. The game bombed, so he and his partners built a photo sharing website that became Flickr.

After Yahoo bought Flickr, Butterfield stayed for a few years. Then he left to start another game company. That game, Glitch, also failed to find an audience.

But the company had built an in-house instant messaging tool to help manage the game’s development, and Butterfield decided to release it.

That side project, Slack, became one of the fastest startups to hit a billion-dollar valuation, and currently has a market cap of over $19 billion.

All because Butterfield wanted an easier way for employees to communicate.


By 2005, the small startup Odeo had built a podcast platform. Then Apple announced iTunes would include podcasting features. 

So the company started holding “hackathons,” where groups of employees would spend a day working on new ideas.

One of those ideas was a system that let users send a text to one number, and that text would automatically be broadcast to all of your friends. They called the side project “Twttr.”

In time, Twttr became Twitter. You know the rest of that story.

All because a struggling company realized it needed a few new ideas.

Which is true for every company, no matter how successful it may currently be.

The opinions expressed here by columnists are their own, not those of

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