Today Shuttlestock is worth over 2.5 billion dollars since IPOing in 2012. That surely is an impressive run for a solo f

“It was still a very new concept. We thought given the number of software India uses, there must be a huge opportunity. This was the driving force though the product has evolved over the years.” — says Vembu

A hostel in Mexico seemed like the right place to pursue his terrible idea, so Kevin packed his flip-flops and bought two tickets out of California — one for himself, one for his girlfriend. That second ticket would become the best investment Kevin Systrom ever made.

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its tongue-tripping name to become ubiquitous with a Subway-like concept where you see your big-ass burrito get stuffed in public. If only the food were as great as the idea. (If you can’t get queso right, you’re not getting high up on this list.)

“We spent like $60,000 to launch Burbn. We raised $500,000 and we were kicking ourselves the second day after… We were like, we had all this money left. […] Turns out, you can bootstrap yourself with Amazon Web Services; you need like 2 engineers these days to do things well.”

However, photos were super expensive to use, so he decided to take his own photos with a Canon he bought. This soon prompted him to realize that other entrepreneurs on the web might want stock photos as he did. With this, he put together the odd 30 000 photos he had already took and paywalled it behind a website with a $49 monthly subscription for unlimited use.

Although the product took a while before it managed to gain traction, it has since skyrocketed in growth. As with all private companies, it’s hard to identify its true valuation but taking a look at some older estimates, we can generate an idea of how much it’s worth.

“I didn’t have a specific idea in mind… I mean, the idea was basically to start a check-in app… Who wasn’t starting a check-in app at that time? […] It was probably the worst idea we could’ve been working on at the time.”

This soon blew up, and Oringer expanded his services by adding on contributors beyond himself. This was all bootstrapped with Oringer raising a small round only once (mainly to help scale his management team) and still maintains a close to 50% ownership of the company by himself.

Starting off with an older name on the list, Zoho is known as the CRM with everything. Having launched in 1996, Zoho was launched when there weren’t that many software companies in India.

Burbn was easy to build, but it was even easier for users to forget. 80 people — that’s how many joined Burbn over nine months. Kevin recalls having his friends meet his parents via the app, and reconnecting with long-lost acquaintances. But whenever he showed the app to ‘outsiders’ — a.k.a. potential users like you and me — they would nod enthusiastically and then dismiss the app minutes later.

Burbn — Kevin’s first grown-up brainchild — sounded good on paper. Unlike other check-in apps, Burbn allowed users to post photos and videos along with their check-ins. Investors liked the idea, and Kevin received two checks — one from Baseline Ventures, and another from Andreessen Horowitz — totalling $500,000.

His next stop was NextStop, a location recommendation app startup. With FourSquare leading the way, check-in apps were all the rage in the late 2000s, and a small team meant Kevin could get more responsibility and take initiative.

As a direct competitor of Salesforce, Zoho competes differently by using two tactics for its growth. They focus on offering a freemium with all the bells and whistles to help entice customers to switch over to their full suite of products eventually.

Another interesting point is that Zoho actually reinvests most of their profit (50% of it!) back into R