In the past few years, we've seen a global cultural shift towards entrepreneurialism. With tech titans like Mark Zuckerberg and Steve Jobs, millennials are discovering entrepreneurship earlier than their parents, thus inspiring them to drop their school bags and start their own ventures.

But, as Reid Hoffman said, "Starting a company is like throwing yourself off the cliff and building an airplane on the way down." Some people may have the courage to take the leap but very few can stand the pressure to build something successful from scratch.

The cold hard truth about growing a startup is that it will always be chaotic no matter how careful you plan. It also doesn't matter if you're a degree-holder or a dropout. When it's crunch time, it all boils down to your ingenuity, resourcefulness, and ability to maintain your composure.

These dropouts prove that they have what it takes to thrive in the unforgiving world of entrepreneurship:

1. Richard Werbe and Jiaming Zhong - Studypool

Designed for students who need on demand tutoring assistance, Studypool is a Microtutoring platform that breaks down conventional learning into smaller, more digestible pieces of learning. The company was founded by CEO Richard Werbe and CTO Jiaming Zhong during their sophomore year in college. After generating thousands of users within a month, Werbe and Zhong chose to drop out of school and dedicate their time to running the website.

Through 500 Startups, a venture fund and accelerator, Studypool raised $2.3 million in seed funding, making Werbe the youngest entrepreneur to raise over a million through the accelerator program. Today, the website serves over a million students across the globe with the help of over 40,000 tutors.

Studypool is, at its core, a Microtutoring platform where students can go for on-demand homework help for for questions that take as little as one minute. It covers a great deal of lessons in fields like business, accounting, writing, and programming. Apart from posting questions, users can also avail live tutoring sessions or browse learning resources from the "Notebank".

In one of his articles, Werbe explains that you need to build startups around trends and not just original ideas.

The idea behind Studypool is to make information as accessible as possible, but it was built around the 21st century trend of trolling the internet to find esoteric information. With search engines, users often need to verify information through different sites to form a cohesive and reliable solution. It's also difficult to find definitive answers to very specific questions -- the kind that's rarely searched online.

For students, Studypool does a significantly better job than search engines. Instead of providing "shallow" information, Studypool brings answers that are tailored to their specific questions with the help of qualified tutors. "We want to be the platform that helps out with very specific questions," says Werbe. "You need explanations tailored to you."

Werbe also said that a little anarchy is sometimes necessary to give your startup some traction.

"Whether it means dropping out of school, ignoring advice from parents, or straying from the herd mentality, your life is going to change in some capacity," says Werbe.

2. Ari Weinstein, Conrad Kramer, and Nick Frey - Workflow

Workflow is an app that gives your Apple device superpowers. It's a personal automation tool that lets users weave together different apps to create a chain of actions - from getting directions to the next event in your calendar to compiling expense reports to Dropbox.

The app was co-founded by Ari Weinstein, Conrad Kramer, and Nick Frey, all of whom dropped out of college to work on the app. Thanks to their hard work and vision, Workflow was named the "Most Innovative App of the Year" by USA Today in 2015.

"We wanted to make something that connected different apps together, in a way that isn't really possible right now," says Weinstein.

Weinstein started working as a software engineer in WiFast when he was 18. At age 19, he dropped out of Massachusetts Institute of Technology to pursue the life of an app developer.

Another selling point of Workflow is its ease of use. Despite being able to automate a string of actions, everything can be done through the simple drag-and-drop interface.

With a little creativity, you can automate complicated tasks like finding the lyrics of a currently playing song. With countless apps to mix and match, there are virtually endless ways for Workflow to make your digital life easier.

3. Keiran and Rory O'Reilly - Gifs.com

The parents of Kieran and Rory O'Reilly got two new license plates when the siblings were accepted to Harvard - "2 N HRVRD" and "HARVRD 2". Sometime later, Rory said they might change it to "2 DROPOUTS".

Instead of focusing on their studies and making their parents proud, the two turned their attention to gifs.com -- a site that allows users to turn video clips into animated gifs -- and made their parents even prouder!

It sounds simple, but gifs.com is now being used by millions of people every month. The site also offers a host of tools that can make animations more unique, including black and white filters, padding, stickers, and captions.

In 2015, the brothers received a $100,000 grant each from Peter Thiel. But before this, they had to withstand homelessness and weeks filled with self-doubt. .

"I almost felt like I could melt," says Rory. "It felt as if every day we'd wake up and move to a friend's place, a hotel, or an Airbnb -- a new distant location. Fun, in a way but incredibly stressful."

During this time, the brothers remained focused on what they had to do. They kept up with sending outreach emails to investors, checking the website's stats, and searching for ways to build a decent user base.

Eventually, Rory O'Reilly had an idea to post about their startup on HackerNews. And within 24 hours, gifs.com was #1 on HackerNews, the /r/technology subreddit, and Product Hunt. The site was even featured on TechCrunch.

It seems that the O'Reillys' website was just in time for the visual content marketing revolution. Not only are humorous animations highly shareable in social networks, several messaging apps today also integrate gifs to spice up conversations.

In other words, aside from casual users who enjoy animations, gifs are also widely used by content marketers to engage their social media audience.

4. Dylan Field and Evan Wallace - Figma.com

In 2012 Field had the opportunity to take a year off from his CS & math undergraduate studies at Brown University to join the Thiel Fellowship where he and 10 other applicants were awarded $100,000 to pursue and develop their own startup.

Field wanted to take on the $6 Billion business Adobe and build a design tool that could rival Adobe's Illustrator but that would also allow users to collaborate on work in the cloud.

"Creative tools like Adobe Photoshop are expensive and very hard to use, to train yourself to use Photoshop is a long, arduous process, and so what we're trying to do is to make it so that anyone can be creative by creating a free, simple and creative tool for the browser."

After teaming up with Ewan Wallace they came up with the idea for Figma, a workflow browser-based collaborative design tool. Barely a year later, the team managed to snag $3.8 million in funding.

Figma differentiates from similar tools such as Wake as it was built as a vector editing tool and allows users to design directly in the software instead of having to import files from other programs such as Sketch or Illustrator.

Later in 2015, Field and Wallace were able to secure even more funding; this time a very impressive $14 million, and Figma was officially launched in September of last year. They are hoping to build a solid following within the design community by offering an easily accessible alternative to Illustrator and are currently offering a 3 month free trial.

Published on: Mar 8, 2017