Learn From 6 Entrepreneurs Who Quit Their Jobs and Became More Successful

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Many people list ‘entrepreneur’ as their planned career choice – but not everyone can handle the lifestyle that’s required. As a result, when friends and family tell us they’ve got an idea to earn millions, we smile and offer support. But when our loved ones suggest leaving a secure job with steady pay and hours, we beg them to think carefully or reconsider.

Yet part of the reason that not everyone can handle the lifestyle, lies in the fact that to start something new you have to harness your passion and ignore the worrisome comments. Despite negative commentary, financial barriers and self-doubt, these daring entrepreneurs flew in the face of “common sense,” ditched their desk jobs – and became hugely successful because of it.

1. Santhosh Tuppad

Santhosh Tuppad was a tech employee that spent his days behind a desk, handling other people’s problems and advancing someone else’s business. That is, until he quit his job without even handing in his notice (not something we’d encourage). He had an idea, and pursued it by cutting ties with his previous job altogether and co-founding his own IT company with a partner.

Tuppad’s first company grew and thrived for years, but if quitting your safe job to start your own company wasn’t daring enough once, Tuppad did it a second time. He left his new IT business in the hands of his partner to create Test Insane, a software testing company. Since then, he’s won several awards, speaks at conferences, and enjoys financial success, all while following his passion.

2. Paul English

When you pair dissatisfaction as a desk jockey with a meeting of minds over a few drinks, you have the success story of Paul English and his business, Kayak. English left his good but dreary hours at a venture capital firm when the founder of Orbitz, Steve Hafner, partnered with him to create a new kind of travel website.


English took the position of chief technology officer at Kayak, and together they created a site which collects, compares, and sifts through the best plane, hotel, and rental car deals available to give customers the best prices. Kayak’s annual revenues now top $292 million, with over 5 million travellers using their mobile travel app each year.

3. Andy Schamisso

The thought of leaving a public relations job and all its security to make tea isn’t a thought many people would entertain. But Andy Schamisso needed only three things to quit his steady paycheck and wander the streets of New York in what would eventually become his startup company; a recipe, a list of health benefits, and his dog, Inko.

When Schamisso discovered the health benefits of a unique and little-known kind of tea his wife liked, he realized there was a demand not yet met in the market. He bought 6,000 cases of tea made from his own unique recipe, and after substantial sales on the streets, he began selling them in stores. The company, Inko’s White Tea – named after his dog, now makes over $3 million a year and has unveiled a variety of new flavors.

5. Dana Sinkler and Alex Dzieduszycki

A job at a four-star restaurant owned by Jean-Georges Vongerichten gave Dana Sinkler and Alex Dzieduszycki a chance to work with a world famous chef and trust in the security of a weekly paycheck. Yet that wasn’t enough, so the pair quit their jobs to open their own catering business, allowing them to create and deliver their own top dishes.

However, while trying to develop a unique menu, Dzieduszycki and Sinkler did more than just help their current business – they started a new one entirely. Terra Chips were born as an appetizer to serve at a bar, and the fried vegetable roots quickly exploded into a startup of its own. Once the two entrepreneurs packaged and started selling them in stores, it only took a few years before success had them making $23 million a year in sales. They were eventually bought by Hain Celestial for $80 million, leaving the entrepreneur pair with the freedom to create more startups, far richer and more successful than they began.

Terra chips

6. Shep and Ian Murray

When an advertising executive and a public relations employee decide to give up their desk jobs at a ritzy corporation in Manhattan, people’s heads turn. When they give up these “safe” jobs to take out advances on their credit cards and sell ties out of their backpacks on the beach, people demand they come back to their senses. Yet Shep and Ian Murray, two brothers who could’ve been sitting pretty in their unhappy jobs, ignored that advice and sold 800 ties by hand in a single day – a venture that would eventually become the company Vineyard Vines.

Their tie business has now made $100 million dollars in a single year, opened 18 stores, and sells in outlets around the world – giving them the opportunity to never wear a corporate tie themselves again.

Got What It Takes?

Whether these entrepreneurs doubled their previous income or made millions, doing the “dumb” thing and ditching regular jobs lead to more success than ever expected. So if you’re at the office dreaming of turning your idea into a reality, check out our startup business loans overview to find out what it takes to make that first leap towards entrepreneurial glory.

Written by:
Rob Binns
Rob writes mainly about the payments industry, but also brings to the table industry-specific knowledge of CRM software, business loans, fulfilment, and invoice finance. When not exasperating his editor with bad puns, he can be found relaxing in a sunny (socially-distanced) corner, with a beer and a battered copy of Dostoevsky.