These 25 Entrepreneurs Gave Up Everything to Pursue Their Passions — and Succeeded

Many of you reading this right now hope to be successful entrepreneurs. You’re not fully there yet, you haven’t fully committed yet, but you are on the edge, waiting for the perfect chance.

But then doubt comes into play: can I do it? How long will it take? Is it even worth it?

You know the handful of stories of Facebook, Google, Amazon, IKEA and the like that have made it big. But for you that’s perhaps too unrealistic.

You also know the million stories of failures that surround businesses. You know that 9 out of 10 startups fail and that almost half of all small businesses close down before their 5-year anniversary.

But what about that 1 out of 10 startups? What about the other half of the small businesses? The successful entrepreneurs that didn’t fail? Where are their stories?

That’s why we’ve brought to you today these stories of not-giving-up, the stories of success that you won’t hear about in the evening news. The real stories of everyday entrepreneurs who quit their jobs to pursue their passions — and succeeded.

These are the real stories that can help you chart your course on your way to success, to give up the fear of failing and begin your new life as an entrepreneur.

Against the odds

These successful entrepreneurs preserved against all the odds — the constant doubts placed on them by their friends, family and others. But they not only survived, they thrived.

Daniel C. Lavery, Writer & Civil Rights Attorney

danielclavery.com |@Danielclavery


My father discouraged me from the practice of law and said I could never pass the bar exam. My wife and I had two children with another on the way, and I wanted to consider a major change by doing something everyone said was impossible.

I was successful in passing the exam and I decided to open a civil rights private practice at 40. Soon I had won the largest defamation verdict west of the Mississippi, and established precedents in slander law.

For new entrepreneurs, I offer the wisdom I learned not to always follow your father’s advice, or anyone else’s who does not know your motivation, passion, and determination. If you have a passion to do something a few people don’t believe possible, you should not be discouraged.

Lori Cheek, Founder of Cheekd

cheekd.com |@loricheeknyc


After working in architecture, furniture and design for 15 years, I came up with an idea that led me into the NYC world of technology and dating with Cheekd, a newly launched hyper speed Bluetooth mobile dating app. However, I had to sacrifice a lot for my idea.

I sold nearly $75,000 worth of my designer clothes at consignment shops and on eBay, doing focus groups, secret shopping, app testing, dog walking, house sitting. I rented out my West Village Studio in NYC on AirBnB while I couch surfed for 14 months, nearly got evicted and ultimately lost my lease of 5 years to my gorgeous apartment.

And finally, after four tumultuous years I landed on ABC’s Shark Tank and was harshly rejected. 48 hours later, Cheekd.com received a record breaking 100K unique visitors and our inbox filled up with thousands of emails (50 from interested investors) insisting that the “Sharks” were “out of their minds” for not investing.

Cheekd has been the most powerful thing that’s ever happened to me. Building this business has been an incredible learning experience. I’ve never been more dedicated to anything. Despite the occasional overwhelming stress, it’s been loads of fun.

Successful entrepreneurs by accident or incident

These entrepreneurs didn’t get to their successful careers fully by their own choices. In one way or another, a decision was made for them or discovered by accident. So they took that opportunity to take their careers into their own hands and become successful entrepreneurs.

Dan Nainan, Comedian

danielnainan.com |@comediandan


I was a senior engineer with Intel Corporation. My job was to travel the world with the company’s senior executives, doing technical demonstrations on stage at events, and I was incredibly nervous about speaking on stage. I took a comedy class to get over the fear, and the comedy kind of took off.

Since leaving Intel to pursue comedy full-time, I have performed at two Democratic National Conventions, at a TED Conference, at several presidential inaugural galas, for President Obama, Donald Trump, Rudolph Giuliani, Michael Bloomberg, Hillary Clinton, Steve Wozniak, Arianna Huffington and for many similar luminaries.

Jessica Mehta, Novelist & Founder of Mehtafor

mehtafor.com |jessicatynermehta


I worked for non-profits and NGOs as a grant writer, events coordinator, admin, etc. For a few years I was indifferent, but in my last two years I really burned out.

In my final position, I was actually hired on as a Director and wasn’t told that my job was *really* to finish up the year’s project before the department was shut down. I then started working on writing and mehtafor.com, a writing services company which serves a variety of clients including Fortune500 enterprises and major media outlets.

I was making six figures within 18 months; however, I attribute that to luck, dogged ambition, and moving overseas where cost of living was much lower and I had foreign earned income exemption.

Jonathan Whitney, Profitable Affiliate Programs

bloggeroid.com |@ProfAffiliates


My story is a bit different. I didn’t quit my job, I was let go. I was a discovery analyst for a law firm in Seattle. The job was alright, but I wasn’t passionate about it.

After I was let go I started driving for Lyft and Uber. With the huge sign up bonuses, I figured I could make some money blogging about the industry and referring drivers. I had no experience with blogging, and didn’t even know how to build a website. It took months to get the ball rolling. But when it started rolling it really took off. I made significantly more than a year’s salary in a short period of time. Moreover, I realized how much I loved blogging and web design.


For the 20 other successful entrepreneurs, visit the original article here.