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25 Successful Entrepreneurs Who Quit Their Jobs to Pursue Their Passions

Written by on November 10, 2016

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 Laver is a successful civil rights lawyer and writer

Daniel C. Lavery, Writer & Civil Rights Attorney

danielclavery.comtwitter-1 @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 Cheekd is a professional and successful dating specialist

Lori Cheek, Founder of Cheekd

cheekd.com |  twitter-1 @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.


Daniel Nainan is a successful entrepreneur comedian

Dan Nainan, Comedian

danielnainan.com |  twitter-1 @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 is a successful writer and founder of mehtafor.com

Jessica Mehta, Novelist & Founder of Mehtafor

mehtafor.com | facebook-1 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 is one of our many successful entrepreneurs

Jonathan Whitney, Profitable Affiliate Programs

bloggeroid.com | twitter-1 @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.


Catherine Wood is an executive life coach and successful entrepreneur

Kristen R. Edens, Founder of KristheScribbler.com

kristhescribbler.com | twitter-1 @ScribblerKris


I quit my job as an exercise physiologist (with a Master’s degree) in 2008 to pursue my preferred career as a freelance writer.

I loved my job, but hated corporate politics. The commute, salary, gas prices, and scheduled hours made it more expensive to work than not to work. Lastly, I wasn’t challenged enough.

In addition to quitting my job, I was unaware of the economic recession building at that time and was in the process of divorce. Things were tough but it motivated me to put all my focus in my business. I started with zero and built it up. Every day I continue to see it grow and succeed. Success is defined in many ways and I define it as pursuing what makes me happy and solving problems that others dread.


Dana Humphrey is a successful PR entrepreneur

Dana Humphrey, Whitegate PR

whitegatepr.com | twitter-1 @danakhumphrey


I started my business in San Diego in 2007. I was working full time for a company called Muttropolis and started consulting part time as Whitegate PR. My grand plan was to go to San Francisco, but I applied for one job in NYC and got it!

I applied, had a phone interview, flew to NYC and moved within ten days. Two months later I was laid off on a Thursday. That Friday, the very next day, the one client I had been consulting for called me and asked that I be available for more hours. I have been running my business full time since that day.

From hobby to main focus

These successful entrepreneurs had their eye on their hobbies the whole time. But when they saw the opportunity to really make gains in their careers, they took their side hustle and made it their main focus.


Christ Brantner is another of our successful entrepreneurs

Chris Brantner, Founder of CutCableToday.com & Scribblrs.com

cutcabletoday.comtwitter-1 @cutcabletoday


I was a teacher up until recently, and I juggled a side job as a freelance writer and blogger. I enjoyed teaching, but after 10 years, I was ready to move on. I wanted to be my own boss and was willing to work hard for it.

Turns out, it paid off. A year ago, I quit my day job as a teacher and went full-time with my website, CutCableToday.com. The interesting part is that the site was just another side gig, but then it took off. I started it in March 2015, and by the summer it was doing really well, and I decided not to go back to teaching the next fall. Now CutCableToday receives over a million visitors per month.


Gene Caballero is a successful entrepreneur with GreenPal

Gene Caballero, Co-Founder of GreenPal

yourgreenpal.com twitter-1 @YourGreenPal


Before I started my entrepreneurial journey, I worked as a sales coach at a Fortune 50 tech company.  Having done both jobs for 4 years, I knew that at some point I was going to have to quit my day job to pursue my startup full time.

My tipping point was when we hit 500 transactions per week with GreenPal, which has been described as the Uber for lawn care.  What this did was prove that our concept was something that could scale and allow me to leave with a better peace of mind.


Thomas Nguyen left his job as an entrepreneur to become a successful restaurant entrepreneur

Thomas P. Nguyen, Partner & CMO at Peli Peli

pelipeli.com | twitter-1 @pelipeli


I left my career as an attorney to pursue becoming an entrepreneur.  I hated my job because it wasn’t what I was passionate about.  I finally quit because I knew at 27 I had to make a move or else be doomed to my career that I hated.  It took me many years to achieve success—almost 10!

I have now opened a successful South African restaurant in Houston with three locations and ranked in the top 3 in Houston on both Tripadvisor and Yelp.


Sumit Bansal left his career to focus on his knowledge of Excel and became a successful entrepreneur

Sumit Bansal, Founder of Trump Excel

trumpexcel.comtwitter-1 @trumpexcel


I am an MBA and worked as a Marketing Manager in a top technology firm.  I loved my job. I had a great team, good quality work that gave me enough opportunities, and a good work life balance. But at the end of the day, I was still an employee in a huge firm.

At the same time, I had a fledgling online business where I was teaching people how to use Excel spreadsheets. I quit when I couldn’t see myself doing what I was doing in my corporate job for long. Having a backup online business gave me the strength to take the plunge. When I quit my job, my blog was already 2 years old. It was growing fast and I was able to give it my full attention. While success means different things for different people, it was 6 months after quitting my job that I could earn enough to think of it as a long term business.


April Davis is a successful entrepreneur involved in the matchmaking industry

April Davis, LUMA (Luxury Matchmaking)

lumasearch.com | twitter-1 @LUMA_search


I was always a hard worker, working my way up a Fortune 500 company. But if there was one thing I knew more than anything – it was how to help people find love. I was a Matchmaker for years within my own circle of friends and acquaintances; I just didn’t know that I was one at the time.

I often wondered why so many of my girlfriends were single – they were all high-caliber women who were beautiful on the inside and out. The challenges involved in singles meeting quality matches became increasingly apparent, and it was then that I realized I needed to take my matchmaking from a hobby to a full time career. My matchmaking service has taken off, with more than $1M in sales last year. I have expanded the company to over 20 locations in the U.S. and plan to expand even more in the upcoming year.


Dave Hermansen is a successful ecommerce entrepreneur

Dave Hermansen, Founder of Store Coach, Inc.

storecoach.com | twitter-1 @storecoach


While working as an AutoCAD drafter for a large electrical engineering company in the early 2000s, I started trying to learn eCommerce. My first couple of sites were not super successful but I kept at it for two and a half years, surfing the web for any help I could get on how to generate traffic. Once I learned SEO and the secret to generating free organic traffic, my website started producing real income.

I come from a family of entrepreneurs and always dreamed of having my own business. When I started seeing real success with my website, I knew it was time to escape the cubicle and devote my efforts full time to eCommerce. Once I had unlocked the secret to success with one website, I knew I could do it again and again.

We currently run more than 50 eCommerce websites of our own, in addition to running our Store Coach eCommerce training course and have owned nearly 100 successful web stores over the past decade.

They needed more

These successful entrepreneurs just felt they couldn’t get what they wanted from their day jobs. This is the main cause of why people quit their jobs—and the main motivator on their road to becoming successful entrepreneurs.


Jovim Ventura is a successful printing business entrepreneur

Jovim Ventura, Founder of InoPrints

inoPrints.com | twitter-1 @InoPrints


I was working as a Sales & Marketing Analyst for SurePayroll (online payroll company that got acquired for $115M). I lived in Excel and Databases.

My Dad always told me to focus more on the learning experience than the paycheck when looking for a job. At my age (22 at the time), with limited responsibilities in life, his advice worked. I knew it was time to quit when I felt I couldn’t add any more value to the company. Also, I always had a burning urge to start my own business again (I failed at starting 7 businesses before finally going corporate). I learned so much from so many smart people at SurePayroll, that it was time to see if I could apply the lessons I learned to my own venture.

  • The 1st year I was working out of my bedroom at my parent’s house.
  • The 2nd Year I was working in a freezing basement storefront (I couldn’t afford to pay the heating bill).
  • The 3rd year, I wanted to quit 2 times after seeing all my friends buying nice cars and driving up to my storefront.
  • The 4th year, I hired my first employee (a friend) and the company finally turned a profit.
  • The 8th year, we spawned off 2 other companies:  CrowdSigns.com & SignMonk.com

Catherine Wood is an executive life coach and successful entrepreneur

Catherine Wood, Founder & Executive Life Coach of Unbounded Potential

catherineawood.com | facebook-1 catherine.a.wood.7


After returning from four years on the Peace Corps to work as a Senior Economist for the Federal Government, I felt stuck behind two computer monitors and a sea of data in comparison to the adventure-packed and rewarding work I had been doing.

For six years, I was very unhappy, although I was really good at what I did given my background in economics.

What finally made me quit was a declaration that I made to myself. I set a time-sensitive intention of having “x” amount of money in the bank, “x” number of clients contracted, and giving my notice by a certain date. Walking into my boss’ office to hand in my two week notice may be the scariest thing I have ever done, but it was almost the most important decision I have ever made. My practice has blossomed, and my lifestyle and level of joy are as different as night and day in comparison to what they used to be.


Spencer Shulem is a successful startup entrepreneur

Spencer Shulem, CEO at WeDo

wedo.com | twitter-1 @spshulem


I was Head of User Experience for Mobile & Desktop at Procore (a 500m software company) and the youngest employee.

At the time I was really interested in starting something of my own. The company wasn’t huge, it had about 200 employees, but it already started to take the plague of a big company. Things were slow to move or change, new ideas were often swapped for simply improvements on existing ideas, and the urgency and passion behind the company was starting to die.

Less than a month after I quit, WeDo—the software company I started that makes a really simple to-do list app that you can use for yourself or collaborate with others—raised $1m from local angel investors. It was not an incredibly easy round to raise, but it started quickly and I was able to start on a company and product that I truly love.


Lisa Chu is now a successful fashion entrepreneur

Lisa Chu, Founder of Black N Bianco Kids Apparel

blacknbianco.com | twitter-1 @BlackNBianco


Before I started my own small business I worked as a sales agent for an apparel company. The job was fulfilling at times, but I never had the opportunity to become more than a sales agent. My passion has always been fashion and I wanted to contribute my ideas and move up the ladder. The moment that I realized I was going nowhere made me quit my job.

Being in the fashion industry for almost a decade gave me a smooth path to creating and launching a small clothing brand. I was able to use the relationships I established to create a high quality apparel goods at a very generous cost.

It took me two years to build up my brand credibility and start earning a profit. Success was not easy and passion was the only thing that didn’t stop me. I now enjoy every second of my day because I am able to do what I love. Expressing myself through my brand was by far the most fulfilling joy I have ever felt. Seeing customers enjoy what I have designed and produced is the frosting on the cake.


Mike Scanlin is a successful finance entrepreneur

Mike Scanlin, CEO of Born To Sell

borntosell.comtwitter-1 @borntosell


I was a venture capitalist in Silicon Valley and had been doing that for 6 years.

Although it paid well, the job is a 60+ hour/week grind. I was on an airplane 3x per week for some Board meeting or conference. The first couple of years were fun but soon it got to be more of a hassle and routine.

I had been thinking about (read: dreaming of) an online business for the last year or so. I had seen other people do it and felt the lifestyle would agree with me. Once I had a really good idea figured out, I quit.

I self-funded the development of borntosell.com (a web site for covered call investors). I hired 35 freelancers to help me with various parts of it (design, coding, SEO, affiliate program, etc) and it took 18 months. Because we had put so much thought into the UI and features, it did well right away. Won some industry awards. It took about 6 months to reach cash flow positive and be profitable. For the last 4-5 years it’s been my primary source of income and is doing well.


Vienne Brown is a successful entrepreneur in the fashion industry

Vienne Brown, Founder of VienneMilano

viennemilano.com | twitter-1 @viennemilano 


I was a Program Manager at Akamai Technologies (a Content Delivery Network business).

Although I did not love my job, I enjoyed the paycheck. To elaborate, I did enjoy working at Akamai mainly because I felt like I was working with really smart people and cutting-edge technology. However, I cannot say that I am passionate about content delivery software – it was not where my heart was.

While working in high-tech, I often found it difficult to find thigh highs that would stay up on my leg. This was the first spark of my business idea. The other reasons are that I’ve always loved fashion and I was turning 30 at the time, and I thought: wouldn’t it be nice to start my 30’s with a new leaf? So I quit.

After about two years, I became successful. By our second year, it was clear that folks had started to take notice of thigh high stockings and that our business was growing.


Maureen Witten is a successful entrepreneur in the health and wellness industry

Maureen Witten, Founder of Be Yourself Wellness

beyourselfwellness.com | twitter-1 @beyourselfwell 


I quit my job as an Elementary School Teacher to become an Emotional Eating Coach. I loved teaching the kids, I hated working with unsupportive principles, uninvolved parents and using part of my paycheck each month for new school supplies.

It took me two years to learn how to market my business online, get my education and craft a signature program. This is my third year and I’m finally starting to generate revenue. I have time for my kids and clients and make more in 8 hours than I did in one month working as a teacher.

The idea just came in a flash

These successful entrepreneurs are the ones movies are made of. They live their corporate jobs until one day an idea just hits them and they can’t shake it off until they follow that idea. And that’s how they became successful entrepreneurs, by taking a chance and reaping the rewards.


Evan Harris a successful real estate entrepreneur

Evan Harris, Co-Founder of SD Equity Partners

sdequitypartners.com | facebook-1 sdequitypartners


Prior to starting SD Equity Partners, I worked as an outside sales representative for a San Diego dental company. I held this position for nearly 22 years!

One day I woke up, put on my work shirt, looked in the mirror, and suddenly said to myself: “It’s time to start my own company.” I didn’t hate my job by any means, but something just clicked and I knew that I needed to pave my own path.

I always held a passion for real estate and while it took some time to find our niche, we become successful in our second year of operation. The road wasn’t easy, but as SD equity is a family business, my wife and I worked together to make this dream a reality.


Anthony Martucci is a successful entrepreneur and co-founder of a marketing & sales company

Anthony Martucci, Co-Founder of Likeworthy Digital

LikeworthyDigital.com | twitter-1 @LikeworthyCHI


A couple years ago, I was working at a large digital marketing firm in Chicago as an Account Executive of sorts—a typical story for people in the industry at my age. My identical twin brother worked in sales at a payroll software company.

He would complain about how the internal marketing teams would hand him “leads” that were never really sales-ready. I would vent about how our clients focused on metrics that were fluffy and didn’t really prove any business impact. One morning we said “wouldn’t it be great if we started a marketing firm that helped bridge the gap between the sales and marketing teams?” And that week we both quit our jobs and started Likeworthy Digital.

We are now approaching year 2 and loving every minute of it. We help generate leads for companies through marketing, and then we work on closing those leads into customers, essentially bridging that gap for companies. It took us about 1 year to be successful— for us, success meant coming into work everyday feeling that what we built was legitimate: Having clients on retainer, doing work for them we believed in, seeing results that helped us win new business. It took about a year of fine tuning the strategy to get there.

There are many other ways to become successful entrepreneurs

Not all these successful entrepreneurs followed in similar paths. Some had quite different stories and winding roads on their journey.


Alina Adams is a successful entrepreneur who found her new career in a different wayAlina Adams, Founder of NYCSchoolSecrets


I had left full-time corporate work when I was pregnant with my third child, and was freelancing as a writer for a variety of parenting and media publications.

I had to apply my children to Kindergarten in NYC (yes, even your local, zoned one) and realized it was a full-time job – and I did it three times!

As a result, other parents started coming to me for advice. So I gave out advice. Then they invited other parents, and it turned into a workshop. Preschools began offering to pay me to give a workshop. And parents at those workshops begged me to write a book so they could have all my information in one place.

I realized that, with the Kindergarten admissions, I would be the one calling the shots and making the schedules. In April 2015, I published the book parents had been clamoring for, Getting Into NYC Kindergarten, and now I regularly go to schools, religious organizations and other businesses, giving talks to help people navigate the Draconian NYC school application system.

I began offering private consultations, which turned out to be the most lucrative part of the process, and now it’s a full-time business.


Erin Morris is a successful design entrepreneur

Erin Morris, Founder and Lead Designer at Evergreen Design Studio

evergreendesignstudio.com | facebook-1 EvergreenDesignStudio


I quit my graphic design job with USC in 2010, moved to Costa Rica, took some time off to play in paradise, then started my own nomadic graphic design business so that I could continue living in Costa Rica.

My previous job was great – good coworkers, relaxed schedule, nice office. A lot of people would call it a dream job. I just found myself happier in the tropics closer to nature.

When I quit, I took a few years off. Once I started the business, it took about a year to grow my online client base to success. It’s been a lot of hard work to market myself online, but very rewarding to be able to run my own business from a place that inspires and makes me so happy. Working from the jungle is my passion!


Sara Grove is a successful entrepreneur in the food industry

Sara Grove, Raw Food Magazine

RawFoodMagazine.com | facebook-1 RawFoodMagazine


I left a job I had teaching my passion Kiteboarding  because the financial returns were little and the physical and time demands were great, so I was left with little time to actually do my favorite hobbies myself.

I finally decided to quit because I dreamed of building a business that could still have a positive impact on others, but give me the time and location freedom to pursue my hobbies (including kiteboarding). I didn’t want my income to be reliant on my physical body. If I was sick, injured or couldn’t teach? No money.  So my partner and I created and launched Raw Food Magazine.

It took 3 months of full-time building, creating, and promoting before we made our first profit, and two years before our income fully supported us.

And one in the process

Outside of the ones who’ve made it—what about the almost successful entrepreneurs? The ones closer and closer to the edge everyday, ready to take that leap. If only they had the right time, the right opportunity, or the right motivation.

Here’s a story of a hopefully successful entrepreneur who’s in the process of quitting his job to pursue his passion. He’s even put up a website so you can track his progress and hold him accountable.


Although not a successful entrepreneur yet, Neil is well on his way

Neil Sheth, Founder of Watchmequit.com

watchmequit.com | yourbrandfound.com 


I work as a Project Manager within Investment Banking where I enable IT change within the organisation.

However, being in finance I don’t get to see the end result. It’s not like I’m delivering a physical product or changing someone’s life or getting more sales for a business. I’ve missed that sense of purpose, and feeling that I’m genuinely helping someone.

I’d like to quit my current job because I want to be in control of my life. I want to be able to spend time with my family or travel around the world when I want. That’s not going to happen immediately as I grow my business, YourBrandFound.com, but that’s definitely my aim.

I’d be very happy if I had a bunch of happy clients, good revenue and was able to spend loads of time with my family and no longer working evenings and weekends after work.  In terms of “good revenue”, I’m targeting £100k by the end of next year. The year after I’d like to double that at least. But as far as being a successful entrepreneur, I’m not sure I’ll ever really feel like I’m successful because success is, in a way, endless.

Who will be the next successful entrepreneurs?

All these disparate entrepreneurs had one thing in common (or in Neil’s case, almost in common): they did it. Somehow, one way or another, they felt their passions pushing them forward to their own careers, their own dreams.

They had the stick-to-it-iveness to push themselves beyond the pain of probable failure, against all the odds and naysayers, and through to success.

And they’re people just like you and me. They have done it. You can do it.

Good luck.

Know of any other successful entrepreneurs who’ve persevered and come on top? We’d love to hear their stories. Let us know in the comments below.

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  • Woohoo. Great insight from all the fellow Entrepreneurs. Great stories.

    • Bernard Meyer

      Hi Jovim, you are absolutely right. These stories, including your great one, will be so important in helping hopeful entrepreneurs take that crucial and scary step into the business world. We are so happy with these results. Thanks!

  • Great stories!! Love to see entrepreneurs take risks and become successful! Thanks for sharing!

    • Bernard Meyer

      Hi Eduardo, glad you liked it and hope you were inspired as well!

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