When I told my former boss that I was quitting my high-paying engineering job to start an eco-friendly clothing boutique, you can imagine how close his eyebrows got to his hairline. From an outside perspective (i.e. according to my co-workers, friends, family and the public at large), this decision might have made me seem a little off-my-rocker. Maybe the toner in the laser printers I was designing was finally getting to my head? Who knows. But for me, a retail store seemed like a perfect fit and what I was “meant to do” at the time.
When you want to start your own business, how do you know what type of business to start? Or if you do come up with a business idea, how do you know if it’s the right idea to pursue? How can you tell if this is the idea that you’re “meant” to implement? So many questions…
To answer these questions, I reached out to 20 entrepreneurs who quit their day jobs to pursue businesses in a completely different lines of work and I asked each of them these 2 questions:
How did you determine what kind of business you wanted to start? How did you know it was the right business idea to pursue?
If you’re still trying to land that perfect business idea or find the right entrepreneurial path for yourself, now is your chance to get ideas and get inspired by these amazing stories:
Kori Jock | Owner | La Vie en Orange
Non-profit Fundraiser ➜ Underwear Designer
My business picked me. In my family, making underwear is normal: my Granma makes my Granpa’s and my dad’s underwear, and I’ve been making my own since 2006. I moved to Seattle from Michigan to follow love (it worked out; we’re married now), even though I loved my work as a non-profit fundraiser, by 2011 I was feeling a little bit lost and sharing my undies with the world was a way to create a touchstone in my new surroundings.
When my first brave clients shared their rave reviews on Etsy, I knew I was onto something. Since then, I’ve launched my own website, started selling face-to-face at craft shows, begun offering an Underwear of the Month Club, and I’ve featured a broader and bolder range of art that I hand screen print on each pair- I just launched a mini-collection of period panties. In June I left my day job to make a full-time go of it, and since then, I’ve been adjusting to becoming my own full-time boss and making sure my values are incorporated in the business at every turn. From using re-purposed t-shirts for the raw materials to donating undies to women’s shelters every year, my non-profit and social justice roots shine bright. And my undies’ bright colors give women allover a secret something to smile about.
Ian So | CEO/Founder | The Chicken and Rice Guys
Marketing Coordinator ➜ Food Truck Operator
I quit job as a marketing coordinator to start a food truck. Didn’t have any food experience, not even as a waiter or cashier. We didn’t even know how to turn on our rice cookers until 30 minutes before our grand opening and ended up running out of rice in 10 minutes. Since that disastrous start, we have started 2 more trucks, a catering business, and opening up a restaurant in May.
We started with a list of business ideas. Of the 17 we first thought of, food truck seemed most likely to succeed since we were copying a food concept in NYC. The concept was Chicken and Rice from the Halal carts in NYC. Plus, a food truck would take less investment. The popularity of the cart in NYC was the strongest indicator for us. Someone got stabbed and killed because he cut another person in line. The cart has their own Wikipedia too! So we thought, this must work in Boston. Good food is good food, regardless of the location.
David Jacobson | Owner/Producer | TrivWorks
Nonprofit Event Planner ➜ Corporate Trivia Event Producer
I used to be a professional event planner with a major nonprofit cultural organization, in charge of planning/producing adult education programs. During that time, I also held side jobs hosting pub quiz nights at a local bar, as well as freelancing with a professional scavenger hunt company.
Once the financial crisis hit in 2008, I saw people being laid off and others having to pick up the slack, with little to no additional compensation (myself included). I realized that there was a unique opportunity for a new form of corporate entertainment/team building, which could effectively boost morale and allow companies to say “thank you” to hard-working employees, without having to break the bank. In 2009 I started TrivWorks, NYC’s only corporate team building company specializing exclusively in live customized trivia events; in 2012, I left my job to pursue TrivWorks full-time, and have been doing so ever since!
Michael Chasin | Co-Founder | LawKick
Transactional Analyst ➜ Online Startup
I quit my day job last January during my 3rd year of Law School to pursue my own startup venture. My job was to be head of transactions for a small business management firm in Beverly Hills. Loved the job and loved my boss but didn’t have the passion and drive I was looking for in a career. I quit to start LawKick.com, a marketplace where individuals can receive price quotes from lawyers regarding a specific legal need they have.
I started the business with my co-founder, a fellow law school student. We both were coming out of school and about to enter into, what we knew was, a broken legal industry screaming for innovation and more transparency. So we sought to fix that problem by starting LawKick!
Shola Akintobi | Owner | Best Face Forward Makeup Studio
Director of Alumni Relations ➜ Chief Beauty Officer
I fired myself from my full time job last year. I was the Director of Alumni Relations at a university and knew that I could no longer ignore the call to do something else. Back in college, I began selling makeup and performing beauty services in my dorm room. I absolutely loved helping women to look and feel their best. After I graduated with my MBA, I entered the working world and all but shut the door on that hobby. Like a fly to honey, no matter where I worked, the idea of owning my own business and defining my destiny kept coming back to me. I began part-time (often in the wee hours of the night) planning what is now Best Face Forward Makeup Studio.
I knew this was the right business to pursue when I began composing my business plan. I did a great deal of research (conducted surveys and interviews) and found out that there weren’t many companies that offered the same combination of services (in the same way) that my company would. That would dissuade most, but for me, it was confirmation that I was on to something great.
Seth Peterson | Co-Founder & CEO | All You Can Arcade
Stockbroker ➜ Arcade Business
Three years ago, I was a full time stockbroker with little to no mechanical skills. After buying myself an arcade game on my birthday, I almost immediately set out to see if I could try and monetize the game by putting it into a bar or laundromat. When I saw how little the arcade games were returning, my mind went into overdrive to try and come up with an alternative business model and ultimately struck on something that we knew would work.
Our idea was simple, if we could rent the games out by the month and let customers swap the games when they wanted a new one, we could earn more renting the games on freeplay, than we would make by putting the games in traditional coin-op locations or simply relying on arcade party rental income. Fast forward three years and we’ve gone from 1 game to over 200 full sized arcade cabinets, two vehicles, a workshop and our own shipping containers.
Michaela Cristallo | Founder | For the Creators
Marketing Manager ➜ Creative Blogger
I’ve always had the creative spark but had never pursued it as anything more than a small side hobby. I was growing restless with my marketing role in the corporate world a few years back and knew I needed to do something more creative. When I first left my job I pursued a fashion design business but soon found myself writing about my creative experiences and helping others make the same jump I had made from corporate world to creative career path. As time went on what started as a small side project quickly grew in scale and I realized I was onto something. Today I run a website where thousands of people come from around the world to be inspired to live a more creative life. My business is growing by the day and I’ve never been happier.
Mary Kearns | President + Founder | Herban Lifestyle
Scientific Review Coordinator ➜ Soap Maker
In 2012, I left my job coordinating the scientific review of cancer prevention programs to dive full-time into my handcrafted soap business. I had started the business in 2008 as an Etsy store, and bootstrapped it. It had gotten to the point where the soap business was getting too big to continue as a side-gig, and I received a lot of satisfaction from it. Plus, it had grown steadily over the years, even though I had started it at the worst possible time economy-wise. So, it just seemed like the right thing to do.
Steve Silberberg | Owner | FitPacking
Software Developer ➜ Weight Loss Backpacking Leader
I quit my day job as a software developer at an investment firm in order to take people on backpacking trips to get fit and lose weight. When I had the corporate job, I’d sit at my desk every day wanting to stick a fork in my head, wishing I was out doing something fun and active in the wilderness. During vacations, I would go backpacking and found that when I returned, I lost a little weight, my clothes fit better and I was stress free. I figured that this is something I could offer other overly stressed, not-so-active corporate workers. So I started a company called Fitpacking.
Brett McCollum | Co-founder | Gramr Gratitude Co.
Tech Sales Rep ➜ Thank-You Card Designer
I quit my Tech Sales job at Oracle to start a thank-you card company. Yes, you read that correctly. We are trying to change the greeting card game. Our cards are top-quality and feature images from Instagram and VSCO photographers (100k-700k followers each). We offer our cards as standalone and as a monthly subscription.
I knew it was the right idea to pursue because I saw an opportunity to upgrade an industry (greeting cards) that hadn’t been significantly updated in nearly 75 years. Also, my partner and I were driven by the opportunity to push gratitude to a conscious consumer community.
Our Kickstarter has much more info about the company: https://www.kickstarter.com/projects/gramrgratitude/gramr-gratitude-co-the-habit-for-happiness
Courtney Smith | CEO | Coco’s Kloset
Customer Service Rep ➜ Online Boutique Owner
I quit my job as a Customer Service Representative to start an Online Boutique. From a little child, I always dreamed of having my own Boutique, so I started it as a side job while I was working for this Internet Company. It just started of as a side job/hobby and something to make some extra money then next thing I know it took off! Working both my day job and online Boutique became too much so I figure why not go and work for myself full time and that’s exactly what I did and I have been doing that every since. It also helped that the job wasn’t paying very much and it was very stressful so I figured I can pay myself the same and maybe more working for myself.
Shaun Eli Breidbart | Executive Director | The Ivy League of Comedy
VP of Corporate Banking ➜ Stand-up Comedian
I left corporate banking (was a VP) to become a stand-up comedian and comedy show producer. My company, The Ivy League of Comedy (www.IvyStandup.com), produces clean comedy shows for all sorts of venues/groups, from theatres and comedy clubs to yacht clubs, houses of worship, corporate events… I wanted to start a group producing clean comedy shows because when my banking colleagues came to see me at comedy clubs this was their reaction: That was a lot of fun! And your comedy was clean- but most of the other comics were not. We’d love to take clients to a comedy show- where are the clean shows? And there weren’t any, so I realized I needed to start producing them. As a working comic at the same time I was a banker I essentially had two full-time jobs- and one had to go. So I got rid of the higher-paying (but less fun) one.
Rahti Gorfien | Founder | Creative Calling Coaching
Restaurant Hostess ➜ Certified Life Coach
As a struggling actor and standup comic, I used to start support groups for myself around writing, getting to auditions, etc. I really liked Julia Cameron’s ‘The Artists Way’ and worked my way through that book 3 times…once solo and twice in groups I formed with friends. I started a Wishcraft group inspired by Barbara Sher that collectively resulted in a yoga business, a book store and a DJ. I seemed to have a gift at facilitating change.
I knew it was the right business to pursue at the time because my husband frankly said “You’re good at this stuff. Start charging.” Since I was burning out on temping and serial day jobs I hated, I took his advice.
Michelle van Looy | Founder | Women’s Artists Network of Toronto
Social Worker ➜ Women’s Nonprofit Leader
I quit my job as a social worker to start a women’s non-profit art network! I did for myself, what no other job could do. I created a non-profit based on my skills as an artist, a social worker, a childcare provider, a traveler , an academic with 12+ years of post-secondary education and brought in all the skills I had acquired from day jobs to support my art and education. At the time, I didn’t really know it was the right idea. I knew that Sunday nights I didn’t loathe the week ahead. I was always excited to wake-up even in challenging times and I was happy. Really happy.
Michele Velazquez | CEO | Proposal Planner
Event Coordinator ➜ Proposal Planner
I walked away from a 6-figure corporate job to become a Marriage Proposal Planner! My former job was in Information Security where I helped to protect company intellectual property. When my then boyfriend proposed to me, I was sad that he didn’t hire a photographer to capture the moment. I was also a little bummed when he didn’t take me to celebrate my proposal but took me back to my apartment. I felt that was very anti-climatic. In talking to him, I realized there was a huge gap in the market and that men needed help planning their perfect proposal. I have now replaced my income from my boring corporate job and am happy as can be.
Gabriel Mays | Founder | Just Add Content
Captain in Marine Corps ➜ Website Designer
I spent 8 years in the Marine Corps before leaving as a Captain last year to work full-time on my company, Just Add Content, which is a website builder for businesses. While in grad school I built a website as part of my thesis and became interested in web development.
I love web development and I love small businesses, so it only made sense for me to focus on helping small businesses build websites. While on a 12-month deployment to Afghanistan I found how much I loved working on my website builder project in my free time. In the 2 years I spent between Iraq and Afghanistan operating on small teams I had some close calls and realized that life is too short and too precious to do anything but my best work. When I returned from deployment I left the Marine Corps to work on the company full-time.
Jude deTar | CEO | Bottlerocket
Chief Marketing Officer ➜ Social App Creator
I quit my CMO position at a consulting firm to become CEO of a tech startup. I was able to determine what type of company I wanted to start very easily because I had been thinking of the idea and testing solutions for over a year. Like any startup, you are never sure if it is the exact right time to start, but it looked like the market was right for the idea from a variety of angles and I had very little to lose. As a young entrepreneur, I haven’t experienced the high salary and lifestyle that older execs get used to and make it so much harder for them to make the jump. In regards to knowing if it was the “right idea”, it really came down to how much I knew about the area and how passionate I was about it. Our passions and experiences change over time, but I felt that this was something that I had at a least a couple more years on and already knew far more than the average entrepreneur.
Teagen Andrews | Owner | Ecossential Solutions Inc.
Bank Customer Service Rep ➜ Environmental Consultant
I didn’t pursue my Environmental Consulting career, but it certainly chose me. Four years ago I was approached by a friend putting on a music festival who needed an environmentally-minded individual to handle the waste management issues of the event. Turns out, I can move some serious garbage. After an extremely successful event diverting 65% of the waste stream from landfill to recycling or reuse, word spread quickly of my services. The next year I had booked an additional 2 events, 1 of which served 30,000 music fans in Chillicothe, IL. By the third year we had 3 local events under 1000 people, 2 large scale events 15-25000 people, and traversed two states. Definitely the right call.
Betsy Johnson | President & Founder | SwimZip
Advertising Account Manager ➜ Protective Swimwear Designer
I was working for a Fortune 500 company when I was diagnosed with skin cancer at age 26. I loved my job, but helping others avoid my fate inspired me to start my own small business, SwimZip (www.swimzip.com). SwimZip makes “affordable, adorable” UPF 50+ sun protective clothing and swimwear to keep kids sun safe all day long at the beach or pool. I was pursuing a passion and helping save lives – so becoming my own small business owner was really a no-brainer for me. Looking back, when you do find the “right” business idea, it changes your life and makes work a labor of love!
John Przybylo | Co-Owner | Vapor Haus
Warehouse Manager ➜ Electronic Cigarette Store Owner
I quit my day job as a maintenance and warehouse manager last summer and opened my own retail business with my best friend, Steve Lotz. At our new store, “Vapor Haus,” we sell electronic cigarettes (personal vaporizers),accessories and nicotine juices. I knew it was the right kind of business because I had just used an electronic cigarette to quit my 20 year smoking habit and since then, I had other smokers begging me daily to know where they could get their hands on one.
We didn’t want to just be an online-based retail business because then we couldn’t help people quit smoking analog cigarettes. We needed to be able to meet the customers face-to-face and teach them what type of product was best for them and how to use it, as well as the most successful way to ditch their “smokes.” We could only accomplish that with a retail storefront. So far, business continues to grow and despite the fact that I work harder now than ever before, I have never felt better.