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18 Entrepreneurs Explain What They Did Prior to Starting Their Businesses

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It’s always a special time when you take the “leap of faith” and start your own business. But it’s rare that an entrepreneur or business owner doesn’t leverage their background in some way to launch their business. It could be studying entrepreneurship in school or it could have been working with a government contractor or maybe someone had a sales job. No one even “born entrepreneurs”aren’t born as CEOs. It’s usually a process.

We decided to ask some entrepreneurs and business owners what they did before they started their businesses.

#1 – Medical Device Sales

Image Credit: Tom La Vecchia

My last job prior to starting my own business was in medical device sales within the aesthetic space.This led me to start a digital marketing firm specializing in the aesthetic industry. As a sales representative I noticed that the promotional efforts for Plastic Surgeons were held by a few large firms that overcharged. Three years later we are a boutique player in the aesthetic space, specializing in the niche of male plastic surgery. We launched one of the first ever website dedicated to men’s aesthetics and recently expanded to LA.

Thanks to Tom La Vecchia, X Factor Media!

#2 – Advertising Agency & Boutique PR and Advertising Agencies

Image Credit: Natalie Harper

Prior to starting my own public relations and marketing consultancy, I worked for one of the largest global advertising agencies as well as smaller boutique PR and advertising agencies. The boutique agencies taught me everything I know, and gave me all the experience I needed to start my own company, however one of those agencies truly gave me the motivation to leave and start my own business. The owner was not equipped to manage people. While brilliant in the advertising world, he was actually quite miserable to work for. He also didn’t believe in supporting the community and supporting local organizations through our skills. This was one thing I wanted to do more of, and in order to do it I started my own company. Six years in business later, we continue to grow. More importantly, we continue to help the community through pro-bono projects, supporting non-profits and charitable campaigns, and giving back where and when we can. Ultimately, it was being able to do this that compelled me to leave the agency world and start my own business.

Thanks to Natalie Harper, Harper PR

#3 – Google Regional Sales Manager

Image Credit: Steve Benson

Before starting Badger, I worked at Google as Regional Sales Manager. Google is in my opinion the best big company to work at. They do a great job at building an amazing culture, and they are able to keep a small company feel in terms of speed and agility because they keep the teams small and have basically broken the company up into a whole bunch of companies. They have the resources from their cash cow to attack some of the largest and most interesting problems that we’ll be facing in the next 20 years. They really care about their employees, and have enough money to buy a fair amount of happiness. Remember when someone told you money doesn’t buy happiness? That was not totally true, if your employer spends a lot more money on you and pays you a lot more money, it makes your job satisfaction rise. And it helped me start my own business! I believe that Sales experience is particularly useful when founding a company, because a lot of the time it will live or die based on your ability to make sales. And making sales early on when a product is not nearly what it will be one day is especially hard. If I did not have the background in sales, we would not have made it. Because of my experience at Google, I understood the challenges faced by field sales people first hand. When I was working on the Google Maps team, I got to know how powerful mobile mapping was, and what mobile was capable of doing. Because of this background, I was well positioned to launch a company to solve the problems of field sales based on a mobile mapping platform. Google was a fantastic place to work, I truly believe that they are among the best employers in the world, but for me, nothing compares to creating something from scratch. It was definitely a huge leap to leave the corporate world (and the salary and security that comes with it) and start a company. But I was confident that if I could put together the right team, we could solve a problem that would help a ton of people save time, and do better at their job.

Thanks to Steve Benson, Badger Maps!

#4 – Sr. Sales Account Manager

Image Credit: Perry Petrozelli

In my previous role I was a Sr. Sales Account Manager for a leading NYC based StartUp. We had every Google-ly employee perk one could fathom, catered meals, happy hours every day, back massages, bring your pet to work, unlimited vacation… I watched the mismanagement of VC funding lead to the termination of high performing, superstars on my team. I came to the conclusion that 30% of my adult life is too much to dedicate to a company focused on making headlines for crazy perks rather than creating a sustainable and stable working environment. My team and I have created Happster, the first product created to take employee happiness to new heights through positive psychology. We enable managers to see what really matters to their teams and repair the bonds of mistrust between HR and employees.

Thanks to Perry Petrozelli, Aventr!

#5 – Teaching

Image Credit: Jason Bond

Not too long ago me and my wife wife were hopelessly buried in debt. After putting our family’s net worth into a spreadsheet one day, I was shocked to find out that my net worth was – $250,000. I suddenly realized that no matter how hard I worked or how good I was at my job, as an elementary school teacher, I would never get ahead. As much as I loved teaching, I could project what I would make across the next 20 years as a teacher, as well as what my wife would make also. Between the student loans, mortgage, credit cards, personal loans, car loans, we were weighed down. So I decided to become an Entrepreneur and start my own company for people who wanted to learn about trading in the Stock Market. It benefited me, that my previous job was teaching, because I could take that skill and transfer it to my new company. Today I own and manage a company specifically designed to help people grow their portfolios. I even have 100,000 FB followers and over 200,000 active traders and subscribers.

Thanks to Jason Bond, Jason Bond Picks!

#6 – Investment Banker

Image Credit: Janet Wu

I founded SilkRoll in 2015, I spent 10 years developing my style and taste in fashion while working around the world as an investment banker. My lucrative career gave me access to create the closet of my dreams and left me always wanting more. With a wealth of financial knowledge, I took a risk and became the CFO of a clean tech startup and eventually moved to San Francisco where my entire high end wardrobe became obsolete. Everyday I looked at the fashion I loved but no longer wore and was unsatisfied with the options to purge this valuable collection. I contemplated, ”how can I keep the value of this fashion and share it with someone who would appreciate my style?” On the 4th of July, 2015, I shared my vision with Erin. Erin always dreamed of owning this kind of fashion but with an abundance of student loan debt my ability to invest in high quality fashion was limited. By this time, Erin had already spent 4 years in operations at a startup that was in skyrocket growth mode, so she knew her knowledge in scaling operations was as valuable as this idea; she became my co-founder.

Thanks to Janet Wu, SilkRoll!

#7 – From Building Structures to Building Relationships

Image Credit: Lori Cheek

I’m an architect turned entrepreneur, Founder and CEO of Cheekd a mobile dating app that makes missed connections obsolete. After working in architecture, furniture and design for 15 years, I came up with an idea that lead me into the NYC World of Tech and am now solving missed connections. I completely threw away my design career and I’m no longer building structures, I’m now building relationships. Although I did a complete 180 in my career, my design experience has been extremely fruitful in building Cheekd. Architecture is the art, science and business of building and requires an extreme social awareness and understanding of social change as well as a strict attention to detail and design. These elements of my previous corporate career have been crucial in my attempts to reverse engineer an existing industry by simply adding an element of human interaction to a seemingly saturated (online dating) market. My design background has also been extremely beneficial in giving me an innovative approach to building my business, designing the brand and marketing the product.

Thanks to Lori Cheek, Cheekd!

#8 – TV News Reporter & Anchor

Image Credit: Katie Wagner

Before opening up my full service digital marketing agency, Katie Wagner Social Media, I was a TV news reporter and anchor. My last position was with CNN. What I learned about storytelling and engaging an audience in that role as a journalist propelled me to create a different kind of marketing agency, one staffed by journalists who really focused on telling our clients’ stories online. We know how to ask the right questions and create compelling content. We find talking points that others may miss, and offer a unique social media angle for our clients. My prior role not only prepared me for what I do, but inspired me to offer a service that no other agency offered – social media management and brand marketing with an emphasis on authentic storytelling. I couldn’t get it wrong on the evening news, and I can’t get it wrong on behalf of the brands I represent.

Thanks to Katie Wagner, Katie Wagner Social Media!

#9 – Developing an Entrepreneur Program

Image Credit: Anna Renault

After graduating high school, I was hired by the Maryland State Department of Education, Division of Rehabilitation Services (DORS). I worked for them for 31+ years.  One of the assignments I experienced was the development of their Entrepreneur Program. Little did I know at that time that I would use some of the information to start my own business – develop a business plan, get a business license and so on. After retiring in 2001, I also joined a ladies networking group, On Purpose Networking for Women (OPN).  With the support of some of the OPN ladies and with the knowledge from my pre-retirement job, I launched a business writing poetry for customers.  These poems were personalized based on what the customer told me about the person who would receive the poem… their likes/dislikes, their hobbies, their job and their families. I wrote poems for births, birthdays, weddings and anniversaries, graduations and retirements and so on. The poems were printed for fancy papers, then framed or put into photo albums.  Poems by Anna was a great little business until I developed breast cancer in 2009.  Following the completion of that battle, my business changed to Anna’s Journey as I published my first of many books.

Thanks to Anna Renault!

#10 – Lawn Care Business

Image Credit: Bryan Clayton

I’m Bryan Clayton CEO of GreenPal which is best described as Uber for Lawn Care. Before starting GreenPal in 2013, I ran a lawn care business for 15 years. Starting with just a push mower I grew that business to 70 trucks and 145 employees. Running that business and growing it from infancy is what showed me the inefficiencies in the lawn care industry and the pain points that service providers go through. GreenPal’s vision is to become the operating system and platform that makes the lawn care industry run smoothly. Our vision and mission was born from my previous experience and frustrations running a traditional lawn care business.

Thanks to Bryan Clayton, GreenPal!

#11 – US Army Classified as a Computer Engineer

Image Credit: Matt Benhke

I worked for the US Army as a civilian employee classified as a computer engineer. This benefited me in that I was motivated to leave an un-rewarding environment where programs that a ton of money was spent on were just cancelled. Another benefit was that I was able to complete two master’s degrees, one in Software Engineering, and another in Engineering Management. While I applied myself at the Army, the programs I worked on eventually were cancelled so it felt pointless. Building OrthoticShop.com was more than rewarding in that we get to help people find comfortable footwear that helps them stay active.

Thanks to Matt Benhke, Orthotic Shop!

#12 – Knocked on Doors

Image Credit: Lauren Watkins

I knocked doors for a living. That’s right, I did door-to-door sales for four years straight in the armpits of America. I sold alarm systems to homeowners in the kinds of neighborhoods you accidentally drive through, clenching your steering wheel and making sure your doors are locked as you frantically search for the fastest way out. I was dropped off every morning in an unknown ‘hood’, and wasn’t picked up until 9 or 10pm (sometimes even later). I had a cup of soda thrown at the back of my head as I walked away after receiving hard refusals. I was grabbed by the neck of my polo and threatened that if I didn’t get out of the neighborhood, I’d have a gun put in my mouth and be raped. There were days when I considered having a door slammed in my face mid-sentence graciously passive compared to other rejections I’d already had. I was nauseous with anxiety from the moment I woke up just from knowing the reality that awaited me. Despite everything, knocking doors was the best thing I could’ve ever done for myself and my career. It thickened my skin, instilled in me an unbreakable work ethic, and showed me that if I didn’t swim, I was simply going to sink. The entrepreneurial world sounds much more glamorous than my life in door-to-door sales was, but the challenges I now face are arguably worse. As a business owner, you’re called selfish by your closest friends. You’re abandoned by partners you once relied upon. Employees you care so much for, sacrifice your time for, and put your heart into paving a future for, can come to stab you in the back – stealing from you. You’re criticized in your most creative moments. During times of uncertainty, you’ll even hear your own boyfriend and family tell you it might finally be time to, go get a real job. In those moments, I’m so grateful for the Philly curbs I sat on when my feet were blistering, the trees I found refuge under in the suffocating Arizona sun, and the Kansas City neighbors who weren’t home (so I could pee in their bushes when no convenience store was in sight). In those moments, I learned how to reach inside myself and figure out who I really was, what I wanted, and what I was willing to go through to get it. Growing my own business has taught me more about myself than an entire lifetime of working for others could have. I’m unceasingly grateful for the lessons I learned in those hard neighborhoods because they made me. I wouldn’t give those experiences up for anything.

Thanks to Lauren Watkins, Urbana Custom!

#13 – Real Estate Development Industry

Image Credit: Christina May

Prior to beginning my business I worked in the real estate development industry. After debating the choice to start a business for three years, once the choice was made I jumped in. I planned a nine month transition where I began working on cultivating my business’ name, plan and initial client work. As I prepared myself mentally, financially and emotionally to begin a career as an entrepreneur, I decided six weeks in advance of my departure and notice to not only inform my employer, but schedule a time to meet. That exit conversation was memorable. It afforded me the chance to thank my employer for the opportunity and ask questions pertaining to my future venture. The advice and affirmation I received in that meeting gave me a sense a closure for the career I was wrapping up and a boost of confidence heading into the uncertain waters of entrepreneurship. In almost four years time since that meeting, I have never looked back and regretted my decision in part because I had the benefit of a positive send-off from my previous employer.

Thanks Christina May, Illumine8 Marketing & PR!

#14 – Independent Sales Rep

Image Credit: Candice Simons

My previous position held was as an independent sales representative at a small, outdoor advertising firm in Chicago. I don’t believe in any situation necessarily hurting you, as I am confident that there is something to learn from the good, and more importantly, the bad. Being at a small company from nearly inception, I had a unique experience in wearing as many hats as I could possibly get my hands on and about the necessity of building the sales tools vital to be successful in my own field and path. I was able to learn from the positives and negatives throughout my time in Chicago and utilize those experiences in creating my own company and culture on my terms.

Thanks to Candice Simons, Brooklyn Outdoor!

#15 – Interest Rate Options Broker

Image Credit: Rebekah Bailey​

Before I founded Shoreditch I worked in the city as an Interest Rate Options Broker. Throughout my education a job in the financial markets was my motivation but after 6 years I decided it wasn’t for me. My role and company lacked meritocracy and I was bound to the same desk from 07:00 to 18:00 each day. However, my time in the city allowed me to develop a number of skills which have helped as a startup founder, I am more resilient, analytical and I make decisions quickly. All of which are very useful as entrepreneur. Going back to at 07:00-18:00 is not an option which provides additional fuel to my hunger to succeed.

Thanks to Ryan Shaw, Shoreditch!

#16 – Corporate Development

Image Credit: Scott Phillips

Before starting Rise Art, I ran corporate development for Rightster, now Brave Bison. In this role, I was responsible for our seed and series A fundraise with the CEO and developed and managed our partner outreach. The experience was great because it gave me exposure to every element that the founder and CEO of the company were working on as well as a depth of experience across practical elements that are critical when launching a startup. The role was also very useful in building up my own network of contacts, some which have helped us through strategic and financial support as we have grown Rise Art. I still regularly meet with many of the people from that company, some which continue to be mentors.

Thanks to Scott Phillips, Rise Art!

#17 – Travel Agency

Image Credit: Grainne Kelly

Before founding BubbleBum car travel innovations, I worked at a travel agency. I became an entrepreneur to fix a common parenting issue I was experiencing. As a mother of two, my primary goal was to offer travelers a safe way to transport their kids. I was frequently traveling between my native Ireland and England to visit a sick relative, and I always had to transport cumbersome fixed booster seats back and forth on the plane due to the lack of car booster seats available from car rental desks. I came up with the simple idea for an inflatable car booster seat and invented BubbleBum as an affordable, lightweight car booster seat that could travel easier than a child does. It weighs less than one pound and can deflate in minutes, making it easy to throw in a backpack when not in use. BubbleBum also includes belt positioning clips in place of arm rests, so it’s possible to fit three boosters across the back seat of a car! BubbleBum helps ensure that every child has a safe booster seat on every ride.”

Thanks to Grainne Kelly, BubbleBum!

#18 – Worked in a Call Center

Image Credit: Skyler Dennis

Before starting SnJ Empowers, a Coaching and Consulting company for entrepreneurs, I worked at a call center for Accent Marketing. There we were responsible for selling and providing customer service for a grill and motel company. It was okay as far as jobs go but I realized quickly that it was not for me. Everyday I felt like I was dying, sitting in that cramped cubicle. A life of having to ask when I could eat, and when I could use the bathroom, and when I could see my family was not worth the “chump change” I was being paid! Starting my own business has been the best decision I have ever made but having a job helped me significantly because any time I feel overwhelmed or like giving up, I think back to that moments of corporate slavery and I push through! So, for every person reading this, my message is this: “Your dream job does not exist!! So go out and create it!!”

Thanks to Skyler Dennis, SNJ Empowers, LLC !

About Gresham Harkless Jr.

Profile photo of Gresham Harkless Jr.
Gresham Harkless is a Media Consultant for Blue 16 Media and the Blogger-in-Chief for CEO Blog Nation. CEO Blog Nation is a community of blogs for entrepreneurs and business owners. Started in much the same way as most small businesses, CEO Blog Nation captures the essence of entrepreneurship by allowing entrepreneurs and business owners to have a voice. CEO Blog Nation provides news, information, events and even startup business tips for entrepreneurs, startups and business owners to succeed.
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