21 Amazing Online Entrepreneurs— inspiring stories I’ve learned from business mentors I’ve never met

09/23/2016 01:26 am ET Updated Sep 30, 2016

I sat in my home office feeling alone and isolated, staring at my computer screen for two years while building an online business. I accepted this feeling of loneliness, newbie overwhelm, and self-doubt was the life of a start-up online entrepreneur. With no co-workers or boss to get feedback and guidance as I had experienced being an employee, I often second guessed if I was doing things right. As a new solopreneur you wrestle with your own thoughts. You have to be your own cheerleader. You have to constantly be educating yourself. Most of all, you have to have the courage to keep the belief that you can be a success in this ever-changing brave new world online.

One day it hit me, success as an entrepreneur is not so much about technical skills or even marketing strategies. Entrepreneurial success requires a certain set of mental tools. Not only business sense, but an entrepreneurial mindset. It never occurred to me how much of a mindset shift would be necessary to go from being an employee to an online entrepreneur. As a successful television news and talk show producer in Los Angeles, I had proved to myself that I could find success at anything I put my mind to. So when I left my television career to move to Maui because I met the man of my dreams (Lucky me!), I became a stay-at-home entrepreneur which made the best sense when I became a stay-at-home mom. I took online digital marketing courses, but still felt lost and overwhelmed with the internet world. Fortunately I stumbled upon the most inspiring and educational mentors to help me make this big mindset leap. They have helped in ways that most people would pay good money for-- to a business coach, life coach or even a psychologist. They have kept me sane, helped me overcome self-doubt, helped me to focus and take action, helped me to not take myself so seriously, helped me to overcome fear of failure, and the crazy thing is that I have never met a single one of them.

Entrepreneurial statistics show that I am not alone (in the virtual sense)...

According to a recent report on entrepreneurial growth by the Kauffman Foundation, The Growth Entrepreneur Index shows a rise in entrepreneur business growth over the last year and for the third year in a row. It’s the largest year-over-year increase in entrepreneurial growth in the past decade.

Most of my inspiring entrepreneur mentors, I found through podcasts on iTunes. I would put my children to bed, fall asleep with them, then wake up to clean the kitchen between 2am-4am while educating myself through podcast listening.

Here are the inspiring stories and the life-changing lessons I’ve learned from these amazing, successful online entrepreneurs.

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1. Pat Flynn- Creator of Smart Passive Income Blog and Podcast, Ask Pat Podcast, Author of Will It Fly, Software App Designer, Philanthropist

Pat Flynn was fired from his job as an architect just a few months before his wedding. He turned this terrible time in his life into a multi-million dollar business, and he does it all “passively” by offering helpful information through his websites and podcasts.

In the beginning, Pat had some expensive failed attempts at creating software products and apps that he pursued for the money-making potential. (source) His real success came when he followed his intuition to focus on helping people. He gives away all of his tried and tested secrets on the “reciprocity principle”— that giving freely causes the receiver to want to give back. His income is generated through affiliate sales, podcast sponsorships, book sales, niche sites, speaking engagements, software and apps. He publishes his income reports which shows he has made $1,633,594.28 in the last 12 months (at the time of writing of this post).

Lesson: What I learned from Pat Flynn’s story is that being fired (or a terrible, stressful crossroad) can be the greatest turning point of your life! For him, it lead to a way of his definition of passive income-- earning money to enable a lifestyle where he could choose when to work and choose when he wanted to spend time with his family. Rather than spending hours away at a job, both Pat and his wife choose to maximize their time as a family. They both walk their young children into school each day (something most parents can't do because of their jobs). I heard his story after being fired from a job that sucked the life out of my soul, and excruciatingly kept me away from my family for 40 hours a week. He inspired me to discover the entrepreneur within and spend time with my family while making money where I dictate my own schedule. He also taught me that failure as painful as it may be, is necessary trial and error learning for an entrepreneur.

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2. Tim Ferriss - Entrepreneur, #1 New York Times Best Selling Author, Public Speaker, Angel Investor/Advisor (Facebook, Twitter, Uber and 20+ more), The Tim Ferriss Show Podcast

Tim Ferriss is the reason that so many people become convinced to take their initial step onto the online entrepreneurial road, including myself. His book, The 4-Hour Workweek continues to inspire so many with the idea of the “Freedom Lifestyle”-- the notion of not having to trade hours for dollars working a traditional job. Tim is known as a pioneer, a maverick for the digital age. His name is synonymous with success being listed as Fast Company’s “Most Innovative Business People”, Forbes Magazine’s “Names You Need To Know”, and the “7th Most Powerful Personality” on Newsweek’s Digital 100 Power Index for 2012 (and that’s just to name a few “success lists”). His iconic blog The Four Hour Work Week has 1 million+ monthly readers and his Twitter account @tferriss was selected by Mashable as one of only five “must follow” accounts for entrepreneurs. (source) He is the first American to hold a Guinness World Record in tango dance; he speaks five languages; he’s a national kickboxing champion, Japanese horseback archer, and a sought-after speaker and thought-leader. (source)

However his journey has not been an easy one despite his notoriety and success. He talks about being fired multiple times and suffering from depression even during some of his most financially successful times. Tim had even contemplated suicide. This was a secret he kept for years from his closest friends and family while he had a reputation of living a charmed, famous life of world travel, and the ability to conquer anything he wanted in life.

Lesson: I was greatly inspired by Tim Ferriss’ notion of the “Freedom Lifestyle”, but even more inspired by him revealing his deepest hardship in life (his mindset of self). This helped me to realize that even the best of the best are fallible humans, and we’re really on a road of personal development, not just business development. This helped me to see that in the big picture it’s not just about achieving that goal of selling that product, making millions or gaining thousands of followers. When you become an entrepreneur, it is a journey of discovery about yourself.

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3. Kimra Luna - Personal Branding and Online Business Strategist, Creator of Freedom Hackers Facebook Group

Kimra Luna went from welfare to a million-dollar online marketing business in just a year. She was broke, had two young kids and a husband out of work. Living with in-laws, desperate when money ran out, she agreed for her husband to take a job as a FedEx driver in another state. With her husband's tax return money, they bought a computer, and Kimra started selling organic skin products through network marketing. She ravenously studied online business through webinars and podcasts that other entrepreneurs were offering for free. Soon Kimra started teaching what she learned, and built her Freedom Hackers mastermind group to now 30,000+ members. Her husband was able to quit his FedEx job and move back home to help her. Kimra continues to teach hundreds of entrepreneurs her successful methods through online courses and offers a supportive community to Freedom Hacker members. (source)

Lesson: What I learned from Kimra Luna’s story is that if you believe in yourself, and you're determined to succeed, you will find a way to make it happen. Kimra’s story made it easier to keep my belief that I could start with no capital, conquer the technical sides of online business and learn a massive amount through free podcasts and webinars.

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4. Marie Forleo - Life and Business Coach, Motivational Speaker, Author, and Web Television Host of MarieTV

Marie Forleo is an entrepreneurial relationship-building rockstar!

Marie’s story has inspired me because I can identify with her random beginnings and her unusual combination of interests and skills that most people would find as, well... random. She and I are both what she calls a multi-passionate entrepreneur. Like me, she tortured herself by trying to "niche down" (source) to focus on one interest, but she says multi-passionate people need to pursue multiple paths until we discover our "unique convergence point". (source) Marie was a bartender and got her foot in the door on Wall Street when a customer asked her what she wanted to do with her life. That led to recommending Marie for a job at the New York Stock Exchange. She left that job as well as the next job in magazine publishing to pursue something with a fulfilling purpose -- life coaching. She had never been a life coach, but took courses while she taught fitness and dance classes, still bartending on the side. (source) She built her clientele through people she met in her various jobs. Marie started her own YouTube show on her living room couch more than 5 and a half years ago, and has grown into multi-million dollar empire-- Marie Forleo International with Marie TV web show and personal development and business training programs. (source)The connections she made with celebrities like Oprah, Tony Robbins and Richard Branson brought her recognition to celebrity status. Oprah recently named Marie “thought leader for the next generation”.

Lesson: Because of Marie Forleo's model as a successful multi-passionate entrepreneur, I no longer feel guilt or shame for having many interests that I house under one brand. I also learned from Marie to stay true to yourself, follow your inner wisdom, and it’s all about building solid relationships for the long-term, rather than short-term, immediate gain. As an online entrepreneur, we are often compelled to focus on growing our following through finessing our website copy, growing our email list through appealing opt-in gifts, and pumping out content on social media that we often forget about the power of relationship building, especially offline.

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5. Chalene Johnson - New York Times Bestselling Author, Build Your Tribe Podcast, Chalene Show Podcast

Chalene's story is about reinvention while sticking to who you truly are. She morphed from used-car saleswoman to paralegal to fitness trainer to business and lifestyle coach, taking the skills from one job then translating them into building a whole new career, over and over again. (source) In a time when internet marketing was a guy’s domain, she stuck to her feminine intuition, know-how and her way of doing business with bright lipstick, sassy outfits and a bleach-blonde mane of hair. Chalene found her success formula and gained noteriety in the fitness world with her PiYo workout, TurboJam, TurboKick, TurboFire, and ChaLEAN Extreme video series. She says, ”It’s not luck, it’s know how. There is a formula for everything” (source)

Lesson: One of many golden nuggets I gleaned from Chalene Johnson is that YOU define who you are, and you can take what you know to reinvent yourself. I have done the same, going from hairstylist to television producer/reporter to online business owner. Chalene has inspired me to stay true to myself and not be afraid to “flavor my brands” with the girly feminine, yet the emotionally deep essence of who I am.

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6. Amy Porterfield - Social Media Marketing Expert, Author, Online Marketing Made Easy Podcast

Amy's dad was a firefighter and was big on having good work ethics. He told her the way to ultimate freedom is to be your own boss, which encouraged her toward the entrepreneurial career path. She finally took his advice after years of working for motivational coach Tony Robbins managing marketing campaigns. Her ah-ha moment came when she sat in a meeting with some of the brightest minds in online marketing, and that’s when she realized the internet was where she needed to be to grow her own business. As scary as it was to leave a great job, she left to start her own online marketing agency. She has made a name for herself as a social media expert as co-author of Facebook Marketing All-In-One For Dummies. Amy shares her step-by-step secrets for social media and online marketing on her podcast called Online Marketing Made Easy. (source)

Lesson: Amy Porterfield gives away epic content, meaning there is so much value in what she shares for free. This helped me to feel better about my urge to write epic blog posts and record epic podcasts during a time when it was the trend to post short yet frequent content. But like Amy, I cared too much and felt an inner responsibility to put out quality content rather than quantity. Another quality about Amy is that she is a perfectionist, so when she talked about letting some of her personality come through in her podcasts by not editing out every “mistake”, that was an ah-ha inspirational idea to me. I realized that the more of our personality, our humanity, and our authentic imperfect selves that we show to our audience, potential customers or followers, the more they get to really know who we are. Amy surveyed her podcast audience, and found that they actually will trust you more if you don’t seem so “perfect”. When followers feel they know the real you, this builds a trusted relationship which often translates into more sales of your products and services.

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7. Brendon Burchard - High Performance Coach and Motivational Trainer, The Charged Life Podcast, Blog

At age 19, Brendon barely survived a car wreck. He stood there in the dark of night bleeding on the hood of his crumpled vehicle thinking about his life after being spared from death. When he thought his life was about to end, Brendon asked himself life’s last questions, “Did I live fully? Did I love openly? Did I make a difference?” This was Brendon’s turning point leading to his great success as an inspirational business marketing coach and personal development trainer. Asking himself those three “life’s last questions” led Brendon to become a #1 best selling author and one of the first online educators at 32 years old. Now Brendon is a world renown authority on "human motivation" and business marketing. Success Magazine named Brendon one of the Top 25 Most Influential Leaders in Personal Growth” (source)

Lesson: I’ve learned along with Brendon Burchard that when we are faced with our own mortality, the importance becomes about the impact we are leaving on this world. (I was diagnosed with a life-threatening degenerative disease recently and soon after discovered Brendon’s podcasts.) Our motivation then comes from a different place where success is defined by human impact rather than in dollars and accolades. Brendon Bouchard’s success comes from his focus for what he can do for others, not about what he can gain.

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8. Michael Hyatt - Host of This Is Your Life Podcast, Author, Blogger, Speaker, Former CEO of Thomas Nelson Publishers

Michael Hyatt calls himself “Your Virtual Mentor to win at work and succeed at life”. Michael comes from an impressive background of being the former Chairman and CEO of one of the seventh largest trade book publishing companies in the U.S. Thomas Nelson Publishers was acquired by HarperCollins in 2012. That’s when Michael started Michael Hyatt & Company, growing it to a multimillion dollar online training company. He has written two New York Times Best Selling books: Living Forward: A Proven Plan To Stop Drifting and Get The Life You Want and Platform: Get Noticed in a Noisy World. Forbes magazine named him one of “Top 10 Online Marketing Experts to Follow” and one of the “Top 50 Social Media Influencers. His podcast, This Is Your Life, is consistently in the top ten in the Business category on iTunes and downloaded by more than 300,000 people a month. His blog MichaelHyatt.com is a favorite of entrepreneurs worldwide with more than one million page views a month. Forbes magazine named him one of “Top 10 Online Marketing Experts to Follow” and one of the “Top 50 Social Media Influencers. His podcast, This Is Your Life, is consistently in the top ten in the Business category on iTunes and downloaded by more than 300,000 people a month. Michael offers several practical and inspirational personal growth and business development online courses for entrepreneurs including Platform University an online membership community.

This man is the picture of success, but what is most inspirational about him is that he shares his real life challenges in business, family and his personal life, then he offers his practical solutions in do-able bite-sized steps.

Lesson: Michael Hyatt has a method to his success. He calls it being intentional in the four corners of your life (family, health, faith and community). He says when you are not living intentionally, you are leaving your life up to chance. Rather than being on the treadmill of life and letting things fall through the cracks, when you plan your life with intention, you create joy and success on purpose. His podcasts offers solid advice from a man with a track record of success. Michael has helped me to live a more “balanced” life by being intentional about where I put my focus and energy. This helps me to feel less guilt about where I am “falling short” and feel satisfied with what I intentionally do in my life each day.

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9. Danielle La Porte - Author, Inspirational Speaker, Blogger

Danielle LaPorte was broke, did not finish college, was rejected from art school, and didn’t know what to do. This was just after the dot-com crash and there were not many job opportunities. So Danielle took up bartending and work at a retail store called The Body Shop selling lotions and soap. She worked her way up the ranks of that company to the corporate side, then got a job at a non-profit Washington think tank. She always got to where she wanted to go by charm and personality, and being her own quirky self rather than trying to fit into the expected corporate culture. (source) She started a consultancy for “soulful personal branding” and that turned into her first book, Style Statement: Live By Your Own Design. Oprah’s producers became interested in her book and Danielle leveraged that interest into a media blitz. Danielle turned down many offers for her own TV shows, but became a commentator for the CBC, became a sought-after speaker and was featured in many popular publications worldwide. Next came a major turning point for Danielle when her business team had a “clash of wills”, and they fired her from her own incorporation. Danielle instead poured her energy into online success and personal development training programs for entrepreneurs, and inspiring people through speaking engagements worldwide. (source) Her commitment to helping people change their lives led to several books, including the most popular The Desire Map which has sold over 125,000 copies. (source) Forbes named her website the “Top 100 websites for Women.” This online news site The Huffington Post named Danielle’s Twitter account as the “12 Wisest Twitter Accounts Worth Following.” Her multi-million dollar company runs with the help of nine women and one man working virtually from four different countries.

Lesson: Danielle LaPorte is such an inspiration to me in the way that she helps people lead their lives from a self-knowing of inner desire. And even when life threw her some “hardballs”, she hustled and was determined to get where she wanted to go in life by expressing herself in her own personal style. Expressing who I am has not come easily for me because as a child raised with a dad who was in the Chinese Military, my siblings and I were not allowed to have any kind of facial expressions or express any individuality, even a smile or a glimmer in the eye was a reason for discipline. I got very good at being invisible, but was painfully shy and socially inept. I vowed to myself when I was 12-years old that I would cure myself of this isolating shyness and lack of confidence. This is one of the reasons that I created my online brand to guide women in finding their inner wisdom and inner knowing to navigate their lives. Danielle has shown me that success can be found on your own terms by sticking to your inner knowing of who you are.

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10 & 11. Jason Van Orden and Jeremy Frandsen - Hosts of Internet Business Mastery Podcast & Bloggers, Internet Business Mastery Academy Creators

In Jeremy Frandsen and Jason Van Orden’s entrepreneurial journey they both talk about escaping the cubicle office kind of “9 to 5 work”. After Jeremy Fransen read the book Rich Dad, Poor Dad by Robert Kiyosaki, he couldn’t wait to get out of his “cubicle job”. He happened to meet Jason Van Orden who was a pioneer in online marketing, and they created one of the first business podcasts in 2014. The Internet Business Mastery podcast soared to number one in the business category, and people started asking, “where is your online course”? So they created one and it sold out overnight. Now they have a thriving community helping people create successful online businesses. One of their star students is Pat Flynn of Smart Passive Income success.

Lesson: One of the greatly needed lessons I learned from Internet Business Mastery is something Jeremy Frandsen and Jason Van Orden call “Just In Time Learning”. I’ll explain: as a new entrepreneur in the ever-changing scope of the internet, you have to soak up a lot of information at once when you first jump into this world. This can lead to overwhelm and a feeling of being lost in the myriad of ways you can approach building your business. As many of us educate ourselves through blogs or podcasts that are spewing out the newest information every day, we tend to focus on that “shiny object” that catches your attention and leads you down a deep learning rabbit hole. “Just In Time Learning” is the principle that you only need to focus on what you need to learn right now. Don’t worry about what you will need to learn and do two or three steps from now. Just focus on what will help you move forward in your business where you stand right now. For me and most new entrepreneurs, this prevents the all too common feeling of overwhelm.

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12. Cliff Ravenscraft - Host of The Cliff Ravenscraft Show Podcast, Motivational Speaker

Cliff Ravenscraft, aka “Podcast Answerman” started a fun hobby that turned into a full-time, satisfying lucrative career. He and his wife started a podcast in 2005 about their favorite television show Lost. He knew the podcast would take off because he already built an audience following his blog posts about his thoughts on each episode. With the success of the Lost Podcast, he created others on entertainment, technology, faith and family. From there he noticed a community of people who loved the podcast medium, and he saw a need to share his knowledge about podcasting. That prompted Cliff to create the Podcast Answerman Podcast, now called The Cliff Ravenscraft Show. After a couple years, what became most enjoyable to Cliff was connecting and building relationships with his listeners and that’s when he realized his true calling was to entertain, educate, encourage and inspire which was what his podcasts were doing for people. His turning point came when he read Dan Miller’s book 48 Days To The Work You Love, and listening to Dan’s podcast. Dan said, “Find something you love so much, that you would be willing to do it all day for free, then become so great at that one thing that people would be willing to pay you for it”. Cliff had been working for his family’s insurance agency, made good money and was poised to take over the business. He always had a feeling that he would leave the business for a life of ministry. At that point he started to resent his insurance job, felt it was sucking the life out of his soul. His podcast community cheered him on to quit his job when he shared about it on the podcast. He finally made the jump to full time podcasting when his wife explicitly asked him to please quit his job so that she could have her husband back. Today Cliff, his wife and children love their life and he makes a half a million dollars from podcasting, consulting, digital product sales, mastermind groups, speaking engagements and contributors from listeners. (source)

Lesson: Cliff Ravencraft’s words are exactly why I started podcasting in 2014 when I launched my brand Your Sensible Girlfriend’s Guide To Life.

“By just sharing what’s going on in my life, I’m having a powerful and positive influence and impact on the lives of the people who listen.”

“Podcasting has no rules… it is the Wild West of communication with the world.”

“Having an audio podcast is probably one of the best investments you can make to take your message or business or your brand to the next level.”

“There’s nothing more powerful to communicate excitement and passion and, just really, your humanity in a digital form than through an audio podcast.”

These quotes are from Cliff Ravenscraft. (source)

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13. Dana Malstaff - Host of Boss Mom Podcast, Nurture Your Business Podcast, Author, Online Business Coach For Entrepreneur Moms

Dana Malstaff saves us moms from the all-too-common guilt of choosing to be a passionate entrepreneur while also being a dedicated mother. She felt this guilt big-time as soon as she got pregnant and knew she did not want to be a stay-at-home mom. In 2013 she had just left her job to start her own consulting business and soon found out she was six weeks pregnant. Once her baby was born, she would pray that he would take a nap so she could get down to business and that made her feel like a terrible mom. After a couple of years feeling guilty, she came into her role as a mother with more confidence. She realized that this guilt was just coming from a false ideal of societal standards. This idea grew when she was talking to her book coach about writing a book about content strategy, and their conversation led to the discovery of her highly successful brand Boss Mom. (source) Her book Boss Mom: The Ultimate Guide to Raising a Business & Nurturing Your Family Like A Pro and her Boss Mom Facebook group are the go-to business mom’s guide to feeling like a champ in both areas of your life.

Lesson: Dana Malstaff’s story helps moms like me who are passionate about their work to feel understood. Just being understood helps to let go of the deeply felt “bad-mom” guilt that most working moms automatically feel. Her podcast and Facebook community provides a huge sigh of relief for me and thousands of other mompreneurs like me.

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14. Lewis Howes - Host of The School of Greatness Podcast, Blogger, Author, Motivational Speaker

Lewis Howes grew up thinking he might end up in jail like his older brother, but has become a millionaire, an inspirational speaker, a podcaster and author with his brand called The School of Greatness. Growing up in an unhappy home with parents struggling to make ends meet, Lewis’ future looked dim. Lewis struggled in school and had no friends— unable to learn to read past 2nd grade level and feeling ostracized by kids making fun of him for mumbling to cover for his illiteracy. (source) Lewis knew the only shot at finding his way out of poverty and unhappiness was to focus on a sports scholarship. His laser focus got him into professional football with his sights on becoming an Olympian. His dreams were crushed after breaking his wrist. After major surgery, Lewis found himself falling deeper and deeper into depression living on his sister's couch trying to figure out how to make money. He didn’t have any savings or a college degree, also the economy had taken a downturn with companies downsizing and people losing their jobs. He couldn’t do manual labor with his arm in a cast, so he sat on his sister’s couch with his laptop, and read a lot of blogs and saw how people were building their personal brands online. He started looking on LinkedIn trying to connect with people for a job, and that’s where he realized he could connect with successful people and ask them how they made millions or got to where they are. One by one he grew his network, and started up his own website around the sports industry and the sports executives he interviewed through LinkedIn. Lewis took all those success interviews and turned them into a book called The School of Greatness. He also learned how to monetize his website by promoting products, services and live events. He hosted more than 20 live events in one year, and was exhausted. Then he discovered webinars, and from his first webinar made $6300. The lights went on in his head, realizing this is where he can reach an audience without having the to deal with the physical logistics of live events. He then wrote an e-book called The Ultimate Webinar Marketing Guide. Lewis turned his soul-crushing tragic story into a life of empowering online entrepreneurs with his books, his podcast The School of Greatness, and hosts motivational summits with renowned thought leaders. He turned from despair to creating a seven-figure business in a just couple years. (source)

Lesson: What I’ve learned from Lewis Howes is that when you strive for greatness rather than success, (taking you out of “playing the comparison game”), you reach beyond what you believe to be your own potential. That is what brings ultimate passion, joy, empowerment and richness to your life. I also have learned from Lewis to use what you already know to move in the direction of your goal, so I am now using my experience as a television producer and reporter to build a new online brand (for shy, introverted online entrepreneurs who are fearful to get in front of the camera to promote their business through video).

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15. Reina Pomeroy - Life & Business Success Coach, Founder of Reina + Co, Creative Empire Podcast and Heart Centered Biz Bosses Facebook Community

Reina Pomeroy was a social worker, a full-time working mom driving two hours each way work from Reston, Virginia to Baltimore with her 8 month old baby strapped in a car seat the entire time. She felt so helpless when the baby would scream and cry in the back seat, and she couldn't stop to hold and comfort him. She enjoyed her job, but questioned if daycare and hours in the car was the life she wanted for her family. Reina’s turning point happened when a mentor came to her office and revealed she had just left her unsatisfying full time job after losing a best friend to cancer. Reina gave notice shortly after with zero job prospects, but left anyway. (source) She took time to think about the one thing that really makes her happy. Reina says, “The #1 thing that makes me happy is being able to connect with people. I feel most fulfilled when I can take the time to get to know somebody and see them for what they are”. (source) Before becoming a social worker, she had dabbled in wedding planning where she met creative entrepreneurs, and always envied how they got to choose what they wanted to do. She ended up helping a fellow wedding planner with online business coaching, and that lead Reina to create her dream business with her empathetic social worker skills — coaching creative entrepreneurial women from a psychological, yet practical approach. She encourages women to define their own meaning of success which does not have to be centered around creating wealth. For Reina, her definition of success is never having to write a resume ever again.(source)

Lesson: Reina Pomeroy has inspired me with her “heart centered”, empathetic approach to business where “nurturing relationships” is the foundation to a successful business. Her Heart Centered Biz Bosses Facebook Community has taken away the lonely, isolated feeling of being an online business owner by helping hundreds of women (including myself) to connect with other creatives to support each other’s entrepreneurial journey. Reina shows women entrepreneurs like me that a woman’s way of listening to your heart, aka your inner wisdom, leads you to create a heart-fulfilling business and a no-regrets life.

14. Steve Chou - Host of My Wife Quit Her Job Podcast, Creator of My Wife Quit Her Job Blog

Steve Chou’s success story started with his wife hating her job, and both of them feeling like lifeless zombies because their work life was so uninspired. Once she got pregnant, she followed her heart by wanting to be a stay-at-home mom, and started selling wedding handkerchiefs online. One wouldn't expect handkerchiefs to be a lucrative business, but within a year, she replaced her job salary making over $100,000 dollars. Steve documented their entrepreneurial journey in a blog and has turned that into a thriving 6-figure business and a podcast while he still works at a full time job! (source)

Lesson: Steve Chou taught me that fulfilling a need, no matter how small that niche may be, can be turned into a satisfying, lucrative business. And sharing your journey holds value. People are willing to pay for your knowledge even if they are just one step behind where you are. His story helped me to not worry about second-guessing my niche and body of knowledge. I learned that if a specific target market needs and wants what you have to offer, if marketed well, it can be grown into a successful business.

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15. Tara Gentile - Digital Business Strategist, Author, Creator of Quiet Power Strategy, Host of Profit Power Pursuit Podcast with Tara Gentile

Tara Gentile’s start in working online began because she was angry. She didn’t get a promotion that she was expecting and was waiting on for a very long time. She decided that she “wouldn’t be beholden” to someone else agenda ever again. During her maternity leave she realized that she couldn’t go back to a job she hated and would have to figure out how to make a stay-at-home job happen. While nursing her baby and surfing the web on her laptop, she saw there was so much happening online and people were making money at it! Her mom suggested she create a website for Pennsylvania crafters and artists, so she did. One thing led to another and she became editor-and-chief of a website called Scoutie Girl. Just a year after she was denied that promotion at her old job, she replaced her full time job income with her new online career. (source) Tara is the author of Quiet Power Strategy , the creator of Quiet Power Strategy® customizable business planning system, and host an online community for entrepreneurs.(source) She is a bestselling instructor at CreativeLive, an online training workshop platform for creatives. Tara’s work has been featured in Fast Company, Forbes, Design*Sponge, and in the New York Times bestselling book The $100 Startup by Chris Guillebeau. (source)

Lesson: I felt the same way as Tara Gentile working for someone else and not being valued, so I can’t imagine being an employee ever again. I realized that it takes a certain kind of person to be an entrepreneur. It takes being able to handle risks, thinking outside of the box and being resourceful, qualities not needed to be an employee. I am inspired by Tara in all that she shares on her blog and podcast on the strategic and tactical components of how creative people make money and pursue what is most important to them including their mindset. Her interviewing style digs deep to parse out revelations of truth and wisdom to reveal the golden nuggets of those she invites onto her podcast. She gives straight-forward, sound and actionable insight. For me, her linear approach to business inspires my creative brain to become more organized in the way I approach my work.

Photo Credit: Christa Meola

18. Nathalie Lussier - Digital Business Strategist, Creator of AmbitionAlly Software & Off The Charts Podcast

Nathalie always knew she wanted to be an entrepreneur. As a child, she self-published and sold a magazine to friends and family. At age 12 she started designing websites and thought about making that into a business. But instead of following her heart, she went to school to learn software engineering, and worked in Silicon Valley. Finally when she was offered a job on Wall Street she stopped to listen to her intuition and started up an online business around one of her passions--healthy eating. She taught herself how to make money online, and people began asking her to teach them how. She quickly turned that into a six-figure business offering online courses, a membership community and wordpress plugin software. She shares expert insights through her podcast called Off The Charts. (source)

Lesson: I learned from Nathalie Lussier that following your intuition trumps a career that sounds good on a resume. Being a “Type-A”, very mentally driven person, I find it easy to let my rational brain speak loudly, and discount the little voice that is my intuition. Nathalie’s story has helped to remind me that there are times when we let our practical side lead us and that is not a bad thing. But there comes a time when your intuitive inner wisdom must be the guide, even if family or friends think you are “throwing away a good opportunity”. Ultimately listening to that inner voice to do what you love leads to great success and inner fulfillment.

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Heather Crabtree’s parents did not go to college, so they made sure that their children got a good education hoping they would become doctors or lawyers. So Heather went to law school, and during school her dad passed away. That made her take a look at her life and helped her to realize that she had been pursuing a law degree for her dad, but really wanted to start her own business. Without any experience, she started an event planning company. She said, “it just felt right.” She learned online marketing to promote her business, and started coaching other women. She now does group coaching programs and is launching an online shop for digital downloads, trying to maximize time to spend with her children and husband. Heather is so well loved by the 8000+ women in her Savvy Business Owners group because she really takes care to make it about supporting each other in the entrepreneurial process. (source)

Lesson: Heather Crabtree is a model of how to manage and scale a group by being engaged and accessible, yet using what she calls “ambassadors” to take care of portions of the workload inspiring and moderating the group. She has clear rules so that the group of 8000+ women stays in line with her vision of sharing tips, successes, failures, support, inspiration, connection and encouragement. Heather has helped me to realize that we don’t have to overwhelm ourselves by being all things to support other women and keep to the overall vision. She has taught me that other women want to be your wing-women if you have a clear vision, and a good cause.

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20. Oprah Winfrey - Media Proprietor, Talk Show Host, Actress, Producer, Philanthropist, Thought Leader

Oprah Winfrey is an inspiring entrepreneur, an icon, a role model to so many aspiring entrepreneurs online and offline that I had to include her in this list. She came from humble beginnings growing up in a working-class family in a small farming community in Mississippi, living with her grandmother while her unwed mother looked for work in Milwaukee. At age six she was sent to live with her mother in the inner-city apartment where she endured sexual abuse by male relatives while her mother was working as a housecleaner. She tried to run away, was sent to a juvenile detention home, but couldn’t stay because their beds were full. After giving birth to a baby boy who died as an infant, she was sent to live with her father in Tennessee. He was strict with Oprah in order to help her to become her best at anything she pursued in life. Oprah became an honor student, winning prizes in speech and drama classes. At age 17, Oprah won the Miss Black Tennessee beauty pageant and was offered an on-air job at the African American radio station in Nashville. She won a full scholarship at Tennessee State University majoring in Speech Communications and Performing Arts, but left school to take a job as an anchor and reporter at a local television station. WJZ-TV in Baltimore offered her a job as a talk show host where she became known for her outgoing, yet empathetic style. A television station in Chicago hired her to help lift their morning show ratings, and in less than a year it became a hit show, renaming it The Oprah Winfrey Show. In the early ’90’s Oprah’s show became even more popular when she shifted the show’s content around personal development, healthful living and spirituality. Oprah has won numerous awards and was named one of the “100 Most Influential People of the 20th Century” by Time Magazine. Forbes listed Oprah as the first African-American to become a billionaire. She publishes O Magazine and The Oprah Magazine. Oprah’s Harpo Productions and Discovery Communications came together to produce The Oprah Winfrey Network (OWN) which replaced Discovery Health Channel (for which I have produced a women’s health show). Oprah.com hosts inspirational programs such as the famed Super Soul Sunday and online courses including the newly released Thrive with Arianna Huffington. (co-founder, former president and editor-in-chief of The Huffington Post Media Group which hosts this blog post.) (source) (source) (source)

Lesson: Oprah is an example of a woman of color rising through the ranks of television news and media stardom showing us her vulnerable, imperfect sides as well as being a role model for so many women of all ethnicities. Oprah helped me to realize that the color of your skin and a less-than-perfect family background does not have to hold you back from becoming a successful role model, leader, visionary and business woman. Oprah showed me it was possible. At age 23, I dared to jump from being a hairstylist financially supporting myself and my younger siblings, to finding my way into a television newsroom without a college degree or journalism background. As news writers at NBC in Los Angeles, my friend Tracy McMillan and I talked about how we aspired to be as influential as Oprah one day. Tracy is now one of Oprah’s Super Soul Sunday superstars. So many women entrepreneurs (including myself) aspire to inspire and give to the world like Oprah has and continues to do.

21. Arianna Huffington - Creator of Thrive Global, Author, Co-Founder, Former President and Editor-in-Chief of The Huffington Post Media Group (which hosts this blog post.)

Arianna's incredible passion and drive lead her to become a media mogul as co-founder, former president and editor in chief of the award-winning online news platform The Huffington Post. Arianna is on Time Magazine's list of the world’s “100 Most Influential People” and Forbes “Most Powerful Women” list. She is a journalist at heart winning a Pulitzer Prize in 2012, and author of 15 books, most recently Thrive and The Sleep Revolution. Her latest venture, an online platform called Thrive Global, came about from a breaking-point in this push to succeed, and then a realization in what it really means to live a successful life. Her life took a surprising turn-- a personal wake-up call when Arianna collapsed from sheer exhaustion— working too hard, not getting enough sleep and keeping that pace that many of us entrepreneurs do to push ourselves to “get ahead”. She suffered from a broken cheek bone, a deep gash over her eye. That prompted a breakthrough in her paradigm of how to go about achieving a life of success. She realized that our “traditional metrics of success— money and power— has led to an epidemic of burnout, stress related illnesses, and an erosion in quality of our relationships, family life, and ironically our careers”. (source) This accidental epiphany prompted her to write her latest book Thrive: The Third Metric to Redefine Success and Creating a Life of Well Being, Wisdom and Wonder and also to create the online platform Thrive Global. Thrive Global’s mission is to “provide trainings, seminars, e-courses, coaching and ongoing support based on the latest scientific findings to improve people’s health and increase productivity for both companies and individuals around the world”. (source)

Lesson: Today, Arianna is showing us a new way to define success and our ability to truly "thrive" in our lives. She lived a life of money and power found by relentlessly climbing the career ladder. In this new way, we can thrive by allowing success to come through using our intuition, tapping into our “inner wisdom, our sense of wonder and our compassion and kind-hearted generosity”. I can personally relate to Arianna’s entrepreneurial journey with my family emigrating to the U.S., striving in my career as a journalist nominated for an Emmy award, nearly married into a family of notoriety involved in politics and the old "Hollywood Dynasty" of movie-making and entertainment, and that drive for so called "success" in this land of opportunity that many of us strive for. I too had a personal wake-up call when my surfboard slit open my forehead, and the tetanus shot at the hospital brought on a degenerative, autoimmune disease which caused me to reassess my way of life. I am no longer pushing to succeed, but rather allowing my inner wisdom to tell me when to act upon business opportunities. In this new way of living, I feel healthier, happier, and see that I am also thriving in a new way of achieving great success.

Angeline Chew Longshore (aka Your Sensible Girlfriend) was an Emmy Award nominated television news and talk show producer for 15 years in Los Angeles. She left her career in television to become a wife and mother in Maui, Hawaii, and is now an online entrepreneur. Angeline owns three online brands— Your Sensible Girlfriend’s Guide to Life Podcast & Blog, Mr. Right, Right Now ~ manifest your “soul husband” (the man just right for your soul), and Be Yourself On Camera ~ create loyal customers & raving fans with your authentic on-camera presence for the camera-shy entrepreneur. Angeline is a motivational public speaker and coach helping women navigate their lives by intentional mindset shifting and finding inner wisdom. She also works nation-wide with camera-shy online entrepreneur women to use compassion, empathy and self-worth as mindset tools to overcome their fear on camera, and become dynamic online personalities as a personal coach and through her Camera-Shy To Confident & Authentic On Camera online courses.

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