Five FEMALE entrepreneurs who achieved greatness after struggle. A closer look at how humans often fail into greatness.

It’s not hard to find stories of entrepreneurs whose first ideas flopped before they had their breakout moment.  I especially get fired up reading stories of female entrepreneurs who kept pushing through resistance towards their dreams. As females, the way we appear outwardly to the world can feel so important, but all great female entrepreneurs had to at some point stop caring about how other people perceived them and just keep fearlessly pushing forwards. 

Many great success stories often come on the heels deeply vulnerable moments.  When we forge our own paths as entrepreneurs, we might have moments of looking a bit stupid, or we may experience full blown failures that make us want to quit.  Still, avoiding failure at all costs is not only unreasonable but also robs us of life’s greatest teaching moments.

Like most entrepreneurial kids I did the lemonade stands, I went door to door raking leaves and shoveling snow, I babysat the entire neighborhood and did anything I could do to earn a dollar without having to get an actual job.  I recently found a picture of my very first clothing business.   No, not my first etsy shop, that also failed, this was way earlier.  See that pointy hat on my head?   A literal dunce hat made out of upholstery fabric from a forbidden book of samples that my mom kept in her sewing room. I didn’t technically ask to use the samples and I was definitely not allowed to use the sewing machine but one summer day inspiration stuck and my first physical product was born.

You could say this business was a failure because in almost every way it was.  But rather than decide I’m a terrible designer who has no business making garments, I learned some amazing things that I’ve carried with me to this day.  I learned how to thread a machine and sew a straight stitch.  I learned that having people tell me “no” is not the worst thing that can happen, nor is looking stupid.  I learned that I love creating things with my hands and that will forever be my happy place.  I learned that people will buy silly things just because they like the person selling them and I began to imagine how easy it would be to sell things that were actually good.  This very short-lived business of terrible hats was a gift, it was a spark that ignited decades ago, and that has smoldered in me all these years.  It was the very first failure (of many) on a path that has led me to where I am today.

Today my business is still a tiny baby and so I imagine I will fail many more times as I go through the process of raising this baby into a woman.  I’m positive that at some point I will look back on where I am now and cringe, but I’m ok with that.  If we aren’t cringing at our earlier selves, we are not progressing at our craft.

We needn’t look far to find examples of entrepreneurs who have faced adversity and risen to greatness, but I wanted to dig a bit deeper into the female side of things.  There are some household names that immediately popped out at me but are also some lesser known individuals whose stories have inspired me.   So, here’s a look at some ladies who have achieved greatness and have done so not in spite of failure, but also because of it…        

J.K. Rowling

This is one of my favorite rags to riches stories.  Not just because I am the biggest Potter-head of all time, but because this bad ass woman was a single mom on government assistance when she began writing the epic series that would make her a billionaire. It took her six years to write The Philosophers Stone but she persevered, finished her masterpiece and then proceeded to be rejected by 12 different publishers.  There were many points in her journey where I’m sure she felt like an epic failure and she has even spoken publicly about a brief period where she had considered taking her own life, but she kept pushing and eventually became the first writer (female or not) to earn a billion dollars from her work. Boss babe 101.

Cathy Heller

This beautiful soul has been hands down the biggest source of motivation in my own pursuit of entrepreneurship.  She moved to L.A. to become a recording artist and ended up being dropped from not one, but two record labels.  Rather than wallow in despair at a failed music career she created her own music career by selling songs to businesses for huge royalties and built a six figure course teaching others how to do the same.  But she didn’t stop there, she has since gone on to start the “Don’t Keep Your Day Job” podcast (get into it), write a book and build a coaching empire that brings in 8 figures annually.  Not only is she crushing it financially, she now gets to help other entrepreneurs learn from their failures and rise to greatness all while doing their life’s work.   

Madame CJ Walker (Sarah Breedlove)

I first learned about this QUEEN way back in the day while attending hair school.  She was my first peek into the world of female entrepreneurship and living proof that we truly are in the drivers seat of our lives.  This icon was born to  former slaves and by the age of seven she was orphaned.  Left to grow up alone in a world where she faced incredible limitations, not just as woman but also as a person of color, she married at 14, became a teen mom and was living in poverty when struggles with hair loss sparked a calling within her. She had been born into a life that had set her up to fail, but instead she would go on to become the first black American female self made millionaire.  How did she do it? Pure hustle.  She created her own hair growth formula, hit the pavement and sold it door to door.  This would eventually lead to her own hair empire and a netflix special a century after her death.  Talk about leaving a legacy!

Jamie Kern Lima

This amazing woman is the founder of IT cosmetics which she ended up selling for 1.2 billion dollars.   I’ve recently listened to a few podcasts where she is graciously details all the failures she had to endure to achieve such a high level of success. With every penny invested in a business she believed would change the face of the beauty industry she fearlessly knocked on doors and heard all the no’s before her big break would happen. When that break finally did come in the form of a 12 minute slot on CVS, she was down to her last $1000 and one slip up away from total bankruptcy. In spite of all the experts urging her not to, this brave woman allowed herself to to show her bare skin and represent for those struggling with rosacea on national television.   Real woman finally saw a makeup brand representing faces that looked like theirs, these same women fell in love with the brand, and the business went to the moon!

Suze Orman

Hers has become a household name, but not everyone is familiar with her humble beginnings.  At the age of 29 she was working as a waitress making $400 a month and managed to scrape together 50 000 to open her own restaurant.  Sadly, that fifty large ended up badly invested, she lost every penny and was forced to close the restaurant.  Wanting to help others avoid similar situations she educated herself on financial management, scored a job at Merrill Lynch and has since appeared regularly on Oprah and written books on financial literacy with an emphasis on helping women gain financial independence.   Hers is an inspiring rags to riches story featuring female empowerment if there ever was one. 

There are so many other stories that didn’t make this list.  Perhaps you’ve seen success stories of women killing it posted all over Instagram and perhaps it’s those same success stories that make you feel unworthy to start your own thing.  Just remember, anyone doing anything great most certainly has some form of failure behind them.  Don’t compare your mess to someone else’s curated feed. Just don’t. Give yourself the permission to do that thing that makes you really lit up but also a little bit terrified. Make messy things, wear stupid hats, persevere and allow yourself to fail into greatness.

Success! You're on the list.


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