12 entrepreneur stories you should watch for inspiration

Can't stop, won't stop

By Tegan Mouton

12 entrepreneur stories you should watch for inspiration

12 entrepreneur series

2020 has been awful, I mean really, really awful. Businesses have been forced to close their doors, countless people have lost their jobs, and we’ve all had to put a lot of our dreams on hold. 

Without getting too “woe is me”, I’ve found it fairly hard to feel motivated about my career recently, so it was particularly satisfying when I enjoyed a big enthusiasm-upswing after watching (and by that I mean solidly bingeing) Netflix’s series Girlboss. 

While the show isn’t perfect (more on that below) the true-life story of entrepreneur Sophia Amoruso’s hardcore hustle to get her e-commerce store off the ground had me excited to put the time and effort into certain goals I’d lost track of in the chaos of the pandemic. 

If you’re like me and you sometimes need a little inspiration to get your head back in the game, here are a few other entrepreneur success stories (both fiction and non-fiction)  in film and TV format. 


As mentioned above, Girlboss (loosely) follows the true story of entrepreneur Sophia Amoruso (Britt Robertson), a 23-year-old college dropout/ anarchist who wants to make her own way in the world. After realising that she can make a decent living selling vintage clothing on ebay, her e-commerce business Nasty Gal is born (with a lot of challenges, some heartbreak and one hernia along the way). 

Admittedly the 2017 series, which is produced by Amoruso herself and based on her book, may not be the most impartial version of the story (Nasty Gal went from being valued at 200 million to filing for bankruptcy and being sold to the BooHoo shortly after the series debuted, and Amoruso has had big legal troubles with former employees) but it had a few feel good moments that left me feeling pretty perked up overall. I suggest viewing it alongside a pinch of salt 😉 

Self Made: Inspired by the Life of Madam C. J. Walker

Based on the biography On Her Own Ground by A’Lelia Bundles and starring the always spectacular Octavia Spencer, Self Made tells the tale of, you guessed it, Madam C. J. Walker (real name Sarah Walker). Walker was a pioneering black woman, entrepreneur and former laundry washer who built a hair care empire and became one of the richest self-made American women of her time in the early twentieth century.

While some critics have taken issue with Netflix’s artistic license when it comes to the story of Walker and her business rival Annie Malone, Spencer’s portrayal of the entrepreneur’s hustle might give you the dose of inspiration you need to tackle your goals head on, and if that doesn’t do it for you, tune in for Tiffany Haddish as Walker’s daughter Lelia.

Chef’s Table – Christina Tosi 

Sure this one part special isn’t a full-blown series or film, but it will leave you feeling inspired, (and dying for a sugar fix). Chronicling the story of pastry chef and restaurateur Christina Tosi, this special episode of the Netflix series shows how her love of tasty treats, comfort food and good ol’ fashioned hard work made her trend-setting bakery Milk Bar an overnight sensation in New York City (I stopped there twice during my trip to the Big Apple) and later in hot spots all over the world. Think cereal ice-cream, birthday cake truffles and crack pie…yum.

The Pursuit of Happyness (This is actually how the title is spelt, we’re not just bad at English)

This 2006 classic stars Will Smith as Chris Gardner, a real-life homeless salesman turned successful broker. Smith’s son Jaden Smith co-stars in this tear-jerker, making his film debut as Gardner’s son, Christopher Jr. The screenplay by Steven Conrad is based on the best-selling 2006 memoir of the same name written by Gardner with Quincy Troupe, and the story follows Gardner’s one-year struggle being near homeless while single-handedly raising his toddler son. Spoiler alert, Gardner overcame some serious setbacks and became a stock broker, eventually forming his own multimillion-dollar brokerage firm. There will be tears.

Grace and Frankie 

After their husbands come out of the closet and admit they’ve been more than just law partners for the last few decades, polar opposites Grace and Frankie (marvelously played by Jane Fonda and Lily Tomlin) shack up as roommates and support each other as they try to start all over again in their sixties. One of the biggest changes they make as they hit reset on their lives is going into business together, selling things like a yam lubricant and a vibrator for mature women. We love this hilarious and heartwarming series that proves it’s never too late to chase your dreams or start something new.

The Intern

This delightful, that’s right I really said the word delightful, movie follows Robert de Niro as senior citizen Ben Whittaker, who reintegrates into the workforce as an intern at a clothing e-commerce space founded and run by CEO Jules Ostin (Anne Hathaway). While the movie may show the less glamorous side of success (think board members trying to wrestle you out of your own company and insecure, cheating husbands) it’s a sweet tale about two very different people finding and leaning on each other for support as they work together. Frankly, I’m here for any film written by Nancy Meyers!


This comedy/drama film tells the true story of entrepreneur Joy Mangano, a self-made millionaire, who created her own business empire with the invention of a self-wringing mop. I’ll be honest this is far from my favourite Jennifer Lawrence film (though it did earn her a Golden Globe for Best Actress) but Mangano’s story of serious hard work, commitment and grit is extremely inspiring, especially after learning that she had to file for bankruptcy, deal with competitors stealing her inventions and having her own family try to sue for her company. This lady is tough!

Working Girl 

Take it back to the 80s (there are shoulder pads galore) for this absolute rom-com classic. It sees Melanie Griggith star as Tess McGill, a working-class girl from Staten Island, assigned as an administrative assistant to Katharine Parker (Sigourney Weaver), a business exec who plans to steal Tess’ idea for a big merger. Luckily, Tess finds out about Katharine’s diabolical plan, and decides to go ahead with it on her own, with heartwarming and hilarious results. Oh and Harrison Ford is also around being a heartthrob (it was the 80s OK). 

Julie & Julia

I should state right off that I’m incredibly biased because Nora Ephron is my forever idol and anything she has ever written is total gold in my mind, but this film is really fantastic, even if you haven’t checked out any of her other work. Julie & Julia simultaneously tells the (true) stories of chef Julia Child in the early years of her culinary career and New Yorker Julie Powell who aspires to cook all 524 recipes in Child’s cookbook in just 365 days, a challenge she shared on her popular blog, eventually leading to her becoming a published author. (You can see why the story of a successful blog is popular over here at Blondie&Co.). Frankly, this movie is heartwarming perfection, and the more of Meryl Streep and Amy Adams I can get, the better.

(Just a warning you’ll be hungry after watching this)

Jerry Maguire 

Prepare to tear up and swoon over a super hot, young Tom Cruise (I hope pre-scientology) as he shines in this Cameron Crowe classic (“Show me the money!”). Part iconic sports film, part forever fave rom-com, the movie follows Jerry Maguire (Cruise), a sleek and successful sports agent who has a crisis of morality and decides to start his own, more ethical agency with the help of single mother and eventual love interest Dorothy (Renee Zellweger). I cry every time because… “you had me at hello”.

Baby boom

This was a hard one for me to include because frankly, sitting through any Diane Keaton movie is tough for me (too much frantic energy and turtlenecks), but it was written by Nancy Meyers so I feel like they cancel each other out. This 1987 oldie-but-goody stars Keaton as J.C.,a career-driven Manhattan advertising executive, who discovers her long-lost cousin has died, leaving her a fourteen-month-old baby girl, Elizabeth. While she grows fond of the little girl, her new parental role harms her high flying career, and she finds herself living in a farmhouse in Vermont and struggling for cash. To make ends meet, J.C. starts making and selling her homemade “gourmet” baby food, which grows into a fully-fledged business. When she gets a tempting offer from her old company to buy out her new business, she’s faced with a tough choice. Definitely worth a watch! 

Like a boss

The most recent addition to our list, this 2020 film is a fun watch, even if it’s unlikely to win an Oscar. Starring Rose Byrne and Tiffany Haddish (love ‘em both) as lifelong besties and business partners Mia and Mel, the movie follows the duo as they make the decision to accept the help and money of benefactor Claire Luna (Salma Hayek), head of a major cosmetics empire. When they find out Luna is trying to steal their company out from underneath them, they have to overcome their differences in their approach to business and start a new company to take her on. It’s a fun watch if you’re with your girlfriends, but I do wish they would stop throwing random musical numbers at the end of non-musical films…

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