What Startups Can Learn from The Wizard of Oz

July 12, 2014

10:00 am

This year marks the 75th anniversary of the premiere of “The Wizard of Oz,” a movie that captured my youthful imagination (along with millions of others’) whenever it was shown during the holidays on network TV. In addition to being a huge fan, I also have a visceral connection to this cinematic classic due to playing the part of Dorothy in a children’s theater adaptation when I was just 12. Having memorized the scripts for both stage and screen, you could say that I know the movie version of the story pretty well.

Playing the part of Dorothy in The Wizard of Oz.Auditioning for the lead role was my mother’s idea and, since I hadn’t hit my rebellious phase just yet, I went along. The director was a crusty, middle-aged guy who shushed the excited group of children and adults as we gathered in a relatively large auditorium and then boomed, “Ok, who here thinks they can play the part of Dorothy?” Without waiting for me to protest, my mother forcibly nudged me in the back so that I appeared to be standing… as if I had all the confidence in the world. To this day, I don’t remember walking on stage or singing the first few bars of “Somewhere Over the Rainbow,” but I ended up getting the part. Turns out the director wanted someone who wasn’t afraid to take the lead and watched to see who stood up first.

So what does this have to do with entrepreneurship? My adult years find me on quite a different stage – taking an active, decade-long role in the world of startups – so this confluence of milestones got me thinking about ways The Wizard of Oz can inform entrepreneurs. Because, as someone in the startup trenches and an Ozmologist, I think that Dorothy’s character can teach us a few things about launching a business:

Follow your passion

Dorothy chased after her heart even when it appeared that Ms. Gulch was going to get her way. Granted, Toto looked like a goner, but that didn’t stop our Dorothy from trying. Passion also fuels startups. Just look at restaurateur/philanthropist Sean Meenan as proof positive that following your heart is an essential trait for business. He used passion to drive his pitch, his motivation for growth, and confidence to trust his instincts. This enthusiasm led to his successful chain of Café Habanas, which then allowed him to be an initial investor in Etsy. Not only is passion profitable, it can be scalable!

Be ready to pivot when your world changes

What? We’re not in Kansas anymore? Then, let’s see if this Yellow Brick Road can get us to where we need to be. Conditions aren’t always ideal for the budding business venture but if you have a “particular mindset,” says innovator, thought leader, and partner at IDEO, Diego Rodriguez, “one that allows you to do anything with nothing, when you decide to relentlessly pursue a dream no matter how little you’ve got, you’ve already taken the biggest step on that journey.”

Pick your team carefully

Our heroine knew that to reach her goal she would need some help. Her companions were a pretty diverse bunch, but everyone was on board and shared the vision. The same axiom holds true for startups: having diversity on the launch team lowers failure rates and improves long-term returns.

Position yourself to be at the right place at the right time

Ok, Dorothy’s crash landing wiped out a pest and created an enemy but, more importantly, she found herself right at the start of the Yellow Brick Road with supportive throngs cheering her on. Cheerleaders are important for nascent businesses as well. Did you know that some cities in the US are better positioned to help startups than others? Entrepreneurial thought leader Gary Schoeniger says that the key to success is for entrepreneurs to hang out with people who are entrepreneurial. This supportive environment then creates the circumstances that allow entrepreneurs to thrive. Does your city have incubators, accelerators, small business support systems, etc.?

Be courageous

As a child, I thought Dorothy was pretty gutsy to go after the wicked witch’s broom, not to mention those flying monkeys. She was courageous in my book. Turns out that this same attribute is also vital for entrepreneurs. Geoffrey James, a featured writer for, argues that the one simple thing necessary for an entrepreneur to succeed is (you guessed it) courage. Most of society is risk-averse, so he asserts that possessing the courage to say no to a steady job with its medical plans, PTO, 401Ks, etc., to pursue a dream is bold stuff. Forget innovation, forget management skills, and forget access to capital. “Courage!” is what they’ve got that most others ain’t got, to bowdlerize a familiar quote from another Oz character.

I didn’t go on to pursue acting but I did glean some life lessons from Dorothy’s exploits that have applications in just about every endeavor I have ever faced (including two failed startups). The entrepreneurial journey is guaranteed to take you “over the rainbow” and you need to be equipped for all kinds of adventures. Perhaps the best takeaway comes from my theater audition: stand up when you get the nudge and don’t be afraid to take the lead.

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I'm a serial entrepreneur and veteran launch team executive in high tech, e-commerce, and biotech. Based out of Austin, TX, I support women’s entrepreneurial initiatives and teach university courses on business/technical writing.