Melinda Sue Gordon/Everett Collection

Tell me if this sounds familiar: you’re sitting at home, exhausted from work, and staring at your television wondering what you should watch. As an entrepreneur, you feel like you should spend your time watching something educational, but you really just need a few minutes respite from every day.

This leads to a phenomenon I call Netflix roulette. You scroll through the endless suggestions of content, unable to make a decision. Eventually, you settle for something that sounds ok, even though it isn’t what you originally intended. This makes you feel a little guilty for wasting time, and not entirely relaxed either.

Well, you can rest easy, for I’ve got you covered for the next 15 hours. Here’s a list of movies that are both entertaining and still educational for every entrepreneur.

Big Night

Have you ever been in the situation where you’ve created a product, and you are so convinced that you’re right about it that you won’t change it no matter what? This movie, about a chef who refuses to compromise on his vision, follows a last-ditch effort to save his restaurant from foreclosure.

After watching, you’ll come away with a better understanding of the importance of customer experience and product/market fit.

Catch Me If You Can

This biopic of former con-man Frank Abagnale follows him across the world as he lives a flamboyant lifestyle — while being investigated by the FBI for check fraud. It highlights both the creativity of Abagnale and the diligence of the FBI auditors.

For entrepreneurs, the lessons here are especially relevant in a post-Theranos startup world.

The Commitments

Alan Parker’s 1989 film about the rise and fall of a band in Dublin is packed full of lessons for every business owner. You’ll learn about recruitment, financing and team dynamics from a real-world perspective.

Most of all, you’ll find that creating a beautiful product isn’t the surest sign of success.

Jerry Maguire

For entrepreneurs, there’s a moment where you dream of standing up and walking out on their own to start their own business. This movie is the epitome of what that’s like from struggling to find your own clients, to trying to build a reputation and being shut out from things because you simply don’t have the corporate bankroll.

It’s a must watch — especially if you are looking for the blueprint on how to leave your corporate job in a spectacular way.


By now, we’re all aware (or should be) that we can leverage data to make better decisions in pretty much every business, however that hasn’t always been the case. Back in 2003, the Oakland A’s manager was given the smallest recruiting budget in the MLB and had to come up with a new method to put his team together – and this is the result.

What you’ll learn here is how to bootstrap your way to a successful business model.


A fish-out-of-water story about an American sent to India to run a call center, this is a humorous look into the world of corporate expansion, cultural dynamics, and ultimately, corporate takeover.

When considering taking on a partner or working with another team, the lessons you can learn from this movie are relevant andvaluable.

Thank You for Smoking

Have you ever heard the term “lobbyist” and wondered what it really meant? This movie goes into hilarious – and sometimes painful – detail about where exactly our tax dollars are going, and what our rights as individuals and small business owners actually mean.

While there are many aspects to this movie that are excellent, bonus points go tomodeling how to show up every day to a job you’re not passionate about.

Tucker: The Man and His Dream

Sometimes, even when the timing is right, the financing is in place, and you have the perfect idea, your business still won’t work. Preston Tucker did everything right – and his competitors did everything they could to take him down.

For entrepreneurs, this is the ultimate lesson: no matter how much money you have, how hard you work or how much you want it, your business still may not succeed.

With these movies to take you through the rise and fall of entrepreneurship, you’ll be ready to take on the business world in no time.

Dec 4, 2018
Jeffrey Costello and Robert Tagliapietra of JCRT
Jeffrey Costello and Robert Tagliapietra of JCRT

When New York State went into quarantine in mid-March, Jeffrey Costello and Robert Tagliapietra had just moved JCRT, their direct-to-consumer shirt company, to a new office on Pier 59 in New York City. Founded in 2016, JCRT celebrates all things plaid and camouflage, with colorful patterns named after David Bowie and Kate Bush albums and movies such as the Lord of the Rings trilogy.

Stuck in a rentalhome in rural New Jersey,the married Costello andTagliapietragot to work. Heartsick that the city that had been their base and home for years was the epicenter of the Covid-19 outbreak, they wanted to do something to help friends on the frontlines.Costello began sewing masks from whatever sample fabrics he had on hand.Tagliapietra boxed them “by the hundreds” and the couplesentthem to wherever they heard PPE was needed.

“Everything was sort of unknown at that point,” Tagliapietra says. “We were very happy to be able to even do that.”

After sewing about 600 masks (“My hands were tired!” Costello jokes), they were able to reopentheir factory in the Dominican Republic, which been closed due to government quarantine and curfew rules, and began producing masks for sale and donation, giving more than 12,000 to first responders. They’re donating a portion of their retail sales to the New York City Covid-19 Emergency Relief Fund, benefiting health care workers, supporting small businesses, and vulnerable workers and families. Without any marketing other than their social feeds, Tagliapietra and Costello estimate they’ve sold 45,000 masks through JCRT and raised more than $65,000.

Now they’re selling masks and collared shirts made from a black, red, and green plaid, with proceeds going to Movement for Black Lives. Over the Father’s Day weekend, which also included the commemoration of Juneteenth, they donated 100 percentof the sales of those goods to the organization.

JCRT is a second act for Costello and Tagliapietra, who previously founded a women’s wear business called Costello Tagliapietra in 2005. Their runway shows were written up in glossy fashion magazines and the founders got a lot of press for their shared plaid-on-plaid aesthetic and impressive beards, which led to theirbeing dubbed “the lumberjacks of fashion.”

Keeping their operation small also allows the foundersto decide where and how to focus their energies, including supporting the causes they careabout. They’re nowat work on another fundraiser, this one for Pride month,with proceeds going to the Ali Forney Center, a New York City-based program for LGBTQ homeless youth.With their factory up and running, JCRT also continues to release new designs, sellingdressshirts, pants, jackets, bags, and accessoriesthrough their website.

Jun 23, 2020

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