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Winemaker contest offers $75,000 to spend on your side hustle


If you’re working up the nerve to start a new side hustle or passion project, there’s a wine company that might be able to provide that needed bit of extra courage. 

But rather than a stiff drink, the Prisoner Wine Company is offering $75,000 in cash to help one lucky person pursue their passion, whether that means finally launching your idea for a side hustle, embarking on a new career, or finding the time to tackle a creative pursuit. 

This week, the Napa Valley winemaker announced a new contest it’s calling “The Great Unshackling.” The company says the giveaway is inspired by the millions of Americans who have quit their jobs since the start of the pandemic in what’s been dubbed the Great Resignation

It’s worth noting that not everyone feels good about the changes they’ve made in their work lives. A recent survey from job-seeker platform Joblist found that more than a quarter of those who recently quit their job now regret that decision.

‘An extra push to pursue a passion’

Prisoner Wine is inviting anyone in need of “an extra push to pursue a passion” to enter its contest by posting a video to Instagram in which you describe how you would use the $75,000 to take on an exciting new phase of your life and career. 

The contest, which takes its name from the Constellation Brands-owned company’s Unshackled portfolio of wines, is looking for entrants who are “ready to break free from the day-to-day grind to pursue their dreams,” the company said in a press release. 

“Want to design your own capsule collection? Have at it. Want to create a speakeasy Instagram only bakery out of your kitchen? Be our guest,” the company added.

The winner does not actually have to quit their day job in order to claim the prize. The company says the contest is simply meant to give someone more freedom to pursue a side hustle or passion project.

“We want this [$75,000] to give someone the same freedom we had when we launched Unshackled — to follow their passions and chart their own course,” Bukola Ekundayo, Prisoner Wine’s general manager, said in a statement.

A panel of judges will comb through the Instagram video submissions for the contest. You have until September 7 to post your pitch. Entrants must be U.S. residents and at least 21 years old in order to be considered.

You’ll also have to tag and follow @unshackledwines on Instagram and your video entry must include the hashtags “#TheGreatUnshacklingContest, #21.” Read the official rules here.

The company says the judges will narrow the submissions down to five finalists based on the “originality, feasibility, and sincerity” of their pitches. After finalists are selected, the winner will be chosen through a public online vote.

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