For small and large businesses alike, the holidays can be an extremely lucrative season. Consumer spending is expected to be higher this year compared to last year, with an average spend of $1,778, up 8% from 2023, according to a report from Deloitte.
Despite the shopping frenzy, many brands grapple with the challenge of standing out in a crowded market — which often requires a bit of creativity. One method that’s gained traction in recent years? Advent calendars.
The original advent calendar goes back to 19th-century Germany, where Protestants marked the days left before Christmas in creative ways — lighting candles, placing straws in a Nativity crib, etc. — with the first known handmade wooden advent calendar appearing in 1851. The earliest calendars with chocolate have been traced to the 1950s.
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Nowadays, those chocolate-filled calendars you might remember from your childhood have made a big comeback. You’ll still see traditional ones on the shelves, alongside various inventive renditions toting makeup, skincare, jewelry, candles, coffee, socks and so much more.
“As adults, we’re like, ‘Cool, where’s my adult advent calendar?'”
This year, Portland-based ready-made cocktail brand Straightaway Cocktails is jumping on the advent calendar trend for the first time. Entrepreneur sat down with co-founder and CEO Cy Cain to learn more about the company and its take on the holiday tradition.
A long-time cocktail enthusiast with extensive experience helping founder-led brands enter the market, Cain joined forces with fellow cocktail aficionado Casey Richwine to launch Straightaway Cocktails in 2018.
Image Credit: Andrea Morris. Cy Cain, left; Casey Richwine, right.
The goal was to create ready-to-serve cocktails made with the highest-quality ingredients. Straightaway roasts its own hazelnuts and picks its own fir needles to craft its house-made bitters, and it even produced a double-gold-winning amaro to feature in its beverages.
Straightaway’s distillery and tasting room are in Portland’s “Distillery Row.” The company also partners with Alaska Airlines, which serves its margarita and old fashioned offerings.
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Straightaway is committed to quality cocktails, and it’s also on a mission to give back. As a certified B Corporation, Straightaway gives 1% of its profits to environmental partners via 1% for the Planet and 1% to organizations that serve marginalized communities.
Image Credit: Andrea Morris
Although Straightaway has released holiday gift sets since its first year in business, this season marks its first foray into advent calendars, which deliver a “surprise and delight” factor for customers, Cain says.
“Advent calendars just have a spot culturally in all of our minds, [going back to when we were] children,” Cain explains. “As adults, we’re like, ‘Cool, where’s my adult advent calendar?’ This is a fun little thing for people to open.”
“Make sure your timing is right for your brand [and] that you can [pull off] the business.”
Straightaway began preparing for its advent calendar, “12 Nights of Cocktails,” which features a dozen 3.5-ounce drinks and retails for $59.95 on its website about a year before the release. It had early conversations with Costco, where members can also purchase the calendar. The retailer is adept at finding maker brands that deliver on authenticity and quality, Cain says.
Image Credit: Courtesy of Straightaway Cocktails
Even with the head start, readying the calendar was “really a sprint,” according to Cain — but being a vertical maker with its own process helped Straightaway reach the finish line in time.
The process began with some crucial information-gathering: Cain and Straightaway’s director of brand and marketing, Caitlyn Pura, traveled to Washington state to check out other models on the market. The duo came away with a few ideas and sketched them out on the drive back to Portland.
Ultimately, Cain and Pura decided to honor Straightaway’s origin story, which stems from a 1930s cocktail book by Charles H. Baker. “He left after prohibition and traveled the world and cataloged his favorite cocktail recipes,” Cain explains. “Casey’s wife bought that 12 years ago; we found the recipe for lintik in it.”
Straightaway tied that concept in with the idea of classic holiday novels, so the calendar “opens and reads a little bit like a chapter book.” Instead of the 12 nights of Christmas, it’s the 12 nights of cocktails. Cain says the calendar’s been well-received, and the company plans to release another one next year.
For other businesses hoping to put out advent calendars of their own, Cain recommends having a great supply chain team in place and not taking on more than you can handle. “Make sure your timing is right for your brand [and] that you can [pull off] the business that you’re asking for,” he says. “You have to deliver the goods.”
