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    Home»Startups»This couple’s $1.5M holiday side hustle uses ChatGPT to grow
    Startups

    This couple’s $1.5M holiday side hustle uses ChatGPT to grow

    PineapplesUpdateBy PineapplesUpdateDecember 15, 2025No Comments8 Mins Read
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    This couple’s .5M holiday side hustle uses ChatGPT to grow
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    key takeaways

    • The married co-founders teamed up with an engineer to launch White Elephant Online in November 2020.
    • Here’s how they turned a flexible, seasonal side hustle into a “semi-full-time business” with an eye on their next growth chapter.

    At the height of the pandemic in August 2020, David Mancarella was working remotely as director of product management at a property-tech firm based in New York City when he and his coworkers wondered what might happen to their holiday party tradition. The office held white elephant, gamified and often humorous gift exchanges each year.

    ” I was like, Well, there must be a way to play White Elephant virtuallyMancarella tells entrepreneur,I’m sure it exists. But of course, after the call, I started googling And realized it didn’t exist. Because it didn’t really need to exist up to that point. People will only play individually. “It wasn’t really something that people were trying to do virtually until the pandemic hit.”

    Mancarella’s wife, Lilia Kishbaugh, remembers her husband announcing his new business idea at their home in Bethlehem, Pennsylvania, where they moved a few weeks before the pandemic hit. She notes that this was not the first time that he had come up with an idea for a business – rather it was the first time that he had come up with an idea that did not already exist.

    RELATED: ‘I Just Hustle’: She Made Over $300,000 Wrapping Gifts Last Year — And It All Started With a Side Hustle

    After a few days, Mancarella reached out to Andrzej Brinzka, an engineer he had worked with, to run the project. Bryanzka was on board, and the side hustle came together fairly quickly after that. Mancarella and Kishbaugh wanted to launch the business before Thanksgiving to make the most of the holiday season.

    This couple’s .5M holiday side hustle uses ChatGPT to grow

    Image Credit: Courtesy of White Elephant Online. Lelia Kishbaugh and David Mancarella.

    This was the official start of his new business: white elephant online,

    Kishbaugh, who worked in finance before starting her own real estate development company and co-founding a women’s apparel brand bluetaAdmits that she’s attracted to business names that are “a little more effective,” but in this case, her husband’s preference for a “straightforward, optimized” name paid off.

    “There weren’t really any competitors, so if someone was looking to play white elephant virtually, we were there,” Kishbaugh says.

    White Elephant Online’s website went live in early November 2020, and the co-founders were excited when they collected nearly 400 email addresses, but that was just the beginning. “It kind of exploded,” says Mancarella. By the end of the year, her side had more than 165,000 users.

    RELATED: This is the Highest Paying Winter Side Hustle – Plus 7 Others That Can Increase Your Income

    Initially, White Elephant Online was free for individual games with up to 25 people and $99 for corporate use. white elephant online pricing strategy A tiered system has since evolved for businesses and organizations ranging from $69 to $299, depending on how many players participate. The service is free for personal use for up to 10 players.

    Naturally, getting the product up and running so quickly came with some challenges – like a glitch in automatically filling in customers’ first names in both the first and last name fields, which resulted in hundreds of customer service tickets – so the co-founders had to be proactive.

    They created robust support content and used ZenDesk from the start to keep the side hustle running smoothly with their small team, which is only three of them to date.

    Mancarella left his job in product management in the spring following the launch of White Elephant Online; Now, the co-founders consider this venture their “semi-full-time business.”

    Since its inception, White Elephant Online has hosted thousands of virtual gift swaps for over 350,000 users, with lifetime revenue exceeding $1.5 million.

    RELATED: Dry January, anyone? After a ‘scary’ night of drinking he started a side hustle – and grew its revenue to over $50 million with 0 outside investment.

    When the impact of the pandemic subsided and people began returning to the office, the co-founders noticed a significant decline in the number of individual games played on the platform and considered how to scale the business.

    That’s why he launched a Secret Santa generator a few years ago, hoping it would be “like a lead funnel.”

    Kishbaugh says it didn’t work out that way, because the couple didn’t want to promote the free tool too widely to their business audience and didn’t want to risk destroying White Elephant Online. The Secret Santa location is also extremely saturated.

    RELATED: How to Organize a Last-Minute Holiday Party With Your Calendar

    The gift generator is a way for us to touch those who just play the white elephant role, whether in person or virtually.

    Then, recently, the couple landed on another concept: a gift idea generator that complements White Elephant’s offering.

    “The one thing that’s limiting our business is obviously (we’re) virtual,” Mancarella says. “You don’t really need any equipment to play in person. You just need a hat or bucket to throw some numbers in, and you’re good to go. The gift generator is a way for us to touch people who just play White Elephant, whether it’s in person or virtually.”

    The gift generator tool was launched last month and is monetized through Affiliate Links,

    Additionally, as White Elephant Online celebrated its fifth anniversary last November, the business has compiled a significant amount of data on some of the most popular White Elephant gifts.

    White Elephant Online’s platform doesn’t use AI, but in the end, the co-founders used ChatGPT to sift through some of that gift data and gain insights that in the past would have taken a lot of time to understand in depth.

    Although the white elephant exchange has a reputation for silly gifts – Snoop Dogg’s From Crook to Cook: Platinum Recipes from Tha Boss Dogg’s Kitchen The platform has been in the top 10 every year — the co-founders say, adding that tech gadgets like the Apple Air Tag and Bluetooth speakers are also steadily gaining popularity.

    RELATED: I Used a Recently Launched AI Tool to Find a Christmas Gift for My Fiance. It didn’t go as expected – but it was definitely eye-opening.

    It’s not like a lot of companies where you’re iterating every week or two.

    Naturally, White Elephant Online is a highly seasonal businessMancarella and Kishbagh work on it from September to December, which comes with both benefits and challenges.

    “It’s great because it gives us a lot of flexibility,” Kishbaugh explains. “Before having a baby, we traveled in our camper van and visited a lot of national parks. Now we get to spend a lot of time with our daughter, which is amazing.”

    however, Season It also means businesses have a very short window to test and implement the tools they need to capitalize on the holiday rush.

    “It’s not like a lot of companies where you’re recapping every week or two and adjusting the numbers compared to the previous month,” Mancarella says. “It’s like, ‘Okay. It’s a brand new season. Let’s see what we can do.'”

    We love being an entrepreneur…you learn a lot.

    White Elephant Online has maintained a strong year-over-year revenue streak, but the co-founders are looking forward to the next chapter of growth and expansion for the business.

    The co-founders found success by implementing their business idea early on, and they caution aspiring entrepreneurs Against staying in the planning phase too long: It’s important to get a product out into the world and see how people react.

    This goes along with knowing where to focus your precious energy.

    “We love being entrepreneurs and doing things ourselves,” says Kishbaugh. “You learn a lot. It’s fascinating. But to be really successful you have to know where to spend your time.”

    Want to read more stories like this? agree money makers, Our free newsletter is full of creative side hustle ideas and successful strategies. Sign up here.

    key takeaways

    • The married co-founders teamed up with an engineer to launch White Elephant Online in November 2020.
    • Here’s how they turned a flexible, seasonal side hustle into a “semi-full-time business” with an eye on their next growth chapter.

    At the height of the pandemic in August 2020, David Mancarella was working remotely as director of product management at a property-tech firm based in New York City when he and his coworkers wondered what might happen to their holiday party tradition. The office held white elephant, gamified and often humorous gift exchanges each year.

    ” I was like, Well, there must be a way to play White Elephant virtuallyMancarella tells entrepreneur,I’m sure it exists. But of course, after the call, I started googling And realized it didn’t exist. Because it didn’t really need to exist up to that point. People will only play individually. “It wasn’t really something that people were trying to do virtually until the pandemic hit.”

    The remainder of this article is locked.

    Connect with Entrepreneur, For access today.

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