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Home » This Couple’s $1.5M Holiday Side Hustle Uses ChatGPT to Grow
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This Couple’s $1.5M Holiday Side Hustle Uses ChatGPT to Grow

News RoomBy News RoomDecember 15, 20253 Views0
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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 grew the flexible, seasonal side hustle into a “quasi full-time business” eyeing its next growth chapter.

In the throes of the pandemic in August 2020, David Mancarella was working remotely as a director of product management at a property-tech firm based in New York City when he and his co-workers wondered what might happen to their holiday party tradition. The office played white elephant, the gamified and often humorous gift swap, every year.

“ I was like, Well, there must be a way to play white elephant virtually,” Mancarella tells Entrepreneur. “I’m sure that exists. But of course, after the call, I started Googling and realized it did not exist. Because it didn’t really need to exist up to that point. People would just play in person. It wasn’t really something people were trying to do virtually until the pandemic hit.”

Mancarella’s wife, Leliah Kishbaugh, recalls her husband announcing his new business idea at their home in Bethlehem, Pennsylvania, where they’d moved just weeks before the pandemic struck. She notes that it wasn’t the first time he’d come up with an idea for a business — but it was the first time he’d come up with one that didn’t exist already.

Related: ‘I Just Hustled’: She Earned More Than $300,000 Wrapping Gifts Last Year — and It All Started With a Side Hustle

A couple of days later, Mancarella reached out to Andrzej Brynczka, an engineer he’d worked with, to run the project by him. Brynczka was on board, and the side hustle came together fairly quickly after that. Mancarella and Kishbaugh wanted to launch the business ahead of Thanksgiving to make the most of the holiday season.

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

That was the official start of their new business: White Elephant Online.

Kishbaugh, who worked in finance before starting her own real estate development company and co-founding the womenswear brand NILETA, admits that she gravitates toward business names that “are a little bit punchier,” but in this case, her husband’s preference for a “straightforward, optimized” name paid off.

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

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

Related: This Is the Highest-Earning Winter Side Hustle — Plus 7 Others That Can Boost Your Income

Initially, White Elephant Online was free for personal games with up to 25 people and $99 for corporate use. White Elephant Online’s pricing strategy has evolved since then, with a tiered system for businesses and organizations ranging from $69 to $299, depending on how many players participate. The service remains 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 auto-filling 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 materials and used Zendesk early on to keep the side hustle operating smoothly with their small team, which remains just the three of them to this day.

Mancarella quit his job in product management the spring following White Elephant Online’s launch; now, the co-founders consider the venture their “quasi full-time business.”

Since its founding, White Elephant Online has hosted tens of thousands of virtual gift swaps for over 350,000 users, with more than $1.5 million in lifetime revenue.

Related: Dry January, Anyone? He Started a Side Hustle After a ‘Scary’ Night of Drinking — and It’s Exceeded $50 Million Revenue With 0 Outside Investment.

When the pandemic’s impact waned, and people began to return to the office, the co-founders saw a significant drop in the number of personal games played on the platform and considered how to keep growing the business.

That’s why they launched a secret Santa generator a couple of years back, hoping it would be “sort of like a lead funnel.”

It didn’t quite work out that way, Kishbaugh says, as the couple didn’t want to promote the free tool too widely to its business audience and risk cannibalizing White Elephant Online. The secret Santa space is also highly saturated.

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

The gift generator is a way for us to touch the people who just play white elephant, regardless of whether it’s in person or virtually.

Then, more recently, the couple landed on another concept: a gift idea generator that complements the white elephant offering.

“One thing that’s limiting our business is that obviously [we’re] virtual,” Mancarella says. “You don’t really need a tool to play in person. You need a hat or a bucket to throw some numbers in, and you’re good to go. The gift generator is a way for us to touch the people who just play white elephant, regardless of whether it’s in person or virtually.”

The gift generator tool launched last month and is monetized through affiliate links.

What’s more, as White Elephant Online celebrated its fifth anniversary this past 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 on the back end, the co-founders have used ChatGPT to sift through some of that gift data and gain insights that would have been too time-consuming to drill down on in the past.

Although white elephant exchanges have a reputation for silly gifts — Snoop Dogg’s From Crook to Cook: Platinum Recipes from Tha Boss Dogg’s Kitchen has been in the platform’s top 10 every year — the co-founders say that tech gadgets like Apple Air Tags and Bluetooth speakers enjoy consistent popularity too.

Related: I Used a Just-Launched AI Tool to Find a Christmas Present for My Fiancé. It Didn’t Go As Expected — But It Was Definitely an Eye Opener.

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

Naturally, White Elephant Online is a highly seasonal business; Mancarella and Kishbaugh work on it from September through December, which comes with both benefits and challenges.

“It  is great because it gives us a lot of flexibility,” Kishbaugh explains. “Before we had a child, we would travel in our camper van and [visited] a lot of national parks. Now we just get to spend a lot of time with our daughter, which is amazing.”

However, the seasonality also means the business has a very small window in which to test and implement the tools it needs to capitalize on the holiday rush.

“It’s not like a lot of companies where you’re iterating every week or two and kind of adjusting the numbers compared to last month,” Mancarella says. “It’s like, ‘All right. It’s a whole new season. Let’s see what we can do.’”

We love being entrepreneurs…you learn so much.

White Elephant Online has kept up a strong revenue rhythm year over year, but the co-founders look forward to the business’s next chapter of growth and expansion.

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

That goes hand-in-hand with knowing where to focus your valuable energy.

“ We love being entrepreneurs and doing all of the things by ourselves,” Kishbaugh says. “You learn so much. It’s fascinating. But you have to know where to spend your time in order to actually be successful.”

Want to read more stories like this? Subscribe to Money Makers, our free newsletter packed with 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 grew the flexible, seasonal side hustle into a “quasi full-time business” eyeing its next growth chapter.

In the throes of the pandemic in August 2020, David Mancarella was working remotely as a director of product management at a property-tech firm based in New York City when he and his co-workers wondered what might happen to their holiday party tradition. The office played white elephant, the gamified and often humorous gift swap, every year.

“ I was like, Well, there must be a way to play white elephant virtually,” Mancarella tells Entrepreneur. “I’m sure that exists. But of course, after the call, I started Googling and realized it did not exist. Because it didn’t really need to exist up to that point. People would just play in person. It wasn’t really something people were trying to do virtually until the pandemic hit.”

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