Traci Lipple is one of those lucky girls who not only landed a gift-giving boyfriend, but was smart enough to marry him and turn it into a business.

“My boyfriend was super thoughtful, always doing really nice things for me,” she says, ticking off the list of gifts that were delivered regularly to her at work and home. “He became branded around my office for his thoughtfulness.”

After the honeymoon, Lipple decided to spread the love by helping others to engage in more regular gift-giving. With her husband Joe as advisor, they created a personal shopping service, calling it Thoughtfulhusband.com.

They took their idea to Startup Weekend in Pittsburgh last March and won outright. The win gave them seed-funding and incubator space at Thinktiv, where they began by conducting market research in support of their plan.

What they learned was that thoughtfulness—defined as finding the time to pick the right gift and delivering it in a timely fashion—wasn’t a male problem at all; everyone is challenged in their busy lives to make time for thoughtfulness, Lipple says.

With that in mind, they rebranded and launched Lily&Strum in private beta this year. The name was invented from the lilies that Joe still sends and a favorite guitarist, Joe Strummer of The Clash. The mission, says Lipple, is simple: to make everyone a better gift-giver.

Lily&Strum is a subscription-based service that assists the gift-challenged with a management plan, reminding them when important dates or opportunities arise. Web-based and mobile optimized, the platform surveys users to determine what gifts an individual would like, whether a whimsical notion, serious present or something in between.

The startup also works with retailers from small boutiques to big chains like Nordstrom to generate a customized list of suggestions for each person on the gift list. Users select the gift  based on those suggestions and purchase and send the gifts themselves.

The team of four plans to launch a public beta soon.

“Nobody out there is aligning with the user,” says Lipple. “By providing organization, inspiration and validation, we guarantee you never miss a moment and always get it right.”

Deb Smit

Deb is an award-winning journalist who loves ancient places and cool technologies. A former daily newspaper reporter and Time-Life Books editor, she writes mostly about Pittsburgh. Her stories have appeared...