Chamber Insider Blog

32nd Annual Loudoun Small Business Awards Finalist Spotlight: Dare Gift Boxes

Thank you to Rebekah and Colleen for sharing Dare Gift Boxes’ story with us. Congratulations on being named a finalist in our Co-Working & Home-Based Business category for the 32nd Annual Loudoun Small Business Awards!

Tell us the story of your business and how it has evolved. 

Dare Gift Boxes actually began as a very different business. I (Rebekah) originally founded a women’s clothing company in 216 and spent years designing our own line and working with domestic and international manufacturers. When COVID dramatically changed the apparel industry, I leaned more into offering gift boxes as another way to serve our customers.
What started as a pivot continued to grow, and eventually my business partner, Colleen, and I decided to leave clothing behind entirely. We renamed the company Dare Gift Boxes and built a new direction around gifting, with an increasing focus on helping businesses care well for their clients, employees, and communities! Today, we ship gifts nationwide and work with everyone from individual professionals and small businesses to large national brands.

Rebekah and Colleen (co-owners)

What are you most proud of?

I’m most proud that we have grown without losing the heart behind what we do. As the company navigated difficult seasons and exciting growth, our guiding light has remained seeking quality in our products, our customer service, and our care of our team. I’m also incredibly proud of our team. We have built a workplace where people genuinely care about each other, find ways to be flexible for each other’s priorities outside of work (caregiving, motherhood, volunteering) and bringing different strengths to the company.

What sets your business apart?

We never want gifting to feel transactional. We try to put ourselves in the shoes of the person giving the gift and ask, “Would this make someone I care about feel genuinely special?” We have worked hard to combine the infrastructure and convenience businesses need with the personal touches that make a gift feel thoughtful.

That means that as we scale, very human things like a handwritten note are still done by a person with a pen, not a machine. We also work with companies at very different scales. One day we may be creating hundreds of custom gifts for a national brand on a tight deadline, and another day we may be helping a local real estate agent thank one client. We want meaningful gifting to feel accessible whether someone is managing a large corporate program or simply wants to show one person that they matter.

How do you give back to Loudoun?

Loudoun is the community that has supported our growth, so being involved here is very important to us.

We donate weekly to local organizations, love supporting small and independently-owned businesses, attend as many local events as we can. We love getting to know other business owners, referring business, and supporting the people building companies throughout the county. As we grow, we hope our contribution to Loudoun grows too, through jobs, charitable giving, business relationships, and simply being a company that shows up for its community.

What would it mean to you and your business to win a Loudoun Small Business Award?

Loudoun is home to all 5 of us on our team, so this would be an incredible honor by our community.

It would be an incredible recognition of our entire team and of everything that has gone into building Dare through pivots, challenges, long days, and a lot of faith. It’s very humbling to be singled out for any recognition! More than anything, it would be an honor to represent the Loudoun small-business community that has given so much to us.

When you’re not working, where can we find you or what is another passion you have?

Rebekah and Colleen (co-owners) became best friends through traveling the world, and we wish we had more time for that!  Closer to home, we love playing pickleball and volleyball, spending a lot of time with our mutual friend group, caffeinating, and exploring outside. Colleen also takes frequent volunteer trips to Central and South America with an organization that partners with local churches to provide free medical clinics and outreach. She took 7 trips already this year!