Supplier Spotlight: Happy Box

Published on March 20, 2025 | Webster Bank

As a regional bank, we understand the importance of economic development and the role of local small businesses within our footprint.

Our Inclusive Vendor Engagement Program reflects our commitment to community investment. By providing local small business with opportunities to compete for contracts in a fair and equitable environment, we help create positive economic impact in the neighborhoods where we live and work.

To spotlight the real-world value of our program, we recently spoke to Ariel Redmond, who co-created and owns Happy Box LLC with her sister, Hannah Redmond.

What was the defining moment for creating the Happy Box concept?

We say we went from breakup to business because that’s truly how we started. My significant other and I broke up in college and my sister, Hannah, and I were states apart. She wanted to send something to cheer me up, but she wanted to send something personal. She didn’t want flowers or chocolates; she wanted to send something that I would really love. She ended up going to seven different stores and had a really bad experience with USPS. I loved what Hannah curated and sent; it was so meaningful, with a handwritten note and all my favorite products. I loved that package.

Fast-forward, I became a creative director, and Hannah was a marketing and branding strategist, but she’d always had an entrepreneurial spirit and thought about that package she’d sent. Customizing a care package with fun gifts didn’t really exist. There were vendors who were kind of stuffy, but there wasn’t anything out there for us as young women.

How did you move from that defining moment to actually launching Happy Box?

We became an LLC in 2015, testing our product ideas on Etsy, and very quickly sold out of everything. Of course we didn’t have any vendor relationships, we were buying retail and just seeing what would sell and at what price point. We didn’t know anything about logistics. We just knew we had a pretty good idea, and since we were the target audience (millennial women), we were confident we were building something that we loved, and our peers loved.

We knew we wanted to offer an Engagement Kit and a Breakup Kit. We evolved to our own e-commerce store and our customers said, ‘I really like your Happy Birthday Box, but I really want to add this and that to it.’ The ability to build your own care package was still not something that was out there so we decided to break the industry.

When did Happy Box become a full-time career?

Happy Box was a side hustle until 2020. We were both still working our full-time jobs and doing this at night and on weekends, which was crazy. When COVID struck, big box companies pulled back their ad spend, and they couldn’t keep up with supply for e-commerce/shipped goods when stores were closed. Since we always had the mindset of buying local and supporting our local businesses, we were able to still source and sell products online.

Companies and brands like Uber, Showtime, Facebook, Pinterest had to start finding ways to engage teams remotely as employees were almost 100-percent working from home. They started asking if we could brand products/boxes and gifts, and of course, we said yes, since our backgrounds in branding/marketing helped us really understand how to interpret brand logos, colors, and brand guidelines. This unique positioning helped pivot our business into what it is today, and really launched our corporate gifting line of business. This propelled us so much that by October 2022 it was no longer sustainable to do this on nights and weekends, so we quit our full-time jobs that month.

What do you offer that sets Happy Box apart from your competitors?

Our creative and marketing backgrounds allow us to be flexible and create partnerships that we never thought we would have. We have so many different products that can appeal to different people at different times of their lives. The biggest thing is customization. The ability to put the occasion in the customer’s hand is unparalleled.

What are some challenges you’ve faced as a Women-Owned Business?

I think everybody in business has challenges. Women and minorities definitely have unique challenges. It is so challenging, especially when you don’t have a background in it like me. My sister has her MBA and she’s super smart. She knows what she’s doing. But I have a creative background, and successfully operating a business is challenging for everyone.

Women and minorities have been underestimated for years. Do you know how many times I’ve heard, ‘What a cute business you have! How adorable that you run that with your sister. That is darling.’ It’s the most frustrating reaction when I tell someone I run a business with my sister. And then they ask, ’What does your husband do?’

The underestimation that women and minorities face is appalling. You have to prove yourself a lot more. But we use that to our advantage and have this ‘watch me’ mentality that’s empowered us. So, even though we’ve heard demeaning comments, we’ve been able to do pretty incredible things because of that chip on our shoulders. We made the Inc. 5000 list in 2022 and that was a huge accomplishment for us.

It sounds like the differences between you and Hannah are a good illustration of how having diverse people and personalities affects business in positive ways. 

I’m an executor. If I see something I want to do I’m going to do it. She is a planner. She is a strategist. She asks if something makes sense at this exact time, or should we wait and plan?

That tension is what has led to our success. It’s the push and pull that every business should have. If our job were to build a plane, I would be in the air, but without an engine and no seatbelt. Hannah would be on the tarmac, never leaving, but would have everything ready. We couldn’t fly a plane on our own, but together we can fly really well.

How is advancing technology changing the way you do business?

Systems are the future. We love the idea of AI and when you use it in an appropriate way and have the right people activating AI it makes sense, but I don’t think we’ll ever want to replace what our people are doing; I just think it could be our secret weapon.

There’s definitely a marriage between technology and people, and I don’t think we’ll see a world without either. Our job as business owners is identifying where something could be replaced by AI so that someone can do something else. That’s the sweet spot of AI.

Everyone today is pretty much available 24/7. How are you balancing running Happy Box with your personal life and keeping things sane? 

When running a business with your sister there is no separation between your personal life and your professional life.

The biggest shift in our work/life balance has been motherhood. It is impossible to run a business and watch your kids. Hannah and I have adjusted our business to fit our lives. It looks different for us, and it looks different for other people. But we both have daughters around the same age, so we stop at 5 PM. And, when they go to bed, we are back on. It’s about making it make sense for you.

We love what we do so we tend to talk about it all the time; we’re together for family outings and family vacations so that enabled us to advance the business more quickly than other people because we’re collaborating all the time.

How does working with other diverse businesses help your business?

We recently did a conference for the Association of African American Financial Advisors, known as AAAA or Quad-A, and they wanted something unique. They didn’t want a traditional swag kit, so we worked with a Black artist to create a beautiful T-shirt that was a celebration of Black culture. We were so proud of it; our partner was so proud of it and our clients were over the moon. I want to push our clients to be more intentional with what they’re doing, not necessarily just checking boxes. We can make a really big impact and support amazing communities and do something that celebrates culture.

It’s always our mission to source from diverse vendors. We are one ourselves and we’ve been underestimated, so why wouldn’t we do that? Sharing business is core to who we are as a company. As consumers on an individual basis, we can make a difference by shopping small. So, from a corporate standpoint, the amount of business you can do is amplified. The amount of good you can spread is amplified. We love that we can, and our clients are requesting diverse businesses so we’re in this really great spot where we believe in it and our clients believe in it too.