Hannah & Ariel Redmond

Founders of Happy Box

Meet two sisters — Hannah and Ariel Redmond — on a mission to send gifts that are affordable, convenient, and most importantly, don’t suck. In college, Ariel got dumped, & Hannah wanted to send her something to make her feel better. A few trips to some generic stores and a 20-minute wait at the post office left her with an idea…to shake up the gift-giving space by creating a build-your-own care package platform that is personal & convenient: with handwritten notes and free shipping. She partnered up with Ariel, and together they started Happy Box!

They are all about women supporting women and are proud to feature product options that are from female-founded companies. Hannah and Ariel believe in making it easy (and cute!) to be thoughtful, supportive friends, sisters, cousins, coworkers, and humans. Couldn’t we all use a little more of that?

Right now, Happy Box is operated as their side hustle. By day, Hannah is a Marketing Strategist and Ariel is a Creative Director. They use their combined years of experience to truly shake up the gifting space and provide an innovative and easy service to all who want to give meaningful gifts.

Where did the idea for Happy Box come from?

While my sister and I were in college, she was studying at the University of Maryland and I was at Parsons School of Design in NYC, and I got dumped. Not like, 3-month heartache dumped, we had spent years together. If that wasn’t bad enough, it was 3 days before Valentine’s Day.

So Hannah, being the great big sister that she is, set out to send me a care package, but couldn’t find anything personal, or anything for our age group. Her options were expensive flowers (that die) or dated gift baskets (think: Harry and David). So she decided to build a care package with my breakup in mind. Fast forward 7 stores and one VERY long (and frustrating) wait at the post office, she sent her very first “Happy Box”- a break up care package, which included a voo-doo doll and chocolate. I absolutely LOVED it! She picked everything out perfectly and wrote me a note that I couldn’t help but chuckle at. It was exactly what the doctor ordered.

Years later, after graduating and after Hannah got her MBA, she approached me with a thought — what if we made building custom, snarky, care packages for modern women at scale – while making it super easy offering free shipping and sweet hand-written notes? I instantly loved the idea, which we named Happy Box!

The best part? We’re just two sisters who fell in love with the gifting space, and who love working with each other and learning together every day.

What does your typical day look like and how do you make it productive?

By day, we work in marketing and advertising. Hannah is a content and social marketing director and I am a creative director. By night, we’re entrepreneurs – the co-founders of Happy Box. Weeknights and Sundays are devoted to Happy Box. We’re lucky to have our mom and an amazing team of part-timers who run our warehouse, manage our clients, and who make sure everything continues to run smoothly day in and day out, managing our warehouse and shipments and customer service.

How do you bring ideas to life?

Teamwork. We always share and bounce our ideas off of each other.

What’s one trend that excites you?

We absolutely love that tech is allowing for more and more ways to create custom solutions for consumers in an efficient manner; whether that be through AI, or more simply, through direct-to-consumer businesses like ours. It’s consumer empowerment at scale.

What is one habit of yours that makes you more productive as an entrepreneur?

Hannah is a master planner. She is the most organized person I know – from leveraging every to-do list app, to Google calendar to the shared folder structure she basically mandates. Without that level of organization, being a side-hustle entrepreneur would be near impossible!

What advice would you give your younger self?

I’d tell myself to stop doubting yourself; you are smart and deliberate and you don’t give yourself enough credit. I’d also tell myself to enter more business plan competitions and pitch contests.

Tell us something that’s true that almost nobody agrees with you on.

Hannah doesn’t like peanut butter very much and nearly always gets arguments about it when it comes up – people really are passionate about peanut butter!

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Long and short term goal setting. When you achieve your goals, keep setting new ones. We continuously set our goals higher (and create “reach” goals) – and we never get comfortable. We believe in constant growth and innovation in order to chase our dreams.

What is one strategy that has helped you grow your business?

It’s funny, we each had something that meant a lot to us to keep in the business: always have a free shipping option, and always offer a handwritten note. We did this because no where else you can find BOTH of these things as a standard part of the offering. It differentiated us and delighted our customers; it feels like an extra perk.

What is one failure you had as an entrepreneur, and how did you overcome it?

One summer we outsourced our fulfillment of boxes – and within two months realized it was a huge mistake. We realized we did not want to be far from our products, we wanted to own quality control and we wanted to be closer to what the customer was experiencing so we could always optimize our offering. Bringing fulfillment back in house allowed us to learn and grow exponentially as a result.

What is one business idea that you’re willing to give away to our readers?

Create a different type of e-commerce fulfillment center! When we shopped around there was no good option that was affordable but offered custom solutions like ours and had strong quality assurance. We always joke that that will be our next business idea.

What is the best $100 you recently spent? What and why?

A task rabbit to help us move stuff to our storage space – for that matter, ANY money we spend on our team is the best money we’ve recently spent! We’ve learned it is super important to hire help and delegate – it’s the only way to focus on growth and scale.

What is one piece of software or a web service that helps you be productive?

We love using Pirateship to mail out our boxes. It uses a one-step form and allows us to import orders and receive tracking information quite easily. The batch workflow makes it a pretty seamless process to drop ship our boxes and ensure they get in the hands of our recipients quickly and safely.

What is the one book that you recommend our community should read and why?

I have to recommend two: Tim Ferris’ “Four Hour Workweek” to help learn lessons of efficiency; as well as “Simple Numbers, Straight Talk, Big Profits!: 4 Keys to Unlock Your Business Potential” by Greg Crabtree and Beverly Blair Harzog that help guide you on the road to profitability

What is your favorite quote?

Hannah: Fail often so you can succeed sooner. Ariel: “Lo que sera, sera” [what will be, will be]

Key Learnings:

  • Be positive, friendly and helpful to others and build relationships along your journey – you never know who you might need a favor from.
  • Hire people who know more than you. Outsource and delegate to people who are experts in the things you’re not an expert at, and focus on GROWTH.
  • Find a mentor who you aspire to be like who you can ask for critical feedback from.
  • Network! The entrepreneurship community is incredibly resourceful and helpful.
  • Stay curious. Always read entrepreneur interviews, read business books to learn, go to industry panels, go to alumni continuing education opportunities. Be hungry to innovate and always be better.