In Conversation with Hannah Redmond & Ariel Redmond of Happy Box

Happy Box_Blog Header

Describe your business in a few words?

Happy Box is an innovative gifting platform that does consumer and corporate gifting. Our most popular option is our build-your-own care package offering where customers pick a box design, fill it with a variety of gifts (we have 100+ to choose from!), pick a card, and our team hand packs each box, hand writes the user’s gift message and ships it right to their recipient’s door. We like to say we’re at the intersection of customization and convenience.

What made you take the leap to start your own business?

We’re sisters, and had this idea based on a gift I sent to Ariel after she got dumped by her boyfriend back in college. We had both been working in branding and advertising and wanted to build something, a brand of our own,  together. Since this was an idea that in our minds filled a gap in the industry, we decided to go for it and we began creating our MVP.

What was your background prior to starting your own business?

My (Hannah) background is in innovation and digital marketing strategy – I worked both at agencies and brand-side on major DTC brands; and Ariel was a creative director at major agencies leading large creative advertising campaigns and commercial shoots. We both were fortunate to have worked on strategy and branding for some of the biggest brands in the world, from which we learned quite a bit! We are incredibly lucky that our skill sets compliment each other so well.

Did you always know you wanted to be an entrepreneur?

Yes! We’ve always discussed business ideas together (we still do) and had an itch to create something for ourselves. This won’t be our last business together.

Take us back to when you first launched your business, what was your marketing strategy to get the word out and did it go as planned?

Originally it was exclusively word of mouth and referrals – we are lucky that our product has two touchpoints: even in one sale, we’re giving two people an experience: one on the gifter side and one on the recipient side. It also doesn’t hurt that we were building instagrammable care packages as we saw most of our growth come from social media.

We always learn the most from our mistakes, share a time with us that you made a mistake or had a challenging time in business and what you learned from it?

Oh, we’ve made plenty of mistakes and faced many challenges as all startups do! Facing a moment of increased demand and growth during a pandemic, while still working full time jobs was hands down our most challenging period to date. First of all, nothing prepares you for growing a business during a pandemic; we suddenly became more relevant and we struggled with growth and expansion during a time where we had to be so careful with how we operated for the safety of our team. What we learned most from that time is that we can’t plan or make processes for every single situation (which definitely goes against my nature as a natural planner!) we must be super nimble and ready to pivot.

What is the accomplishment you are the most proud of to date?

We’re most proud of getting this side hustle to the point where we could quit our full time jobs. It’s an amazing feeling to see something built from a few dollars. We had no financial help from friends, family, or investors – it’s been a bootstrapped business all the way. We’re proud and grateful every single day that we’ve been able to grow something, create jobs, and send so many people happiness all over the world.

When hiring for your team, what is your go-to interview question? Please share any hiring tips you can share from your experience?

I’d say my favorite interview question is “tell me a challenge/problem you faced and walk me through the process of how you solved it.” Then, if the problem they bring up is not super relevant, I’ll give them an example problem they would face in the prospective role and ask them to map out what they would do to solve it. What info would they collect? What questions would they ask? At what point would they escalate to their boss? This shows me a few things: how they react to a challenge, how independent they are, how solutions-oriented they are. There is no specific wrong answer, but having someone walk through step by step pieces of problem solving has always served me well when hiring.

How has your business or industry been impacted by the COVID-19 pandemic?

E-commerce retail has increased across mostly every industry, so we were lucky to be on the e-comm side of things when the pandemic hit. Since we are a handmade business and run our own warehouse and fulfillment center, we did have the challenge to figure out how to safely operate and take the proper precautions for our staff to continue working. We shut down for a bit and we did have to move and expand our space to accommodate social distancing, but the added expense for our teams’ safety is of course worth it.

What is the biggest lesson you have learned in 2020?

The biggest lesson is BE NIMBLE, especially after a year like 2020. But another big lesson learned in this time is to hire people who have the right, relevant experience to guide you on areas of the business that need work. That sounds super obvious, but when you’re a startup you kind of grab onto anyone who will roll up their sleeves and help you out – friends, family, etc – but it’s really important to hire people who have the right skills and experience you need to get the job done.

What do you know now that you wish you knew when you were first starting your business?

I wish I knew that it’s okay not to know it all. Coming from a business school background and having worked on Fortune 50 brands, I held us to this expectation that we would be as prepared and buttoned up as they were. It’s impossible – especially when you’re innovating something, inventing something, or when you’re in a pandemic! You have to be scrappy, roll up your sleeves, brainstorm and figure it out, and that is totally okay.

How have you managed to stay grounded this year?

Hah – not sure we always felt grounded this year! This year was like being on a rollercoaster, truly. I think the two things we do well are we vocalize how GRATEFUL we are, for this experience, for each other, for our amazing team, and for what we’re building. We also know when we’re hitting burnout and we “call it.” We’re sisters so at times tempers get high, but we have learned how to work together. Once we start getting into an argument, one of us says “ok – time to ‘call it -’ we’re not being productive and need to reset our mindset – let’s work on something else or call it a night,” and the other always respects it – it’s a deal we’ve sort of made with each other we’ll do, and it works out.

Do you believe in work/life balance? What are some of your best tips?

Of course! It’s really hard to find balance being a founder and growing a company, but it’s incredibly important. We’re still learning how to do this. It’s really hard especially when you’re small and growing, because there is no shortage of work to do. 

We set goals and boundaries for ourselves. I’ll be packing up my computer for the night and Ariel will look at me and say  “no, leave it here, you can do it tomorrow.” When Ariel celebrated her birthday with her husband in a hotel “staycation” in Brooklyn, I told her NOT to check email and Slack, I’d handle it, and I told the team she was unavailable so she didn’t get pinged. We try really hard to give each other the time we each need to recharge and spend time with our families.

For some tips: as silly as this sounds, I follow a lot of female entrepreneurs on social media and watch their self care routines and I just try them out. Yoga before bed, self-facials, baths, etc. A general tip that I always give people is find a few amazing people who you aspire to be like, who are about 10-20 years older/more experienced than you. See what they do. Ask what makes them successful, and just try some of it out. I try to follow my mentors and these instagram CEOs’ leads and see what works for me to make me feel like I’m striking a balance and taking care of myself.

Another great (and underestimated) tip in being an entrepreneur is to get some sleep – everything is more clear and you work better and can solve more problems when you have had a good night’s sleep. To Ariel’s credit, she has ALWAYS pushed this and believed this. I struggled with sleep and anxiety for years, but since the last company I worked for before diving into Happy Box full time was Casper, a sleep company, I ended up learning so much about how important a good night’s sleep is, which has definitely motivated me.

What’s something our audience would be surprised to learn about you?

Probably that this was a side hustle until pretty recently, most people are pretty surprised by that!

What are your top 3 tips to stay productive each day?

  • We always make to-do lists at the end of the day for what we hope to accomplish or need to remember for the following day. It clears the mind for the night and aligns us on our focus on what’s most important first thing the next morning.
  • We’re big fans of Tim Ferris’ book, Four Hour Work Week, and we believe in 1) batching similar work for efficiency and 2) focusing our attention on the important things and finding help /outsourcing the smaller things to maximize our productivity
  • We always try to do the hardest tasks of the day first (when we’re fresh-minded, and more creative) – so we feel accomplished by lunchtime. This was inspired by Mark Twain’s quote “If the first thing you do in the morning is to eat the frog, then you can continue your day with the satisfaction of knowing that this is probably the worst thing that will happen to you all day”.

What does being an Entreprenista mean to you?

Being an Entreprenista means being confident, resourceful, and an active part of the amazing and powerful women-owned business community. Having smart and informative discussions with fellow female entrepreneurs is incredibly important, because starting and running a company is no cake walk.

Share it!

Posted in

Leave a Comment

8 Inspiring Latinx Entreprenistas that have launched groundbreaking companies

In celebration of National Hispanic Heritage Month, we’ve put together a list of 8 incredible Latinx women founders that have launched groundbreaking companies. Check it out: Jessica Alba: The Honest Company Founded in 2011, The Honest Company makes sustainable, well-designed products that work – built on transparency, trust, and a deep sense of purpose. In…

Susan Sarit of Operations-Made Easy on achieving your goals by getting organized

Describe your business in a few words: I am a mom, daughter, sister, business owner, and more! I started my business for both financial freedom and to be a work-at-home mom. I created Operations-Made Easy to help diverse women with the Operations of their business. Deliberative, disciplined, and detail-oriented are just a few words we…

Lisa Nutt of Make Every Minute Count on personal and professional growth

Describe your business in a few words? The Make Every Minute Count ecosystem encourages us to go (do that thing), grow (personally and professionally) and give (through a membership based family to family giving circle). What made you take the leap to start your own business? I’m a serial entrepreneur. This is the third time…

Connection Coach Kristjana Hillberg on trusting your intuition and having an open mind

Describe your business in a few words: I’m a Connection Coach who helps women unearth their deepest desires, move from auto pilot to intentional action and prioritize their wellbeing. What was your background prior to starting your own business? I’m a multipotentialite – meaning, I have tried multiple things and tested multiple careers ranging from…

Martha Stewart & Marley Spoon: Finally Back to Delicious Meals For Everyone

Cuisine varies by culture, but no matter how societies segment and define themselves, certain foods show up in households across the globe — only differing in their forms. Some of a culture’s time-honored meals are created by its culinary icons.  Among America’s culinary icons, Martha Stewart is, without question, its most trusted. In 2014, Martha…

7 Entreprenista League Members share the biggest business challenge they overcame and what it taught them

Brand Photographer Brittney Guy-Atakpo of Brittney Jean Photography The biggest business challenge I have faced is sticking to a schedule that made me feel productive and good about my work ethic. What I have learned is that there is no right or wrong schedule or routine that produces success. I have been more grateful for…

Courtney Spritzer of WorkRobe on her “secret sauce” for a successful product launch

Describe WorkRobe in a few words? WorkRobes are designed to have you looking your best during any video meeting, so you can go from bedroom to boardroom in seconds and in comfort. My mission is to reimagine what you wear to work (from home).  Can you pinpoint the moment you knew you wanted to create…

Brand Photographer Brittney Jean Guy-Atakpo on helping women show up confidently on camera

Describe your business in a few words? I’m Brittney with Brittney Jean Photography & Company. I help women show up confidently in photos and on social media to grow their brand and business. I’m a Brand Photographer and Strategist. I have over 5 years working for Fortune 100 companies in sales and marketing and over…

Lorena Tapiero of Conscious Consulting on the power of networking

Describe your business in a few words? Conscious Consulting is a Latina-owned, bilingual marketing and public relations agency with 20 years of experience in the hospitality, sports and wellness sectors. Our thoughtful, comprehensive approach helps brands establish clear communication priorities and a long-range vision for meaningful press coverage, value-added partnerships and sustainable influencer relationships. As…

Lindsay Applebaum Stuart of Mamalux on the beginning stage of business

Describe your business in a few words? Mamalux is a first-of-its-kind leakproof sleep solution for breastfeeding moms. Our Kickstarter launches on 10/19! What was your background prior to starting your own business? I spent the first 10 years of my career as a sports journalist for the Washington Post and Sports Illustrated! So this has…

Jessica Bargenquast of Lady ChangeMakers on organic marketing strategies that work

Describe your business in a few words? Lady ChangeMakers is an exclusive e-commerce platform for women-owned businesses to gain valuable exposure and sales. Most of my life I’ve been encouraged to be seen and not heard. Growing up extremely introverted and shy I felt invisible. I wanted to create a platform so women-owned businesses could…

Jennifer Gligoric of EntrePods on the importance of mindset

Describe EntrePods in a few words? Cutting-edge entrepreneur and investor network answering the question “So Now What?” for business owners powered by fractional consultants and coaches with decades worth of experience. What made you take the leap to start your own business? I had no choice.  My mother owned a staffing company for 54 years…

Certified Financial Planner Maggie Gomez on investing and building wealth

Describe your business in a few words? An accessible place where anyone can learn to invest and build wealth, regardless of their net worth. What made you take the leap to start your own business? I realized that it was only those who were already wealthy that had access to quality financial guidance. I got…

Claire Jones of Cushy Couture on shifting paradigms in the fashion industry

Describe your business in a few words? Cushy Couture is a customer-driven clothing brand that creates high quality sweatpants in a wide range of colors and patterns that come in three different inseam lengths because we believe that you don’t have to settle for less. We create functional sweatpants that will last you for multiple…

Writer, Speaker, Podcaster, and Life Coach Chelsea Austin on taking care of yourself first

Describe your business in a few words? I advocate for others to find their own self-worth and acceptance through self-care, love, respect, and storytelling. What made you take the leap to start your own business? When I started writing my book and my blog, I don’t think I ever realized it would become a business.…