This transcript was generated from the episode audio and may contain minor errors.
[Music]
Hello, hello, what's up? Welcome to Side Hustle School. My name is Chris Guillebeau, your host. Welcome as well to Throwback Thursday. This is our weekly segment, conveniently happening on Thursdays, where we take an in-depth look at someone whose story has evolved since we first featured them.
We have had more than 2,000 episodes so far, so it's really great to go back and see, okay, we talked to somebody three years ago, you know, how are they doing now? And in lots of cases, they have expanded their business, they've grown a lot, sometimes they have transitioned to a new business, lots of different kinds of updates, along with some lessons learned, which I hope you will find helpful. Today's is definitely interesting and helpful. So last week we heard from the founder of Go Last Minute. He operates a travel booking portal that now offers a whitelist option for licensing.
Today in our latest feature, we'll hear from Hannah Redmond, co-founder of Happy Box. Happy Box. Hannah and her co-founder, who happens to be her sister, quit their New York City advertising jobs in the height of the pandemic because their side hustle was doing so well. I love it. Hannah will tell us a bit about that, among other things.
She'll also include some advice on when is a good time to quit. I get that question from listeners all the time, so it's great to have her take on it. Let's hand the microphone over to Hannah. [Music]
My name is Hannah Redmond. I'm currently in Hoboken, New Jersey.
The name of my side hustle, now turned full-time hustle, is Happy Box. And yes, we were on episode 531 of Side Hustle School. So Happy Box is a build-your-own-care package company. We specialize in custom gifting, which basically means whether you're someone gifting for a friend or a cousin who lives across the country, or if you're a corporation that needs to gift all new hires, something super custom and unique. We do it for you.
So you can go right on our site, you can build a custom care package, and a few clicks, you can buy some of our curated care packages that are refreshed seasonally and for relevant moments, or you can work with our concierge team to create something super custom and branded if you are a company that is looking for a box or a care package that has your branding, your logo, has items that has your logo on it, that kind of thing. So we started the idea back in 2015, actually. We were discussing kind of this care package that I had sent my sister, so I co-founded the company with my sister back in college. And in college, she got dumped and broken up with in college, as we all did at some point. And I was living states apart, and I wanted to surprise her with a care package.
And I thought it was bizarre that you couldn't customize a care package online. I mean, at the time, you could customize a car online, but you couldn't customize a care package. So I kind of looked around, saw if there was anything like it in the market. There really wasn't. I graduated college in 2008.
So fast forward quite some years later, this kind of still was bugging me that this didn't exist. So pitched the idea to my now co-founder and sister and saying, hey, remember that care package I had built? And I kind of vented to you about not being able to do it easily online. You know, Amazon's great, and they have great options for quick shipping, but there's no real website where there's like the intersection of customization and convenience. I want to customize something super personal.
I want a handwritten note. I want to pick every item, but I really just need it done for me. So I was like, hey, want to try this and see what people think. And we really just started that way. When we were side hustling Happy Box, we were both working in corporate jobs in Manhattan.
I was working actually brand side after working at ad agencies for quite some time. And Ariel was working in ad agency still. We side hustled it for, let's see, five years, five years total since we really launched the brand and the company. And then since then in October, 2020, we finally committed to quit our jobs. It was really smack of the first year of the pandemic.
It was right after that kind of started. And we were working again, long distance gifting became very relevant. So we were working all night to get the Happy Box work done. And we finally decided we were like, we have to sleep sometimes and we decided to take a leap. It was incredibly scary to jump from pretty cushy, very successful corporate jobs, steady paycheck in the middle of a pandemic, for sure.
That was, I think, one of the things that made me the most nervous, but we did it. And I think once we realized that spending 100% of our time on the business would make it propel even further. And once we realized that and it happened, it made it all worth it and made sense. We also now have a full-time staff, which is unreal. And I still, you know, every time I go to the warehouse and I see everyone, it still blows my mind.
So we have a full-time staff. We have lots of amazing part-time staff. And I mean, on a personal level, my sister and I both just had our first babies. So lots have changed in our lives. Our biggest challenge currently is scale and growth.
We are self-funded. So every penny matters, every effort we do, every strategy is about business growth and scale. And I think for us, we're at a point where we have grown to a level that media dollars really matter. Every kind of strategic decision really impacts the next steps. The advice I would give to someone who wants to, let's say turn their side hustle into a full-time job, is really plan for it and really think about the opportunity cost of you taking your brain 100% against your idea and making it full-time.
I think the moment we realized we had to quit our jobs was when we were like, wow, if we had all day to focus on this, I think we can grow at 10X, not 2X every year. And that was a huge realization. I think we both sat there and we were like, oh my God, if I had more hours to do this, we could just kill it. And I think there's, everyone kind of faces that when they're side hustling is how much more time would it take to really blow this up versus, okay, it's fine to just work on it at night and make some extra cash. So I think that is the biggest advice, is really plan as much as you can to quit if that's what you're looking to do and really think about what could you achieve if you spent 100% of your time there.
Thanks so much to Hannah for sharing her updates with us. Listeners, I want to encourage you to check out her website, happyboxstore.com, happyboxstore.com, just like it sounds, or on Instagram, @happybox. In fact, if you're looking for a gift item, perhaps might be a great place to go. All right, let me know what you think and who you'd like to see featured from our archives of more than 1,000 stories, 2,000 plus episodes, in fact, 1,000 plus stories. If you've got a question or an update for us about your hustle, sidehustleschool.com/questions.
Thanks so much for tuning in today. We've got a new episode coming out tomorrow. You can subscribe or follow wherever you like to listen to podcasts. That's it for now. My name's Chris Guillebeau.
This is "Side Hustle School." [Music]
from The Onward Project.
