Getting Candid With Candy Queen Rosie O'Neill Of Sugarfina


Falling in love took Rosie O'Neill on the most unexpected twist — a completely new career path. The former PR and marketing executive for Mattel was ready for something new but it wasn't until a shared passion for candy with her boyfriend turned fiancé Josh Resnick transformed into a booming business, filling a niche for other adults who wanted a candy store/experience to call their own.

Enter Sugarfina, a luxury candy boutique and growing candy empire. Since launching in 2012, they've added 25 boutiques, 15 mini boutiques inside Nordstrom plus their huge online and wholesale business.

So, how did Rosie go from corporate executive to successful entrepreneur — all while her relationship thrived under the pressure? Read on as Rosie explains how she knew they were onto something big, why her relationship has been the best thing for growing the business and what she wants all aspiring entrepreneurs to know before turning their own worlds upside down!

Rosie O'Neill and fiancée Josh Resnik

1. How did you and your now fiancé and business partner Josh Resnick realize you shared a passion for candy?

On our third date, he took me to see Willie Wonka and the Chocolate Factory, at an outdoor screening in LA. Afterwards, we started this brainstorm of why should kids have all the fun? Why has candy become kind of like, junky? You're shoveling scoops of candy into a plastic bag and it's all about getting the cheapest candy possible and the biggest quantity possible and kids are sneezing into all the bins and it's just gross. Where's the candy store for people like us who want something of higher quality, beautifully presented? and a little more expensive than gummy worms shoveled out of a bin.

2. So, how did that conversation turn into a business plan?

We had it as this back-burner idea that we worked on in our spare time. We travel a lot so whenever we would travel, particularly in Europe, we would discover these beautiful, high quality, amazingly made candies. And then we started tracking down the candy makers and visiting them. We discovered incredible stories behind these candies — these are candy makers that have been doing it for generations and most of these candy makers needed convincing to come to the US. They only sold it in their region. We had to show them the vision and how much respect we were going treat their candy with. We convinced a bunch of them to sell to us and we were just buying super small quantities in the beginning and sharing it with our friends and family. After two years of that exploration and discovery phase, we said, 'Hey, why don't we launch this?' Three months later we got the website live and very quickly — I mean within three weeks — it just started snowballing and all these huge things started happening.

3. When did you know you hit on something big?

The (former) site Daily Candy did a piece on us three weeks in to our launch. And then after that, Facebook asked us to be the exclusive candy supplier in a gift program they were running. It was us, Starbucks and Apple — which was crazy because we were running the business out of our basement then. It got us a ton of exposure and then from there, it kept compounding because we were very nimble and very flexible. We recognized that whatever we had in our mind for what the business was not what it was going to end up looking like. So, we needed to pivot and make changes along the way. And, we went from selling candy with interesting stories from different countries to becoming a gifting company. About 2/3 of our purchases are gifts and so that was a meaningful pivot. Ultimately, we wanted to go into retail — we just needed to prove the concept first.

4. What were some of your earliest challenges?

It's hard to focus and prioritize when you're in that new stage and you're getting these different things thrown at you. It is very tempting to say "yes" to everything, but you must be disciplined. If you do say "yes" to everything, you end up doing a bunch of things poorly. We went through a phase where we were jumping in, not really understanding what was going to happen, not being prepared and then having all these problems — missing orders, shipping late, shipping the wrong things. There were plenty of headaches and heartaches along the way. The thing that was easy, in a sense, was that customers really got it and wanted it but the operational side of growing and filling that demand was very hard.

5. What is it really like working with your significant other?

You must understand who you are as a person in your relationship. All our friends told us we were crazy, there was no way in hell they would work with their partner and what were we doing? I had no apprehension whatsoever. Josh was a little more cautious just because he felt like we really did have a good thing going and he didn't want to introduce anything that would put a lot of stress on the relationship. But, it's been easy to be totally honest. I think we're lucky in that sense. We just happen to have a chemistry that makes us work together very well. And, we have a clear separation of roles. Josh is the back of house and I'm the front of house. I do all the creative product development, marketing sales, all the retails channels and he handles all the operations, finances, legal — all the stuff that I cringe when I even think about it. We have a really healthy respect for each other and I just completely trust him to do those things and vice versa. This way, we're not stepping on each other's toes at all. We come together for all the big strategic business decisions and sometimes we have different opinions but I think we're good communicators and we debate in a healthy way that doesn't get personal.

6. How does your team feel about working for a couple?

I think our team sees that our dynamic is healthy and productive. If anything, we support each other in ways that we just couldn't if we weren't in a relationship. It's worked out to our advantage competitively. The fact that we're together all the time and pretty much work and strategize and brainstorm 24 hours a day — you usually can't have that much interaction with your business partner. I think that's enabled us to move quickly and take these projects on together.

7. What's your team dynamic like?

Our corporate office now is about 60 people. We have a lot of people in their early 20's and Sugarfina is their first job out of college. They have a really different set of motivations than people who have maybe been in the business world for 15 or 20 years. So, with that said, the team members who are early in their career value being part of something that they see is a bigger cause. Not just pushing paper, not just showing up but they're really doing something and contributing to something they're excited about and passionate about. We really communicate the vision of where we want to take the company and show them the big role they play in that. They also value the ability to cross-train. I think of Sugarfina as a second college where you might come in and have no idea what you want to do in your career — and we embrace that. We want to help you figure out what you like doing and we're totally open if you want to switch groups or functions. We've had a ton of people make pretty dramatic role shifts. We had a woman in her early 20's start out in our sales team. It just wasn't her favorite thing and she saw an opening in our operations team and is thriving there. I think that flexibility and really caring about people being happy in their careers is important. I would say for the people who are more experienced, autonomy and being able to truly have ownership is key.

8. So, what's your philosophy as a boss?

Josh and I are very much about, 'Hey, we hired you because you're smarter than us in this area. We're here for you, support you, will give guidance and direction and keep you apprised of the bigger picture — but, we want you to run your business!' As we get bigger and bigger, keeping people feeling connected and empowered is key. One of the things Josh and I recently introduced is an anonymous question box at our monthly staff meetings. You can ask us any question, no matter how difficult or how uncomfortable. We'll read the question out loud and answer it in front of the group. We've had some doozies! We try to be incredibly transparent but it's hard. You have managers not living up to our values of empowerment or maybe they're micromanaging their team. My office sometimes feels like a revolving door of people just wanting to talk about their situations and how they're 'feeling.' I think we live with a generation that's much more comfortable speaking up when they aren't happy. I have had to get used to that because in my career, I wasn't really exposed to that. I was exposed to, 'stay focused, stay positive, keep moving, things will be fine.'

9. What's the biggest business strategy you've learned since launching Sugarfina?

I'm not going to say I've become a tough negotiator because it doesn't come across that way — but I've been able to get a lot of things that most people are afraid to even ask for just by asking in the right way. I learned that by watching Josh. He's really a master at it and so I sat through a few negotiations with him and was so impressed that he asked bold questions without it feeling aggressive. I think if you're in a negotiation, you can help the partner see your side and see the challenges you're facing by saying, 'Hey, I recognize this is a big ask but here's the challenges we're facing as a business and here's why it will help us be a more successful partner for you.' Nine times out of ten they get it and we either get what we're asking for or very close to it. They don't feel bad, we don't feel bad and it just comes out in a win-win situation. People think you must be really tough and stand your ground when you're negotiating and I think it's the opposite. You must be very flexible, you must be very communicative, you must have things that you're willing to give up that get you what you really do need. If you can leave the negotiation and they think of you as a very thoughtful and sweet person — they're going to support you. It's that 'kill people with kindness' thing. We've had a lot of opportunities where people said, 'Hey, you're really nice people, you're good to us, you're a good partner. We want to help you.' I cannot oversay enough the value of being a nice person.

10. What advice do you have for other entrepreneurs looking to get things off the ground?

I would say first and foremost, make sure that you truly understand what it means to be an entrepreneur and that it's the right fit for you. Now that we're in these Shark Tank days, I think everyone has great ideas and everyone has an opportunity to become an entrepreneur but it's not right for everyone. You must have a tremendous amount of internal willpower to keep going and be successful. You will fail every day and you have to get up every day and say, "Okay, I failed yesterday. I'm going to learn from it, I'm going to overcome it, I'm going to do better today." It can be draining. You're taking a beating a lot of the time. So, know yourself and know if that's what you want to sign up for — because as wonderful as entrepreneurship can be, the path to getting there is hard. You'll likely have a good few years of your life where you're not going to be able to pay yourself or you might just have days where you just wake up and totally want to quit. Knowing that going in makes it a lot easier to deal with.

11. What have been some 'happy accidents' while growing Sugarfina?

We've launched a couple of April Fool's jokes, that in our mind were the most wacky, stupid ideas. But, last year, we introduced “cold pressed juice gummy bears" ˘as a joke. But, we got so much response and people were freaking out over the email! They were like, 'Where is this? I'm ready to buy it!' Because of the response, we decided that maybe there's something here and we should develop it. So, we partnered up with Pressed Juicery and created this green juice gummy bear that we're launching at the end of April. This year, our April Fool's joke was “Sugar Fido" — a luxury candy boutique for dogs. We got even more of a reaction than last year's juice gummy bears and people were sad when they found out it was a joke. I'm not saying we're going to do that too — but those are the kinds of things where now we're saying, 'Well, what if we did that?' and bringing that playful exploration to the company.

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How Postpartum Mesh Underwear Started My Entrepreneurial Journey

"Steal the mesh underwear you get from the hospital," a friend said upon learning I was pregnant with my first daughter.

It was the single best piece of advice I received before giving birth in December 2013. My best friend delivered her daughter eight months previously, and she was the first to pass along this shared code among new moms: you'll need mesh underwear for your at-home postpartum recovery, and you can't find them anywhere for purchase. End result: steal them. And tell your friends.

My delivery and subsequent recovery were not easy. To my unexpected surprise, after almost 24 hours of labor, I had an emergency C-section. Thankfully, my daughter was healthy; however, my recovery was quite a journey. The shock to my system caused my bloated and swollen body to need weeks of recovery time. Luckily, I had trusted my friend and followed her instructions: I had stolen some mesh underwear from the hospital to bring home with me.

Unfortunately, I needed those disposable underwear for much longer than I anticipated and quickly ran out. As I still wasn't quite mobile, my mother went to the store to find more underwear for me. Unfortunately, she couldn't find them anywhere and ended up buying me oversized granny panties. Sure, they were big enough, but I had to cut the waistband for comfort.

I eventually recovered from my C-section, survived those first few sleepless months, and returned to work. At the time, I was working for a Fortune 100 company and happily contributing to the corporate world. But becoming a new mom brought with it an internal struggle and search for something “more" out of my life--a desire to have a bigger impact. A flashback to my friend's golden piece of advice got me thinking: Why aren't mesh underwear readily available for women in recovery? What if I could make the magical mesh underwear available to new moms everywhere? Did I know much about designing, selling, or marketing clothing? Not really. But I also didn't know much about motherhood when I started that journey, either, and that seemed to be working out well. And so, Brief Transitions was born.

My quest began. With my manufacturing and engineering background I naively thought, It's one product. How hard could it be? While it may not have been “hard," it definitely took a lot of work. I slowly started to do some research on the possibilities. What would it take to start a company and bring these underwear to market? How are they made and what type of manufacturer do I need? With each step forward I learned a little more--I spoke with suppliers, researched materials, and experimented with packaging. I started to really believe that I was meant to bring these underwear to other moms in need.

Then I realized that I needed to learn more about the online business and ecommerce world as well. Google was my new best friend. On my one hour commute (each way), I listened to a lot of podcasts to learn about topics I wasn't familiar with--how to setup a website, social media platforms, email marketing, etc. I worked in the evenings and inbetween business trips to plan what I called Execution Phase. In 2016, I had a website with a Shopify cart up and running. I also delivered my second daughter via C-section (and handily also supplied myself with all the mesh underwear I needed).

They say, “If you build it, they will come." But I've learned that the saying should really go more like this: “If you build it, and tell everyone about it, they might come." I had a 3-month-old, an almost 3 year old and my business was up and running. I had an occasional sale; however, my processes were extremely manual and having a day job while trying to ship product out proved to be challenging. I was manually processing and filling orders and then going to the post office on Saturday mornings to ship to customers. I eventually decided to go where the moms shop...hello, Amazon Prime! I started to research what I needed to do to list products with Amazon and the benefits of Amazon fulfillment (hint: they take care of it for you).

Fast forward to 2018...

While I started to build this side business and saw a potential for it to grow way beyond my expectations, my corporate job became more demanding with respect to travel and time away from home. I was on the road 70% of the time during first quarter 2018. My normally “go with the flow" 4-year-old started to cry every time I left for a trip and asked why I wasn't home for bedtime. That was a low point for me and even though bedtime with young kids has its own challenges, I realized I didn't want to miss out on this time in their lives. My desire for more scheduling flexibility and less corporate travel time pushed me to work the nights and weekends needed to build and scale my side hustle to a full-time business. If anyone tries to tell you it's “easy" to build “passive" income, don't believe them. Starting and building a business takes a lot of grit, hustle and hard work. After months of agonizing, changing my mind, and wondering if I should really leave my job (and a steady paycheck!), I ultimately left my corporate job in April 2018 to pursue Brief Transitions full-time.

In building Brief Transitions, I reached out to like-minded women to see if they were experiencing similar challenges to my own--balancing creating and building a business while raising children--and I realized that many women are on the quest for flexible, meaningful work. I realized that we can advance the movement of female entrepreneurs by leveraging community to inspire, empower, and connect these trailblazers. For that reason, I recently launched a new project, The Transitions Collective, a platform for connecting community-driven women entrepreneurs.

As is the case with many entrepreneurs, I find myself working on multiple projects at a time. I am now working on a members-only community for The Transitions Collective that will provide access to experts and resources for women who want to leave corporate and work in their business full-time. Connecting and supporting women in this movement makes us a force in the future of work. At the same time, I had my most profitable sales quarter to date and best of all, I am able to drop my daughter off at school in the morning.

Mesh underwear started me on a journey much bigger than I ever imagined. They sparked an idea, ignited a passion, and drove me to find fulfillment in a different type of work. That stolen underwear was just the beginning.