Ariel Pasternak and Atara Bernstein believe that food is more than just what’s on your plate. It is how you express your values, your identity, and even your style, which is why the powerhouse duo launched Pineapple Collaborative, a platform that brings people together both on and offline through food; making it, enjoying it, and sharing it. 

What started as a humble potluck dinner with 30 guests in Washington D.C. has grown into a vibrant community with over 100,000 members across the country and has even expanded into a line of elevated pantry staples. (ICYMI, their olive oil and apple cider vinegar have been praised by every publication from Goop and Vanity Fair to Bon Appétit and Food & Wine.)

From bringing people together over a potluck meal to launching their elevated pantry staples to building a digital community during a pandemic, the co-founders of Pineapple Collaborative share how they’re lifting up deserving voices in the food industry and why they believe community is much more powerful than competition.

How did you make your first dollar and what did that job teach you that still applies today?

ATARA BERNSTEIN: I worked part-time at a pizza shop when I was in high school, which was my first real job outside of the odd babysitting gig. My manager was relatively unapproachable, so the main lesson I learned there that I still practice to this day is to lead and solve problems on my own. I've developed a pretty scrappy and DIY attitude because of that experience which I'm proud of! 

Take us back to the beginning. What was the lightbulb moment for your business/career and what inspired you to pursue this path?

ARIEL PASTERNAK: Pineapple Collaborative is all about connection, community, and lifting up deserving voices in the food industry. The idea for Pineapple really began in 2015 with a potluck dinner attended by 30 women in Washington, D.C. who came together over their shared love of food. We officially launched in 2017 as a national platform for people to build real, meaningful connections through their shared passion for food. 

We truly believe that food is more than what’s on your plate; it is how you express your values, identity, and even how you express your style. Before launching Pineapple, we didn’t really feel like there was a space for people to go and share their thoughts and passion about food, aside from well-known food professionals. We felt strongly that the narrative should change. Food is for everyone and Pineapple Collaborative welcomes your ideas, values, and beliefs no matter your background or day job.

Entrepreneurship is all about taking calculated risks. What’s the most pivotal risk you’ve taken, and how did it change your path? 

ATARA: The biggest risk I've taken is leaving my freelance career to launch Pineapple Collaborative without any guarantee of success or fulfillment. (Noting my privilege here! The concept and degree of risk are very different depending on your class, socioeconomic status, race, gender identity, etc.). It was a scary leap, but I had to listen to my gut.

I've never shied away from commitment, so I kept telling myself that we could always re-evaluate after a few months if things were not going as planned. Fast forward three years later and we're going strong. We’ve brought together a community of over 100,000 people who love food, developed a team of seven, and created a thriving multi-channel ecosystem with a diverse revenue stream to boot. I am really thankful that I took a risk on Pineapple Collaborative and excited for where it’s going.

What career mistake has given you the biggest lesson?

ARIEL: As much as we all try, nobody can avoid mistakes. When I’ve made mistakes in the past, I’ve pretty much let the stress and anxiety over it get the best of me. There is no reason to replay your mistake over and over in your head. Just make sure that you absorb it, learn from it, and move on. Whether that means you need to take a few minutes to collect yourself, schedule a call with your boss or colleague to problem solve, or write down the next steps, it’s important that you don’t let your mistake define you. You are much more than your career, whether you are working for someone else or yourself.

2020 presented everybody around the globe with new, unprecedented challenges. How did you #FindNewRoads + switch gears towards your new version of success?

ATARA: 2020 has certainly been a doozy of a year. First and foremost, we are so thankful for the support our community has shown this year. As a company that started out of a love of gathering with others, it has been really special to see our community of over 100,000 strong come together in new ways for one another over the past year and we are so excited for how we will continue to show up for each other in new ways in 2021.

With the onset of the pandemic in the U.S. back in March, Ariel and I really had to think long and hard about how to pivot what makes Pineapple special: Our events and gatherings. We knew that without these things, we had to show up for our community in new and creative ways amidst a time of so much uncertainty, fear, and loneliness. We didn’t want to rush into anything, so as a team we took several months to develop a careful plan that had our community’s needs at the center. We received dozens of emails and DMs from our community asking us to share about their respective pandemic relief initiatives, so we created a Community Bulletin Board that anyone could add to. We hosted Zoom events that still brought warmth and hospitality to a digital space. A top priority was ensuring that these events were a safe zone for all people in our community, so we created a Digital Code of Conduct, chatted with our moderators before events, introduced ourselves using our preferred pronouns (and encouraged those who were comfortable to do the same), and let people know to turn their camera off if that was what made them feel best. 

2020 has not been easy on anyone, but finding these pivots that kept our brand ethos of togetherness at the center was really rewarding.

How are you making a difference and pushing your industry forward?

ARIEL: Pineapple Collaborative started as a place for people in food to gather, connect, and collaborate. We strongly believe that community is much more powerful than competition. When we decided to launch our first two pantry staples last year, The Olive Oil and The Apple Cider Vinegar, we prioritized our ethos of collaboration into how we sourced–working closely with women producers and experts in our Pineapple network. We care deeply about working together with our partners not only to make the best possible products but to lift up the deserving voices in our industry and help them tell their stories. Both Kathryn Tomajan (the maker behind The Olive Oil) and Joanne Krueger (behind The ACV) have incredible stories, ethics, and processes and we are truly humbled and inspired to work with them.

The food industry can honestly be really shady sometimes, and in reality, most people in America don’t really know where their food is coming from or what it took to get it into your kitchen. We really want to break that narrative by elevating the stories behind our products—from the incredible growers to the type of olives and apples you’ll find in our staples—because we should be rooted in real connection to our food and our planet. We should know who makes it and we should understand what effect it has on the environment. With so many brands trying to outsmart each other with different innovations and or hyper-niche categories, we’re actually trying to get back to basics. For us, that means a company built on community first and one that celebrates sustainably and honestly made food products as a meaningful way to connect to one another.

Going after what you deserve in life takes confidence and guts. Does confidence come naturally to you or did you have to learn it? What advice can you share for women on cultivating confidence and going after their dreams? 

ATARA: Confidence does not come naturally to me at all, and so for me, it’s an active practice and a skill that I’ve honed over many years. I’ve learned how to be confident by facing rejection and being comfortable with it. At this stage, I would go as far as to say that I welcome it! To me, rejection means that you’re confident enough to put yourself out there. And the more rejection you face, the more work you’re producing and proliferating. My single focus when the going gets tough is to focus on creating and making great work. Confidence comes when you care more about the intrinsic factors that drive you (the work, the growth, the learning) and less about the extrinsic rewards that tend to leave you feeling empty regardless.

What is the biggest challenge to achieving success in life?

ARIEL: Defining your own version of success and being really clear and honest about what that means for you. It’s a natural tendency to compare ourselves to others and their version of success, but at the end of the day, it’s pretty much comparing apples to oranges. If we are constantly chasing someone else’s version of success, we never get to realize the joy and accomplishment that comes from achieving our own goals on our own timeline.

When you separate yourself from your job title and the bells and whistles of your business or career, who are you and what do you like to do? How have you remained true and authentic to who you are?

ATARA: I like to think that I'm true to myself both in and out of the business. I stay true to myself by not comparing myself to others (a tall order in the age of social media). A bit about me: I’m a 30-year-old Jewish white woman. Judaism is a big part of my identity. I grew up in an extremely Orthodox home, and while I'm not currently practicing in that way anymore, it's an important part of who I am. I’m also very into my dog Luna (she’s a pitbull/boxer mix), music (have recently been jamming to My Analog Journal), and most of all, FOOD. Food is the most important thing in my life and I’m wholly consumed (ha!) by it. There are many aspects of food that keep me inspired. I love food history, delving deep into the significance and source of a single product, food justice, and, of course, cooking and eating too.

For those who haven’t started a business (or are about to) what advice do you have? 

ARIEL: Ensure you have at least six months’ worth of savings so that you give yourself time to figure it out in the really early days of your business without being worried about paying for your essential living costs. Also, surround yourself with people—friends, family, team members—who believe in you and the mission of what you’re doing because you’ll need them to support you (and remind you why you make the decisions you did) when the going gets tough. Lastly, hire people who are smarter than you and can excel in certain areas of the business better than you can. 

What is the biggest mistake entrepreneurs make with money early on? 

ATARA: Not prioritizing their own financial wellness. When we started Pineapple, we were not paying ourselves and that, honestly, became very hard to sustain. (P.S.: I want to name my privilege in having multiple safety nets and being able to dip into savings rather than being paid by the business). Looking back, I think that prioritizing our financial stability would have alleviated a lot of stress. Over time, we’ve made it our mission to balance both taking care of business and being taken care of by the business. Financial stability is a big piece of that dynamic. 

What is your number one piece of financial advice for any new entrepreneur and why?

ARIEL: For us, it was really important to bootstrap Pineapple Collaborative from the beginning. We used sales from our very first events and established a partnership with Caviar early on to help kickstart our business, but we wanted to be really strategic with where our money was coming from and where we were putting it. We definitely recommend being scrappy—especially at the beginning—and finding a couple of partners that believe in your brand and that you can see as a long-term, mutually beneficial partner for years to come. 

When it comes to investors, we also recommend being really strategic and taking your time in choosing who to work with. It is critical that anyone who invests in your business not only believes in your mission but also aligns with your core values. We feel super lucky to have a small but mighty list of investors on our side who truly understand what Pineapple is all about, and want to see it flourish as much as we do. Approaching investors with the utmost intentionality definitely makes for a more lean business structure, but it has allowed us to be on a really healthy growth trajectory year after year.

It’s easy to celebrate the wins, but how do you handle failure or when something hasn’t worked out for you?

ATARA: Just a few weeks ago, I made a mistake (that stemmed from a silly typo in Shopify of all things) which cost the business thousands of dollars. This error fell squarely on my shoulders and I took it pretty hard. Admittedly, I did indulge in a few hours of self-pity. Once the pity party concluded, I decompressed with my team and my loved ones. Together, we reflected on our learnings and brainstormed a solution. Ultimately, I always like to remind myself that while fortune favors the bold, failure does too. If you’re not failing, you’re not challenging the status quo. This failure ended up leading to some really meaningful connections and honest conversations with our community that would have never have happened otherwise.

With success comes opportunity, but that also means you have your hands full. What keeps you inspired and motivated to keep going even on your most challenging days?

ARIEL: I’m really inspired by talking to other entrepreneurs and creatives and hearing about their experiences and what’s driving them. Also, hearing positive feedback from our community and seeing our products being used and enjoyed in people’s kitchens keeps me motivated to continue doing the work we do, despite the tough moments. It really makes all the hard work worth it.

If you could go back to the beginning of your career journey—with the knowledge you have now— what advice would you give yourself? 

ATARA: One adage that we repeat a lot at Pineapple is “seek to understand rather than to be understood.” It’s an idea that I learned early on in my career and has taught me a lot about the importance of empathy in business as well as life. It's been a guiding force in how we approach and resolve conflict. I've reflected on this saying in so many scenarios from contract negotiations to interpersonal conversations, leadership, and more.

Fill in the blanks:

When I feel fear, I… 

ARIEL: Acknowledge the fear and keep moving forward.

ATARA: Remind myself that scary things help me grow.

To be successful, you need to be… 

ARIEL: Persistent (don’t quit!).

ATARA: Learning and growing.

If I wasn’t in my job now, I would be… 

ARIEL: Pursuing a new industry, like real estate.

ATARA: Making pottery.

Three qualities that got me to where I am today are… 

ARIEL: Persistence, creativity, and professionalism. 

ATARA: Empathy, creativity, and grit.

The change I’d like to see in my industry is…  

ARIEL: True equity for those who power our food system, like farmworkers and restaurant workers.

ATARA: DITTO TO ARIEL’s ANSWER!