Women and Business: Ali Kriegsman, Kim Kaupe and Polly Rodriguez On the Ins and Outs of Being a Woman Leader

 
 WORDS BY CARA BEST, PHOTOS OF POLLY AND KIM BY CARA BEST - PHOTOS OF ALI COURTESY OF BULLETIN

WORDS BY CARA BEST, PHOTOS OF POLLY AND KIM BY CARA BEST - PHOTOS OF ALI COURTESY OF BULLETIN

Being a woman leader comes with its fair share of unique joys and challenges and no one knows that better than our panelists from 'The Modern Woman Entrepreneur' event we held in February. We met back up with Ali Kriegsman (COO / Co-Founder, Bulletin), Kim Kaupe (CEO, Zinepak), and Polly Rodriguez (CEO, Unbound) to get the down low on what it truly means to be a woman leader in 2018.


WHAT ADVICE DO YOU HAVE FOR WOMEN HOPING TO STRIKE OUT ON THEIR OWN?

Ali Kriegsman: I feel like so many women are tricked into thinking they need to be “ready” to start a business or freelance or follow their dreams. I agree that there are certain things you need in place – money saved up, confidence in tow – but no external validation or “moment” will force your hand. A lot of women think they need to be at a certain place in their career or have XYZ on their resume first, but the sooner you start, the sooner you’ll start failing, succeeding, rinse and repeat.

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HOW DOES YOUR EXPERIENCE AS A WOMEN SHAPE YOUR LEADERSHIP STYLE?

Polly Rodriguez: I think women tend to be more open to vulnerability and more empathetic, which are essential traits when it comes to team building. No one tells you that as your startup scales your job becomes wholly focused on managing and cultivating people as opposed to the business. I think women are far more comfortable with being vulnerable leaders who are empathetic to the needs of their teams. Being able to sense what your teammates need is the single most important thing for your startup to thrive. 

HOW DID YOU LEARN TO LEAD ON THE JOB AND BUILD A CULTURE FROM THE GROUND UP?

Kim Kaupe: Because I had worked in a corporate setting for three years, I had an idea of what built culture and what destroyed it. I took the best of what I learned in corporate and applied it to my business. What I try doesn't always work, but I try to fail fast and fail forward - improving little by little as I go. I also ask our team to weigh in on what they think is working for the culture as it's shaped by everyone, not just me!

HOW DID YOU KNOW THAT YOUR STARTING YOUR OWN COMPANY WAS THE RIGHT OPTION TO PURSUE?

Polly: The most successful founders are those who are solving problems they personally experience. Not only because you can empathize with your customers but also because it will keep you motivated during the inevitably tough times. I knew in my gut that there should be a household brand name in sexual wellness, but it was getting my hands on the market research that illuminated how broken the industry is. Learning that gave me that feeling of, "I have to do this." It's important to have a firm grasp on the solutions that exist in the marketplace and what you're going up against. 

YOUR COMPANY HAS GONE THROUGH A SERIES OF REINVENTIONS, HOW HAVE THEY AFFECTED BULLETIN'S IDENTITY?

Ali: Every time we pivoted, it was because the existing version of our company just wasn’t working. Alana and I had quit our full-time jobs to build something together, and three months in, that “something” (the Bulletin digital magazine) was in shambles. But we couldn’t just turn around like, “hehe nevermind!” and go back to our nine to five. We were really insistent on pushing forward and making it work. We polled the independent brands who sold with us through the magazine and as it turned out, they were all really eager for more IRL retail opportunities - a space in NY where they could sell consistently. So, that’s when we immediately pivoted to doing pop-up markets in Williamsburg. We were making money on that model, but we were essentially running a huge event every single weekend and working seven days a week. We needed a more sustainable retail environment (as opposed to the 18,000 sq foot, outdoor parking lot we were in) and that’s when we decided to open our first store, which is on North 7th and Wythe in Brooklyn.

After the disappointment of the 2016 election and going through a very male-dominated tech incubator, we decided to exclusively spotlight women-owned businesses in our stores and create an inclusive space where women could support other women in a direct and explicit way. We really locked into the brand’s identity in 2017 once we infused it with our own personal values and goals as a team. We’ve always been extremely invested in supporting small brands and business owners, but once the political climate started to challenge our identity as female business owners and as women period, we were really motivated to transform our retail experience into something that empowered, supported and financially benefited women.

WHAT COMMON BUSINESS ADVICE DO YOU WANT WOMEN TO IGNORE?

Kim: "Keep ideas to yourself." Don't be shy or scared to ask others, "What do you think about this?" The best feedback comes from those outside of your day to day. I've asked students, people in elevators, and people sitting next to me on planes what they think of an idea I'm toying with. What skill should every female leader have? The ability to ask for help. Your greatest tool is your ability to ask and rely on others. You cannot do everything, you are not Superman, nor should you be.

HOW DOES YOUR WOMANHOOD INFLUENCE YOUR LEADERSHIP STYLE?

Ali: Prior to Bulletin, I never thought of my womanhood affecting my leadership style or how it might inform my experience as a manager. I do think my experience as a female founder in tech has influenced how I treat my team. I think Alana would say the same. Through all of Bulletin’s ups and downs, Alana and I had to very deliberately convince ourselves that we were capable of building something big. When you’re in an incubator program filled with tech dudes or pitching a ton of male investors with few women in the mix, it’s easy to feel out of place or question your potential. That experience definitely inspired Alana and I to teach our team that the sky is the limit.

Many of the women who work in our retail stores have side projects that we actively try to encourage. We give a lot of ownership to the women on the corporate team and motivate them to really dominate their piece of the business. At the end of the day, it’s important to me that an employee feels like she’s working on herself and developing her own strengths and skills while supporting Bulletin.  I kind of lead knowing that the women on my team (sadly) won’t be with us forever, and I want them to feel like post-Bulletin, they can accomplish their wildest dreams.

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YOU FOUND YOURSELF IN AN INDUSTRY THAT IS A BIT LEFT OF CENTER. WHAT DREW YOU FIRST TO THIS AREA OF INTEREST?

Polly: For me, it was going through a cancer diagnosis that resulted in menopause that made me first realize how overlooked female sexuality is. My doctors just framed my menopause as the "inability to have children" and didn't mention anything about the lifetime of side effects. I went to buy a vibrator for the first time and the shopping experience just left me feeling embarrassed and overwhelmed. 

Risk is inherently the trade off to any huge opportunity. It’s true that if there isn't anything uncomfortable about what you're building, it's probably not an idea that is going to shake up things in a way that's truly disruptive and innovative. If it feels uncomfortable, unconventional, and scary - pursue it. It means there's something bigger there.

FOR YEARS, ZINEPAK OPERATED UNDER THE ‘BOOTSTRAPS’ METHOD OF ONLY SPENDING ON WHAT WAS NECESSARY, WITH NO OUTSIDE FUNDING. HOW DID YOU PRIORITIZE WHICH ELEMENTS OF THE BUSINESS TO INVEST IN AND WHICH TO DO WITHOUT?

Kim: We weigh each decision by saying, 'If this were to completely fail, how bad of a position would that put us in?" Often founders get excited and look at the upsides, but the real decision making happens when you pick apart the downsides piece by piece and figure out what kind of situation you are going to be in if you end up there. Once we feel like we’ve picked apart a problem enough and figured out just how bad it can get, we know then if we can afford to take the risk. 


Miss our last panel? Don't fret, we'll be hosting events this season in New York and Los Angeles at our Holiday / Resort '18 shows! Join us for a deep dive into the science of networking on June 11th at 6:30pm at Studio 450. Not in NYC? Join us on June 18th for a cocktail mixer in partnership with some amazing brands at The Freehand in downtown Los Angeles. RSVP to kristina@brandassembly.com.