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5 female entrepreneurs on how they turned their passions into careers

For the working woman, life can sometimes be stressful.

There’s always something to do. Whether it’s tending to your family, your friends, your social circle, or most importantly, yourself. Being a woman and pursuing a career hasn’t exactly been the smoothest ride since the dawn of time.

Joanna Lau, founder and CEO of Jemma products, knows exactly what that feels like. During an intimate panel discussion at the Jemma headquarters, five female entrepreneurs and founders discussed their journeys, from the birth of their ideas, the work they put into executing them, and the eventual launch of their companies.

#mytwocents ❤

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If you’re a working woman who’s always on the go, you’ve probably heard of Jemma handbags. They come in all different shapes and sizes, from gym bags to totes, backpacks, wallets — you name it, Jemma has it on deck.

A quick scan of the Jemma website tells you all you need to know about the products, the convenience, the variety and the audience. Still, getting Jemma to the position it is now wasn’t an easy feat.

The panel shared it all, how their ideas came about, how they operate their businesses when they first realized their businesses were a success and the trials they faced throughout their vision. They bought forward topics that often arose when interviewing entrepreneurs, but it seemed that all the founders held different opinions.

There are a couple of questions to broach when figuring out how to structure your new business. Details in things like money, time, audience, partnerships are essential deciding factors in whether or not you make it or break it.

Here are a few key points to feel out and tackle when first engaging in a new project. If you’re feeling doubtful about your decision, consider these stories as a lesson and guide for your own ideas.

If you’re considering…

An entirely new career

If you’ve been thinking of jumping into a new career but find yourself hesitant since you’ve been working something on a different spectrum, just use Helena Crawley, founder and CEO of SweatStyle, as an example.

Her career started off as a tax associate in New York City. Working long hours as a lawyer was tough, so she found herself at the gym, often exercising to eliminate her stress.

Delving into a healthier lifestyle, she joined a women’s fitness studio to better empower herself emotionally and physically. It was here that she noted the subtle differences in ensemble between women’s workout gear. “There was a disconnect,” she shared. The notice of that little detail was the sole reason she came up with the multiplex of workout clothing that is SweatStyle.

“SweatStyle customizes the gear for you depending on the type of workout or fitness that you’ll be engaged in.”

The company familiarizes you with the different types of workout products that are possible to get you your best fit. While Helena’s original job was focused on the law, the leap from files to fitness proved to be a successful one.

A path of familiarity

If you’re anything like Olivia Landau, the founder, and CEO of The Clear Cut, you’ve been disregarding your career’s calling for too long.

Olivia has always had a part in the jewelry business. Her family has been in it for generations. Growing up, they instilled in her that she should not go into jewelry because they considered it to be a “dying industry.”

After graduating with her BA and working for Tiffany & Co.’s corporate office, she found herself unfulfilled in the corporate sector and turned her passions towards a different direction.

Enrolling and graduating from Gemological Institute of America, she set off on her own venture, starting a company as a private jeweler who picks out and designs diamond rings. Olivia says,

“A lot of people are overwhelmed with hundreds of thousands of options. We get a sense of your preferences, budget, design, and timeline. All diamond rings take about 2 weeks to create.”

Clear Cut first started off as a blog, which caught traction on Instagram. From there, the company grew organically. People began reaching out to Olivia, mentioning how opaque the diamond industry was and how difficult it was to shop for a diamond.

“When you commit to it full time, it’s really different from when it’s a side-hustle. Nothing is the same than by when you live or die on whether this is going to succeed or not.”

Committed to making it easier and more worthwhile for their consumers, the company set out to create bespoke rings, handmade and sold at wholesale prices.

The real importance of networking

Of course, networking is important. Anyone who’s anyone doing anything can tell you that much. But when asked the question by Joanna, a different opinion surfaced.

For Helena, every meeting she has is a new opportunity.

“I think that’s the number one thing you can do for your business. I always take any coffee, lunch or drink meeting that anybody suggest for me, because no matter what, there’s always something that comes out of that conversation. Like a question I hadn’t considered before, or a connection to someone else that may be useful, or just becoming an advocate for your brand.”

She also mentioned that although these connections may not seem useful at the time, they may become evident later on.

“Putting your name out there, making connections and building your brand and down the line letting them know that hey, our brand is 3x the size, you’re much more likely to get a response from them than if you never made that connection in the first place. Many times things have circled back around.”

Estee Goldschmidt, founder, and CEO of the ShopDrop, has a different idea in mind.

Rather than utilizing all of her networking tools, she focuses more on her consumer’s opinions, and heavily sorts out the different types of entrepreneurial relationships available to her, placing a particular case of selective choice on investors.

“There’s networking with other entrepreneurs, which for me is a lifeline. I feel that other entrepreneurs have helped me so much for maintaining sanity, and in terms of exposure and connections, there’s this community and understanding in terms of helping each other. In terms of networking with our users… So. Important. It’s customer discovery every single conversation I have. We’ll get coffee, or jump on the phone and all of our product improvements has come from our user base. In terms of networking with potential investors, I started saying no to those meetings, and they’d be like ‘send the deck and I’ll forward it.’ Initially, I was taking those meetings and then I started feeling like an empty canister, used and discarded.”


For ShopDrop, an app that links brand engagement through consumer analytics, the most crucial information lies in the hands of the users. Estee says,

“Reaching people and having people find out about you costs money and energy. User acquisition costs money. Most companies start with a blog that people are reading, but aren’t making money off of it, so they decide to create a product with a solid profit market and sell it.”

ShopDrop’s most difficult transition was the aspect of payment. After getting into the NYU Entrepreneurship Accelerator, ShopDrop garnered an audience of over 800 active users, which then grew to 2,000 active users.

“Reaching people and having people find out about you costs money and energy. User acquisition costs money. Most companies start with a blog that people are reading, but because they aren’t making money off of it they decide to create a product with a solid profit market and sell it. Spend tens of thousands of dollars in PR in order to reach their audience ‘organically.'”

But ShopDrop remains self-funded to this day. Estee continued,

“There were moments that were difficult when it came to finances. Sometimes there would be a clear uptake and other days it was much harder to get by.”

When Joanna first started Jemma, she was contemplative on whether or not she would raise money for capital or self-fund her business.

She chose the latter, sorting out which direction to take her business, and was scrappy with money when needed, such as getting her friends to model the product.

“The first question you ask yourself is, ‘Do you want this business to be your business or do you want it to be a business that you sell the next 5 years?’ When you’ve figured that out, then it becomes easier to organically grow your product.”

This year, Jemma will hit $1M in sales revenue.

Taking a risk

For Lia Winograd, Founder and CEO of Pepper, it was the opposite. Lia was excited when she launched the idea for her bra company that gears it’s merchandise to small chested women.

Pepper’s funding came from Kickstarter, more than quadrupling its original goal of $10,000. The official launch of the product was this year, though it’s been in the works since 2017.

Pepper was Lia’s side project after hours and on weekends. She and her co-founder were working for a year on building the company and waiting for the development of the actual product.

Lia also informs us that quitting her job before Pepper’s official launch would have been a bad idea all around.

After Pepper proved successful through consumer spending, it became a question of whether or not the product would be able to deliver, which took yet another six months.

Combating loneliness

“As founder and CEO do you ever feel lonely?” Joanna asked the group. A reactive agreement bursts throughout the room, each woman giving their own take on how to beat the matter.

Discussing the importance of work, life and family balance, Lia mentioned that sometimes, being surrounded by too big a community and balancing a few things at once can also feel overwhelming and that it’s important to prioritize your work-life (and self) in times like this.

“Find your community,” Helena advocates.

“My team has been my lifeline,” Estee follows, sharing a story of how her team helped her get through being rejected from a company accelerator.

A shared trait between them all was the importance they place on their community. Whether it’s your co-founder, family, network, classmates, friends, the people that want to see you succeed are the most important in crucial times, especially when first launching or starting an idea.

As women, we’re gifted with natural abilities that can help overcome arising obstacles; our intuition, our ability to multi-task, the utilization of our femininity to grow new ideas, the list goes on and on.

Whether your business is new, old, small, big, your focus or a side project, the most important lesson is that it starts with you. Focusing on yourself comes first. Once you’ve found your harmonious balance, it seems that everything else falls into place effortlessly.