This Women’s History Month, we are shining a light on the incredible journeys and achievements from women-owned and run businesses. We asked our Community members to share the story of their businesses with us: their milestones, how they push past fear or self-doubt when making big decisions, and their advice for other women business owners and entrepreneurs.
We were blown away by their responses and want to highlight some of the amazing stories that our Community members kindly shared with us.
What is a defining moment or important milestone for you in your journey as a business owner?
“A defining moment in my journey as a business owner was winning "Favorite Dessert in San Diego" for 5 years in a row!” — Nancy, @sugarmamma
“The most defining moment in my journey as a business owner was the day I decided to go for it—to jump in with both feet.
I had spent over a decade sitting in a cubicle at my corporate job, daydreaming about the freedom and independence of owning my own business. I wanted to control my own destiny. I wanted my hard work to come back to me—not just fill the pockets of faceless executives.
Then I got really sick. I nearly died. I was medically terminated just as the COVID lockdowns began. I found a remote desk job, but the misery followed. One day, while staring out the window, I asked the big questions: I survived. I lived. So now what? Is this really what I’m supposed to be doing?
I knew I was capable of something more.
Not even an hour later, my husband came home from a walk with our boys and said, “I met a couple on Main Street today—they said we’re opening a coffee shop.”
And I said, “OK. That’s what we’re doing.”
That was it. We were all in. Whatever it takes, we’re going to build something big and positive for our community.” — Briana, @BrianaJo
“A defining milestone in my journey was launching my brick and mortar beauty supply store, My Shade & Texture, just months before the pandemic. When COVID-19 hit, I had to quickly pivot and innovate to keep serving my community. I created one-of-a-kind shopping services including virtual shopping consultations, curbside pickup, and personal delivery options. This challenge ultimately strengthened my business and showed me how resilient and adaptable I could be as an entrepreneur.” — Pamela, @MyShadeandText
“A defining moment for Amityville Apothecary was hosting our first Alchemy Academy last year. We had people traveling from all over the country—some from across state lines, others flying in from thousands of miles away—all drawn together by a shared desire to deepen their spiritual practice and understanding.
What made it truly unforgettable were the incredible teachers who brought their unique wisdom and energy into the space. Each session was powerful, from hands-on spellwork to deep-diving into ancient practices. But the most profound moment came during our Silent Supper Ritual. As everyone sat together in sacred silence, sharing personal stories, ancestral connections, and spiritual breakthroughs, the energy was palpable. Walls came down, hearts opened, and a deep sense of connection was forged—not just with each other, but with the unseen realms as well.
That experience confirmed that Amityville Apothecary isn’t just a shop—it’s a sacred gathering place where people come to awaken their magic, find community, and reclaim their power. Hosting the Alchemy Academy showed us the true depth of what we’re building—a space where transformation happens, spirits are honored, and magic is real.” — Dina, @DinaLRosenberg
How do you push past your fear or self-doubt when making big decisions?
“I work hard to remember that I have extensive experience to depend on and I'm not alone. I have a wonderful community to support me, including Square.” — Raelinn, @TWR
“Ask myself "what's the worst that can happen?"” — Sandra, @GandGPaleo
“There is always something better on the other side of fear. That guides my decision process” — Monika, @creativemphoto
“When I have to make big decisions , I give it great thought and sometimes will ask for outside opinions before making my decisions. When I finally make a decision it is for the long haul and I am willing to see it through to the end.” — Gizelda, @Toomerz
What's the best piece of advice another woman business owner or entrepreneur has given you?
“The best advice we’ve received from another business owner is that success is a self-awareness game—you have to know who you are, what you’re good at, and where you need support. It’s easy to get caught up in trying to do everything yourself, but the real power comes from understanding your strengths and knowing when to lean on others.
For us, that means embracing the balance of our partnership. Dina and Danielle each bring different strengths to the table—where one excels, the other offers support. That self-awareness allows us to divide responsibilities, trust each other’s instincts, and focus on what we do best without burning out.
Success isn’t about hustling harder—it’s about knowing yourself, trusting your intuition, and building a team that complements your vision. That advice has shaped how we run Amityville Apothecary and allowed us to grow with confidence and alignment.” — Dina, @DinaLRosenberg
“You can't eat an elephant all in one bite." I say it all the time to others.” — Carey, @CareyJo
“The best advice I’ve received from another woman entrepreneur is: ‘You don’t have to be perfect, but you do have to be fearless.’ As a female and a minority business owner, I’ve faced challenges that could have made me second-guess myself. But I’ve learned that success isn’t about having all the answers—it’s about showing up, making bold moves, and trusting that you’ll figure it out along the way. That mindset has helped me push through obstacles and build a business that thrives against the odds.” — Salwa, @XProduction
![Salwa @XProduction, owner of [PICKLES] by Evergreen and Market](https://community.squareup.com/t5/image/serverpage/image-id/50377i46A8C8E259AF2BF5/image-size/large?v=v2&px=999 "MM-1478 - Salwa Kisswani.jpg")
“If it feels wrong, don't do it. Your intuition is usually correct.” — Jackie, @jhascek
What's a game-changing trend that you think more business owners should pay attention to in your industry?
“A game-changing trend more business owners should pay attention to is the growing demand for functional foods with clean ingredients. Consumers today aren’t just looking for snacks—they want foods that offer health benefits, gut-friendly ingredients, and real functionality. We’re seeing this with the rise of prebiotic sodas, fermented foods, and now, even pickles. The opportunity is huge for brands that can merge bold flavors with wellness benefits while staying authentic and transparent. Business owners who lean into this movement, especially with strong branding and storytelling, will be the ones who stand out and scale.” — Salwa, @XProduction
“One of the most important “trends” is actually something old: real human connection.
Before the internet, we had to talk to each other. We were face-to-face, present, and connected. That’s what the younger generation is craving now—genuineness, groundedness, realness.
Sure, we’re using more technology and AI to be efficient. Yes, you can now buy a coffee without ever speaking to another person. But convenience can’t replace connection.
The real opportunity? Use the time tech saves us to be human again. Look people in the eye. Ask how they’re doing—and actually care about the answer.
It’s not about customer service anymore. It’s about human to human connection.” — Briana, @BrianaJo
“A game-changing trend in the beauty industry that more business owners should embrace is educational entrepreneurship—teaching the business behind beauty rather than just selling products. My "Passions & Profits: Beauty Edition" program demonstrates this approach by teaching young girls how to transform their beauty interests into viable businesses. This creates not just customers but future innovators and business owners. The beauty industry needs to focus on empowerment through knowledge transfer, especially for underrepresented communities who often face barriers to business ownership.” — Pamela, @MyShadeandText
“Unreasonable hospitality. Too many businesses, especially larger ones, are moving away from the one on one experience and making sure that clients are actually taken care of. They're more concerned with getting things done faster and more efficiently. They're focused on using AI, digital everything and call centers. They're getting away from the human connection and the most important thing - the customer.” — Carey, @CareyJo
Thank you to everyone for taking the time to participate in this article ♥️ You can learn more about their businesses here:
- @BrianaJo is the owner of Random’s Coffee, a cozy, community-driven coffee shop in Belton, Missouri
- @CareyJo runs Arctic Heat in Boulder, Montana, specializing in sales, services, installation and repair for HVAC systems.
- @creativemphoto owns Demel Portraits, Chicago’s premiere portrait photographer
- @DinaLRosenberg runs Amityville Apothecary in Amityville, New York where you can find carefully curated products from crystals to tarot reading and more
- @GandGPaleo is the owner of To Go Paleo, offering delicious, allergen-friendly foods at Salem Saturday Market
- @jhascek is Reverend High Priestess Jackie, creating bespoke ceremonies that welcome and satisfy everyone
- @MyShadeandText is behind My Shade and Texture, a beauty bar for naturalists based in Tampa, Florida
- @sugarmamma is the owner of Sugar Mamma,
- @Toomerz runs Zelda’s African Imports, where you’ll find a fabulous and fashionable selection of African clothing and accessories
- @TWR is the brain behind Travel With Raelinn, providing tailored travel advice whether you’re solo explorers or families
- @XProduction brings healthy, flavorful and unique pickled products through [PICKLES] by Evergreen and Market
Did you know that the Square Community has a group specifically for women-owned businesses and entrepreneurs? Join togetHER today.
Tra is a Square Community manager at Square. She is responsible for several programs, including Question of the Week, Seller Groups, and our new Mentorship Program.