Today we’d like to introduce you to Stephanie Ross.
Hi Stephanie, please kick things off for us with an introduction to yourself and your story.
Five years ago, my sister Cathryn and I were on one of our regular phone calls when I blurted out an idea that would change the course of both of our lives:
“What if we created an experience where women business owners could come together to learn from speakers and experts while building genuine relationships?”
It was in the wake of the pandemic, and we were searching for exactly that kind of community ourselves. We wanted a place where women entrepreneurs could meet in person to learn, grow, connect, and truly support one another. What we found instead were mostly networking events that felt transactional or happy hours that never quite went beyond small talk.
There simply wasn’t a space that combined meaningful education, authentic connection, and a lot of fun.
Then we realized something that has guided us ever since: when you can’t find what you’re looking for, sometimes you’re the one meant to create it.
So we did.
I designed a simple logo in Canva, we invited a handful of local women business owners to a picnic, shared our vision, captured the energy of that first gathering, and launched Sister Circle. We had no five-year business plan—just a belief that women deserved a different kind of entrepreneurial community.
After sharing photos and videos from that very first picnic, our inbox filled with one question: “When’s the next one?”
That led to our first social event, which sold out. Just a few months later, we hosted our very first conference—what has since grown into Sister Circle Summit.
For the first year and a half, we poured our hearts into hosting pop-up events, socials, community calls, monthly gatherings, and our annual conference. Along the way, I noticed a pattern. Women would leave our events energized and inspired, but once they returned to the day-to-day demands of running a business, that momentum often faded.
That’s when we realized inspiration wasn’t enough. What women needed was consistent support, accountability, and a community that would walk alongside them month after month.
That realization became the foundation of the Sister Circle Membership.
Now, more than three and a half years later, our membership remains the heart of everything we do. What began in La Crosse, Wisconsin has grown into a thriving community that serves women across the Midwest and beyond through local chapters and online membership.
Looking back, it’s incredible to think that one conversation between two sisters sparked what has become so much more than a business. Sister Circle has become a movement rooted in a simple belief: that women don’t have to build successful businesses alone. We can build through our core pillars of sisterhood, soul, and strategy!
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
We’ve had many challenges along the way as we’ve beta tested, grown, evolved, and are now scaling across the Midwest and beyond! Here’s a few…
We started before we had it all figured out. Sister Circle started with one picnic, about 10 women, and a whole lot of faith. We had the vision, but we had no idea just how big this dream would become.
We took the time to beta test and learn what our community truly needed. We tried a little bit of everything in those early days—free socials, workshops, webinars, conferences, coaching—you name it. Every “yes,” every “no,” and every experiment helped us discover what actually worked, what the women wanted, and what I actually enjoyed creating as an experience.
We stayed the course when it was discouraging. When we officially launched the Sister Circle Membership, only one person signed up at the launch event. I’ll be honest—it was extremely discouraging and I almost quit right then and there. But instead of taking it as a sign to stop, I took it as challenge to keep refining, keep believing, and keep showing up and we ended up launching with 18 Founding Members!
We’ve outgrown our systems time and time again as a growing community which only forced us to create systems and structure around our membership. As more women joined, we realized that passion alone wasn’t enough. The bigger the community became, the more we needed intentional structure and frameworks for our meetings, clear communication of what we’re about and who we’re for, and healthy boundaries to create an incredible experience for everyone.
I learned rather quickly that I was never meant to build this business alone. Building Sister Circle while running other businesses—and then becoming a mom—made it impossible for me to keep wearing every hat. It challenged me to redefine what leadership really looked like to step into the role of CEO. One of the biggest mindset shifts has been letting go of being the person who does everything and becoming the leader who empowers others to do it alongside me. Building a team, creating systems, and trusting others has been one of the most challenging and rewarding parts of this journey.
And last but definitely not least, scaling without losing our soul. As we’ve expanded into chapters across the Midwest, my biggest priority has never been growth for growth’s sake. It’s been protecting the heart of Sister Circle while creating systems that allow more women to experience the same sense of belonging, support, and connection that started with one simple picnic.
Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Building a business can be hard, but that doesn’t mean it can’t be FUN! Small Business Sister Circle is not just another “networking group”. Sister Circle is a business education community for women entrepreneurs who are serious about their growth, where sisterhood IS the strategy!
While business can be hard, it doesn’t mean it can’t be fun! We believe you can do hard things and have fun by doing it in community! Our first local chapter started in my hometown of La Crosse, Wisconsin to fill a need and is expanding to other Midwest cities to create a ripple effect of collaboration over competition.
Our brand is all about dreaming big, even in a small town! While you can join an online community anywhere, what makes our community unique is our in person opportunities to connect each month through your local chapter and our emphasis on implementation. While many communities focus solely on networking, our focus is on practical, tangible business education that we help you implement and hold accountable. The networking, connecting, and referrals that come from our community are simply a byproduct of showing up and engaging!
Can you share something surprising about yourself?
I have never taken a single formal business class in high school or college. My business education has come solely through my own research and first hand experience of growing and scaling my first business, a fitness and yoga studio for 10 years starting at the age of 20. As my mentor says, I’ve earned my PhD through the ‘School of Hard Knocks’!
Pricing:
- $99/month membership
Contact Info:
- Website: https://www.sistercircle.co
- Instagram: https://www.instagram.com/smallbusiness.sistercircle/
- Facebook: https://www.facebook.com/SmallBusinessSisterCircle
- Youtube: https://www.youtube.com/channel/UC_Fhd7_aGJOaT51_UCVAkRw
- Other: https://www.stephanieleaross.com
