Our Founder answers some questions about Lady Boss Collective.

Michelle Calcagni

Founder, Lady Boss Collective

Founder/Managing Director, PhoneBox Group


What inspired you to create Lady Boss Collective?

When I started PhoneBox, I realized that the perks of working for yourself were sometimes outweighed by how isolating the experience could be. I also recognized how easy it would be to miss out on the chance to collaborate with people of diverse experiences and thoughts. When you add in the unique challenges of being a woman in business, it’s not an easy path for any women entrepreneur.

That understanding led me to create Lady Boss Collective. There are many talented and insightful women who share the unique challenge of starting and managing a small business, and I wondered what might happen if we came together in a more focused way. I kicked off the first LBC cohort in 2017, and I’m incredibly excited to bring that sense of connection to other women as LBC moves forward. We are so much stronger together than we can be on our own.

What is your background?

I’d imagine my background is a lot like that of many women who have decided to start businesses later in their careers. I spent the first part of my career working for evolving companies of varying sizes, then spent the next part working at very large companies. In 2016, I decided to combine my professional network and professional background to launch PhoneBox Group, which has been a fulfilling and challenging experience. Beyond my “work life”, I’ve always been passionate about volunteering and giving back as part of non-profit/educational organizations and creating Lady Boss Collective continues that commitment. 

How does Lady Boss Collective affect women’s lives?

Our Member testimonials speak more eloquently than I can about Lady Boss Collective’s impact, but I believe it creates an environment that encourages each of us to succeed in our businesses in a way that is true to our values and vision. There is no substitute for the strength that comes when you realize you’re not alone on a journey, and that you are valued and appreciated for everything you are (and want to become). 

What has surprised you about Lady Boss Collective so far?

I’d expected that the women who would join would be amazing, but I’m truly awestruck when I look back at conversations we’ve had and at the way members have come together to provide support for each other. I’ve seen Members share their biggest fears and celebrate huge successes so openly and honestly that it took my breath away. Members feel as though they have a trusted army of extraordinary, insightful women on their side, and that is more powerful than I could have predicted. 

Why do you think Lady Boss Collective works?

First, it brings structure to something we might otherwise try to do on our own – finding connections, sharing experiences and seeking input. The way we’ve set up the cohorts, how meet-ups are managed and many other details ensure that the time we spend together is valuable. Second, it fits easily within normal business activities. You already have meetings, you need to solve problems and you want to celebrate success – Lady Boss Collective helps you do all of that, and more!

You’ve said that you’d like to have Members from across the globe; why does that matter to you?

One of the highlights of my life has been living/working with terrific women all over the world. Those experiences taught me that many challenges aren’t geography-specific – they’re more universal. I believe that’s true for women entrepreneurs; we aren’t all the same, but we share more than we might think and can come together in ways to help all of us. Plus, because the cohort model allows for a lot of customization, it can work almost anywhere.

How is Lady Boss Collective different from other women-focused organizations?

There are terrific organizations out there that focus on women in business, on networking, on educating entrepreneurs, etc., and that’s good news for all of us. But I couldn’t find any other organization that solely focuses on providing support, guidance and inspiration to women who create/manage small businesses. We’re not the place to come for networking or for education – there are other organizations doing a great job providing those services and we hope to partner with them as we grow. After all, the more we can all collaborate to make women entrepreneurs be successful, the better we all are. 

How do you define success for Lady Boss Collective?

When creating the organization, I was clear about our primary objective: to help as many women entrepreneurs connect as possible, anywhere in the world. That means adding Members and creating cohorts, but also expanding Member services over time. I’m so glad we have a terrific Advisory Board to help shape our future; I couldn’t do it alone.

Do you have questions? We have answers!