Meet Bailey Feldman - Anne Arundel Moms

Meet Bailey Feldman, an Annapolis mom of three daughters, one dog, four chickens and the founder of Fount + Flourish. Her mission is to create intentional space and interactions that deeply connect women to each other and to their most-whole selves.

Bailey shares how her past jobs have inspired her, why you need to reinforce your “village” and her BIG plans for the new Fount + Flourish physical space that will enhance the way we gather and redefine how we work.

Discover the power of gathering with the vibrant Fount + Flourish community and become a member – they’ll create the space. All you do is show up and step into a world of connection, empowerment, and nourishment.

Tell us a little bit about you and your family! Where did you grow up? How long have you lived in Annapolis?

My husband and I met here in Annapolis, or we like to say we met in the middle with him coming from the North (Duxbury, MA) and me coming from the South (Delray Beach, FL). We have called downtown Annapolis home for the last 12 years, however I have retained many of my south Florida ways with love of bright colors, bare feet, and a very low tolerance for the winter time. You will often see us boarding a plane to visit my family in South Florida around March when I just can’t handle the cold any longer. 

Brad and I have been married 7 years and have three little girls – Isadora (5), Juniper (4), and Etta May (18m) and have fully embraced our girl gang life. Brad is a high school Math teacher at Key School and loves dropping off Izzy and Junie in the lower school each day. We live with a few chickens and were able to get some male energy into the house with our dog Bowie (like David Bowie, not the city). 

Congratulations on your brand new adventure at Fount + Flourish. Tell us how you started Fount + Flourish and your inspiration behind it.

After 9 years working across international non-profits and management consulting, I’ve spent most of my career helping a lot of men and that just wasn’t working for me. I decided I wanted to use my gathering, consulting, and coaching skills to help more women. Women add such unique value to communities but are lacking the support systems needed and are often forced to choose and sacrifice –  Work or Motherhood, Play or Care, Boss or Wife, Friend or Selfcare. F+F wants to fill the gap of the support systems that we are currently lacking, with the hope that one day we become superfluous because these systems exist without us. 

As for the inspiration, honestly, it was a strong desire to revolt. To break down walls that felt like they were suffocating me regarding work, community, and family. To fight for women who put everyone and everything above themselves. To break cycles of self-sacrifice, guilt, and loneliness. It started with creating space for women and continues to evolve into a much larger experiment to change behavior of how we see ourselves in the world and how the world sees us. 

What are the big things planned for Fount + Flourish this year?

Major, big, amazing things. I can’t wait. We just launched and expanded our social membership program to not only offer monthly meetups and events, but also establish a directory that connects women to each other and to experts and resources in the area. We opened our physical office space on October 1st alongside the launch of our community membership. This membership includes social membership but also gives M-F daily access to the office space to connect and work alongside other women. We are also expanding our Fount Fitness program which allows us to partner with women-focused wellness experiences around the city and host classes that raise money for local charities. Finally, we are going to be launching some digital course work on leadership and a new leadership lab program that helps rising female leaders and mothers powerfully navigate their careers. 

What can people expect when they come to a Fount + Flourish event or become a member? 

Space created with them in mind. Whether it’s a Fount community event or Flourish Leadership coaching and consulting programs, our main mission is to create intentional spaces that allow for a deeper connection to self and others. When you walk through the physical or virtual door, I want your shoulders to drop, your chin to lift, and for you to have time to nourish your mind, body, and soul. It’s about making space available for creativity, play, movement, and connection. It’s about creating space for the things in our lives that often get put on the back burner amidst the daily grind. I often tell women at my events that I will take care of creating the space, all they have to do is show up.

How has your job shifted your perspective of Motherhood?

I think it’s less about how it shifted my perspective on motherhood and more about how it has forced me to confront the perception of motherhood and women in the workplace. I never fully understood the breadth of bias and stereotypes that women can face in the workplace, and this is coming from a middle-class, white woman. From young women starting their careers to maternity leave and returning to work after raising children, the challenges, stigmas, and labels that exist are mind-blowing. It’s one of the major driving forces behind launching Fount + Flourish: to redefine the female experience for women in the workplace.

What’s one thing people would be surprised to know about you?

I wanted to be an environmental scientist growing up, and it’s even what I studied in undergrad at the University of Florida along with a minor in sustainability. I thought I knew exactly what I was going to do but the world had different plans. My career path completely shifted when I moved to DC. However, my background in sustainability has been a huge anchor in how I approach my work in leadership and behavior change. At the heart of sustainability you’re looking at how people interact with the world around them and what motivates them. It’s about finding balance and seeing the whole story, not just pieces of it.

What’s something you love that’s just for you?

I’m an audiobook fanatic, I love to just put in my ear pods and listen to books while I rest, clean, walk, cook dinner, etc.

Best mom hack that makes your life easier.

Honestly, my village. Not just the come by for a playdate village – but the “hey, its been a hard day. Can I bring my family of five over and you feed us on top of your family” kind of village. My family is held up by a thick layer of friendships and knowing that support is there when and however I may need it, just makes life easier in general. We live downtown, so living in close proximity to this village is also incredible.

Name something you hope your children look back and remember about their childhood and you as their mama.

That we were silly and that our house was always full of music and laughter. That we felt freedom to be weird and playful.

What’s your favorite family activity to do in the area? 

We love to be outside as a family, whether we are just on the porch, heading to the pool at Mears/Safe Harbor, eating at dinner under the stars, or playing around at St. Johns.

What have you learned from your children?

Gosh, I am learning from them and through them every day. Recently, after our third child was born, I had a big realization at just how different three kids in the same family could be. It’s such a good reminder at how unique and diverse people are and how much we can learn from accepting, celebrating, and fighting to understand each other’s differences.

Greatest gift about being a mom.

Getting a front row seat to the ‘goodness’ of mankind. There is so much potential for love, kindness, and joy in humans and I just get smacked in the face surprised by it on a daily basis.

Best advice for mom guilt.

Recently we were at a seniors graduation party and by the end of it, my baby was naked on the pool steps and my two older girls were in their party dresses on floaties lounging in the pool (the friendship allowed for this behavior). My advice… Do what you need to do to be present and live fully. If it’s not a bit wild and messy, then is it even real? Our door mat isn’t lying when it says ‘Welcome to the Jungle.’

Who has most influenced you to be the mom you are today?

Embracing and learning from others in different seasons. I learned a ton from my own mom and upbringing (both what to do and what not to do), but I shaped it and refined it because I lived or immersed myself with other families and saw how they operated before having a family of my own.

Fount + Flourish was created by Bailey Feldman in response to her dream and pursuit to honor and strengthen the impact of women in the world around us. Bailey realized in order to achieve this, we must redefine the female experience. We have to document our current experience and then pivot, tear down, build up, and reconstruct the one we want to have. This needs to both occur on a personal level AND a collective level. Redefining what it means to be female in our families, our communities, and our workplaces. As a gatherer at heart, space lies at the center of this effort.

The creation of physical and mental space to learn, enjoy, and connect. Fount, as a space and source to provide deep nourishment to the mind, body, and soul of women in our community, and Flourish as a space to support vigorous development and growth of individuals and groups.


Fount + Flourish

100 Cathedral Street #7

Annapolis, MD 21401

We love to support local businesses! What are your favorite local places to:

Get coffee: Curate (and for wine nights, best of both worlds!) 

Go on a date night: I’ll keep this classic – Vin 909

Go out for a girls night: Preserve to order all the things and eat tapas style! Maybe post drinks at Parley Room 

Go out to dinner as a family: Tsunami (we love our sushi) or meet friends at Forward Brewing!

Get your hair done: Wah – Honestly, I just get the cheapest cut once a year at a walk-in spot, not the best person to ask for hair advice lol!

Shop for your kids: Details + Design carries the brand Pink Chicken and I love a good splurge on something fun for the girls #girlmom

Get your nails done: I do it at home with my manicurist kit these days, but if I need a professional I run into Sun Spa & nails

Have fun as a family: We have been loving family, summer nights at Annapolis Blues games!

Photography by @ashcaitphoto

Join The Anne Arundel Moms Community

Stay up-to-date with what's happening in-and-around Annapolis and Anne Arundel County with local events, community highlights, and exclusive deals.