A Barefoot Stroll With Brenda Della Casa

25 Aug

Hard to believe, but the lovely and talented BDC and I are about to celebrate our “one year anniversary.” We met in a most serendipitous way here in Rome last year over cocktails prepared by one of the world’s best mixologists, and ended up forming a friendship both professional and personal that continues to grow as time goes on. Brenda was savoring her last evening in Rome, and I just happened to grab the bar stool next to her. The rest is, as they say, history. So appropriate for Rome, no?

Little did I know then that Brenda’s time spent in Rome had such a significant role in her life’s journey (read The Fear of Letting Go), and little did I know at the time what a significant impact she would have on mine as well! Here I catch up with Brenda for a chat about life, love, and basically the art and science of being her fabulous self: a role model for women’s empowerment and lifestyle expert extraordinaire. Enjoy!

Photo credit: Graffiti, Aisha Singleton; Makeup: Lauren Cosenza

Photo credit: Graffiti, Aisha Singleton; Makeup: Lauren Cosenza

Brenda Della Casa
Editor in Chief of Walking Barefoot, Author of Cinderella Was a Liar, Director of Online Content for Preston Bailey, Huffington Post Blogger and Managing Partner of I Am Staggered

First of all, can you briefly chart for us the career path that has led to where you currently find yourself? Maybe just a rough sketch or outline of your trajectory: where you started and how you’ve gotten to where you are now, so we can delve further into the particulars.

Though I have always been a writer, as a teenager, I set out to become the next Marilyn Monroe, but when college was in the picture, I was more excited by the idea of spending my days breaking stories and writing than playing on stage. I took drama classes but it was my magazine writing classes that gave me a thrill. I had an incredible, smart and sophisticated professor, Marianne Szegedy-Maszak who really mentored me and changed the direction of my life by giving me an example of the woman I really wanted to become. I interned for President Clinton in The White House Communications and Press office and graduated with tons of ambition, but no job. I took a position casting reality TV shows and did that while trying to break into the journalism business and when we went on hiatus, I took a job at Morgan Stanley working for Ann Thivierge, Barton Biggs and two amazing mentors, Barbara Reinhart and David Dineen. Barbara told David I wanted to write, David had a girlfriend, Cari Wira, who was an editor at Woman’s Day and six years after graduating, I sold my first clip. Two years later, the executive assistant I worked with sent me a link to a comedy site, The Phat Phree and I contacted them to write for them (for free). I became the only female writer and we were contacted by an agent and given a book deal. That same agent accepted my pitch for Cinderella Was a Liar, a book based on my thousands of interviews for dating shows. See how one thing leads to another?

Tell us about how Walking Barefoot, your personal blog and now showcase for your lifestyle expertise, came into being, and a little about the niche that you’ve managed to carve out on the Internet. You started your site back when blogging was just a glimmer in most people’s eyes, so tell us about the exponential growth you’ve experienced, your readership, and your current mission and vision for your site.

In 2005, a colleague mentioned that her sister had started something called a “Blog” and I was intrigued by the idea of playing editor. I have great respect for Hugh Hefner and Diana Vreeland and a blog was a very small way for me to play out my fantasy of having my own online magazine. The posts started out silly, musings about my coffee guy and the shoes I had found on my way home from the market, but it soon grew into something more authentic, a place where I followed Hemingway’s suggestion that writers sit at a typewriter and bleed. The more honest and open and vulnerable I was, the more emails I received from people who were also dealing with this and that. In the past 8 years, this site has grown to be read in over 160 countries and by a very wide demographic. The bulk of my readers range from 17-45 and there is no significant majority when it comes to income or race. That’s pretty telling in that it shows me that we are all dealing with the human experience, no matter where we are in our lives. We all have pains and fears, worries about our future, ties to our past and concerns about how to navigate through life. We also all have reasons to be grateful and joyful as well as the power to change our future by doing the work here in our present. My mission is always to remain authentic and real and to bring some kind of value to my reader, even if it is simply a five minute break in a stressful day, but also to really listen to my readers and give them what they ask for. I’d like to see more guest posts and eventually start videos and a TV program.

You are quite a Renaissance woman, with your talents extending into several different endeavors and fields. Can you share with us the process of writing your book Cinderella Was a Liar and how that project came to fruition? What was your biggest challenge in bringing that book to the market, and what are you most proud of as a result of publishing?

That’s very sweet of you to say, but I really see myself as someone with great curiosity. I am an ambitious creature but only in the sense in that I like to conquer things which I half-jokingly blame on my being an Aries. I have always had the dream of having an empire like Playboy, but have always treated every article assignment like a gift which has kept things exciting. My grandfather was always reminding me to focus on one thing at a time and over time it will build something. I focus on six things at a time and I am grateful a foundation has been built. I didn’t set out to write a book or to start a blog, I just knew that I wanted to write and when opportunities presented themselves, I jumped at them. I pitched several ideas to my agent, Byrd Leavell, after he had approached us about The Phat Phree and we worked through it and took it to the houses. I led the meeting at McGraw-Hill and was later told that it was partly my proposal and partly that meeting that sold Cinderella Was a Liar. I wrote the book in six months. I loved the process and what the book brought into my life (people, opportunities, readers) but I would say, in terms of publishing, I am most proud of having the courage to write about my past for The Huffington Post and a little piece called Twenty-something: Quarter Life Crisis which went viral and continues to be posted and shared by people 12 years later. I am also deeply proud to work for Preston.

Let’s talk about that. You’re currently the online content manager for Preston Bailey, an innovative, world-renowned and highly sought-after wedding and event planner. I think many people would consider this to be a dream job. What’s it like to work in such a high-profile and influential role? What brings you the most satisfaction in this position, and what unique skills and assets do you bring to Mr. Bailey’s brand?

Along with writing for Esquire, working for Preston is my dream job. Preston is an icon, but he is also hilarious, deeply generous, kind and humble in ways no one would expect. I feel I can call, email or go to him for anything at any time and that really says something about him. My other team members are incredible as well. My CFO is like an oracle, terrifyingly smart and charismatic, and my CEO is one of the funniest, ambitious and challenging people I have ever met. My colleagues are my friends and we spend most of our day working and laughing very hard. I was able to play an integral role in the design and development of the new site ( which is an online magazine. I am fortunate that Preston really values each person’s talent and gift and he and my CEO really allow me to own my role and take my suggestions and ideas very seriously while mentoring me to always become a better writer, editor and even person. I learn so much every day and am challenged in ways that really push me. I really grow in this role and I feel I add value while working with a talented and hard-working team, all the while surrounded by the beauty created by Preston Bailey—who can ask for more than that?

Now, let’s talk for a moment on a personal level. You’ve been remarkably open about the difficulties you faced in childhood, as you alluded to earlier when you mentioned the courage it took to share about your past in some of your writing for The Huffington Post. You’re also very open and candid throughout your writing, which I really appreciate. Coming from my own social work background, I like that you consistently maintain a theme of encouraging self-empowerment for women. How much of an influence have your personal struggles and challenges had on your ability to strive for such excellence and succeed in such high achievement in your life, both professional and personal? In what ways do you think you continually model one of your mottos, “Always a soldier, never a victim?”

Great question! I think my struggles in childhood and early adulthood impacted my development, but I was determined not to allow them to define me, in part, because I was so ashamed of where I had come from. I was always treated as though I was “less than” everyone else because of my situation–be it my marks, my clothing or my not having a place to live. I was told by my father that I was the wrong gender, by my mother that I was discardable, and even those who cared for me painted a grim picture of the road ahead. My favorite teacher said that it was a shame that the bus would always run me over and I would not have the chance others would have to go to college or have a normal life because of my circumstances. Quite frankly, that was the worst and best thing to ever say to me. I know I can credit my grandfather’s influence for any decent qualities I have, and as flippant as it sounds, I also think that looking up to Madonna as much as I did really helped me. I fought to finish high school while not having a real home, I fought to get into college, and I moved to New York and emulated Madonna’s “I will get what I want” attitude until I proved to myself and those around me that I was as worthy as everyone else. Lastly, I know what it feels like to be victimized and to feel helpless and powerless, so I really admire true personal power. I have amazing women in my life who are in total control of themselves and who take care of themselves and of those they love and stand up for themselves, and I know what it feels like on both sides. Being in control of your own life and protecting yourself feels better, and I want all of my readers to feel the security of knowing they are enough as they are, even if there are some things they want to polish, and they can handle anything that comes their way but do not have to keep handling disrespect or devaluation, even from themselves.

Can you tell us about one of the most formative experiences of your professional life, the impact that it had on you and how it either directly or indirectly brought you to where you are currently?

Working for Preston. I would say that it has pushed me to be the best I can be each and every day. When you are representing the print portion of a brand like Preston’s, you need to constantly educate and push yourself. It’s a very tough and rewarding position and I am lucky to work for Preston and be a part of his team.

Tell us three (or more!) things you are grateful for every day.

My health, my family of friends, Tony Montana (my chihuahua), my career, my readers, having the opportunity to experience travel and the fun things I get to experience as a result of my job and having a home that is safe, secure and that no one can kick me out of.

What’s next for Brenda Della Casa? Where can we expect to see you go from here, and how can we get involved?

I am launching a new site, re-launching I am Staggered and working on some new projects that will allow me to be more interactive with my readers. I am also off to Puerto Rico with my girlfriend next week and then planning a trip to Spain.

Where can we find you online?

Walking Barefoot, as well as social media: @BrendaDellaCasa on Twitter, Walking Barefoot on Facebook, Google+, and Pinterest.

Lastly, what advice would you give to your younger self, knowing what you know now? And, what advice would you give to a young woman (or man!) looking to make their way in the world?

To my younger self: Don’t try and make things work with someone who disrespects and/or devalues you. The pain of trying to undo that kind of treatment is worse than the pain of loss you will experience. It also wastes precious time and resources better utilized to enhance your life with travel, new experiences and new relationships. I would also tell her to work hard but also work smart and accept that not everything is going to go her way because she is human, not because of where she came from. Lastly, I would tell her to pay attention to what people do and not what they say and to make adjustments in her own behavior based on what they do/do not do. Just because someone was nice doesn’t mean that you still need to be when they start being nasty.

My advice to others is the same and to also know that you aren’t supposed to have the answers, life gives lessons and tests and gold stars along the way. Make a plan and don’t be afraid to tweak it or abandon it altogether when it’s clear that is the best choice. As my friend Lauren says, “Prepare for all scenarios, balance risk vs. reward, and then follow your heart.”


One Response to “A Barefoot Stroll With Brenda Della Casa”


  1. Un Americana a Roma Interview | Walking Barefoot - August 25, 2013

    […] See the interview here (and be sure to check out her wonderful posts!) […]

Comments are closed.

%d bloggers like this: