Entrepreneur and author Jessica Dennehy is redefining the word selfish to help people reconnect to themselves and live a happier life!
Jessica Dennehy, author of the new book Selfish is a Superpower, is redefining the word selfish to help people reconnect to themselves and live a happier life! Jessica’s journey, navigating through highs and lows, triumphs, and setbacks, offers a fresh perspective on the entrepreneurial landscape. Even through a painful divorce that left her as a solo parent, a major career change, and the stress of building multiple businesses, she was able to thrive and reconnect with her purpose and passions.
Timeliness and Relevance: Jessica’s innovative (“selfish”) approach and forward-thinking strategies are both timely and relevant in today’s rapidly evolving business landscape. Her story will resonate with readers who are eager to make their mark in the business world.
Personal Connection: Jessica has made a significant impact in front of audiences across the country as she connects with people using personal anecdotes. This personal touch will create a deeper engagement with your audience, fostering a sense of connection and inspiration.
Jessica’s story is not merely about business achievements; it encompasses personal growth, resilience, and the pursuit of a higher purpose. With her diverse background, from business and entrepreneurship to personal development and self-improvement, Jessica is a powerhouse who knows how to captivate a crowd and leave audiences feeling inspired and energized.
Can you introduce yourself and tell us about your inspiring story? We’d love to learn more about how you got to where you are today.
I am Jessica Dennehy, a best-selling author, national speaker, owner of multiple businesses, and solo mom to two amazing daughters.
I’m a recovering attorney who left an unfulfilling career on Wall Street to prioritize the things that lit me up and create a life full of joy, adventure, and success. I took a chance on entrepreneurship to build my own brand of luxury barbershops in New York, called MadMen.
After scaling that business, I founded my own consulting company, Pivot & Slay, became a published author, and began speaking on stage.
The more I shared my story publicly, the more my followers cheered me on and were inspired to achieve their own big dreams. This fuels my desire to reach even more people with a NY Times best-selling book and a spot on a national talk show.
Living my life and running my companies in a way that is most meaningful to me, while finding harmony between having fun, being present for my daughters, and still maintaining my passion for success is the ultimate win!
What made you decide to go into business for yourself?
Eight years into my legal career, I began to feel a little less inspired and enthusiastic about work. I had really maxed out in my growth there, but I was about to start a family and didn’t have the courage to think about what other possibilities I could explore for work.
At the same time, my then-husband conceptualized a business idea for a luxury barbershop and found the perfect location. Something inside of me told me to go for it, even though I couldn’t pinpoint why. And that was the beginning of my journey into entrepreneurship.
When did you know it was time to become a full-time entrepreneur?
About 3 years after opening Madmen, we had grown to the point where we could open a second location. In order to expand the business successfully, we knew we needed all hands on deck. Plus, if I worked for our business, I’d be able to control my schedule more and also have more time to be with my daughters. That was really the driving force for me because I was struggling to find that perfect harmony between work and family while on Wall Street.
What are 3 websites or podcasts you can’t imagine your day without?
I’m kind of an old soul and don’t really surf the web or listen to podcasts to find inspiration or to learn.
Instead, I can’t imagine my day without a good book. I love reading for fun as well as for personal development. I draw the most knowledge and inspiration from reading, so I always have two books on hand to dive into.
I find psychological thrillers to be really fun to read. It activates my brain to see the foreshadowing and collect the clues through the story. Thinking and guessing my way through the book is not only fun, but it helps me develop critical thinking skills.
When I read for personal growth, I don’t reach for the “rah-rah” books meant to ramp up my enthusiasm. I prefer ones for mindfulness and spiritual growth. One of my challenges as an entrepreneur was learning how to tone down being overly disciplined and controlling. Reading has helped me develop my ability to sit in the quietude and connect more deeply to myself, improving how I manage my emotions.
I’m currently reading You Are the Placebo by Dr. Joe Dispenza. I also enjoyed The Untethered Soul by Michael Singer and The Emotion Code by Dr. Bradley Nelson.
What are your top 3 mobile apps that help you stay organized and on top of your game?
When it comes to staying organized, I prefer a tactical and minimalist approach. Technology has me looking at my phone too much, so I try to stay off apps as much as possible, which helps me focus and get things done without distraction. I even turn off my phone notifications to supercharge my productivity.
My top 3 must-haves are my Google calendar, a hand-written planner, and a weekly whiteboard calendar.
I spend some time on Sunday nights or early Monday morning writing out everything I need to do for the upcoming week so I can hit the ground running on Monday morning- no time wasted! Writing it all by hand in my planner and on the whiteboard keeps me aware of what I need to get done.
How do you use social media in your business?
Social media plays a key role in my marketing and it’s one of my favorite topics to talk about! I use it in a fun way to educate my audience on what I do while allowing them to connect with me. My followers get to peek into my life and be part of the fun I have with friends and family, get inspired to dream big and achieve their own goals as they watch me achieve mine, and recognize that everyone has setbacks as I share my challenging moments.
Showing up genuinely in this way on social media allows me to cut through the noise and reach my ideal audience that vibes with my brand. It also allows me to make connections and opens opportunities on a broader scale than if I relied solely on in-person networking.
What social media platform is the best for business growth and why?
The best platform is the one to which you can commit to having a consistent daily presence. Every business is unique and will have a specific ideal client they are trying to reach. The message is more important than the platform. Begin using the platform you are most comfortable with so it will feel effortless to establish the habit. The key is to be genuine! Create thoughtful posts that align with your personal and brand values so your ideal client will be attracted to you. Once you’ve developed a consistent habit of posting and gained traction, move on to other platforms.
How do you boost your self-esteem in moments of doubt?
When I’m feeling doubtful, I take some time to get quiet and tune into myself. I tap into my good habits like meditating and journaling. I remind myself of my own resilience, of all the times I didn’t know what I was doing but I took a chance and learned along the way. Focusing on my past successes helps me push through the doubt because I know if I did it before, I can do it again.
How did you market your business when it was brand new?
When we opened our brick-and-mortar barbershop in 2012, our budget was almost non-existent. So, we handed out flyers door-to-door, and this was the initial marketing for Madmen since there was no budget for mailing. Keeping close ties with other business owners in the community and using organic social media played a role in marketing the barbershops. 13 years later we are able to have a consistent marketing budget that includes social media marketing, text message marketing, and traditional mailers too.
When it came to Pivot & Slay, I first relied very heavily (and still do today) on organic social media growth. Now, I also mix in some organic press, which has helped expand my reach a lot.
What are the three most important habits to be a successful entrepreneur?
Habits in one area of your life reflect and apply to other areas too. Successful entrepreneurs are consistent, they take action and evolve constantly.
Consistency keeps you on track and allows you to recover from obstacles more quickly. Indecision is a momentum killer in business. When you take action, even if it’s not perfect, will result in either success or a lesson learned.
Evolution is necessary to stay relevant in the ever-changing business landscape or you will face stagnation. Mastering these habits will propel your business forward and will help you win in other areas of your life as well.
What is a typical day like for you?
My day always begins with the same elements, but in various order depending on how I feel when I wake up. Each morning it’s important that I work out. Cardio and yoga clear my mental clutter as I focus on one thing in the moment: stretching and making my body stronger.
I meditate after my workout, then head outside to drink coffee and read a few chapters of a psychological thriller or self-development book. A solid morning routine starts my day off right.
I practice energy batching throughout the day to be the most productive with work. I focus on the task that is the best use of my energy. Whether I’m writing, recording podcasts, or visiting my barbershops, I do that all day. These tasks require specific energy and it’s easier for me to stay on target once I’m in the mode.
Each day I make time for some fun! I might spend an hour at the beach, take a walk on the boardwalk, soak up the sun for 20 minutes, or sometimes I’m able to take a full day off to have an adventure with my girls. Making time for fun is how I maintain a high vibration and positive energy for my family and business.
We all face challenges, but looking back, what have been some of the biggest challenges and pitfalls you’ve had to navigate?
The number one pitfall in my life was navigating my divorce. I had just left behind my corporate career to go all in on the barber shops. Just as I was trying to get my footing in a new career identity, the rug was pulled out from under me in my marriage. This momentous occasion changed who I was as a person.
Instead of getting stuck in self-pity, I turned the microscope on myself in a way that helped me understand what my contribution was to its demise. Slowly tackling one detail at a time, rather than being overwhelmed by all the things at once, I considered what I should have done differently and what I could change for the future. Baby steps toward the positive kept me from negative self-judgment.
Another pitfall was when my barber shops shut down during COVID. I had to make a conscious choice to find a way to create income for myself during the time we were uncertain when, or even if, the shops would reopen.
As the weeks and months passed, it became more difficult to envision how we would be able to financially support the business. I had to care for my children at home and I didn’t have the security of knowing that a job with a steady paycheck was waiting for me when the world returned to normal.
I had to create a business out of thin air in a moment when people were afraid to spend money because they weren’t sure where their next paycheck was coming from, You couldn’t create a physical presence due to the COVID restrictions, and I couldn’t be certain the business I spent a decade building would rebound. This period was a true test of mental fortitude.
Can you share some of the most important lessons you’ve learned from your successes and failures in business?
I’ve learned that there are two outcomes to every action or decision- you either win or you learn. Keeping this mindset as an entrepreneur has allowed me to propel myself out of my corporate job and achieve amazing things. Fearing failure will keep you stuck and unhappy.
A very important lesson I learned early in my entrepreneurship journey was that anything is possible when you let go of your fear of failing and take action on your ideas, even if people think you’re crazy! I took enormous risks to leave my previous corporate career to open a niche business. If I had let my fear of failure and the negative comments from family and friends keep me from that opportunity, I wouldn’t be where I am today.
Listening to your gut instincts is also incredibly important and often overlooked. People spend too much time worrying about what others think rather than leaning in on what they truly feel is the right decision. They allow outside noise to keep them from paying attention to their own “knowing”.
How do you prioritize self-care and well-being while managing the demands of your business?
You won’t have a successful business if you don’t prioritize your own well-being. What’s even worse is you will lose all of the magical energy that makes you unique if you always put the demands of life and business first.
Self-care doesn’t have to take a lot of time. I started with something small, waking up earlier than my children to have quiet time to myself to think about what I really wanted in my life. Not long after, I found something that reignited my inner fire- helping small business owners and speaking on stage. This was just the start, but the result was more joy in my life, more meaningful conversations with my family, and more enthusiasm in my business.
Getting organized, delegating responsibilities to others, and scheduling self-care are key to making it happen. I set up systems so my business can run without me, even if it’s for a short period of time.
Recently I had to take a hard look at things that were keeping me busy but not propelling me forward or contributing to my happiness. I made the decision to cut out some things so I could focus on projects and people that are important, including me!
What advice would you give your younger self when starting this journey?
It’s so important to learn how to trust your gut instinct. As an entrepreneur, you’ll often be faced with making important decisions quickly. If you wait until you know every aspect of something before you make a move, opportunities will pass you by.
What initiatives or actions do you believe are crucial for fostering a more supportive and inclusive business environment for women?
The biggest initiative we can create to foster a more supportive and encouraging women’s business environment is what I discuss in my new book is using “selfish” as a superpower.
I’m redefining this word because it’s so important for women to realize that being selfless all the time is a detriment to your family. By putting others first all the time you are going overboard in the giving department and unintentionally teaching your children that it’s ok for them to always put themselves last in order of importance. I know most women do not want to teach that to their children.
The reason I wrote Selfish is a Superpower is because I want to remove the societal stigma attached to the word selfish. When used strategically, selfishness is an amazing attribute that elevates your happiness. When you come to the table in your business, your brand, and your family as a happier human being, you are actually doing something selfless because you are pouring into your family in a more enthusiastic way.
It’s okay to be selfish sometimes. Take moments during the day or week to do something good for yourself. Be the example to lead a life that lights you up.
Your children don’t do what you say, they follow your example. Show them that it’s okay, it’s actually necessary, to put yourself first sometimes so you can show up in your life as your best self, the best spouse, the best businesswoman, the best parent.
That is the most impactful thing we can teach the female business community and that is why I wrote this book.
What challenges have you faced in the workplace, especially your experience in male-dominated environments?
Challenges in the workplace in male-dominated industries are no stranger to me! Men have underestimated me since my first job in a hardware store at the age of 16. The treatment continued in the legal field, at the NY Stock Exchange, and in my barber shops.
At first, it made me angry and frustrated to not be taken seriously. But I realized I could convert this poor behavior toward me into something positive that drives me forward. Once I removed my emotional reaction, I found it amusing that I could be viewed in such a cavalier manner by others despite being smart and successful with a bright future ahead.
I decided it didn’t matter what these men thought and instead found creative ways to use it in my favor. I became competitive with myself, measuring myself against yesterday’s version of me. Had I not faced this challenge daily early on, it would have taken me much longer to learn this lesson.
When I finally got to my dream job on Wall Street, others would treat me like a joke. Little did they know I would soon flex my underdog powers and sweep the floor with them. Stockbrokers were typically egotistical, narcissistic men I was a young woman, fresh out of law school, considered green and inexperienced. I used my intellect and drive to catch them off-guard and excel.
By the time I ran my own business, I had harnessed the power of being underestimated. Most of the staff and customers in barber shops are male. I was often mistaken for the front-end staff because of my helpful nature. Sweeping floors and serving espressos earned me the title of “hon” and paid me with snapping fingers and entitled demands. I held my head high and kept my response sweet. Once they realized I was the business owner, their demeanor shifted, and they felt silly for behaving poorly toward me.
You can’t change the behavior of people who are closed-minded or short-sighted, but you can change your approach. Your presence and energy are strong and confident when you stand in the power of your best self, regardless of how others act. Your light shines brighter. People see that, they feel it. I don’t have to prove myself to anyone but me!
How do you leverage technology and innovation (like AI) to stay ahead in the rapidly evolving business landscape?
I leverage social media to create new relationships with people of notoriety like Michael Strahan and Louis Gregory. Rather than it being simply a source of entertainment, social media elevates my networking abilities. The real-time aspect of social platforms gives me the edge to open doors to new opportunities and collaborations, as well as make quick decisions based on timely events.
Can you share any specific examples of how you have successfully built and maintained strategic partnerships or collaborations?
When I began hosting free monthly events for entrepreneurs, I quickly outgrew the first venue and needed to find a new location. A guest in attendance at my first event introduced me to the owner of a beautiful restaurant and event space. Chef Eric and I connected and became close friends. He loved my mission to help business owners and offered his venue for my use.
Our partnership gave me a proper space to help business owners learn, scale, and grow, and it brought exposure and business to Chef Eric’s restaurant on a night that was typically slow. Undoubtedly, we both gained in other ways as well through the connections and conversations made during the meet-ups.
It is through genuine networking that I was introduced to Chef Eric. Taking the time to build relationships with other business owners, share knowledge, and provide value has been key to developing partnerships that have helped me grow.
What advice would you give to a new business owner?
Being around the right people will get you to success much faster. Surround yourself with people who challenge your thinking and encourage you to see your greatest potential. Take the time to build real connections with others who are more successful than you, learn from their experiences, and leverage their knowledge to elevate your own growth. Successful entrepreneurs remember the early days and many are willing to help you navigate this new journey.
Which female leader do you admire, and why?
You’ve heard the term “right-hand man”? The female leader I admire the most is the right-hand woman! CEO Constance Schwartz-Morini is a prime example that you CAN have it all, a principle that I believe in deeply and use as a guide for life. This multi-dimensional powerhouse excels in business, family, and life.
She stands in her power as a woman as she walks through the masculine worlds of sports and entertainment, guiding notorious legends like Michael Strahan and Snoop Dogg to their next level of greatness.
Leading the way for women who want to break into male-dominated fields, she reminds them not to leave their femininity behind as they shake up the “boys club”.
Constance Schwartz-Marini doesn’t need to flex her inner boss, her confidence and intellect are at the forefront of an amazing career, balanced by a fun and love-filled personal life she proudly shares snippets of with the public.
She embodies the qualities I stand for, creating her best self by harnessing both her masculine and feminine energies, and showing what you can achieve when you let your light shine.
What would you consider your biggest accomplishment and why?
My biggest accomplishment is creating a happy life for myself so I can show up better in all ways, including being an example for my daughters. Prioritizing myself in a way that creates a positive impact on the people around me, building businesses despite the doubts and haters, and going for my dreams shows my daughters that they really can have it all. I am proof to my girls that leading a happy and fulfilling life is important and within their reach. My successes give them the confidence that they can achieve it too.
How do you set your business apart from others in your industry?
My business is a reflection of my personal beliefs and values. In a time when so many public figures create a persona for the outside world that is different from who they are in private, I have built an authentic brand. You know exactly what I stand for, which allows me to attract and work with clients who are aligned with my brand.
Do you have a favorite quote or motto that inspires you?
Pivot & Slay, of course! It’s the power to adapt to whatever life throws your way so you can reach your true potential.
Want more inspiring interviews? Check out our Interview with Founder Alison Martin on Fostering an Inclusive Environment, Dr. Sonia Chopra’s Toothaches to Triumph Story of Struggles and Success, and Sara Sutton Fell Founder and CEO of FlexJobs Who’s Making Meaningful Work From Home Happen, part of our interview series spotlighting successful women in business.
Melissa Stewart is the founder of SheOwnsIt.com. She is a Purveyor of Possibility, Entrepreneur Advocate and Coffee Addict. She believes that behind every successful woman is her story. What’s your story?
