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Jessica Dennehy of Pivot & Slay: “Women provide an amazingly unique perspective in the world of business”

Women provide an amazingly unique perspective in the world of business. Our experiences drive us to work more efficiently and to find symbiotic rhythms between the different parts of our lives. This makes for a very collaborative and open minded work place, where ideas are welcome and celebrated. Owning your own company also gives you […]

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Women provide an amazingly unique perspective in the world of business. Our experiences drive us to work more efficiently and to find symbiotic rhythms between the different parts of our lives. This makes for a very collaborative and open minded work place, where ideas are welcome and celebrated.

Owning your own company also gives you more flexibility to create a life that you control, rather than a job controlling you. It is a beautiful way to get women in the driver’s seat of their own life so they can craft an ecosystem that doesn’t otherwise exist in the corporate world.

Lastly, there should be more women of all varieties in leadership positions so that we can pave the way for the younger generations. It’s important for young women to see someone who looks like them achieving the things they’ve been dreaming about. Subconsciously it gives them the courage and confidence to take a risk and try it for themselves.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Jessica Dennehy, a business coach on a mission to help other entrepreneurs fulfill their dreams. Through her company Pivot & Slay, she coaches entrepreneurs to be adaptive and evolve so their companies can withstand the test of time. She helps structure companies, create processes to get businesses running more efficiently, and helps protect brands using Trademarks and other legal strategies that most small business owners overlook.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

My dream was to be a Wall Street attorney and for almost a decade, I was a regulator at the NYSE and FINRA. Nine years ago, I started a brick and mortar side-business — a brand of luxury barbershops. The business took off and I was able to leave my corporate job and pivot into entrepreneurship full time. We opened our second location in 2015 and then a third overseas in the Dominican Republic in 2017, which we sold last year. During the pandemic, I started helping local small business owners navigate the shut down and found that my true passion was helping other entrepreneurs emerge and succeed.

Can you share the most interesting story that happened to you since you began your career?

In 2017 we opened a third location of our barbershop in the Dominican Republic. There, the most effective form of advertising is on billboards. We did an entire lifestyle brand shoot specifically for these billboards making barbering sexy and appealing. We launched the billboards prior to our grand opening to get everyone excited for our launch. Seeing myself on a billboard was a surreal experience!! But even more interesting was when we went out to a local restaurant and people recognized me from the billboard! They thought I was famous and were star-struck!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

My first legal job was the summer after first year when I was clerking for a judge. At the time, I was binge-watching the “West Wing” because I was convinced I’d work for the government one day. For the first few weeks, I walked around the office like geek addressing the judge as “sir,” because it reminded me of how the president was addressed in the show. In the moment, I thought it made me seem really professional.

A week later, I ran into another law clerk that had already worked for this particular judge. He informed me that the judge was very casual and liked to be called by his first name only. Apparently, the judge took pity on me as a naïve first year law student and didn’t want to tell me to chill out and call him John.

Lesson learned — stop taking yourself so seriously. Be genuine and you’ll get more relationship equity than if you put on appearances. Since then, I’ve been my unapologetic true self (hence, the pink hair).

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My parents have been a pivotal part of my success throughout my life. Even when they didn’t quite understand or agree with my decisions, or when some of my choices went south, they always stood by me and had my back. Coming from immigrant parents and being the first in his family to go to college, my dad was especially motivated to give me easier access than he had to business opportunities. A lot of his own experiences an entrepreneur shaped the decisions I’ve made in my career. My mother’s dedication to helping me study from a young age and always pushing me to do better in school is what shaped my work ethic and ambition to always keep learning. As a solo parent, I’ve had to lean on my parents more than usual this year as I build my new business and travel often for speaking engagement and training. Without them, my new business endeavors would not be possible.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

The <G> Code by Ryan Stewman is one of my favorite books about mindset, not because it’s extremely motivating, but because it made me realize how strong I was already. In 2018, I began living my life in a more purposeful, positive way each day. Through mediation and yoga I was able to achieve a heightened state of awareness that allowed me to change my mindset completely. I began waking up at 5am to kick my day off with exercise, mediation and gratitude. The people around me didn’t quite understand it. It was something I felt naturally drawn to and that helped me achieve a more fulfilling and productive day. I read Ryan’s book shortly after meeting him and realized he had the same epiphany years ago during his own journey. His book so eloquently put my instinctive actions that I couldn’t describe into a succinct and relatable language. It reinforced my confidence that I could achieve even more if I kept it up.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

It is not a quote so much as a mantra I say to myself often: Start by Starting.

Many people never take-action because they are too busy overthinking. Start by starting. We cannot get caught up waiting for the perfect answer or perfect timing to present itself before starting. This only leads to indecision and procrastination.

I always choose “Done” over “Perfect.” Take a risk, do the work, and get it done. Even if you have to revise or correct something, at least you got the ball rolling. Small action steps lead to momentum so you can then begin to tackle the larger things that have you overwhelmed and stunted.

How have you used your success to make the world a better place?

Well, during the Covid Pandemic in 2020, our barber shops were shut down. We used our manufacturing contacts to procure 100,000 surgical masks at the end of March, before anyone really had access to them. We donated these across Nassau County Long Island to first responders, elderly, and other communities in need. I also began to provide free coaching for other small business owners to help navigate the closures, government loans applications and then eventually the reopening protocols. And lastly, as a 500-hour certified yoga instructor, I taught free community yoga classes virtually to help people keep a positive mindset and outlook.

Since then, I have been a guest speaker at local schools, Girl Scout events, Kiwanis club meetings, and empowerment podcasts to encourage others to embrace their entrepreneurial spirit.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Initially what held me back from founding my own company was fear that I would not be able to manage it all. I wanted to be a present parent but also have a successful career. I mistakenly believed that the way to do this was to work for someone else, so I could leave the office and shut off work. What I didn’t realize, is creating your own company gives you more flexibility to create a life and lifestyle that you control, rather than a job controlling you. It is a beautify way to get women in the driver’s seat of their own life so they can create an ecosystem that doesn’t otherwise exist in the corporate world.

Can you share with our readers what you are doing to help empower women to become founders?

I have been using my social media platforms as a way to inspire and encourage woman to take a risk and follow their dreams. I’ve been speaking to woman and also to Girl Scout groups about entrepreneurship and tips on how to get started and I’ve been encouraging woman to find a coach like me to help them avoid the trials and error that many business owners face. I use anecdotes from my own experience to demonstrate that business isn’t perfect. The woman you see in me now is not the same woman who started out years ago. I am imperfect, I made mistakes, I took risks, and I failed a lot before I became successful and confident. I want woman to see that. I want them to hear that and internalize it. The road to success is imperfect and bumpy, but the trick is to stick with it. Do not be afraid of making mistakes. Learn from them and grow stronger.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

Women provide an amazingly unique perspective in the world of business. Our experiences drive us to work more efficiently and to find symbiotic rhythms between the different parts of our lives. This makes for a very collaborative and open minded work place, where ideas are welcome and celebrated.

Owning your own company also gives you more flexibility to create a life that you control, rather than a job controlling you. It is a beautiful way to get women in the driver’s seat of their own life so they can craft an ecosystem that doesn’t otherwise exist in the corporate world.

Lastly, there should be more women of all varieties in leadership positions so that we can pave the way for the younger generations. It’s important for young women to see someone who looks like them achieving the things they’ve been dreaming about. Subconsciously it gives them the courage and confidence to take a risk and try it for themselves.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders? If you can, please share an example or story for each.

  1. Empowerment starts from within. Start Starting! We can easily get caught up in waiting for the right timing or right moment to get started. Now is the perfect time to take a step forward! Every small step you take towards founding a company will reinforce your goals and empower you to keep moving. Get the ball rolling with one small step and watch how much momentum you gain!
  2. Give Imposter Syndrome the Middle Finger! The voice we hear the most is our own, so it better be a good one. Keep it positive. Valuable people often worry that they aren’t worthy to be in the room with other valuable people. We worry that we don’t have enough to add to the conversation. We often think that the things we know are obvious or the things we’ve accomplished are ordinary. FALSE! There are people watching you that are in awe of what you’ve accomplish or the knowledge you’ve attained. You have different strengths than other accomplished people and just as you learn from them, they can learn from you. So start believing your worthy & get in those rooms now!
  3. Inspiring Others Sparks Inspiration! To all the Women Founders like me, get out there and start talking about your experiences in the business world. Collectively, we will help inspire other women to get started on this amazing journey! Someone, somewhere will feel connected to your story and look to YOU as a source of inspiration. It’s powerful to see a relatable person doing things you’ve been dreaming of doing. Subconsciously, it gives us the confidence to go out and try! Once you start shining your light onto others, the light will come back to you. You’ll find people reciprocating the positive energy & offering up some inspiration of their own to you. The energy is contagious and catapulting!
  4. Be Generous with the Knowledge — use your social media pages to give away small pieces of information that are helpful and add value to someone else in their come up. Be generous with it. Not only will this help you gain credibility in the marketplace, but it will help you build up the confidence to make your power move into founding a company of your own!
  5. Be Genuine. Start a company that accurately reflects you as a person and that you feel passionately about. This authenticity will shine through and attract the right people to your orbit. You cannot fabricate sincerity. When you create a company founded around your true self and true values, the right company culture and branding will follow.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Empowering the individual so that free thought and confidence can flow. Instead of trying to fit within a box of societal acceptance, let’s celebrate independent thought. Embracing our individuality will allow for creativity to flow and more humanistic, logical approaches to problem solving that I believe are underutilized right now.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to meet Lori Greiner. What I’ve always loved about her is that she is approachable and relatable, but continues to maintain her strength in a room full of powerful men. She is a force to be reckoned with: smart, accomplished and quick witted. But she conveys all of that with a feminine touch. So many female entrepreneurs think they have to ditch their feminine energy so that they can compete and thrive in a man’s world. What they don’t realize is that embracing your true self exudes a genuine confidence that no one else can replicate. Watching here makes me feel like I can do anything!

How can our readers further follow your work online?

If you’d like to know more about me and my coaching company, please visit my website and mention this article to get a free 15-minute Strategy Session. https://www.pivotandslay.com.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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