Jessica Dennehy is a business coach on a mission. She wants to “help other entrepreneurs fulfill their dreams.”
As an entrepreneur, Jessica Dennehy started Pivot & Slay. The company “coaches entrepreneurs to be adaptive and evolve so their companies can withstand the test of time.”
Likewise, at Pivot & Slay, Jessica Dennehy also “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.”
Before founding Pivot & Slay, Jessica Dennehy fulfilled her dream of working as a Wall Street attorney. For nearly 10 years, she was a “regulator at the NYSE and FINRA.”
Aside from Pivot & Slay, Jessica Dennehy also launched a “brick and mortar side-business—a brand of luxury barbershops.” This business found success, which allowed her to leave her corporate job and “pivot into entrepreneurship full time.”
In 2015, Jessica Dennehy “opened our second location.” In 2017, they opened their third location overseas in the Dominican Republic, which they later sold.
Later on, Jessica Dennehy found her life’s true passion, which is “helping other entrepreneurs emerge and succeed.”
Throughout her career, Jessica Dennehy learned the valuable lesson of not taking yourself so seriously. When you are genuine, you’ll “get more relationship equity than if you put on appearances.”
Check out more interviews with leading entrepreneurs here. You can also watch her here:
Lesson learned — stop taking yourself so seriously. Jessica Dennehy, Pivot & Slay
Jerome Knyszewski: 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?
Jessica Dennehy: 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.
Jerome Knyszewski: Can you share the most interesting story that happened to you since you began your career?
Jessica Dennehy: 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!
Jerome Knyszewski: 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?
Jessica Dennehy: 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).
Jerome Knyszewski: Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?
Jessica Dennehy: 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.
I always choose “Done” over “Perfect.” Take a risk, do the work, and get it done.
Jerome Knyszewski: 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.
Jessica Dennehy:
- 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!
- 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!
- 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!
- 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!
- 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.
Jerome Knyszewski: 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.
Jessica Dennehy: 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!
Now is the perfect time to take a step forward! Jessica Dennehy
Jerome Knyszewski: How can our readers further follow your work online?
Jessica Dennehy: 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.
Jerome Knyszewski: Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
