Jessica Dennehy is a business and legal strategist on a mission to help entrepreneurs reinvent themselves, transform their ideas into successful companies and scale their businesses. Through her company Pivot & Slay,™ she coaches business owners on how to keep their companies efficient and evolving.
As a serial podcast guest, Jessica discusses the positive impact fitness and mindset have on success. She is a 500-hour certified yoga instructor, teaching private lessons to entrepreneurs who want to cultivate the right mindset for business leadership. Jessica also writes a monthly business column called Soul Proprietor. She left her job as a regulatory attorney on Wall Street after almost a decade to become her own boss and scale a brand of luxury barbershops in New York.
What is Pivot & Slay about?
During the pandemic, my barbershops were shut down, so I started to make videos on my Instagram to help other business owners navigate the closures and apply for PPP & EIDL Loans. When these businesses reopened, they looked to me for advice on how to stay fresh. Many of my followers also wanted to diversify their income by starting up new businesses. I loved helping small businesses so much that it inspired me to become a coach and help other entrepreneurs succeed. Pivot & Slay was born!
Tell us a little bit about your personal background – how you ended up in this career?
My dream was to be a Wall Street attorney, and for almost a decade, I was a regulator at the NYSE and FINRA. Eight years ago, I started a side-business – a luxury barbershop. 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 shutdown and found that my true passion was helping other entrepreneurs emerge and succeed.
What was the biggest problem you encountered starting up, and how did you overcome it?
The inevitable nay-sayers telling me how crazy I was to open a business. I overcame this by tuning them out. I had the confidence to trust my gut and ignore the people who wanted me to believe that I couldn’t Slay It. Remember, to change the path of your life, you’ll have to get out of your comfort zone and go against the grain. This is part of the process. Have the confidence to take the risk.
What are some of the Dos and Don’ts of being a business and success Coach?
You must have a positive outlook and make sure when you are providing insight, it is always in a constructive way with an actionable piece of advice the client can utilize immediately.
Otherwise, we are just critiquing someone, not coaching them.
Do you have any other projects or businesses you working on?
In addition to Pivot & Slay, I own two brick and mortar barbershops, write a business column for a publication out of Brooklyn, I’m a 500-hour certified yoga instructor, a single mom of two beautiful daughters, and I won’t stop there either. I hope to add two additional revenue sources to my income by the end of the year.
How do you stay driven and motivated to keep going in your business?
I love to challenge myself and keep learning because that is how I continue to grow. This motivates me daily. I enjoy seeing how far I can push myself, my business, and my achievements. I love adding unique value to someone else’s life and journey.
What is the one thing you wish you knew before starting your career as a coach?
Business is a constant evolution; a journey with no end. If you set out thinking that one day you will have achieved enough or you’ll be able to coast along, then you don’t have the correct mindset to be an entrepreneur.
What has been your most effective marketing strategy to gain new clients?
The best marketing strategy is to add value to someone’s life at no cost. When you start to do this through your social media platforms or exploratory calls with new contacts, the person will remember it.
They might not become your client right away, but they will keep watching what you’re doing. They’ll keep remembering your generosity and insight. And one day, when they need your advice, they won’t hesitate to pay for it.
When is the ideal time for a new entrepreneur to hire a business coach?
NOW! A business coach is the shortcut you need to get results faster. They can synthesize your hurdles into succinct and tangible action items that will help you skip the trial and error most entrepreneurs face. Collapse time and hire a coach.
What are some of the reasons you would refuse or stop working with a client?
If a client isn’t willing to do the hard work, they’ll never achieve success. So many people get hung up on the details, rather than taking action and tweaking along the way. If a client doesn’t consistently perform the action items we agree upon, then they aren’t worth my time because they aren’t putting in the work necessary to achieve results.
Similarly, if they expect me to do the work for them, they are looking for a business partner, not a coach.
That is a different story altogether.
What is your definition of success?
My definition of success is having the freedom to choose when and how you work so you can make a lot of money on your own terms and still enjoy other important aspects of life. A well-rounded life is a key to happiness.
What are three things most clients have in common?
They don’t get started because they are too busy overthinking. When a client tells me they are struggling, I say – start by starting. We don’t get anywhere if we don’t take action. People get caught up in the “how” and wait for the perfect answer or perfect timing to present itself before starting. This is a huge mistake and only leads to indecision and procrastination.
I always choose Done > 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.
What’s your best piece of advice for people who are just starting their coaching business?
Not all business is good business. Vet clients properly to make sure they are a good fit for your personality and are willing to do the hard work it will take to succeed. You have to hire them as much as they have to hire you.
How can readers get in touch with you?
Readers can contact me through the contact form on my website JessicaDennehy.com or via email at JessicaDennehy @ gmail.com.
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