Jessica Dennehy: How Her Morning Routine Helps Her Achieve Business Goals
Welcome to the Course Creator Series, where you can learn directly from experienced course creators on how you can monetize and grow your online business.
I’m your host, Dr. Destini Copp and I help entrepreneurs scale their digital product revenue with automated sales funnels and reduce their reliance on 1:1 services or freelance work. Today, I had the pleasure of interviewing Jessica Dennehy.
Jessica Dennehy is a best-selling author, legal strategist & business consultant on a mission to empower entrepreneurs to shift their mindsets & overcome the inner hurdles that are holding them back. She left her career as a Wall Street regulator after almost a decade to scale her brand of luxury barbershops in New York, called MadMen. Now, she owns an entrepreneur coaching company called Pivot & Slay. As an advanced yoga instructor and corporate attorney, her unique coaching style intermingles self-development with the business & legal strategies necessary for success.
Please tell us about your business.
My company, Pivot & Slay, is a unique consulting brand that combines lifestyle coaching with legal and business strategies. I’m a corporate attorney by trade, so I am well-versed in business structuring, but I am also a yoga practitioner and advanced instructor. My legal background gave me the technical tools I needed for business, but my yoga journey has allowed me to develop the mental fortitude necessary to be a successful entrepreneur.
Although I established the company just one year ago, it has already made a significant impact in the coaching industry, especially with the launch of my book - Pivot & Slay - which hit bestseller the first day it was available.
Start at the beginning of your journey. What were things like for you? How did you feel? What was keeping you up at night?
In 2012, I started my first business while still working full time as a Wall Street Regulator. My then-husband and I had just bought a house and were one week away from having our first baby. But we saw an opportunity and jumped on it.
He had a great concept to open a luxury brand of barbershops, which was unique at the time because the barbering industry had not yet exploded. We happened to see a property that would work perfectly and, although the timing wasn’t ideal, we decided to take a giant leap and go for it. We opened our first luxury barbershop in New York called Mad Men.
Working full time while owning a business was not easy, even with my partner in the business full time. There were many moments where we had to improvise and pivot, especially since we were working with a tight budget.
What kept me up the most at night was thinking about finances. I wasn’t sure how we would afford the rent if the business didn’t do well. I was scared we would drain our savings floating the company until it was profitable. In any environment, thinking about using up your savings is scary, but this was incredibly stressful to me as we were about to have a newborn and recently purchased our first home. There were a lot of life-changing events happening at once, and it could have all went so very wrong.
Instead of constantly worrying, I change my perspective to think of the immense upside potential the business could have if we were successful! That mindset pivot got me through some sleepless nights.
Thankfully, our hard work paid off, and the concept was well-received. Within three years, I was able to leave Wall Street and jump full-time into the business.
We expanded to a second location in New York in 2016 and a third in the Dominican Republic in 2017, which we later sold.
During the pandemic, the shops were shut down, and I had to PIVOT. I realized I had so much business knowledge between working on Wall Street for nine years and running my own business for 8. I decided to start consulting with other small business owners about how they could adapt to the post-pandemic landscape and not just survive but thrive. And that is when Pivot & Slay was born.
At what point did things change for you? What was the pivotal moment?
Before the pandemic, I didn’t give myself enough credit for the knowledge I had accumulated throughout my diverse career. It wasn’t until I was unemployed that I realized my self-worth. This was a massive lesson in mindset for me.
I could have caved under the pressure of temporarily losing my income and businesses. But instead, I rose from the ashes, fully prepared to do whatever it took to provide for myself and my two daughters.
I started to post tips on social media about applying for pandemic relief, and suddenly my audience from all over the country was asking me for business advice. I quickly established myself as a reliable source for guidance and garnered the trust of my audience. This made me realize that my diverse career had afforded me knowledge that many other business owners did not have access to.
I spent months coaching clients for free while they navigated the shutdown.
After states began to reopen, I decided to formalize my business and coach entrepreneurs to pivot their mindsets and succeed no matter the circumstances.
What are some of the best ways you’ve found students for your online course(s)?
Social media is the best way to organically grow your business and find students for your online courses. Groups on Facebook are beneficial. Rather than cold-pitching your course or services, go into a group and add some value consistently. This will help people get to know you and eventually trust you enough to purchase something.
What is your entrepreneurial life like today? What pain points have vanished? How have things improved?
The pain points don’t vanish. They get easier to deal with because your perspective has shifted, and your mindset grows.
My entrepreneurial life improves daily because I improve myself daily. Often, entrepreneurs dream about the endpoint. They have goals, and they focus on checking those goals off a list, thinking that this is the end of the list is the finish line. But guess what? There is no finish line.
I wake up daily ready to Slay and then figure out how I will make that happen.
The mindset shift is what makes the pivoting acceptable. I managed my expectations by telling myself every day will be a new learning experience.
The comfort zone is an entrepreneurial dream killer. To keep growing, your goals should continuously evolve and challenge you to be a little better than you were the day before.
Have you pivoted in your business?
Constantly. If you aren’t pivoting, you aren’t developing. To me, a pivot is a purposeful turn you take so you can overcome a hurdle that is blocking your path to success.
Every entrepreneur in every industry faces hurdles. If you are not willing to adapt, you will surely fail. The trick is always to be open to changing things up on the fly. This will help you slay it, no matter what is going on around you.
What are your best tips for growing your online course business organically?
Use social media to grow your online course organically. It’s a free platform with a limitless audience. Post consistently and be interesting. Let people get to know you, even if what you are saying or doing isn’t related to your course or business.
People buy from people they like. The audience wants to know you personally before they will trust you enough to make a purchase. If you work daily to build a brand for yourself on social media, organic growth will follow.
What’s your favorite launch strategy? Webinars, Challenges, Video Series, etc. Why do you like this approach?
Video content is my favorite for a launch. It’s more engaging and interesting for the consumer and gives you a lot of latitude on how to creatively approach a sale.
How do you stay focused and productive in your business? What advice do you have for new entrepreneurs?
I believe in the power of a morning mindset. When I start the day with a positive routine, I am my best self. I advise all my coaching clients to get in the habit of developing a morning routine that will set them up to be in the most productive mindset for the day.
For me, this includes an early rise and 90-minutes of exercise first thing in the morning. I follow that up with a ten-minute meditation and then write down five things I am grateful for.
This morning routine is a non-negotiable part of my day. I am disciplined with it because I know that without it, the day doesn’t go as smoothly as it could.
After that routine, I am my most elite self for the day. My focus is precise, which helps me reach my goals for the day more efficiently and effectively.
What do you see as the next steps for your online course business?
I am already developing another course that will launch later this year. It takes new entrepreneurs through the details of how to start up a new business venture and what to expect in the first 12 months after you launch. It will be financially accessible because I love small businesses and want new entrepreneurs to be enthusiastic about ditching their corporate life and taking control of their careers!
What is your favorite quote or business book?
My favorite business book is UnF*CK Your Business by Tomas Keenan. Tomas is a beast when it comes to establishing core values for your business and implementing processes that will help your business sore. Every business owner should implement his strategies because they work for any industry.
What advice do you have for other online course creators/entrepreneurs out there?
Stop waiting for the perfect time to get started. Create your content and put it out there. If the topic is relevant and the purpose is clear, people will purchase it. The only one who will see the imperfections is you! Remember that imperfect action is always better than no action.
How can people find you to learn more?
If you’re interested in working with me or learning more about what I can offer you, visit my website https://www.pivotandslay.com/.