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Nov. 7, 2022

How To Live Life On Your Own Terms - Jessica Dennehy - Pivot & Slay

How To Live Life On Your Own Terms - Jessica Dennehy - Pivot & Slay

Starting a business is one of the ultimate dreams of every person. It is exciting to be your own boss and have complete control over your work and time. You get to decide when you start working, what hours you work, and make decisions on how you want to run your business.

Today on Beyond the Story Podcast, we are joined by Jessica Dennehy. Jessica is a best-selling author, business strategist, & speaker on a mission to empower leaders to Pivot their businesses & mindset so they can Slay their goals & enjoy the freedom that comes with success.  Through her company, Pivot & Slay, she helps entrepreneurs reach out of their comfort zones to find their authentic selves & start taking the risks necessary for success. As a yoga enthusiast, small business owner & former Wall Street regulator, her unique style guides entrepreneurs with actionable items they need to shift their mindsets & take their businesses to the next level. Her expertise & diverse background have landed her features in several media outlets, such as Forbes, NY Weekly, New York Post, Legal Zoom, LA Weekly, Authority Magazine, Women's Daily Magazine, CEO Blog Nation, Thrive Global, Billion Success & more! 

In this episode, Jessica talks about how she started her legal journey at Wall Street and found that she did not enjoy the experience as much as she thought she would. She discusses why she quit her job at Wall Street to start her own business with her ex-husband who was her partner. She also tells us about all of the important things that scare her and definitely leave us with important pieces of advice. Enjoy!


[01:27] How Jessica's legal journey started.

[03:46] How the law and stock exchange match

[07:19] Jessica's experience working on Wall Street, a predominantly male environment

[09:23] Jessica's experience starting a family while still at Wall Street

[11:53] Why did Jessica leave her prestigious job at Wall Street?

[12:24] First taste of business ownership

[13:00] What led to Jessica's divorce? 

[15:30] Jessica's opinions on what helped her and her ex-husband establish a successful business partnership.

[19:02] how Jessica learned about Apex

[23:26] Jessica’s experience on her personal journey of healing and becoming the best version of herself

[25:58] What scares Jessica the most

[30:22] Final thoughts from Jessica

[31:16] Hypothetical duet song of choice for Jessica

Notable Quotes

[00:01:59] “I want to understand something from a different perspective, and I feel like that helps me grow as a person. So, I don't say I guess you could say it's arguing, sure. But like it's not arguing because I want to be right. It's arguing because I want to grow.” 

[00:02:31] “You have to take a side when you're a litigator. But in order to really develop your case and like to cross-examine someone properly or close, using a closing argument, you have to understand and anticipate what the other side is going to bring to the table.” 

[00:04:05] “If you want to be an exchange-listed firm, you need to pay the exchange to be listed.” 

[00:08:00] “So the guys that I was dealing with from the floor, they don't like to be. They don't like to be in the room with a woman who's powerful. And I did not want to conform.” 

[00:08:26] “I think one of the major things that happened to me is that I was able to embrace the masculine energy that drives me to be really successful in life, but also harness that feminine side of myself and not lose it and not yield that to any of the people that I was working with. I just kind of use it as my superpower.” 

[00:11:11] “I kind of got the entrepreneurial bug in me and made me realize how miserable I was on Wall Street. And so finally we hit a point in that business where I didn't really need my job anymore.” 

[00:11:48] “We had started the business, but to be both all in 100% was very scary. So, I did it because my priorities had changed and my freedom became something that was really important to me, not just because I had kids and I wanted to be a great mom, but I also didn't feel aligned with Wall Street anymore.” 

[00:13:54] “I lost myself in being a mom. I was so guilty because I worked on Wall Street for so many hours a week and then I would miss all this stuff with the kids. [00:16:19] I think what ended up happening is we had mutually assured destruction. So, like if you messed up in the business or I messed up, then we both lost.” 

[00:20:51] “The one thing I love about business ownership is that I have the freedom to make as much money as I want on a timeline that matches my lifestyle. I get to go and enjoy my life on vacation when I want. I can work from anywhere, you know. I control my life so much more now and I only have to work with people I like.” 

[00:24:20] “So I'm much more carefree and flowy now and more like whatever is going to happen is going to happen. I'm just going to do the best that I can, and I'm going to keep moving forward.” 

[00:30:38] “No matter what you do, if you own a business or you don't, living a life that's authentic and real is the best thing you can do for your own happiness and the most. Most people who are miserable are miserable because they don't like themselves.” 


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