IAM1384 – Best Selling Author Empowers Leaders to Pivot their Businesses

Jessica Dennehy is a 2x best-selling author, speaker & coach on a mission to empower leaders to Pivot their businesses, Slay their goals & enjoy the freedom that comes with success. Through her company, Pivot & Slay, she helps entrepreneurs embrace their CEO Power, exit their comfort zones, and start taking the risks necessary for success.

• CEO Story: Jessica had an amazing career as a Wall Street attorney. But suddenly she felt she was in a cage and didn’t have all the freedom that she wanted. Seeking the freedom to enjoy her life, the small business opportunity came, and later on, she is helping other business owners achieve their success.
• Business Service: Coaching entrepreneurs where they can get stronger and more confident.
• Secret Sauce: Being an authentic person, genuine and flawed, and showing the fun side to the clients.
• CEO Hack: Having the morning to yourself – a moment with yourself alone- no phone, emails, etc. exercise, or meditating.
• CEO Nugget: It’s better to make a mistake and learn a lesson than to just sit stagnant waiting for the perfect moment.
• CEO Defined: Alignment. Having the time and freedom that you want. Freedom to work with clients you are connected to.

Website: pivotandslay.com

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Transcription

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00:25 Intro

Do you want to learn effective ways to build relationships, generate sales, and grow your business from successful entrepreneurs, startups, and CEOs without listening to a long, long, long interview? If so, you've come to the right place. Gresham Harkless values your time and is ready to share with you precisely the information you're in search of. This is the I AM CEO Podcast.

00:53 – Gresham Harkless

Hello. Hello. Hello. This is Gresham from the I AM CEO podcast. I have a very special guest on the show today. I have Jessica Dennehy of Pivot in Slay. Jessica, it's great to have you on the show.

01:02 – Jessica Dennehy

Thank you so much for having me. I'm excited to be here.

01:04 – Gresham Harkless

Yes, I'm excited to have you on and absolutely love your name and jumping in a lot more to all the awesome things that you're working on. But of course, before we do that, I want to read a little bit more about Jessica so you can hear about some of those awesome things. Jessica is a two-time best-selling author, speaker, and coach on a mission to empower leaders to pivot their businesses, slay their goals, and enjoy the freedom that comes with success. Through her company pivot and Slay, she helps entrepreneurs who embrace their CEO power exit their comfort zones and start taking the risks necessary for success. Jessica, I appreciate you again for being on the show. Are you ready to speak to the I AM CEO community?

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01:41 – Jessica Dennehy

I am so excited and ready, yes.

01:43 – Gresham Harkles

Awesome. Let's do it then. Let's pivot this podcast, as I like to say. So to kind of kick everything off, I wanted to rewind the clock and hear a little more about how you got started, what I call your CEO story.

01:43 – Jessica Dennehy

Oh, okay. So. Well, I didn't plan on becoming a CEO. I actually started out wanting to be a lawyer, and I worked my whole life trying to do that, and I did it. I ended up as a New York stock exchange regulator for ten years, which was a really exciting and amazing job until suddenly I felt really caged and I didn't have all the freedom that I wanted. I didn't know that the key to opening up that door of freedom would be entrepreneurship, but I kind of stumbled into it just because I was feeling all the fields. You know, I wanted to work on my own terms in a way that was aligned for me with people who were aligned with me, and I just wanted to also have the freedom to enjoy my life.

And so as those feelings were pulling on my heartstrings, an opportunity had come up to dive into the small business arena. At the time I was married and my husband had this idea for a luxury barbershop. And so I was like, all right, cool, let's do it. So I kind of, had, like, a loose interaction with it at the beginning, mostly just like investor-related and spouse support. But as it developed and grew, I took on a larger role and was eventually able to leave my nine-to-five and kind of go all in on scaling that business.

And I realized I had learned so much through my years on Wall Street that helped me become a business owner and do it better, and then ten years in that small business, growing and scaling it. So I decided to help other entrepreneurs and small business owners do the same thing for their business so that they can find the freedom and enjoyment that I found from it.

03:36 – Gresham Harkless

Nice. I absolutely love that. And two things that kind of stuck out to me. You know, first of all, you just the, I think the transferable skills might be the word that I'm thinking of. And I think so many times when you're starting something new, we sometimes forget that our experiences before, as you mentioned, that Wall Street experience actually helped you out with your business. And I think that's something that we often think that, okay, I'm doing this position, this career, so that has nothing to do with my next career, but it all kind of goes together as it happens to in life.

04:03- Jessica Dennehy

Absolutely, I agree. And it's not something, you know, until it's happening to you and you pull from the toolbox that you've been building and you're kind of like, oh, this is applicable to so much other stuff in my life. And that's the beauty of business. And what I tell my coaching clients at Pivot and Slay is, you know, business is business. You're all in different industries, but you're all going through the same kinds of struggles, and the same kinds of skill sets are needed to build upon your business and really grow it. That's. And that's the beauty of it all.

04:36 – Gresham Harkless

Yeah, absolutely. And I love, you know, that toolbox kind of analogy as well because one of the other things I was going to say that really kind of stuck out to me is that often we go through things in life and we're not sometimes sure, like why we're going through those frustrations, troubles, sometimes the great things. But I love how you have your own toolbox that you sound like you've accrued over the years and experienced. And a lot of times that toolbox is so that you can kind of give that value and help out so many other people. It sounds like you've had that experience.

05:03- Jessica Dennehy

Absolutely. And it actually, that kind of transpired during COVID because, you know, businesses were shut down and I was applying for loans for my own small businesses. And I'm like, man, this stuff's so hard to understand. And I'm trained to read legal documents and I'm still confused. So how's the average business owner going to, like, like, go through this, especially during a really stressful time? So I started to just help people for free, help them navigate that. And then it made me realize, like, wow, as a lawyer, I have a lot of knowledge to offer in the business world that other people would not necessarily know or have access to.

So that I think, for me, was an eye-opening moment of how much value I actually had to add to the world. Because so many times we think of the things that we know and we say, oh, that's just normal. Because it's normal for us, but it's not normal. Whatever you know is so specific interesting and unique to you. And if you start to share that, you'll realize how much value is inside of those things, you find routine.

06:12- Gresham Harkless

Yeah, I love that you said that because, you know, we have our quote-unquote zone of genius. And the thing that we really do with effort and ease, I wanted to drill down a little bit more, hear a little bit more about your business, see how you're serving your clients, and how you're making your impact for them.

06:26 – Jessica Dennehy

Sure. So pivot. And Slate is really geared towards entrepreneurs who have kind of hit a wall. They've taken the business as far as they can with their natural skill set, and they need that third-party neutral perspective to help them see where they can fill in the gaps and really start to take off. And my approach to business and life in general is, I believe that, yeah, we need those skills that relate to business strategies and we need to implement those things. But if you're not showing up as your most empowered CEO self, your company and your brand are really going to suffer. And it's a part that a lot of people skip. They just go straight to the doing right. They want the strategies.

They want to know what they could do next, but they're going through the motions. They're not really living it in a real, genuine, authentic way. And so my coaching style is, let's work on where you can get stronger and more confident as a CEO, and then you can bring that energy to the company. And when we start to implement these business strategies that I have, you know, that I've used myself and have helped other people use, they'll be stronger, and they'll be more intent, intentional, and purposeful, and it'll get you a lot farther, a lot faster. So that's my strategy, and I think it's a fun group of people to work with because they see it

. They're so close. They're standing on the edge of greatness, and they just don't know how to make it happen. They have the moving parts. They just have to get that focus back and get it all moving in the right direction.

08:04 – Gresham Harkless

Yeah, it definitely sounds so exciting, especially if, you know, as you said, you're standing on the, on the precipice, I guess, of really, you know, taking it off and you feel like you just hit this wall, but you're not sure exactly, you know, what exactly to do. So I know you help your clients in terms of figuring out, you know, what, you know is their thing that kind of sets them apart and makes you unique. So I want to ask you, what for your thing? What do you feel? Is what I like to call your secret sauce, the thing you feel sets you or your organization apart and makes it unique.

08:32 – Jessica Dennehy

I think it's not just one thing. I think my personality is, first of all, one thing I talk about a lot. And even with my clients, we do weekly accountability. And I ask them, like, what do you do for fun? Because if you're just sitting home being a workaholic robot, where's your brand energy going to come from? Like, your energy for the brand comes from your experiences, your happiness, your, you know, your. The life inside of you coming out and, you know, bringing the brand to life. So what did you do for fun? So something that I think really sets me apart is that I show my fun side, and I think it actually enhances my business. So when I was a lawyer, I didn't have pink hair. You know, I didn't have fun clothing.

I was bored. I was in a suit all the time, and I just had my normal brown hair, and I was just doing my thing. Minimal makeup, you know, all the things. No personality to my shoes. Now I'm me, right? So I bring that. I feel like these two things are intertwined. I'm authentically who I am. I bring it to the table every day and I show it in every way in my clothes, in my hair, in the way that I talk, in the way that I emote, in my, you know, my hand gestures that you're seeing right now. Like, all that stuff is who I am, and I bring fun to the business. So instead of hiding that part of me thinking someone might not take me seriously because I'm not taking myself seriously,

I'm like, no, I don't always take myself seriously because I'm not perfect. I'm genuine, I am flawed. I have fun. I have different parts of me that intertwine to create me. And I think not a lot of people do that. They show the highlight reel, they show what they want you to see. And there's not a lot of people out there giving you every part of them.

10:21 – Gresham Harkless

Yeah, absolutely. And I think that's something beautiful and phenomenal that you do. So I wanted to switch gears a little bit, and I want to ask you for what I call a co-hack. You might have already touched on this, but this could be like an app, it could be a book or a habit that you have, but what's something that makes you more effective and efficient?

10:40 – Jessica Dennehy

My number one hack that I use is having the morning to myself without any interruption. And it kind of goes back to what I was just talking about when I wake up at four every day, and I know not everyone's a morning person, the same kind of concept works at night, but just if you block out that time that it's quiet and that you can really think and be with yourself and, you know, just have a moment to you where no one else can intrude upon it. No phone, no emails, nothing. No social media. For me, that's been a game changer because it starts my day with me really focused. You know, I'm not looking at my phone. When I look at my phone, there's several things happening, you know, texts and missed calls and emails and socials and notifications.

So none of that's going on. I'm just in my zone. I'm exercising, I'm thinking, I'm, you know, getting into my mode for the day, and then I meditate and then I do some gratitude. And though that routine, which is about a two-hour window, is pivotal to my day, if I don't have that, my day flows much differently. And that that is my biggest hack because once I got that down pat, my day became more efficient, more productive, more happy, and I can just, you know, take over the world now.

12:04- Gresham Harkless

Awesome, awesome, awesome. So I wanted to ask you now for what I call a CEO nugget. So this is a little bit more of a word of wisdom or piece of advice. I usually say it might be something you would tell your favorite client, or if you were to hop into a time machine, you would tell who your younger business self is.

12:19 – Jessica Dennehy

Oh, if I could happen a time machine man, I would tell myself. And I learned this through trial and error. A wrong decision is better than indecision. It's better to make a mistake and learn the lesson than to just sit stagnant in waiting for the perfect moment or the perfect action. I think that I have done that so many times in my life, and it's worked out every time because I choose to learn a lesson from my mistake instead of wallowing in the fact that I made a mistake. So if you look at the problem from that perspective, there's really. It's a win-win, and it makes you more able to take a risk because there are only two options.

One is you win and the risk pays off. And two you learn a lesson to get back in the groove and make a better choice the next time that might get you the win. So if you look at every problem like that, then you're not going to be scared to take that risk and do that thing, because mostly waiting around is just you afraid to potentially fail. So make a wrong decision, and that is better than indecision any day.

13:36 – Gresham Harkless

Nice. I absolutely love that. So I wanted to ask you now my absolute favorite question, which is the definition of what it means to be a CEO. And we're hoping to have different, quote-unquote, CEO's on this show. So, Jessica, what does being a CEO mean?

13:48 – Jessica Denneh

What does it mean to me? Oh, I mean, to me, alignment is the first thing that comes to mind. Like, by being the CEO of my own company, I get to feel completely aligned all the time because I get the time freedom that I want. I get to work with only the clients that I feel connected to. I get to hire people I feel connected to. And, like, suddenly my circle starts to be these amazing people that I vibe with naturally, and my life just gets elevated from there because then my home life becomes better because I'm just more happy.

And so to me, when I think about being a CEO, that's the first thing that comes to mind, because when you're in alignment you're naturally leading your entire team into alignment, not just at the company that you've created, but throughout their life. Because when they're happier and they're at work and they feel aligned, they go home and they pour into their family differently. So you get the opportunity to create this ripple effect of happiness and alignment throughout your company. And that, to me, is really what the most important thing is.

14:57 – Gresham Harkless

Awesome, Awesome, Awesome. Well, Jessica, truly appreciate that definition. And of course, I appreciate your time even more. So what I wanted to do now was pass you the mic, so to speak, just to see if there's anything additional that you can let our readers and listeners know. And, of course, how best people get a hold of you. Find out about all your books and all the awesome things that you're working on.

15:14 – Jessica Dennehy

Sure. So if you want to find me, you can find me on social media at the Jessica Dennehy. So that's on Facebook or Instagram. You can find me, you know, apply for my coaching program, find my book, find free resources at all@pivotandslade.com and my best advice to you guys is to start starting. Take that one step that will get the ball rolling, and we'll start your momentum moving forward. That one small step means so much more than you think, and it's more manageable than thinking about the overarching vision. So just take that first step, and I'm certain that things will start flowing in the right direction from there.

15:54 – Gresham Harkless

Yeah, I'm absolutely certain as well. And of course, to make everything easier, we will have the links and information in the show notes as well, too, so you can get a hold of Jessica and find out about all the awesome things that she's working on. And I love that last point. I think it's so powerful. Sometimes we forget about the energy that it takes. But a lot of times, by starting something, even if it doesn't go the way we want it to go, it gives you that energy towards starting the next thing or pivoting or doing ever. But you have to start to get that energy to kind of get going. So thank you so much for doing that and reminding us of that as well. And I hope you have a phenomenal rest of the day.

16:24 – Jessica Dennehy

Thank you for having me.

16:25 – Outro

Thank you for listening to the I AM CEO Podcast powered by Blue 16 Media. Tune in next time and visit us at iamceo.co I AM CEO is not just a phrase, it's a community. Be sure to follow us on social media and subscribe to our podcast on iTunes Google Play and everywhere you listen to podcasts, SUBSCRIBE, and leave us a five-star rating grab CEO gear at www.ceogear.co. This has been the I AM CEO Podcast with Gresham Harkless. Thank you for listening.

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