HOSU 38 | Become Your Own Boss

Building Your Brand And Becoming Your Own Boss With Jessica Dennehy

What does freedom mean to you? How do you overcome indecision and become your own boss? Jessica Dennehy, CEO and founder of Pivot and Slay, shares her views on this with Matthew Sullivan. From her role as a Wall Street regulator to being her own boss today, Jessica talks to Matthew about how she left her Wall Street career behind to become an entrepreneur and pursue her passions. Listen in and learn more as Jessica discusses how she managed to integrate her personal brand with her business and why it’s important to do so.

Watch the episode here:

Listen to the podcast here:

Building Your Brand And Becoming Your Own Boss With Jessica Dennehy

Jessica, how are you?

I’m doing wonderful. How are you?

I’m very well. It’s a little chilly. It has been snowing here. A large amount of snow was delivered. It’s quite Christmassy because I’m North of Salt Lake City in Utah, as you can tell from my deep Western accent here.

It snows there all year round pretty much.

Not in where we live. There are places where it snows much better. We must be in these cheap areas where the snow doesn’t quite make it. I don’t ski and my wife does. Everyone says, “Skiing is fantastic.” I supposed, but I don’t understand it.

I’m going there for the first time in February 2022. I’m very excited.

It is a lovely place. I have completely changed my tune but this episode is what it’s all about. It’s change and adjustment. Isn’t that a surprise? As a brief introduction, you are the CEO, Founder, Chief Cook and Head Bottle Washer of Pivot & Slay, which is both the most amazing and also a slightly scary name considering you have this Wall Street background, this idea of slay. In other words, if you don’t pivot, I will slay you through the Goldman Sachs style.

Around Christmas time, everyone is putting the Santa sleigh.

I didn’t mean it like that. I meant to kill and destroy.

I know what you meant. During Halloween, they had Michael Myers with the sleigh. It’s not meant in that way. It’s not about forcing you to pivot, but life is nudging you and throwing things at you. You’re adapting as you go along so that you can still succeed no matter what.

What drove you to this interesting departure from Wall Street? Tell me a bit more about your Wall Street background because that’s always fascinating.

As a child, I wanted to be a lawyer. That was my big dream. I wanted to work on a big firm on Wall Street. I don’t know why. Listening to both sides of the story always fascinated me because it always helped me evolve as a human being. I became more inquisitive than argumentative. My inquisitive nature led me down the road of being a litigator because I got to ask a lot of questions and do some investigatory work. The thing about being a lawyer is usually, out of law school, you get thrown in a room full of boxes. You are looking through thousands of documents.

HOSU 38 | Become Your Own Boss

Pivot and Slay: The Ultimate Guide to Mindset Mastery https://www.amazon.com/Pivot-Slay-ultimate-mindset-mastery/dp/B094CWJMW9

What ended up happening with me was that I met a professor who worked at the New York Stock Exchange. She offered me an internship during my time in law school and I loved it. Because I showed my work ethic there, I was able to get a job right out of law school. I was thrown into litigation on day one, taking depositions, doing discovery and then eventually, getting into a hearing scenario, which was fun. I loved it for a long time until later in my career.

About eight years in, I started to feel a little bit caged. My growth had been stunted. I was forced into taking on cases that they brought me whether or not I agreed with the charges. I started to push back a lot on that and think to myself like, “I don’t want to be doing this work I don’t feel passionate about every single day.” That’s what led me to explore my entrepreneurial side.

That must be quite the challenge for someone like you when you’re at that point where you begin to think, “This doesn’t feel right.” That must be a real challenge for litigators and lawyers generally, where your bosses give you this case and say, “Go and make two plus two equals seven effectively.” I suppose there comes a point. Is that how it feels after a while?

In this scenario, it did to me because the market became over-regulated. A lot of the things they were taking a stance on didn’t resonate with me. I started to feel inauthentic in that job. I wasn’t able to capture my own personality and passion. It became hard for me to send a lot of love in the way of my career. It’s scary because my whole life was crafted to get to this goal. There I was in the goal and it wasn’t panning out the way that I wanted it to. I was scared because I didn’t know what else I had inside me yet. I didn’t know where else to go.

The real tension is you know that this is something that you don’t want to do. It gets to a point where almost every molecule in your body is rebelling against this but the question is, what am I going to do? What is evolution? What is the pathway to writing the book and creating this guidance at Pivot & Slay? Tell me more about Pivot & Slay.

Pivot & Slay is a coaching and business consultation company. I work with entrepreneurs. I empower them to pivot their mindsets and businesses so they can scale and slay their goals and ultimately find their freedom because freedom is what I’m passionate about like allowing people. A lot of times, when we think of freedom, we think of time freedom like, “I could be my own boss and do my own thing.” That’s part of it. For me, the thing that drove me the most was alignment freedom. It’s this capacity to be around people who I feel like I can help the most and I’m doing the most good for.

That was what was missing in my corporate job. That’s what I help entrepreneurs achieve. My book Pivot & Slay is about the way that I did that for myself from pivoting out of my corporate career and starting a business I knew nothing about. It’s how I developed and scaled that business ultimately to a point where I could now teach other people to do it too. Pivot & Slay was not the business I started when I left Wall Street. When I left Wall Street, I started a barbershop.

That’s fascinating. Please tell me more.

I was on Wall Street and I wasn’t happy. At the same time, a lot of us go through this where we are like, “We don’t know what else to do. This is all we know, so we don’t do anything.” We have all been in a scenario like that and we are miserable. Our misery becomes who we are and then it goes on and on. I might have become one of those people if it wasn’t for my then-husband losing his job. He lost his job and we had bought a house. We were about to have a baby.

We were like, “This is not great timing.” He said, “I have a good business idea. What do you think about taking this gigantic risk a week before we have a baby and throwing a bunch of money into a business?” This was years ago. The barbering world wasn’t as popular as it is now. It was like, “That shop has been here for 50 years. No one has changed the tile for 100 years. We are going to go and get a $10 cut.”

We were trying to break through and make a more upscale environment and place for men to go that wasn’t a salon. It’s a men’s place but not a salon and for a normal price point. It’s his luxury barbershop idea and that wasn’t happening at that time. I said, “There is nothing like that. There is a need for that in our area in New York. Let’s do it.”

That was the first time where I solely made a choice based on my gut instincts because there was nothing logical about this choice. We were a week away from having our first child. We had spent our life savings on a house. Me giving the rest of the money to him to start a business that neither of us could cut hair or have ever owned a business, this by all stretches of logic, made no sense.

What possibly could go wrong?

What could go right was the big question, but in my heart of hearts, it felt right? I did it and he did it. I stayed at Wall Street for two years while he did the grind in the business. At night, we talked about what to do, how to pivot and how to hire. We were stumbling along but because of our grit, we made it happen and it exploded. Two years later, I was like, “I’m going to leave my cage and find my freedom by working in the business too and we can scale it.” That’s what we did.

Freedom is the capacity to be around people you feel like you’re helping and doing the most for.

What is interesting is the two things. First of all, you talked about your gut instinct. Secondly, you talked about this concept of grit and determination. Those are two important, if not the most important, characteristics of success generally. It’s the ability to stick at something even though you may not know what is around the corner and having that drive and determination to follow your instincts.

Is that something that you realized you were doing at that time? Looking back, are you able to think, “That was quite a good thing. I could have given up and decided that it was too difficult with all of these changing situations that you forced into?” How do you view that through the lens of your new venture? If you were to look at yourself, how would you process that grit? Does that make any sense?

Yes, it did. I will interpret it for the audience. That was not the first time I had followed my gut, but it was the first time I had followed it confidently. Sometime in law school, I realized that every time I had not listened to my gut, I had failed. Every time I listened to it, even though I didn’t know where it would lead me, I somehow succeeded. At that moment, when I said yes to the business venture, I very much knew I was going off this solely based on my gut. I knew I would figure it out along the way because I’m a disciplined and determined person. I knew if I put my focus and drive towards that, it would succeed.

It’s that confidence that so many people lack where they don’t trust themselves. They hear that inner compass talking to them like, “You should do this.” Their brain talks them out of it, “It’s too scary. It’s not the right time. There’s too much going on. You don’t know what you’re doing.” They follow that logical side of themselves instead of what is in their heart. That’s when they start to lose that momentum and drive. If you follow what your inner compass is telling you, that’s when you can build up confidence.

I could look back now on all my decisions and be like, “I was right all those times. I should give myself more credit than I do.” I have to put my lawyer hat back on. “Look at the evidence. Every time I followed my gut, it was okay. It worked.” That’s what people don’t do. They don’t look back and think about those moments. They need that awareness. It’s like a little switch. It’s a little bit of awareness that creates that confidence.

As an entrepreneur, you’re always piling forward and head down, driving forward. Another interesting thing you said is evidence because there’s this saying that fear is a temporary lack of information. With all of this gut instinct, drive and determination, that is always for some reason balanced by a healthy dose of fear.

The fear normally materializes at 3:00 in the morning when your mind is racing through all of these potential permutations. To be able to say, “Hang on. This is going to be okay because it has been all right in the past,” you have to learn that. I’m sure when you deal with entrepreneurs, that’s one of the big challenges. How do you get people to have faith in themselves? What is the process that you take them through?

I always tell them to challenge themselves on a smaller scale and test it out. If you give yourself those little challenges throughout the week where you’re following the gut on something that you view as nominal, you will start to see the pattern that I’m talking about. A lot of times, I will have them talk about past experiences where they dove into something they weren’t quite sure how it would get them to where they wanted it to be but it worked out.

It’s more of awareness because, by the time they come to me, they have already had all of these experiences. They are so busy with their heads down. They haven’t taken their heads out of the ground to look around and see all of the facts that are laid out around them. The piece that’s missing is that awareness, vision and neutrality that I, as a third party, can see about them. They have to start to see it in themselves is what it is. It already exists before I enter.

This is the concept of a different perspective of mentoring or various similar concepts. Is that something that you had the benefit of when you were building that challenging barbershop business?

No, and that’s why I want to give it to everybody because if I had someone around me that had gone through this before, I could have collapsed time instead of going through years of trial and error, which is how I figured out the barbershop industry. I would have been able to be like, “That is a better move.” I will get to my goal faster because someone else was guiding me. Without that, you’re left to continuously risk some stuff, try some things and see what works and what doesn’t.

That’s exactly what we did when we opened Mad Men Barbershop. It took a long time to get in a rhythm and for me to build up my own personal confidence within that business because the truth was, I knew the business from a corporate Wall Street standpoint. Small business is a different animal. Although I could apply some strategies to the small business, it was a trial by fire.

I suppose one of the frequent responses you probably get from entrepreneurs who necessarily have to have protective egos because that’s what makes people entrepreneurs is, “The thing is that you don’t have any specific industry knowledge about what I’m doing.” The answer is you don’t need that. In your example, if someone came along and said, “I don’t know anything specifically about barbers. I don’t know how to cut hair, but I have worked in this type of business before, which is very similar.” How would you answer this pushback from the entrepreneur who is saying, “I understand what you’re saying, but don’t you need to have industry knowledge about what I’m trying to do?”

HOSU 38 | Become Your Own Boss

Become Your Own Boss: Life is not about forcing you to pivot, but just kind of nudging you and throwing things at you while you adapt as you go along so that you can still succeed no matter what.

My answer is always, business is business. Business strategies apply to industries across the board. There are certain things you can do within the business that will help any business no matter what industry you’re in. The main thing that I love to help people do is show up to that business differently as their more empowered self.

When you’re showing up to lead people, that’s a different feeling than when you’re showing up to boss people. A lot of business owners stumble upon success in a haphazard way. They are still trying to navigate as they are trying to “lead.” What that ends up doing is them bossing everybody around instead of leading by example, showing up empowered and allowing other people to become empowered.

To me, I’m going to teach you the business strategies that you can apply to any industry. On top of that, I’m going to show you how to show up so that your employees and staff want to succeed and help you build up your brand, which is a very hard thing to do in this day and age. You have to build that brand culture and company value in other people below you. You do that by leading instead of bossing.

A lot of that problem comes from business owners who are immersed in the business and working for the business rather than having the ability to take a step back and work on the business. Do you see that as one of the biggest challenges that you come across?

Yes, that’s one of the things I help entrepreneurs with the most. To scale the business, you have to delegate but to delegate probably is one of the hardest things that a bunch of type-A egotistical entrepreneurs can do because they think they are irreplaceable, but the truth is, you are not irreplaceable. Someone else can do what you do inside of your business if you delegate, train them and hire properly. I work with people on the proper way to do all of those things so that they can have a certain level of comfort in allowing these people to do all of the heavy lifting while they work on the brand vision as the leader of the organization.

Do you find that structure is lacking in many of the people that you work with in terms of the ability to delegate is much easier if there is a structure and process that can be used? Do you find that as you begin to start unpacking the way that these businesses are built that many of them are lacking in that fundamental structure that will enable them to grow?

Absolutely. Most small business owners stumble upon success. They didn’t necessarily lay down the proper foundation to build a successful business. It just happened to all fall into place. When they get to the point where they want to grow and scale, they don’t know how because the foundation they built the whole company on is wobbly.

I describe it like a slingshot. You have to pull yourself back a second and lay that groundwork you forgot to lay at the onset before you can have an impact and build upon that further. You made it. Congrats. You went this far alone, but if you don’t get your processes down and solidify it, you will not be able to build anything stronger than what you have now.

Would you say that perspective is one of the most valuable things that you bring to an owner or entrepreneur?

Yes, absolutely. An outside perspective of someone who isn’t in the muck is exactly what these people need because they are trying to ascend to the CEO role. They think they are the CEO, but if you’re at your business every day, you’re an employee like you were before you started your business. To become the CEO, you have to ascend to that 50,000-foot view where you’re focusing on the vision and you’re not inside doing the work all the time. Many people are still inside and they don’t have to be. There is the freedom to be had. You have to know how to achieve it.

In companies where you have got multiple founders that are still part of the management team, not just a sole entrepreneur. As you begin to unpack where they are and show them a different perspective, typically, do you find that there isn’t at the root of everything a clear understanding of what the brand should be or what the company is? Do you find that it begins to get deeper? The more you peel back the layers, fundamental issues start appearing like, “We don’t know what we are or what the message should be.” Do you have any examples or thoughts on that scenario?

For the most part, people are focused on making money because they are leaving their 9:00 to 5:00 or their corporate life or whatever. They don’t even create a culture in the company. They don’t even create a brand. They have a product or service, but they haven’t cultivated a brand. The reason is it takes time to build a brand. It doesn’t take time to build a product. You can put a product or service out there tomorrow. Brand creation is the long game. No one is looking to get in on the long game. They want short-term satisfaction and gratification.

The brand though is what builds wealth, the company and longevity. Lots of people have failed to create that within their company. A product and service are only going to take you so far because people buy based on their emotions. If you’re tapping into their emotion by utilizing your brand, your personality and infusing your energy into the brand, that’s what is going to get you the long-term clients and company. Right now, you just have a product or service if you haven’t created brand awareness.

Is that something that you learned firsthand from the business that you ran? In other words, you have got something that is ubiquitous to a certain extent. There are many people doing that. How do you differentiate yourself? How do you build those brand values that people feel compelled to come back to your barbershop rather than somewhere else’s? What were the real lessons or key points that you learned in that process that you were able to bring to other people?

If you put your focus and your drive towards your goal, you will succeed.

Both of my businesses have a personality infused into them, Mad Men Barbershop and Pivot & Slay. There are tons of barbershops and business coaches. What makes me unique is that it’s me. I’m here. I’m infusing my energy and personality into these brands. When we opened Mad Men, we did focus on creating a lifestyle brand because we knew that it would be important to attract people too. What other reason would they come to us? We had no established barber staff yet. We had no business in the industry prior to this.

We had to attract them by building a culture around getting a haircut. We had to build a men’s place with a men’s feel and attract them in with the branding, which is what we did. Everyone thought that was crazy because, in the beginning, we had to put a lot of money into creating that brand. It didn’t get an ROI the next day. We didn’t have 7,000 people waiting to get a haircut. It took time to build the allure and personality of the brand.

Down the line, when the industry became saturated in the luxury barbershop world, we were already infiltrated in everybody’s mind. We already had brand awareness. People kept coming back to us because we had established that from the get-go. I learned that with Mad Men. I continued to do that with Pivot & Slay by infusing who I am and my values into that coaching business because coaches are a dime a dozen now too. Why would you want to work with me? Because this is who I bring, this is the brand that I bring to the table that no one else can bring.

Does that not cause you scaling issues having that personality-driven business? How do you overcome the problem of not being able to be in 100 places at the same time?

Infusing your energy into a brand is not the same as being the entire brand. I’m not the entire brand, but when you work with me, you know this is the level of service and the type of energy I will provide. Anyone I hire will be aligned with exactly my mission, energy and personality. You know what to expect. It’s the same for Mad Men. As we scale, you know what to expect when you walk in the door. If my customers don’t have a barber, they have a barbershop. They don’t come in to see a specific person. They come in for the brand.

That’s the same with the coaching business. It’s an asset and necessity in order to scale to have a separate personality for the brand that is aligned with who you are and what you bring because you’re the one leading in your business. You’re leading the vision. The vision is going to be part of who you are because that’s authentic. That is the most effortless way to build a brand if it’s authentic to you because it won’t be work. It will be fun.

That’s important because there are business owners that feel constrained that they can’t grow their business. They feel compelled that they need to be the person taking the calls or speaking to the customers because no one else can do it right and has that same energy. What you’re able to do is to take a business, which is dependent on that foundation and those values and yet still grow it. There are valuable firsthand lessons that you have been able to demonstrate in your business. Does that make it easier for you to convey the successful nature of the outcome of your coaching?

Yes, because I have done this for myself. I’m doing it now. The reason that people are attracted to my brand is because I’m doing these things. It has already worked because if you have leaned into me, it has worked on you. You know that these work. You know that these strategies are applicable and successful.

One of the biggest challenges is cases. Do you have examples? If you’re selling a product or service, there are different things. It’s easier to demonstrate a product. In some respects, it’s easier to demonstrate the services. What are the biggest challenges that you have in being able to demonstrate potential success in a business that is very much personality-driven?

Are we talking about the coaching business?

Yes. The haircut is either a good or bad haircut.

When you’re first starting out, sometimes the only proof of concept you have is you. What I started with was showing people how I have done this for myself. For example, I can do it for you because I have already done it twice for myself. That’s how it started. When you’re in a service-based business, it’s important to start showcasing and highlighting all of your client wins. Social media is an amazing place to do that. Creating graphics with things people text you, things people say or reviews people leave is such a beautiful way to show that what you’re doing is working and allowing other people to trust that brand a little bit extra.

HOSU 38 | Become Your Own Boss

Become Your Own Boss: When the things you’re taking a stance on don’t resonate with you, you start to feel inauthentic and what you’re doing won’t be able to capture your own personality, your own passion.

In your legal career, you had positive outcomes. The case goes your way. The judgment is in your favor. That’s the win. In what you’re building with the barbershop, you have got over a decade of success. You have got numbers that represent that. A consultant is one way of describing it but when you’re not working in the business with someone, you’re on the outside as an advisor. Is that a challenge in its own right because you want to roll your sleeves up and get your hands dirty as it were? Is that slightly frustrating when you’re having to always work with someone else who is the owner of the business?

I thought it would be. What happened was I got clear on my role and the types of people I wanted to work with. After several years of doing this, what I have learned is I’m very selective at the onset because I want people who will do the work. If they are not willing to do the work, their results will not shine through and it won’t be good for them or for me.

The thing is, it’s hard as someone who has built several businesses to not go in and be like, “Let me do this for you.” What I have learned is my role is to advise them of different paths they could take and allow them the autonomy to choose which of those feels right for them. It’s almost like children. You want to raise them so that they are independent.

My goal is to get my clients to start thinking and acting like CEOs so that they can spread their wings and keep on growing. I don’t want them to be with me forever. That’s not the goal. The goal is for them to understand how to become autonomous, strong and empowered in their own right so that they can continue to build successful businesses. Their wins in their business are my wins too because it’s teamwork. I can guide them, but they have to go do it.

I was talking to someone who provides top-level marketing services. She was saying that they have a strict policy, which is something that probably developed over time. You say you’re selective, but is that something that you have decided over time? Having gone out and met lots of people, you realized there are some people you cannot help.

It comes back down to systems and processes, believe it or not. If you have a system of questions and a prescreening process, you can weed out almost everyone that doesn’t align with what you want, either by them self-identifying or you identifying them as not the right fit. That’s not to say it’s a perfect system. I have taken clients that I thought would be a good fit and I learned later that they weren’t. You have to pivot in those instances. There are ways to make that easier as you learn and go through. Sometimes, it takes those mistakes. I wasn’t as selective at first as I am now because I have learned the hard way in some instances on who meshes with me and who doesn’t. Now, I see the signs earlier, which is nice.

Do you have a particular story or situation that surprised you in a very positive way with one of your clients?

A client that I still have was very excitable when we first met. I knew he was at the point where he wanted change. When we started diving in and I would give him feedback and tasks to do, I was noticing that he wasn’t implementing. I let it go for a little bit because I believe that people need to accept the advice and implement it in a way that is meaningful to them. I like to back off a little bit and give them some space to feel it out and not get overwhelmed, but then it went too long.

I finally had to sit down with him. I said, “Why are you paying me all this money if you’re not going to implement anything? Nothing is going to get done this way. I feel like you’re avoiding it all.” We had that tough conversation. He was like, “Thank you for the push. I appreciate this. Things are going to change.” I was like, “All right. We will see.”

He went on to implement all the things that I had said he should and he has had massive success ever since. He is now leaning in more than ever. He has hired people. He had trouble hiring before. Now, he has tons of applications. He has grown by three additional employees. He is soaring. It was great to see because I saw the potential in him before he did. Now, he sees it too and he is shining his light.

Many coaches would not have the strength of character to confront their clients in such a way. They tend to be much more passive, “I will provide you with systems and ways of keeping notes.” That’s something that’s probably very much built on that strong foundation of your litigation career. Do you think that’s the case?

I have a knack for being compassionate but also very direct. My delivery is, “I get what you’re going through because I have been there before, but here’s the tough love. This is what you need to do to set your sights on the goals that you told me you want.” For me, it’s not totally selfless. The reason I love this job is because I love to help people, but I’m not going to help people that don’t want to help themselves.

For me, I would rather tell you, “If you’re not going to do the work, I’m not taking your money anymore because this isn’t fun for me. I don’t want you to get nothing done and keep throwing your money my way. Go and take your money. When you’re ready to work, come back.” It’s more interesting for me to work with people who are motivated. Some coaches maybe wouldn’t do that but I want to help and see people shine, but I’m direct and not for everybody. That’s okay. This is my personality. If you don’t like some tough love sometimes, then probably you’re not for me.

That’s hugely important because what you don’t want to do is have an agreement with someone, but at the end of the day, there is no outcome. The interesting thing about Pivot & Slay is that there’s almost like a process. It has to work both ways. I can only work with the willing as it were. I will say, “Don’t think that I’m going to go in and provide you with this cookie-cutter approach. It has to work for both of us.” There’s a bit of checking each other out as it were before you can go forward. That’s quite compelling compared to this feeling that I’m just going to get another sausage-machine approach.

It’s confidence that so many people lack that hinders them from succeeding.

It’s definitely not with me. My program is customized to fit the needs of the person. I give a lot of different ways to interact with me, get feedback from me and learn from me, whether that’s one-on-one, group setting, accountability calls, accountability worksheets, homework or videos. I have it all, but it’s customized with that person. If you tell me you like to learn or communicate a certain way, that’s what we are going to do because I want you to work in the way that’s best for you. This isn’t the Jessica Show. This is to let the other person shine. That’s my coaching style because I know that’s the best way for them to spread their wings and be successful even after they work with me.

Would you describe your approach? Coaching is a word that is ubiquitous and therefore is diluted to a certain extent. Would you position yourself more like an interim CEO to a certain extent?

I wouldn’t because I’m not going to go in and do the work for you. That is something that you have to do in order to learn how to be the best self in your company. I don’t like the word consultant because consultant indicates that I’m going to go in, fix stuff for you and give it to you in a bow. That’s not my style, even though the word coaching is not so positive right now.

It is though a good descriptive term for what I do, which is, “I’m here to be your leadership mentor. I’m going to be your cheerleader. I’m going to give you the tough love when you need it. You’re going to come out being a better leader after we are done.” That is what a coach does. They cultivate the natural talent that you already have inside you. They help you bring it out and position you in the right place for you to shine. That’s exactly what I do for my clients.

The important thing is to be outcome-orientated. In other words, we are going to go through this process, but ultimately, this is the outcome that we want. This is the deliverable. That might be more sales or a greater approach to recruiting. Is that how you work? We say, “What do we want to achieve? What are the outcomes that we want? Let’s find out how we can work together to deliver those specific outcomes.”

The first thing I ask everybody is, “What do you want?” You wouldn’t believe how many blank stares I get because no one is used to that. Everyone is concentrating on what they don’t want. You get what you focus on. If you focus on what you don’t want, that is what will come your way. If you focus on what you do want, then we can create a path together to get you there in a way that makes sense for you.

That’s different for everyone because not everybody has the same personality and that’s okay. There’s not a cookie-cutter method out there. You should take what you hear from people, internalize it and make it work for you. Just because another approach worked for someone else doesn’t mean that it’s what will work for you. You have to be able to pivot within that approach and make it yours. That’s what I teach people to do.

That must be ultimately the most fulfilling thing is when whole heartfelt advice comes from you. It was based on your experience. It’s not based on started intellectualism, but it’s based on your heart one experience. When you’re articulating that to someone and they listen to you and take that advice and positive things happen. That must solve and unwind all of those. Sleep is nicer to you when you were litigating Chapter 43 of the Investment Company Act or something. Does that rebalance everything and put you back on a more humane footing?

Yes, I think so. One of my core values is connection. I value creating that connection with people and not making them feel like a factory number. I want them to have a customized and personalized experience with me, form that bond with me and make them feel all the feels.

I can see from your look then that you are thinking, “There is no Section 43 of the Investment Company Act.” Now would be a good time to switch gears as I sit here, rattling

my piece of paper with my Hooked On Startups’ quick-fire questionnaire. Hopefully, this is a complete surprise. Question number one, what is your favorite word?


Question number two, what is your least favorite word?

HOSU 38 | Become Your Own Boss

Become Your Own Boss: Grit and determination are really important characteristics for success because success is generally the ability to stick to something even though you may not know what’s around the corner.


Question number three, what are you most excited about now?

I’m most excited about my second book that is launching soon about startups and what to expect in the first twelve months.

When is that coming out?

It should be out in January 2022.

Leading on to question four, what turns you off now?

Talking about anything negative is a huge turnoff for me. The news turns me off. I don’t turn on the news. I don’t want to talk about the news. I want to look at my bright future and your bright future and bask in the glory of that.

Question number five, what sound or noise do you love?

My kids’ laughing.

What sound or noise do you hate?

It’s my little one when she screams right in my ear for bugs. Whenever she sees the bug, she loses her mind like someone is murdering her. It’s crazy. I hate that sound.

Number seven and you may plead the fifth, what is your favorite curse word?

Fear is just the product of a temporary lack of information.

F*** is the only one I say. My daughter is only six and she is like, “Mommy, are there any other curse words? All you say is f***.”

Question number eight, what profession other than your own would you like to attempt?

I would probably do something with travel because I love to travel. Maybe I will run a travel agency or something like that. I always thought about following people on their vacations and taking candid photos of them for their memories.

Do you mean following them with their permission?

Yes. They have curated memories from that trip. I thought that would be cool because then I could travel around the world.

Question nine, what profession would you not like to attempt?

Garbage man.

The final question then, if heaven exists, what would you like to hear God say when you arrive at the pearly gates?

Thank you for raising two beautiful, kind daughters.

Jessica, it has been such a pleasure having you on. What is the best way of finding out more about you, contacting you, getting a hold of your new book and generally understanding more about how you can potentially help these people?

You can visit PivotAndSlay.com. You can find my book there and apply for my coaching program. You can find my Instagram, Facebook and everything. Connect with me there.

Thank you so much for being a guest on the show. I very much look forward to following your progress and staying in touch. Jessica, thank you once again.

HOSU 38 | Become Your Own Boss

Become Your Own Boss: If people always follow that logical side of themselves instead of what’s in their heart, they start to lose their momentum and drive.

Thank you.

Important Links:

About Jessica Dennehy

Jessica Dennehy is a former Wall Street regulator turned entrepreneur, who left the investment world after almost a decade to build a brand of luxury barbershops, which scaled over eight years, even expanding overseas. Now, she is helping other entrepreneurs do the same – reinvent themselves, transform their ideas into successful companies and scale their businesses with her consulting business, Pivot & Slay. She has been featured in Forbes, LA Weekly, New York Post, Billionaire Success and more. Jessica would love to bring her expertise to your audience and has some amazing talking points.What does freedom mean to you?   How to overcome Indecision and Become Your Own Boss
-Leaving her Wall Street career behind to become an entrepreneur and pursue her passions
-How to shift your mindset in order to achieve success in business and life and take back control
-What lays behind your indecision. How to overcome it and make the first step in becoming your own boss
-How she has integrated her personal brand with her business brand and why this is important