500: Creating Confidence: Auditioning For The Role Of Yourself | Heather Monahan

Powered by RedCircle

Heather Monahan creates confidence. She is a best-selling author, keynote speaker, TEDx speaker, and Board Member of Healthlynked Corporation.  As a former C-suite executive in media, she was named one of the most Influential Women in Radio in 2017, and Thrive Global named her a Limit Breaking Female Founder in 2018. Heather’s podcast Creating Confidence is a Top 100 show in the Business category on Apple Podcast. Heather was named one of the Top 40 Female Keynote Speakers of 2020 and Top 50 Keynote Speakers in the World 2022 by Real Leaders and her new book Overcome Your Villains is available now.

Heather joins us this week to propose the idea of auditioning for the role of yourself. It’s a new year, and entering a new year typically comes with some new goals and ambitions. These require a new set of habits, routines, and a shift in mindset. How do we maintain and rewire ourselves in a manner that will finally allow us to take those steps necessary to accomplish what we desire? Listen to Heather layout what made her realize she was quite literally building someone else’s mansion. This is when she decided that she had the knowledge and resources to build her own. In this episode, she covers her Beliefs, Actions, and Knowledge model to overcome adversity. Alongside this, how she got Gary Vaynerchuk as her first podcast guest, and how driving the revenue for her CEO of 14 years finally triggered her big move to becoming who she was meant to be.

Conquer Local is presented by Vendasta. We have proudly served 5.5+ million local businesses through 60,000+ channel partners. Learn more about Vendasta and we can help your organization or learn more about Vendasta’s Affiliate Program and how our listeners (like yourself) are making up to $10,000 off referrals.

Are you an entrepreneur, salesperson, or marketer? Keep the learning going in the Conquer Local Academy.


George: This is the Conquer Local podcast, a show about billion-dollar sales leaders, marketers leading local economic growth, and entrepreneurs that have created their dream organizations. They wanna share their secrets, giving you the distilled version of their extraordinary feats. Our hope is with the tangible takeaways from each episode, you can rewire, rework and reimagine your business. I’m George Leith, on this episode, we’re very proud to feature once again, Heather Monahan. Heather is a best-selling author, keynote speaker, TEDx speaker, podcast host, and board member. She’s a former C-suite executive and media, and she was named one of the most influential women in radio in 2017, and Thrive Global named her a limit-breaking female founder in 2018. Her podcast Creating Confidence is a top 100 show in the business category on Apple Podcasts, and she’s had such notable guests as Gary Vaynerchuk, Sara Blakely, James Altucher, and Lisa Lampanelli on her show. She was named one of the top 40 female keynote speakers of 2020, and she actually was on the Conquer Local podcast on episode 119, get ready conquers, my friend Heather Monahan is coming up next on this week’s episode of the Conquer Local podcast. Joining us from the beautiful metropolis of Miami, Florida, Heather Monahan, back on the show. Heather, congratulations on all the success, welcome to the Conquer Local podcast.

Heather: Hello George, thank you so much for having me back, I still appreciate it.

George: I wanna tell folks that Heather was one of our first five guests when we started the Conquer Local podcast four years ago, over 200 episodes ago. And at that time you had written your first book. And now we’re here to talk about the second book, “Overcoming Your Villains,” and I was at a convention a couple of years ago before COVID, if you remember, we met at the Nobu Hotel, had a drink, and you told me about the book and about the speaking and you know, your career has just been taking off, but let’s talk about what it is that, you know, you’re doing a lot of things, but really when we get down to the mission and vision, what’s Heather Monahan up to?

Heather: Oh my gosh, so many things George, it is just crazy. And one of the things I’ve learned, you know, as I just wanna make sure everyone knows that we know each other back from my other life, which was back in Corporate America when we worked together and were partners together in business and loved working with you. But since that time I was fired, oh, it’s about four years ago now, that I was fired from that job and I had to reinvent myself. The first thing I did was write and self-publish my first book as you mentioned, that led to my launching. My podcast led to my speaking career, but then COVID hit and shut everything down. The speaking disappeared, and then I had to reinvent myself as a sales consultant and then a virtual speaker, and then I landed a board seat with a company called House Link, and then I pitched HarperCollins Leadership, you know, on a book deal and ultimately launching my new book. So it’s been a very crazy high and low, last few years as I kind of navigate through this entrepreneurial journey. But it’s definitely not, the way I used to feel in Corporate America was, everything is, you know, very clear and well lit, and I know what that next move and next meeting and next step is and now in this entrepreneurial world, it’s nothing like that, it’s a complete darkness.

Building Your Own Mansion: How Heather Realized It Was Time To Do It Herself

George: I was running through our history, and I remember when you and I met the Wynn Lounge, some of my better sales presentations have been in lounges, but we, you know, it was a legit business meeting 10 in the morning, and you were running a radio company, running revenue for a radio company. And I’ve read the book, and one of my favorite pieces of the book was you were at George’s house in Naples, and Aerosmith plays the concert and that, you know, the leader of the Atlanta Radio Group says, “this is the house that Heather built.” Can we talk a little bit about that story? Because you’re a great storyteller, I wanna hear the story.

Heather: Oh my gosh, that’s so crazy. Yeah, so George is referencing a time back when I was a chief revenue officer in media, the company was headquartered in Naples, Florida. And at least once, if not twice a year, they would bring all the leadership into Naples where the CEO actually had his home as a way to, you know, thank everybody, unify everyone and kind of give direction and guidance. And so on this occasion, he had just completely rebuilt or he had like, you know, built a new house. I believe it wasn’t, this house was not a house, it was a mansion on the ocean, other level with a guest house bigger than any house I’d ever seen. Tiki bar, like it was amazing. And yes, we had Aerosmith performing for us. But when we all arrived, all of the executive team, we were brought in on buses. And when we got off the bus, the leader from Atlanta looked at me and said, “oh my gosh, here we are, it’s the house that Heather built.” And what he meant by that was my job was to drive revenue. I was responsible for revenue in the company for 14 years. And it was that moment where I thought, oh my gosh, this is the house that Heather built, but I’m not living here! Like this, something was so, he was laughing and being funny tongue in cheek when he said it, but it really hit me hard in that, wait a minute, what is it that I’m not doing right? Like why am I not building a mansion right now? ‘Cause I certainly was nowhere near that financially in my life. And how do you go from, you know, being the person that has the capability to drive all the revenue, bring in the talent, you know, achieve all the goals, but you don’t know how to do that for yourself. And that day and that event left me with a lot of questions for awhile.

Getting Fired Doesn’t Mean You’re Bad: Erase Embarrassment And Shame, Big Things Will Happen

George: You know the title of the book is “Overcome Your Villains,” and you’ve been very vocal about the fact that you got fired. And you know, a lot of people look through LinkedIn profiles and it’s not something you go read, I got fired from this thing. I remember a woman that we brought onto our organization and she said, “I see you’re connected to Heather Monahan.” And I’m like, yeah, go listen to the Podcast 119. And she said, you know, “she’s so inspiring because I got fired, and I thought that my life was over and here is somebody that’s leading saying, it’s not the end, it could just be the beginning of something even bigger.” And I’d like you to talk about that, ’cause I know it’s near and dear to your heart. And you should know that this individual is doing very well and learned a lot from the lessons that you taught in that first book. So congratulations on that.

Heather: Oh, thank you for sharing that with me. I so appreciate that. But George, you know, it’s like anything, in business, we need to find a white space. You know, what is different or unique about us? I don’t wanna go to the most competitive space. So when I went out on my own, I thought, what space can I own in this really noisy world? And as I looked around, I didn’t see anyone out there really identifying with, “hey, I’ve been fired and this is my story.” Most people wanna hide that story, right? They feel shame around it, they’re embarrassed, but I thought maybe this could be my white space. And so I tested it, I put a white, right when I got fired, I put a post up that said, I have just been fired, and if I’ve ever helped you in any way, I need to hear from you now. And that post went viral and had millions of people liking it and sharing it and commenting, and that post also landed me on the Elvis Duran show, and that’s where I was given the idea to write my book, which I had never even thought of. So, you know, when I hear people say that it helps them, that I talk about and shine a light on the fact that getting fired doesn’t mean you’re bad, it probably means you’re in a bad situation. And there’s a huge difference there, right? And I think people, when they feel shame around it, they’re feeling bad about who they are. Listen, I was working for a woman who didn’t want me to be there. So for whatever reason it is, it was her right to fire me. I should have known years prior to that, that I would have been better off leaving that company. But I was so familiar with it. I don’t wanna say comfortable ’cause I wasn’t comfortable there, but it was familiar to me. And that idea of taking that leap into the unknown just felt too scary until she pushed me and now I’m grateful for it.

How Heather Landed Gary Vee As Her First Podcast Guest

George: You know, when we met and you know, you commanded attention in a room, you’re a great speaker, you had a great message. Revenue leaders from other organizations would look at, you know, I saw you speak a number of times. And now in this role, when I look through, while I was just looking through the acknowledgements in the book, you got Ed Mylett, you got Gary Vaynerchuk, you’ve got James Altucher like you have taken that, the ability that you had to command attention, and now you’re putting it into a different area. What, you know, what led to that? And I’m sure that, I think you talk about it. The book is a little scary in the beginning, a little bit of imposter syndrome.

Heather: Oh my God! Totally, it’s so scary and that’s what I want people to know on the outside looking in. People might see, you know, me on Gary V show and they think, “oh, this woman’s killing it, and she’s, you know, she’s so lucky.” No, none of this stuff has been easy, right? Really, when I look back at the tactics and even around Gary Vaynerchuk when I wanted to get him on my show, I put my sales shoes on and I think, how can I add value to this person? How can I separate myself from everybody else out there? I took out a Google alert on his name and I got a Google alert one day that he was launching a wine company with a partner. And I thought, I bet the partner is gonna be easier to get to than Gary Vaynerchuk. So I reached out to that partner, I sent him a DM on LinkedIn, where I have a lot of credibility. I show up all the time, and if you don’t, whoever’s listening, if you don’t have a LinkedIn profile show up, you can explode your LinkedIn profile right now. And it will give you reach, it will help your business and it will help elevate you as an expert in your business. So I messaged him and I said, hey, I was in the wine business, I have a lot of experience with what works with wine launches and what doesn’t. If you want me to give you some free advice, I’m happy to help. He said, “let’s get on a call today,” we jumped on a call, we hit it off, we were on the phone for an hour, and at the end of the call, he says, “Heather, if there’s ever any way I can help you, please don’t hesitate to ask.” And I said, funny that you say that, I’d love to have Gary Vaynerchuk as my first guest on my podcast and I’m launching it next month, can you help me line him up? And he said, oh my gosh, I hate you, yes, I will. But it’s really, you know, leaning in, I’m like, what are those things that you’re good at? And sales is my thing, I did it, you know, for over 20 years. And the more that I brought that sales unique attribute and style with me into this new space, the more success I found.

George: Well, I know one thing I also know about you is you’re fearless. So you know the good for you, and I can’t tell you who it is yet, but very, very soon on this very podcast, I used your tactic. I reached out to somebody and we’re gonna get a really big name. I can’t say who it is yet, but it’s thank you. It inspired me, I watched it like, well if Heather can do it, I’m gonna give it a shot.

Heather: Yes.

George: Inside the book, if you were to pick your favorite chapter, your favorite lesson inside, “Overcome Your Villains,” what would it be?

We’ve All Heard It One Million Times But Are You Doing It Yet? “Just Be You”

Heather: I will tell you that my favorite, personally favorite chapter was the one chapter in the book that made me cry, when I read, I narrate the audible version of my book, which I had to try out for by the way, which is so ridiculous. I had to audition to be Heather Monahan, and I got nervous George, about doing it. And I called my friend who has a book with Harper Collins already and she did the audible. I said, what advice can you give me? “She goes, get ready for it, are you ready?” I said, yes. She said, just be you. And it was that awesome advice that if they don’t like me, then they’re not gonna want me. I might as well just show up as me and I turned the microphone on, I recorded. And a week later they told me “you won the part of Heather Monahan and you can record.” And so one of the things that I did.

George: It’s crazy.

Heather: It’s so crazy!

George: It’s so crazy! I read that on a post you put online, I’m like, how the hell is that a thing?

Heather: It’s a thing, this is a real thing. But the cool part was I asked when they told me, “okay, you’ve got the part,” I said, is there any flexibility that I can get with creative ideas that I have for the audible version versus what I did in the hardback? And they said, “you have all the creative flexibility you want.” So what I did was at the end of every single chapter, I just go off book, my producer hits record, and then I share, after two years of writing this book, it was the first time that I was reading it all together, and I share like the behind the scenes of, oh my Gosh, I can’t believe that in this book, I left this part out and I tell them, like, I tell the listener, you know what I forgot to mention or what my thoughts are on it. So there was one chapter that I never thought I would cry on, and that’s the last chapter in the book is a chapter about legacy. And one of my mentors passing away and we had to stop recording that chapter took over an hour because I got so emotional. And it was so emotionally charged for me that I didn’t anticipate it was going to be.

The Value Of Mentors And How Close Mentorship With Your Idols Is More Attainable Than You Think

George: You know, we’re riffing here, there’s no script, mentors really important, right? Like I look back, I’m like, why the hell didn’t I have more mentors when I was young? I was so dumb. Let’s talk about that and talk about some of your mentors.

Heather: Yeah, one of the things I get asked a lot, George, and I’m sure you get this question too, is I can’t get a mentor. That’s BS, right? First of all, with all the content that people create on social media, I could have Ed Mylett mentoring me for years before the day I ever showed up and met him, right? I don’t need to meet someone to ask them a specific question. You know, I can consume their content and begin to understand their way of thinking so I can emulate it at different times, that’s number one. But number two, I go back to add value. I’ll never forget, there was one mentor in New York that he was much ahead of me, he was older than me, had more experience than me, had a bigger title than I did. And I’d ask him all the time, I’d love it if you could answer some questions for me and he’d be like, “I’m busy now, I don’t have time for this.” So I started watching him and I noticed he came into the office so far in advance of anyone else. He’d be there at six in the morning, some days. And so I thought, if I wanna get this guy’s respect and his attention, I should go buy him breakfast and meet him at the office at six. And I wasn’t invited, you know, he didn’t invite me to do this. I just said, I’m gonna take the chance that he’s gonna be there. And so I started getting him coffee, I started picking up bagels and coming in at six or 6:30 in the morning, and suddenly then he had time to talk to me. And then I’d say to him, I can also give you some feedback ’cause I’m the age of your employees and I hear the things they say, and maybe I can help you to understand some of the communication that might be lacking or missing, and maybe that would add value to you. So I was always looking for ways that I could add him value instead of just sucking value from someone else.

George: When I look at the profile, I see this thing that you go up to Boston every once in a while and go to a school there and do some teaching. You are teaching sales at Harvard!

Heather: Well, all right, this is so funny. I’m not like a full time professor at Harvard, no, but what happened was during a couple of years ago, before I wrote this book, I got a DM on social media because of my LinkedIn profile by the way, in the content I create on LinkedIn, a professor from Harvard sent me a DM and said, “I saw some of your content and videos on sales, would you ever be willing to come in and do a guest, you know, as a guest lecture for one class? And I was blown away ’cause I couldn’t have gotten into Harvard, right? I couldn’t believe they would want me to come in. And so I agreed, but then I asked him, but why me? Like, why would you want me? And he explained, “Heather, I’m an older, white male, who’s been out of sales for years and I’m teaching it.” “I think it would be helpful to have someone who’s in sales, who’s a female who’s younger, that has a different perspective.” “You could probably add value and speak to things that I don’t even know about.” And I thought that was so cool that he was, you know, that humble, and seeing that there might be other ways to you know, to teach. So I went in not knowing what I was gonna do, and it was an amazing experience. The students were brilliant, right? But they didn’t have real world experience. So for people like you and I, that’s easy to show up and add value, right? It was easy to answer their questions because they didn’t understand what it was like in real time. And we all know reading a textbook in school versus going out and living it, are two totally different stories. So I was really, it was such an exciting experience. And then when the pandemic hit, that same professor reached out to me and said, “I have a budget to bring on a teacher that would be assisting me, would you be willing, you know, to do this?” “It will be virtually, once a week on every Monday for the semester, would you be willing to do this?” And I accepted the opportunity and did it, I won’t do it again though, I’ll tell you. And here’s why, it was so much more work than I thought it was going to be. You think that you just have to show up and, you know, answer the questions and teach, but there’s so much behind the scenes. You have to read all the content ahead of time. You basically have to take the class and help assistant teaching the class and get with the other professor who’s the lead professor to get guidance weekly. And it just, it does not pay well, by the way, I had a lot of people think that, you know, assisting at Harvard would be, you know, this lucrative job, it was not, but I’m sure if you know, stay the course and get a full-time job at Harvard, it’s different, but it was a really eye opening, unique experience for me to see that, the expertise of sales and sales leadership and real-world experience has massive value and never underestimate the way that other people see you and see your value.

George: You know, I’ve been inspired by that, and you and I discussed that when we met the last time before COVID face-to-face, but it really is interesting when you sit down in a room full of MBA students, and they ask you to talk about what really happens in the street, and they’re just mesmerized by it, but it kind of makes sense. You’ve been going to school for five or six or seven years, taking your MBA. You haven’t been out calling on clients and running a business, or being an entrepreneur that when I read through all of the material, you produce a lot of content. Is that the key to building the brand in your opinion? Is the sheer volume of the content, or is there something else there?

Heather: I mean, consistency’s really important, that I know for sure, showing up every day. So there is an element about volume because you have to show up daily, you can’t, you know, disappear for awhile, you’ll lose the community. So I don’t think volume is the answer, I think consistency is definitely the answer, but now I look back, my first couple of years after I got fired, I was doing every single podcast that anyone asked me to do, even if they had 10 listeners. And those are the things that I wonder was that content necessary for me to create, probably not. Like I had to get to a point where I was saying, my time is valuable, is there an ROI, right? If I’m creating LinkedIn posts, there’s a strong ROI there, ’cause I have a big community now, but when you’re starting out, it’s trying to identify, I almost felt desperate to wanna try to break in, so I would do anything and desperation is not a strategy, right? So I strongly suggest to people, look at what the ROI is, how much time do you have to put into doing something and what is that return and or potential return and constantly reevaluate that.


Adjusting Through A Pandemic And Constant Re-inventions Of Your Plans

George: I remember listening to a Zig Ziglar sales training, like when I started in the radio business, sales manager gave me Zig Ziglar cassettes, that’s how long ago it was. And the story that he tells about Yorishiro Honda, and how every time he would just about get the Honda Motor Corporation going, something crazy would happen. Like the plant got bombed during World War Two. And I relate this back to watching some of your content because you’re very open about the fact, it just started to get going, then COVID hits, and now I got to reinvent myself even again, and I think it’s an important lesson for people to understand. You’re like, oh, Heather’s knocking it out of the park. Boom, she gets hit. Yeah, you didn’t even see it coming, who saw global pandemic coming? How many times have you had to reinvent it, even during this new version of what you’ve been doing?

Heather: Oh my gosh! The biggest one was when the pandemic hit and my speaking business, I had a full calendar for the next year booked out and I was so excited to feel that safety of okay, business is really solidifying and I can start to see out in forecasts, right? And it just disappeared overnight, and then I was confronted with this idea of, okay, what problem can I solve from home that I can charge for? And then what do I charge? You know, I have no idea. I started getting into this consulting and coaching and I didn’t know what to charge, I devalued myself. But the good thing was it gave me an opportunity that first month to develop reviews and testimonials in my work. And the more reviews and testimonials, you have, speak volumes to other people. So you can go get attract new clients that you can charge more for. And during that time, I started seeing people show up online as virtual speakers. And I thought what’s a virtual speaker? Like this wasn’t a thing, you know, before I had never gone to a virtual speech. So I started studying and I thought, can I be a virtual speaker? I guess I have to try. So every time I would take a deal at first, I’d offer 100% money back guarantee, so there’s no barrier to entry, and then I don’t have to feel bad if I’m not a good virtual speaker ’cause I still didn’t really know what that meant. And it turns out I was a good virtual speaker, so I started rebranding, now I’m virtual speaking. Right now, I’m positioning myself in this new way, but then when live events started opening up a few months ago, I started getting scared about going back out because I was so good, I’m this new arena, right? On the computer and with the chat thread, and how does that translate back? So I continually, am re-inventing and transitioning to these different arenas. It happens so often, it’s becoming my new norm.

George: And I think that it’s a good lesson for all of us that you’d need to be reinventing yourself or you’re gonna become irrelevant in a very short period of time with just the way that things are changing. I gotta ask about Gary Vaynerchuk, you know, you’ve done a bunch with him, had him on your podcast. Congratulations, that’s huge. But then I saw some other content online that you’ve been doing. I watched him at the IFA, the International Franchise Association show two years ago, right before COVID, he did a two hour and 40 minute presentation, no slides and just had the audience riveted. He really is that good, isn’t he?

Heather: I mean, he is so incredibly focused. He is so on when you’re with him and so intense. But yeah, I’m a big fan of Gary Vaynerchuk. But again with him, he’s been playing the long game. People forget that, you know, he started off in that wine business and doing wine videos. And this is, you know, more than 10 years ago, 15 years ago, where he had these ideas to start showing up and creating content and really you know, bringing people along for the journey, nobody was doing that. He’s been, you know, a pioneer in this whole entrepreneurial space. So yeah, I do think he is that good.


George: Well, I appreciate getting a few minutes of your time and having you join us once again on the show, we have very few repeat guests, but when I saw the book come out of it, we got to get Heather back the show, we gotta talk about, “Overcome Your Villains.” Congratulations, I’ve got it right here. Here is the book. So we’re gonna put all the information on how you can get more Heather Monahan in the show notes, the website, the virtual speaking, the live in-person speaking, the two books, congratulations on everything. The podcast to people wanna listen to your podcast, and it’s good seeing you again, my friend, and thanks for coming on the show.

Heather: Oh it’s so great seeing you Georgia and for all of your people and anyone listening. If you go to overcomeyourvillains.com put in your order number for the book and you immediately get my $500 bonus bundle for free as a big, thank you. It’s got my confidence video course, my accountability program, my workbooks, everything. So hopefully it will help all of you get over your villains and get onto your best life. Thank you, George.

George: We cannot thank Heather enough for sharing your stories this week. I gotta read this for you out of the book, “Overcoming Your Villains,” ’cause you can tell that Heather is a big personality, but you got to hear this. “To anyone who’s pissed that their name is not here, I’m under deadline and this is stressful, so bring your book over and I’ll write in it personally for you.” “If you don’t know me well enough to come over, then you can’t be pissed.” As you can tell, Heather is a big personality and she’s reinvented herself in this new role and the book is unbelievable. “Overcoming your villains,” there’s some great lessons in there, and I highly recommend her podcasts. She’s got some great guests and some great learnings inside that. The value of posting content, she talked about documenting your processes, being consistent. And the reason I read that quote out of the book, Heather is always Heather, she’s not somebody different. She’s very authentic, this is who she is, you can take it or leave it, and obviously a lot of people are taking it because her career as a speaker and as a coach has been going very well. Well, if you love this episode with Heather, there is another one episode 119, “Confidently Pursuing Goals and Embracing the Unknown.” Have a listen to the next time you’re enjoying a coffee, sitting in the car or walking the dog. Just one of the over 200 episodes we’ve produced in the last four years to help you Conquer Local. If you found value in this episode, please leave us a review wherever you listen to your podcasts. The feedback that you give us helps us to grow and better adapt to what you wanna hear in future episodes and be sure to subscribe to the Finney award winning, Conquer Local podcast. As we continue to welcome extra ordinary sales leaders, marketers and entrepreneurs. My name is George Leith, I’ll see you when I see you.