Damon D’Amore: Helping C-Suite Leaders Build Legacy Through Story & Strength #legacybuilding

Welcome to the Legacy All Stars podcast. We feature inspirational stories from people who dedicate themselves to helping others. Here is your host, Alan Pavloski. Welcome back to the Legacy All Stars podcast where we celebrate people making a difference in the lives of others. Today's guest, Damon D' Amore has spent more than 20 years working directly with C suite leaders across Fortune 500 companies. Applying lessons from Wall Street, Hollywood and entrepreneurial ventures to guide executives on psychological performance, storytelling for stakeholder engagement and building legacy. Founder of Legacy mentor Damon brings a no nonsense, high impact approach to personal growth and professional excellence, especially for female leaders navigating male dominated executive spaces. He's known for telling the truth, forging trust quickly and creating results that stick. Damon, welcome to the show. It's great to have you. How are you my friend?

Doing wonderful. Thank you for having me.

Yeah, my pleasure. Let's jump right in. You've had an incredibly diverse background from Wall street to film, TV, entrepreneurship, and now coaching Fortune 500 leaders. What are the consistent leadership lessons you've carried through each chapter?

Yeah, you did a wonderful pre interview job with your questions, very thoughtful and detailed. So I actually wrote down some notes to make sure that I have them best answers for you. But across all the different businesses, I mean the people really at the top of their game that stay there and last, they're very secure in their identity. They have a very tightly defined identity and they own it. They're okay with it, primarily self validate as opposed to constantly looking for external validations. Especially when it comes to big strategic vision. They're comfortable moving forward with their vision and goals and gathering a team together. If they're only 70, 80% there on the tactics and the actual numbers, they're comfortable taking risk and they pretty much all of them have their own personal systems and processes in place for everything from time and energy management to communication strategies. You know, very detailed, almost a little bit kooky, personalized systems for performance. But they're all different. But they all have a strict system which they are disciplined to that, you know, any demand on their time, energy, resources, labor is going to go through a filter to see if it fits into that system and what they should be focused on.

So yeah, you know, I want to kind of ask a follow up on that. You talked about owning it and being true to themselves. I mean, isn't authenticity in general that which resonates with others in a way that makes people feel powerful and confident anyway?

Yeah, authenticity is big. There's been a trend over the last so many years to go a little bit too far with that. Almost like I think you go too far with things like empathy, too, when you're dealing with team engagement. But yeah, people know whether you're authentic or not, because it used to take millions of dollars of a Super bowl commercial in order to get somebody to focus on you for a minute and see if they could kind of get your vibe. Now it's a cell phone and totally low production value on TikTok. And in a minute, enough people could think that you're authentic about whatever your story is, that you could gain millions of followers and people can see through it, what's scripted and what's not. And now they're starting to see through what's AI and not. Not just video clips, but people that are reading scripts that are generated by AI versus, if I listen to 100 a year podcast and I know how Allan talks, I can tell when something is not authentic. And it's more for buzzwords or clickbait or algorithms to, you know.

Yeah, well, I hope that my process is thoughtful enough to where I don't have any of that come up, but thank you for that. Let's talk about storytelling for stakeholders. Why is it so critical for leaders today? And how do you help them build those narratives?

So, especially since 2020, for a lot of reasons, stakeholder relationships have become a lot more complex. And there's been this inverse relationship between expectations that stakeholders put on their leaders and their brands and the amount of time that you have to actually respond to that and do it in an authentic way that they trust you for. There's also been culturally, over the last decade or so, Jordan Peterson talks about this a lot. A prevalence of story and narrative over facts and data, at least in the short term. But because we live in a society where information's flowing so fast and things go viral and get picked up and the communication means are shorter and shorter. From a blog post to a video clip to 140 characters to a meme. Narrative wins every time. And it's really hard to pull back that narrative once it's caught on. So you want to be in control of your narrative personally, as a leader and of your brand. And you want to be able to have a really quick, concrete strategy for regaining control of that narrative if you lose control of it, which happens a lot. And a lot of people have leaned into stories, especially that they told themselves through lockdowns and economic factors and social unrest, all kinds of things that happen over the last five years. People fall back onto the stories that they tell themselves and how they fit into this world almost as their own avatar. So when you, when you're speaking to your audience, if you can convince them that you see them for who they are in this world and you can help them go from A to B because of your unique value, whatever it might be, they will trust you to be their guide along their journey, whatever that journey is. The story used to just be more for the creatives, but now everybody's telling a story. Whoever you are, especially if you're on social media in any context, no matter how much business it is versus personal, you better be able to tell a story with a concrete beginning, middle and end and explain to the listener why they're better off they spent their time listening to you and not somebody else.

Yeah. Do you have techniques that you use to help your clients learn better qualities of storytelling?

Yeah, I've been really fortunate in that the storytelling I did professionally in Hollywood started off in independent film, but then a lot of documentaries and reality television. So dealing with a lot of non fiction narrative, even from my Wall street days before that and I pitching new businesses. But I'm also a big fan of storytelling. So you start with a base level of something like Joseph Campbell maybe, but you get into this really broad spider web of philosophy, religion, literature, belief systems, all kinds of things that inform it. And actually on my wallet I want to move my camera. But my base storytelling program for Corporate clients has 74 data points on it leading your stakeholders from where they are here today to where you want to take them. And it's constantly evolving. But I collapse that down into even a five to seven point for somebody who's in a jam. I get a phone call and my client says, oh my God, someone's Business Insider is going to interview me. Here are the 10 questions and I look at them and I say, wow. Two of those are your thought leadership platform based on what's going on right now in the world. In your category, here's your 1, 2, 3, 4, 5. You know, you take them on this journey, so yeah, it helps to have that shorthand, but it's constantly iterating with new things that I learn, new things that I research, and also the types of stories that are resonating with the public. You know, I'm not a big social media fan, but I'm on it just to see what people are actually, you know, the attention economy. So why are they spending more time on this than something like watching their favorite show Mad men for the fifth time? Like why are they doom scrolling on TikTok for two hours before bed. So. Yeah, and also being really considerate of your audience. You know, even in for corporate leaders, they have multiple external stakeholders, but they all like to be spoken to through different channels. You know, some are written, some are verbal, some are interviews, some are visual. You better be able to take your facts and data in a really compelling narrative and put it into a simple infographic or meme. So you need to be flexible in your storytelling abilities and the means by which you communicate, because you might have board members who are of different ages, even generations now, you know, and then they like to be communicated to in their own specific way. So you might have multiple deliverables for that.

Yeah, definitely. And I'm really particularly intrigued by the fact that you were able to transfer that skill set from your Hollywood days and your film days and your TV days into coaching.

I was really resistant to it, honestly, because everything I knew about coaching, and you'll never hear me refer to myself as executive coach, coach for various reasons. But I was resistant to it because I saw what was generally known to be that. And having been in business for so long, especially at high levels, even on Wall Street, I was like, that's not for these people. For my C suite group. But I had more and more leaders that I worked with in other areas asking me to help them with board presentations or this or that, or I'm going to Davos and doing my first thought leadership speech. I only have 15 minutes. You've known me for 10 years. What are the three things that people should be taking away and blogging about on their own? So to quote my therapist, like, just give up and just let it happen and see how it goes for six months. And then before I knew it, the first six months, I had 14 Fortune 500C suite clients, men and women, helping with different areas along storytelling or personal performance or a lot to do with resilience. It was kind of a natural progression. And I'm not a big Steve Jobs fan, but one of my favorite quotes is being able to connect the dots looking backwards. And somebody might look at my resume in order and be like, that's strange. But you look backwards and you realize this. Built on this, built on this, built on this. And so now you have like a fully formed recipe.

Yeah.

And then I had to get comfortable speaking in public because I never was, you know, as I did a lot of public speaking before COVID for the six years prior, because that turned out to be a channel that I was not familiar with. But a lot of people that were my client demographic, like in YPO forums, you needed to be able to do it in a really succinct way.

Yeah, for sure. A large portion of your clients are women in the C suite. Why have you had so many high performing women turn to you for coaching and how is your approach different?

Well, I started off, my business is mainly referrals anyway. These days, except for when I do a speaking gig or something, I'm actually writing a book. But that's separate. And at that level a lot of it was referrals. Oh, I did this. Who helped you with that? And additionally a good portion of those are women. And just from a, at least back then, they tend to hang in their own cliques. You know, there's like female YPO form or female this or their female Silicon Valley book club that they were going into and you get referrals that way. So I was kind of forced to build separate curriculums for men and women for certain parts of my program because men and women are obviously different. The initial feedback which carries through today is always, I don't feel like you treated me like a woman. I don't feel like you put kid gloves on or treated me different than you would a man. And I'm very conscious of that. A because I grew up with a single mom and sisters and believe that things aren't fair even to this day, that the things I hear that you'll never see in the press, behind these walls, in these big companies, it's shocking. It's almost like 1980s style bias. And it's not fair. But if you think that it's not fair and therefore it shouldn't be tolerated, then you shouldn't have to play the game then you're not a player in this game. All of my clients, very forward leaning, very strong women who would say things like, I read your email about what I need to work on and even though, you know, I might think some of it could be interpreted as mansplaining, but you know, these are traditional male qualities they need to get familiar with. It's not fair. I recognize it, but I want to overcome it. And I said, we're going to work great together because I want you to be optimistic but pragmatic. I think also growing up around just a bunch of women, my feminine side of my storytelling, archetypical stuff is really, really tuned in. But I really am a fan of women. Even when I coach CrossFit in LA years ago, I love coaching the women's class. It was different to have somebody truly who thought that they couldn't do something, learn how to do something than teach a guy like me to go from pulling 350 to 400 pounds, like, literally, who cares? I think they're a lot stronger than men in a lot of ways. A lot of this came through in Covid when everybody went remote. I had clients call me, you know, that were CFOs or CMOs, and they would say, my CEOs on a Zoom, and he's in his home office and he sees me with like a kid on my lap, another one running around, and husband's sick. And they're like, oh, my God, how do you do you do all this with, like working 80 hours a week? For me, I'm like, yeah, like, you're so much tougher than this guy who's golfing by 3pm on Friday. Not that I'm not a fan of men. I work with male clients, but there's definitely a difference. And I feel like the current culture is not going to change. There was a flip 2015, and especially closer to 2020, where the leaders who have a more diverse and inclusive talent pool that's qualified to choose from, and the perspectives as they're implementing their decisions, those higher degrees of empathy, compassion, team building, they're all incredibly valuable and nobody can really survive in the long term without them. So these voices have to be there. And also to that point, there are a lot of. There are a lot of times when a crisis is brewing and a lot of female executives prove during 2020 that they are much further superior in mitigating crises as they are on the horizon. We give this number of reasons as every tidal Wave rolls past 2020, whether it's supply chain disruption, talent wars, geopolitical inflation, all these tidal waves could become another big storm. It's been incredibly helpful. These leaders are learning to have female perspectives just from the critical thinking process they go through versus a man, how they look at threats and opportunities. I love being part of that equation. And also from an age gap, a lot of the leaders that went through 2020, unless they're really older, they weren't around for 08, the last big global crisis, but those people transitioned into the board. So you have people who were Gen Xers or even Boomers, and you have C suite people and big brands like, know, Verizon or Duncan, like 40 years old. And there's a generation gap, but there's also a gender gap between how women communicate with those male stakeholders and what those men hear. Versus how they process it. So somebody negative would call it mansplaining. But a lot of my clients appreciate going what they're going to present, going through a filter of what I'm hearing as the demographic of these people on this board and helping them craft it so that it's inclusive to everybody. And the things I love the most are when I get a call after a board meeting and they say something like, I got everything I wanted. You know, even in the middle of Q4, 2020, with second lockdowns coming, when budgets were tight, people got increases in budgets to go after things they wanted. They told a more compelling story backed by real data, and they wove that masculine and feminine narrative so that they could get everybody's advocacy around that table. Instead of the old way of just pounding on this hero's journey, we're going to go out and slay the dragon and bring the unicorn. You know, it doesn't work anymore. It doesn't work for most. There's always exceptions that people can point to. But I always tell my clients, your business is in the lottery ticket. You shouldn't just roll the dice and hope you're one of those people that could do whatever you want.

You know, this is a question that you and I have discussed before, but can you speak about trauma or early life challenges and how they've shaped your understanding of resilience? And furthermore, how do you guide clients.

Through their own without turning it into like a grief porn session? It'd be into also because there's family and stuff. But a lot of people, I've learned, experienced a lot of trauma regardless of their background, especially working a lot with women. The degree of even lower case a abuse from, you know, physical to verbal to financial to cultural is shocking. What people have had to put up with. Me myself as a kid just saw and experienced a bunch of stuff kids aren't supposed to be around. And it made me, A, very protective of other people around me. I became a protector and B, it made me very indignant, which became one of my superpowers later on. And I try to teach this to my clients. Like anybody that tries to put you in a box or limit your self actualization or ability to thrive because of your gender or sex, your economic status, where you're from, how you look, how you speak, your education level, I push back against that like I'm being buried alive. And it's helped me a lot through my journey because I wound up leaving college full time early to work on Wall street and be very successful. Without a finance degree. And then when they wanted to transfer into entertainment, I was told, you got to go to film school. And I was like, no, I have all these skill sets. Transfer somewhere else. And I went. Produced the biggest reality shows in history. Along the way, whenever somebody said, well, you're not the type of person that could do that. No. And a lot of the women I work with, even at the highest levels, still experience this bias where it seeps into them, and it makes me sad. I've had people with incredible resumes call me up and say, when things aren't going well, say, do you think I was a diversity hire? You really think I was the best person for this job? And it's like, what are you. Are you insane? Like, I can rattle off 20 data points. And they're like, yeah, you're right. And it's like, by the way, all the men around you going through this, like, 20, 20, 20, 21. They're all falling apart, too. I had people call me and say, I can't get my CFO to return an email for a week. He's just paralyzed. And I thought this guy was a, you know, steadfast rock. So I think that everybody can tap into their trauma history, and even if they don't, you don't need it to happen. But somewhere in their life path, personally, professionally, they've been told, that's not for you. If you remember Caddyshack, you know, Bill Murray wanting to go in the pool, and Chevy Chase is like, well, the pond's better for you. You're more of a pond guy than a pool guy. Yeah, I hope that answers your question. I didn't want to get too.

Yeah, it does.

Too gory or anything with stuff.

No, that's perfect. Look, I always encourage vulnerability, and I always encourage people to. To speak their truth. And not to a point where you're like, you talked about making a grief porn. But ultimately, it's important that people embrace their experiences and apply those experiences to make them the best person they can be.

I've seen the opposite, both professionally and up front. I mean, out of the number of women that I've been around growing up, there are some that said no and were indignant and actually physically left and endured a bunch of stuff just so that they could go have their own life. And I saw other women just say, I'm a victim and never recover from it, and decades of lost time. And I also tell, for female clients especially, sometimes I'll coach people just below the C suite. I'll get A phone call and they'll say, oh, there's three candidates for the next coo. One of them's a woman. Would you coach her and give us some feedback? Say, great. There's a scarcity mindset where there's so few women at the top that they're afraid to push because they say, well, you know, I sacrificed a lot. My family did xyz. I make great money. I'm number two in this position. Maybe I shouldn't rock the boat. And I always say, imagine you were a man. Would you ever think that you should put some self limiting restraints on? And no, it's like, well, then don't. So, you know, I've seen the, the negative part of lives and careers when people impose their own restraints because they think they're not worthy or imposter syndrome, or they've accomplished so much they never thought they would that they're afraid of losing it all, you know, if they keep pushing too hard. I'm like, now, not at all. Like, who would ever. Somebody told me, like, you should stay in your lane for the next 40 years of your life. I'd be the first one, you know, knocking down the door like Hulk, you know, running into the dark. I don't even know the path. But you're not gonna, you're not gonna restrain my self actualization journey to happiness and fulfillment. Even if I fail, it's mine. You don't get to define it. So, you know, a lot of these women not get defined by and also culture. There's a lot of pressure on them to define themselves a certain way with that executive presence. And I'm all for it, but I always tell my clients, you know, they're not hiring you to have a woman in the position to check a box that acts like a man. They want you to retain your femininity, but you need to express these other characteristics of leadership traits that are traditionally more male, better or worse, and own that. You know, like, you really need to earn your identity up there in that C suite. You need to accept it, you need to own it. So that when people look at you, hear your name, read your name on an email chain, there's a feeling and a vibe. You know who that person is and they know who they are. And that when they walk into a room, they're comfortable with who they are, you know, not asking for permission. I had somebody go to their first board reporting meeting in their new job, and I said, show me the deck. And you show me the deck. And the very last slide said, Questions, comments, question mark. They said you delete that. What are you talking about? They just promoted you and gave this position because you are the authority on this pillar of their business. You going to ask them to tear your thought leadership and authority apart after a presentation? No. You sit there and you delivered your gold to them, your treasure, and let them ask if they have a question. But, you know, you don't ask somebody to tear apart your thesis. No, you're.

You describe your coaching style as intense, honest and empathetic. Can you walk us through what a breakthrough moment looks like in your work with clients?

Yeah, it's funny, one of my clients actually called me a hardliner with empathy in that semi in one of my quotes. And sometimes they're surprised when they get the empathy part. Actually, I've had times where they've had really horrible stuff happen. And I was just nurturing on the call for an hour or 90 minutes and at the end they were like, oh, we were waiting for, you know, Nietzsche, Damon, like, you know, like hardcore. I was like, well, like everybody else, you're allowed to grieve. But if you call me a week from now and you're still like this, we're going to have a problem, you know, So I really think that I call it pragmatic optimism. I wrote an article about it that's one of the foundations of my book, that the strongest people can look at the world and be optimistic but see it for what it is like. See their challenges, challenges of the world, obstacles. And I think that that plays a lot into being honest, mostly with yourself. There's a stories quote says lie to no one, especially yourself. And I'm a big believer in that. And I always talk about this. The first Rocky movie in the beginning, he goes and gets beaten up by some thug and he goes home and he looks in the mirror and he sees a picture of himself when he was like 12 years old, this beautiful kid, almost like a movie star, and then looks at this bashed up face and he thought of this with himself. He even tells people when they ask him to fight the champ, I'm a bum, you know, So I think there's this honesty, but without being unfair to yourself or brutal. And regarding a breakthrough moment, I had a client who, I won't say male or female, but big Fortune 200 company, very difficult time with their board and went in for a board meeting that we prepared months for and specific communication strategies for each board member who's an ally, who's an enemy, even though they're internal and afterwards called me from the hallway and said, not only did they approve all this, but one of them pulled me aside, one of the older board members, and said, we don't understand why we can't push you around. And that, to me, is a big breakthrough. You know, it took a lot of honest introspection and some really tough love on their part with themselves leading up to that. How am I being seen? And why is that? And how do I change that? How do I change it in a confident, authentic way and, you know, having intense, honest, empathetic conversations but being unrelenting about it? I think that's a real skill set. And I've had other people tell me, you should just focus on being happy. It's like, you know, what if I was a child? Yeah, happiness is a thing. But, like, you know, something, you could act. I have a different take. And I have friends who are happiness coaches, and I love them, but I believe that happiness is like, you know, a smile from somebody you love or a rainbow, or you're doing that feeling when your dog snuggles on you or whatever, and you can't manifest it. You can capture those moments. You could savor it. So you work all your life for fulfillment. How to be fulfilled is different than being happy. It's not settling. But I think that the most fulfilled people I see, who are most comfortable in their skin and navigating the world and gaining advocacy for people walking by and being like, you know what? That's the new chief sales guy. I'm not totally on board with him, but he's not an asshole, and he looks like he's walking through the world, kind of like he owns his space. And they will follow you. You will gain advocacy and engagement from your stakeholders. I think it's very, very, very important. And a lot of people, especially these days, after Covid, you don't have to walk into a meeting and pitch for a job. You're on zoom. You're in the comfort of your own home, probably in your pajamas, waist down. Like, there's this discomfort from having to be really brutally honest with yourself because you don't let anybody else do that with you anymore, you know? And it's also one of the reasons that a lot of the people at that level work with me, because they're shrouded in fear on some low level, and they can't ask their employees for advice because they're going to tell them whatever they want to hear. They don't want to get fired. They can't tell the board that they're having a problem because they're going to question whether or not they made the right hire. Some of them can't even tell their families. So they need an external stakeholder in their success to be brutally honest and have that intense empathy with. And then once you get, once you peel away all that stuff, somebody who nurtures you as you're building it back up, you know, the practice isn't just like some drill sergeant or Gary Vee to rip you apart and tell you you're not successful because you're a piece of crap. You know, you don't work hard enough.

Today's episode is with Damon d'. Amore. This is the part one of a two part episode. I hope you all enjoy.