Damon D'Amore (Part 2) - Giving More Than You Take: A Masterclass in Purpose-Driven Leadership

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. All right, this is part two of a two part episode with Damon d'. Amour. Really powerful episode. I hope you all enjoy this. There's some really great takeaways here. You know, what you said resonated with me in another way that really affects like the way I think about things. You know, you think about performing artists and musicians. It's not always the best, most prolific musicians that are the most compelling to watch. It's those that are having the most fun and those that are most comfortable in their own skin. And something you said as a response to that last question really hit me at that moment. You know, I'm also a musician and when I just go in there with reckless abandon and have fun, I mean, that's when I perform my best as well.

Yeah. And you know, some of the great Miles Davis, I'm a huge fan, but he was so uncomfortable in his skin. Even though he had so much talent. He would go on stage, turn his back to the audience, play for two hours and walk off. Like not even let them look in the eye. Cause he was afraid of seeing a glance of. Really. This guy's supposed to be that good, like feeding his imposter syndrome. But if you can be in yourself in the moment and like find your flow state, for lack of a better word, people will gravitate towards you. And it's really, really impressive to watch and be a part of. And it gives people themselves hope, you know, oh, if that guy who's uncool can find that much artistry and like joy and peace and flow and being a Zen, that why can't I kind.

Of thing, you know, on the Miles Davis side and because I really relate to that. A big Miles fan, I saw Miles live a couple times and yes, exactly the same experience. He'd turn his back and just blow. Purple is what he would say, basically. But listen, Miles, he may have had imposter syndrome. Purple publicly to the point where he didn't want to be seen by the public. But in the band practices and in his band, he was a tyrant. He was known to be a fierce tyrant to make sure that the music was right. So again, you know, you can pull out multiple parts of your personality and make sure that you're utilizing those parts of your personality to get to your means. It means to your end that would.

Be like a Steve Jobs, modern day. I mean, very few people can get Away with it. But it's like, I don't care if you're Bill Evans or whoever. Like, if you're on this record, you're on a Miles Davis joint, period. This is my show.

That's right.

And there's a few Hollywood producers, because I worked at Hollywood for a long time that, you know, when you walk into a movie and you see that name, no matter who the director is, it's a Jerry Bruckheimer film. You know, it's got a certain. It's Top Gun, it stays the thunder. It's all these things, you know. It used to be the same way with Miramax, even though it's a bad word today because of Weinstein. But when the independent wave hit again in the early 90s, I recognized walking into a theater in Jersey in Red bank, like, oh, wow. The last few movies I saw with that Miramax City logo were really good independent films. Like, you know, so, yeah, I think. And leaders need to let people know you have a collaborative process, but in the end, it's your strategy that they're all helping to drive. So if they're on board with a great. If they're not, can't have multiple generals running around the battlefield, you know, that's right. And it's a little bit contrary to some of the more Kumbaya culture stuff that I see these days, but if you build something for everybody, then it's for nobody. It really loses value. Needs to have a very concrete through line.

Let's move on to Legacy Mentor. Tell me the story behind Legacy Mentor and what does it stand for today and how has it evolved from its early days?

Yeah, I believe that there's plenty of reasons to work and work hard and sacrifice on whatever. There's that line from thank you for smoking where everybody has to pay a mortgage, so people do what they do. But I believe that once you've gotten to the senior ranks of leadership in large companies, even not even the C Suite, but you could have a lot of power and influence. You should be using some of that political brand capital, whatever, to leave the world a better place than when you were here. And it could be anything, whatever your jive is, you know? But Legacy Mentor initially started because I had a couple of large clients that were from Undercover Boss when I worked with them, when I produced that show. And they were getting ready to sunset their careers and trying to figure out, like, how do I get my big network of business people to want to donate, support these causes when they'd never really heard that. That's part of my. Part of my personal life. So initially, I would work with these executives on how to organically use their brand's weight and presence and things in order to introduce people to the fact that they support breast cancer awareness or, you know, recovery and addiction, whatever it might be. And then it morphed more into when the pillars of my system that I coach on, those that you mentioned at the beginning, really dialed into my niche. My average engagements were a year, a lot of longer than that. I don't want to work with somebody who's just stocking up piles of cash. You know, there better be something behind all that. Not that I'm not a capitalist. I am, but. But I still want to work with somebody who's just concerned with the red and the black line. So all of my clients have something that, whether they're in their business now that they're running in order to make an impact on, but it should be a measurable impact far beyond your gone. Whether it's beyond you in that CEO role or it's beyond when you're on this earth. So that's how I define it. You make a measurable, meaningful impact that lasts way beyond your time and your access to those resources, and you inspire others to do the same. And so many people tell me they went to their local, whatever groups, they go to their poker game or their clubs, local business clubs, Rotary, and inspire others to start thinking about like, oh, man, I'm turning the corner around 50, you know, I mean, supposedly the best earning decade for my career after working for the last 30 years. What are the relationships I want to build to carry after this? What are the skills that maybe I can learn while I'm here, and how do those carry over? So, yeah, I really think it's really important. I mean, I had great mentors along every part of my career and even growing up. And I think it's really important to find people that want to make a difference and even if it's not in your wheelhouse, help them figure out how to make that difference. If I've helped multiple people start charities and do all kinds of stuff, I.

Mean, there it is. That's the real reason, candidly, why you're on the show, because your philosophy about giving back and about encouraging others to make a difference just really is congruent with the theme of this show. So I appreciate that.

You know what, if I think about it enough, I'll get upset. But, like, I remember being younger, wanting to do things and being put in those boxes by people Who I thought I looked up to, who look like successful, had good lives, healthy families, nice house, whatever. And being like limiting. What are you talking about? You know, and then organically meeting people that wanted to help. But it doesn't mean you give people everything, but you help them learn and help themselves. And I've done it so many times. I've been at Big Brother, Big Sister program, pro bono. Mentored dozens of kids from bad neighborhoods in la all the way from high school through graduating college. I'm going to one of their graduations in Houston in December. First one in the family to get a four year degree. But and making that commitment, you know, my girlfriend, since we've been together, once in a while, in a weekend, my phone will ring and it'll be one of my MBA students from USC from 2015 who's going through a life thing or a divorce or having a baby or a career change. She's like, wow, you still talk with those people. I was like, you make a commitment to somebody who's looking at their life plan, you should be available for them as long as they're still living that life plan, you know, so. And I love that. I love the fact that I get hit up on email and text message and Instagram or whatever by students from a decade ago celebrating stuff. I'm going to one of their weddings in a foreign country. Yeah, I mean, mentoring is very, very, very, very important. And I'm a big fan of the book the Go Giver. And not so much that from a transactional money perspective, but every relationship is a transaction and you should always be giving more than you're taking. Building this big karma bank, not selfishly, but because that's the way that it's supposed to work. Like, be a good person. My grandmother used to say, that guy's good people. You want to be known as, hey, that guy's got a big heart. He's always helping. He's always helping when he can.

I love the whole give more than you get philosophy. I think that's really well said. So thank you for sharing that as well.

Somebody recently get really sick and I was like, you know, I can't imagine facing possibly dying. But I was like, don't fear the reaper, baby. Like, if you wake up every day and you know that you've given more than you've taken while you were here, that should comfort you. And not that I want to die, but I'm not afraid of it. I've lived a really incredible life. And outside of the one on one relationships, the hundreds of people. I have this file on my computer, like notes, texts, emails, whatever. LinkedIn messages. I heard you speak here. I was here. I did this. You know, something you said in the workshop in 2020 during COVID I still have on my desk. I refer to her constantly. It's like, I know I personally impacted hundreds of people for the better, including those I mentored. And I feel good, like my time to check out. Like, I'm not saying, oh man, I should have been a better person to other people. Anybody who's thinking that is living pretty low. And they got to correct that, like now.

Yeah, most definitely. I want to expand a little bit more on that. I know philanthropy and purpose driven impact are a big part of your life and your client work. What are some examples of legacy building that you're especially proud of?

Yeah, well, the one that I actually wound up being really involved with and joining the board of is the charity by Don Fertman, the former chief development officer of Subway before he retired. He was there for years. 30, 30 years. I put him on out of COVID boss. And he exposed his recovery journey on national television to 15 million people and initially was worried about it. And then got emails from Subway employees all over the world, like India, like, I've always been ashamed of my recovery, but you're so successful now on xyz. And he was a musician also. He had a couple albums as an amateur and he wanted to start an organization for musicians in recovery where there were safe places to jam and practice and meet each other, because usually it's a bar in your local town, you know. And he wound up putting together this idea for this organization. And I watched him gather all the corporate resources of Subway and they sponsored this big concert of musicians in recovery like Dave Matthews and Steven Tyler and all these people on the mall in D.C. and have a big blowout and then attract other charities in the recovery space. So he's been going with that and really affecting and changing people's lives now for, gosh, I don't know, eight years or something. And that was somebody. I said, look, you've got one of the biggest brands in the world. You have more stores than even McDonald's on the planet. People care about what you say now. You have this platform and the number one television show. And specifically with him, there was a challenge. And a lot of the storytelling work came in. It's like when I met the Lung Cancer foundation people, they were like, it's hard to raise money because most people think people with lung cancer is Their own fault because they smoked, you know, or most people think that addiction is because people are weak and don't have explicitly. And I have addicts in my family, and I know that's not true. So it's really fulfilling to see. Wow. I met this person through this other part of my professional career. They have this need which intersects with my legacy. I want to help people be able to build and leave theirs. And they have the resources and the microphones and the attention to do this and the logistics to actually build it. Really, really, really satisfying. And I've had other ones, too, but that's always one of my favorite examples because.

Yeah, that's a big one. That's. That's something to really be proud of. Sure.

Yeah. And he always mentions it, you know, he's like, I wouldn't do this without you. I said, come on, dude. Yeah, you would. You're an unstoppable force, you know, And I happen to have this. But no, very, very, very proud of that. As well as the other people have been a bit of a founding of some military veteran charities for very specific issues and other things. Cool.

Let's talk about what men in leadership can learn from your work, especially when it comes to working with women in meaningful and respectful ways.

Yeah. So one of the things I talk about a lot when I talk about storytelling for stakeholders is in 2020, there was this shift from, you know, whether it was a big brand, commercial or an ad or movies, or the narratives people were used to seeing and hearing, or whether they knew it or not, were traditional hero's journey for forever. You know, hero willingly or unwillingly goes out into the world on some adventure, meets the mentors, suffers a bunch of stuff, finds some treasure, but slays some external resistance. You know, the dragon, the matrix, whatever it might be feminine. The heroine's journey, or sometimes called the Virgin's Promise, is all about overcoming internal resistance. And for the first time in 2020, with lockdowns and health scares and scarcity and everything going on, everybody hit this same low point in their own personal heroes journeys of this feminine challenge. Right? They had to overcome this internal resistance. They were scared, they were afraid. Some of them, you know, lost people, lost jobs. First time a whole generation of workers heard the word furlough on the news. Like it's terrifying, Right? So since then, consciously or unconsciously, the stories from leaders and brands that people most engage with have been those that merge traditional masculine and feminine archetypes in these stories. Jamie Dimon is a brilliant example. If you go read his like 25 page letter shareholder letters, which I love, there is this empathy and compassion but with a limit because they're still a business. But he really touches the average person. You can see it when he walks into a bank branch in Detroit, people hug him. You're know, and he's a tough guy. He said some tough things. So for men, I always tell them you need to start to appreciate and learn your own relationship with a feminine narrative and what those story points traditionally are on an arc. Stakeholder engagement, team building. Empathy is so important. Communication so important. Talk about diversity and inclusion. I believe that nothing is more valuable to a leader and especially to male leaders than having a diverse pool of candidates for roles that are all qualify but represent a bunch of diverse backgrounds, cultures, perspectives, xyz. And then once a leader makes a decision on what that they're going to do, being inclusive of all those different perspectives and feelings and concerns. And that only comes with learning more about how women in business think and communicate and the things that you learn that they wanted to say but we're afraid to say. There's a lot of stuff that women don't say. These beings are mentioned. So I believe that the more that they can mentor women in meaningful and respectful ways, they're only strengthening their own. If you want to call their network or the political capital of a company. But it's like they're so much stronger because they, these women now trust having a male advocate. They see men that are open to giving political and capital or network over to help them over their bros from Michigan or they were in a fraternity or whatever because they have a very specific unique skill set and value to add. So I think it's incredibly important I tell them if you're allowed to show up in the next women's leadership zoom, just stay silent, you know, because I guarantee there's issues going on at your company that you have a certain perspective through that you're seeing through your 52 year old gen X male dude eyes. And the same thing that you're seeing these women are experiencing in a completely different way. Like I'm a member of some female peer mentoring groups in corporate and they let me be a member and I never take up their time on these calls, but I listen and it's like, wow, this is the perspective of what's going on. So I encourage men like be a mentor at your company. Ask for female upcoming leaders to mentor and if you can't do it there, go to a local organization, whatever it might be and have a lot of grace and realize, like I've, I've had some men tell me, oh, you know, I started working with this gal at work and she holds back a lot. I'm like, yeah, you're the first man to ever like without an agenda try to help them. It's unnerving and it's scary. Or they're a little bit not unsure. But just keep proving to her that you're going to show up every time, you know, and you got to build that relationship and that trust. Some of us, culturally, media based, whatever, most men are not monsters. Most women are not these like helpless corporate on some floating data river just because they get socially promoted. That's absurd. You know, like a lot of people still work based on merit and there needs to be a better communication and men need to see the value in it and women need to see the value in having a male real stakeholder in their career. And I always tell people, some people say, oh, why would a woman at that level hire you? Why don't you hire a woman coach? Oh, she can and she probably does. Probably got three different coaches. But even at the highest, most balanced, equitable levels, you're one of three or four women in that boardroom with eight other dudes. Right. There needs to be some communication filter. Not to correct you, but just to let you know, like this is likely how somebody with their worldview is going to and their experience in corporate America before they got there is going to hear what you're saying. And even the most like feminist capital F guys that I've met, there's something that's going to be said or done or seen that's going to trigger some memory or their grandfather dealing with the grandmother had or something. Like they can't get away from the bias that's like decades embedded in there. Especially before there was HR was a real thing. When I was on Wall street, we had HR department. It was, you know, like a zoo, an X rated zoo. And so this is a new thing for everybody and there'll be missteps, people will take an inch, go too far, roll back. But I think that we're so much better in a place with male engagement of female employees and mentees and executives and balancing everything than we were 10 years ago now 2015, you know, and a lot of men realized, yeah, during COVID like when teams were falling apart, a lot of these teams felt like they could talk to their female leaders more than they could their male leaders. Like very specific, unique value that you should not be ignoring or minimizing at all, regardless of what your background, your bias is, you know, so yeah, for sure.

What advice do you have for emerging leaders who want to lead with purpose and power but don't have access to a mentor like you?

Yeah, number one, do the work to really define your purpose and what that is that you want. Like I'm a big essentialism fan from Greg McCowan talks about your essential intent and mine personally. Like my log line in my head, like why I do what I do is I love working with leaders because they have an exponential force multiplier effect if they're doing positive. Right. So my essential intent is to help leaders self actualize and successfully make a meaningful measurable impact on stakeholders, you know, beyond them. But really do the work to define that purpose and go from as broad as you can to as niche as you can and then develop a thesis on your industry, your category, what you do and constantly validate it and check it, you know, even if nobody's reading it, you're writing to yourself, you should have a constant log running of, oh, this is where I think B2B marketing is going in the next decade with all these disruptions and pulling out validations from the news or other companies and pulling up things to challenge it. So that when somebody asks you, oh, you work in B2B SaaS marketing, where's everything going to be in 18 months with all this AI, like how's the ad market going to be effective? They know that you have an opinion and it's been well thought out, you know. And the other thing would be find mentors that will help you along the way and know how to ask them to be your mentor. You know, a lot of people have never been mentors and they assume it's some massive time energy, maybe even financial commitment. So have a process which I always help people with, find those mentors to find your purpose, have a thesis and validate it and constantly be updating and talking about it and then know who are the people that can help you along the way, like know the gaps in your knowledge and skill sets. And I always tell people if there were 10 steps on your journey to fulfilling your purpose. Right. Maybe you're at step number two right now, right? Can you get to three on your own? No. But if you did, you could probably crush 4 and 5. Find a mentor and show them all this work you've done and based on their history, you respect their opinion, their knowledge, their help, would they help you with this and then go back and do it and then Months later be like, hey, remember me? The guy you talked to helped. Not only did I do that, I'm all the way over here now, so do you. How do you recommend I get to here? And most people, once you show them that you appreciated their time so much that you actually did the work, they're going to be so happy to be on a monthly quarterly call or whatever with you to find your purpose, develop a thesis, constantly test it, and find mentors that are strategic to your success of filling that purpose. And hopefully they want to do it because it's also going to help them fulfill whatever their long term goals are and have filters on your demands for your time and energy and resources. Right. If you have a day job, maybe you're working on your purpose 10 hours a week, five hours Saturday, five hours Sunday. Like be willing to make trade offs in order to stay on path for that purpose.

Yeah, for sure. I have one last question for you, and I like to ask this of all my guests, but what does legacy mean to you and what do you hope to be remembered for?

I hope to be remembered as the guy that helped a lot of folks self actualize and successfully make whatever impact they wanted to in a really big, broad way because of their positions or their media presence or the breadth of their company's scope. But because I'm a Wall street guy, I'm a very by the numbers black and white guy, every year I do this exercise where I reach out to five professional and five personal contacts and I say, if you saw my name tomorrow morning on your Instagram feed or in your email, and it says that I died, like, what's the first thing that would come to your mind? And I measure them every year, you know, all 10 of them. And consistently I've been doing this since 2014, 11 years. I mean like the 70 percentile for the first thing that comes to is helping those who, who need it. Like underserved under whatever. So that's, I'm crushing my legacy there and helping people who need it. And the second thing, which is just under that is like resilient. Like, dude, you're always coming back from whatever that challenge is and you're always wanting to help people figure out how to add that resilience to their lives. So I got to work on the other 26% of the people in my group. But as of right now, you know, if I'm with 70 to 73% and they say, oh man, I always know he's helping these people, whether they're students, pro Bono clients or, you know, charity people or whatever. He's always helping those people that beat it and appreciate it, you know, have a big heart.

I don't know.

Gave back more than he took. Yeah.

Great stuff. Well, Damon, we've come to the end, but I really want to thank you for coming on the show to share your insights on empowerment. It's so powerful to our audience. Keep leading with purpose. And remember, legacy isn't only what you leave behind, it's what you build. Today, I'm Alan Pavloski signing off from Legacy All Stars.