I interview Damon about the power of coaching executives. He discusses the process he uses to drive change and goal attainment among his clients. We also discuss how he lands new clients and how to accelerate “referral marketing.”
Damon is a performance specialist working with two types of leaders: corporate C-Suite executives and founding teams of venture-backed firms. His work focuses on: mindset, resilience and storytelling.
He has worked one-on-one with hundreds of CEOs at Fortune 500 brands. His experience spans Wall Street, Hollywood and consumer brands.
Damon is a global keynote speaker, serial founder, board member, investor and adviser to multiple international companies.
Frank Bria: 00:00 The 6 to 7 Figures Show. Episode 73, Let’s hit it.
Announcer: 00:04 Broadcasting from the Valley of the Sun outside Phoenix, Arizona. This is the 6 to 7 Figures Show. Tired of working so hard and having no time? Take your six figure practice and turn it to a thriving seven figure enterprise. And now your host, author, speaker, mentor and strategist Frank Bria.
Frank Bria: 00:29 Hey everyone, Frank Bria here with the 6 to 7 Figures Show and I’m pleased to be here with my guest, Damon D’Amore and we are going to be talking about his background, his experience and Damon is actually a performance specialist. It’s working with basically two kinds of leaderscorporate C-suite execs, founding teams of venture backed firms and his work really focuses on mindset, resilience and storytelling. He’s worked one on one with hundreds of CEOs of fortune 500 brands. His experience spans Wall Street and Hollywood and consumer brands and he’s a global keynote speaker. Serial founder, board member, investor and advisor to multiple international companies. So Damon, thanks so much for being here, really thrilled to have your experience.
Damon D’Amore: 01:19 Thank you for having me. This is wonderful.
Frank Bria: 01:21 Yeah, absolutely. So you and I share a little bit of a common background here in having worked with some fortune 500 companies before and some CEOs of those folks. What would you, for those who have never experienced that before, what is it like going toe to toe with a fortune 500 CEO and trying to get them to do something that maybe they didn’t want originally do in the first place?
Damon D’Amore: 01:50 It’s funny because most people get intimidated because, you know, but what you need to realize is that if they’re asking for help, they really, really want help and feedback and that they want to play in your sandbox. They’re in their own sandbox all day long, where they’re the king in the castle and one of the first big CEOs ever met who had like a $6 billion company. I showed up at the meeting in a suit. His secretary opened his office door and the guy was wearing a Grateful Dead tee shirt and jeans and sneakers. He looked at me, he said, “why are you wearing a suit”? I said, “why are you dressed like that”? I said, I’m here. He said, “because this is the day I get to be with the cool LA guy, the coach, I get to be like, in your world”. I was like, Oh, this whole perspective just shifted. So it’s not so much about, you know, it’s much easier to pull than to push. So if somebody’s coming in to me, they want the help and they want to be open and authentic. The hardest thing is really getting them to trust you so they can tell you all the things that they can’t tell their board, their employees, their spousesand everything’s confidential. It’s getting that trust. It’s really, really difficult. And I gained that trust through saying what my background has been and telling them stories about, you know, loss and resilience. Once they get comfortable, then they open up.
Frank Bria: 03:12 Yeah. I do think that’s something that’s interesting that people who don’t have a lot of experience with fortune 500 executives. You know, CEOs as well as a lot of the senior executives, is that a lot of them, not all of them, but a lot of them, they already are pretty self aware about their blind spots and they don’t really have a lot of issues. It’s not like they have to wear some kind of external armor to pretend like they’re something they’re not. They’re not trying to prove themselves to anyone. There are exceptions to those rules clearly, but usually if you’re standing in their office, we’ve kind of already passed that point. It is interesting that I find actually a lot of these folks very open to feedback. You know, they’ve got opinions and they’ll challenge you on your opinions and you’ve got to have a really good reasoning and some framework and experience to bring that to them. Cause they’re used to having that kind of intellectual debate with people, you know, with their teams. But that they are, they’re very open to to say, you know, all right, let’s go, where are we going. Which I found really refreshing. So it’s, it’s interesting you’ve had that experience too.
Damon D’Amore: 04:23 Yeah and it applies across all industries. After my Wall Street time and before my corporate American time, I worked in Hollywood for awhile and I got to work with a big A-list actor from The Godfather, whose name I won’t drop but you could imagine, he was looking for feedback on something and everybody in the room was just telling him whatever he wanted to hear and you could tell he was getting very pissed off. And in my head, “Well this is why I left Wall Street. This could be my shot. I’m going to tell this guy what I think”. And I did, and we developed a rapport over it and he actually called my boss the next day and said, “Thanks for sending that guy over. He’s the only one that had the balls to tell me what he thought”. Not in a rude, crass way, but you need to give constructive feedback because their time is the most valuable thing and if they feel like you’re wasting it, even by being polite to them, it’s not, it’s the same thing in coaching, you knowyou dont get rough or really down in the weeds with people just for the sake of it. If they need to hear something that nobody else is telling them, that’s my job in order to hold up a mirror. And they ultimately appreciate it.
Frank Bria: 05:24 Yeah. I think that that’s true. Again, you know, it’s a self-selection thing. There are definitely people who don’t have the strength of ego to hear bad news, but they’re also then probably not hiring you or paying you for very long. I don’t have a lot of patience for that. It’s like, “Hey, you know, you hired me. Like, why are you arguing with me”? It sort of doesn’t make a lot of sense to me.
Damon D’Amore: 05:49 When I first started coaching, I had a big suite(?) client and we were in person for our fourth or fifth meeting and I could tell they were just like spinning the wheels and I was nervous cause it was, I was new at this. I was like, “You know what, you’re wasting my time too”. I was like, boom, boom, boom. And they got, they got up and stormed out and like literally stormed out of the meeting and they got on a plane in LA and flew back to where they were going. I assumed our engagement was over. From the air, I got an email that was like two pages long and it’s like, you’re supposed to be supportive. Nobody’s ever spoken to me like that, but once I cooled down I realized you’re 100% right and if you’ll still work with me, how do we address this? So yeah, it’s a…
Frank Bria: 06:30 It is a rollercoaster for sure. There’s something about that I just find it fascinating. I still when I get an opportunity to work with a large corporation executives there, it’s still a lot of fun. But let’s talk about kind of how you got to where you got to. What you’re dealing in the area of resilience and comebacks right? So what is your journey through that? How did you get to where you are, where you’re working with these folks on those subjects now?
Damon D’Amore: 07:04 Sure. And I know we have a time constraint so you could ask me to any dive into any specific part, but the high level wasI grew up in Jersey and I started working on Wall Street at 21 while I was still in college going for undergrad. One of my first jobs after six weeks of being told that I would be an assistant until I graduated, I was actually on the trading floor. And by the time I was 22, I was running a trading desk for one of the biggest bond trading firms in the world and building new businesses for them, reporting directly to the C suite, the CEO and the COO. So very early on at 22, just interacting, I realized these people think differently than everybody else in the company. They see their challenges, their strengths, their weaknesses differently. They communicate differently and over a five year period, I built businesses in New York and London at the trading desk and essentially FinTech before it was called FinTech. Loved it, got burned out went into Hollywood and when I transitioned to Hollywood, I wound up being a producer of reality TV. And the first show I produced was The Apprentice with Donald Trump. When I got there, they said, “Well, you’re the only producer who has producing experience”. Cause I did some before that. But also could talk to these executives about their business. Nobody here knows anything about business. So I became the liaison between the CEOs on the show and doing grant integration, built up a number of relationships, big brands. It was wonderful, did that two seasons transitioned into interactive gaming for a bit with Dreamworks and AOL working with their C-suite and then ultimately went to Undercover Boss. When the show came out, I helped them select the CEOs for the first season and then ultimately a second season. Being around these business folks all the time, at that point I had gone through two careers, a marriage and an implosion, and 9/11, because I worked in Tower One, on Wall Street. So a lot of the questions that I get from people initially were, “Man how do you do it? Like you’re so resilient”. In my mind I’m like, “I’m not really, I’m just living my life”. So after Undercover Boss, I interviewed probably about 700 C Suite execs for the first year and a half to be on the show. Ultimately when I left, I started a consumer products company that I was passionate about with a friend, raised a small venture capital fund. I had this other business life after Hollywood, but always these CEOs were my investors, my advisors, my mentors, channel partners. The soft trade that we were doing was they were giving me their advocacy, their brand or their investment, whatever. But I was giving them at the time, performance coaching. All the conversations were around mindset, focus, resilience. How do I tell my story? Ultimately in 2016, one of them reached out to me for a formal coaching relationship. I’d never done it. I agreed to do it. I loved it. And just through referrals, I built up a book of about 14 CEOs that first year, and now it’s what I do for a living and i love it. I realized the coaching business is so large, I needed to find a niche. So initially it was legacy and now it’s these three pillars. Because I’ve gone through a tremendous amount of wins and losses and always figured out a way to pick one positive thing from the ashes that I can build upon. I can really draw a line from 1993 to 2019. The people who have worked with me appreciate that and they want to know like, how do I, how do I do that? How do I transition and survive and thrive? So that’s a long, long answer.
Frank Bria: 10:26 Yeah, that’s a really fascinating journey. It’s really interesting, I think the people who are really successful and making an impact don’t have that straight line path. You know, it’s like a pinball machine bouncing between different things, and again, you look back and you go, “Wait, what was the one thing out of that experience I can pick out and build on”. So it’s really interesting you call that out because that is something that I’ve personally seen, not just in my own life, but in a lot of people who I think are successful or are really building off of those experiences. That’s the one thing they’re able to do. So that’s interesting.
Damon D’Amore: 11:12 You can tell a lot about somebody, the way that they perceive that journey. Some people are like, “Oh man, you haven’t stuck to anything in the last 30 years”. Other people, are like, “You’ve experienced so much growth in so many different ways”. That’s like, “Oh, I want to work with you”. Not just because you’re giving me props, but because you understand the value in failure and, and you don’t know how to win until you fail, and you can’t really grow unless you suffer, which sucks. But that’s life.
Frank Bria: 11:38 Well, and I think that it makes people better for it. I mean, I remember a conversation I had one timeyou know, one of the tech startups that I was involved in, we were raising $6 million to get it kicked off. And we had just come off a really, really, really lucrative exit. Of course, when you do that, you got a lot of wind at your back and there’s people asking a lot fewer questions than they would otherwise right? So after a really successful presentation where it looks like we were about to close the deal, I felt like one of the investors in the fund, I kinda needed to come clean, you know, and say “Listen, it hasn’t always been like this. This last one was great, but I gotta be honest with you, I’ve had a couple of others where it was a complete failure, like we carried the furniture out in the middle of the night kind of stuff”. He looked at me and I just thought I was having to clear my soul before they invested money, and he goes, “You know what, good, we only invest in folks who have failed” because they said, “You know, people who have never had that experience, they think they’re God. They think that everything they touch is going to be perfect and every decision they make is awesome”. He’s like, “We want people who can reflect on the experience and pause and go, wait a minute. Is this going to turn out badly”? There is value in that for sure.
Damon D’Amore: 13:02 My first couple of months of running a trading desk, I lost a ton of money and I put my head down, thought I was gonna get fired. I went to my boss and he was like, “Yeah, I’m pissed that you lost the money, but this is the best thing that could have happened to you because the guys who make a crazy amount of money their first year of trading think that they’re superheroes and invincible and they have the biggest, worst crashes you could ever imagine”. So, yeah.
Frank Bria: 13:24 Yeah, I believe that for sure. So, I want to pivot quickly cause you just launched a really successful mastermind with some great folks in there that I’d love to talk about. Can you tell us a little bit about this that you just got kicked off with some of these CEOs?
Damon D’Amore: 13:42 Sure. Somy work generally with coaching is two types of people, Fortune 1000 style CEOs, a hundred million plus, usually billion plus revenue or C suite or venture backed people that are top startups that have the cash to scale. But I do a lot of public speaking and I work a lot with early stage entrepreneurs. I love doing it and I always get asked to coach them, but I can’t do it one on one, it’s a time resource issue. So I’ve been in the mastermind for 12 years in LA and we had some people with massive nine figure exits. We’ve had other incredible implosions. But I know the format well that works for me and my peers, so I decided to do it online and it’s called Legacy Mentor Mastermind. Our first cohort is running now and I limited it to 12 people even though we have less than that because in order to get in, you need to be an early stage entrepreneur, founder or at least an executive that’s in the mid-level of your corporate structure but trying to get ahead. We had some people that were way too early stage who applied where they would offer no peer mentorship to everybody else. So I had to weigh revenue now versus bad experience for my people. But basically it’s a wonderful format, it’s a lot of one on one time. We have two large interactive zooms a month where everybody goes over 30 day personal professional goals. Everybody goes over their business issues. We have a big two hour AMA where they get to tap into my brain as a coach and not pay some crazy corporate rate. Then they all get one-on-one zoom with me also. So there’s a consistent, trackable, measurable system that we work on and we launched and we have people that are in corporate America and leaving and starting a company, in corporate America who are basically running a startup within a corporate structure, we have a founder who started a high eight figure, low nine figure business and sold it and now is starting all over again from a bootstrap mentality and wanted to be around these fresh energetic mindsets, and we have someone who’s just left, a big, big industry who is doing a tech startup for the first time. He’s not a technical person but he’s already gotten validation and presales in a SAS model. So people were off and running. It’s funny, it’d be the people who were in corporate already on the first call offered so much value and perspective to the founders who thought that, you know, they know everything but they’re in a four wall mirror room all the time. So it’s wonderful and I tried to keep a price point high enough that it meant something to these people as individual to pay for it, but not prohibitive. Otherwise they’d be full time coaching clients. And it’s a six month program.
Frank Bria: 16:16 Six months. Okay. Very nice. One of the things that you mentioned, which is really key, and we kind of talked about a little bit before we started the interview too, but something I think a lot of people leave out is this curation, this very active curation work you did upfront. Because things live or die on this, you know, it’s really great that you spent the time to make sure you were getting peers in the room because we’ve all been in groups where we’re kind of like, “Is this the right group of folks to be around? Am I in the right room, you know”? If you’re going to do this, and again, have it at a price point where it’s a significant commitmentyou do, you wanna make sure that you’re creating the right room. So that’s good that you did that. I think a lot of entrepreneurs get mixed up in this cause again, this is something we talked about before, it’s like you also have to kind of turn the revenue down when it’s not the right person and if you’re in the wrong mindset about it. It’s kind of like, but I can take the cash.
Damon D’Amore: 17:21 But if you think the long game, because I’ve started so many businesses, six months from now when it’s over, if these people had the most amazing, fulfilling experience and they’ve grown, their testimonials and going after their networks, they’re going to fill two or three more mastermind classes rather than collect an extra 40 or 50 grand now, which isn’t going to be a game changer. In my personal mastermind, I’ve had people that we let in because we wanted to grow and it wasn’t even about money, it was about growing by ego. We have this big group, and they’re just sucking up time and energy so. I match off our current members with accountability partners so they have somebody to talk to throughout the month. And they were all so happy with the partners they got. So it takes time to call everybody who applies to your mastermind all around the country, but I did, I got on the phone with everybody because you need to have a vibe for this conversational piece because the whole thing is conversation.
Frank Bria: 18:13 Yeah, you do that’s so true. Glad that you’re, that’s modeling great behavior for anyone who’s listening to this, who’s trying to create their own group that you really do need to actively curate. That’s great. So you’re working with them for six months, they seem to have different backgrounds, but do they have common threads in the goals that they’re trying to create? Are you building off of that?
Damon D’Amore: 18:38 They do. They’re all overwhelmed with opportunity and possibilities and figuring out what to prioritize and work on and why. More than three quarters of them are struggling with, “I can keep bootstrapping as I am or I can go raise money” and they see these big unicorns questionably failing now like, (?) and these companies going public crashing and they’ve been living in this venture capital unicorn world for a long time now, but they had a scarcity mindset. “Should I raise money and take it while I can at whatever price I can get so that I can sustain this” or “Is it bette to bootstrap”. The answer is different for both depending on your business. So my general response to people is, “What are the metrics you need to hit your next milestone”? If you can do that with bootstrapping and presales and whatever and spend minimal amount of money, do it cause you’re going to have a better valuation, more validation. But at some point, if you think that your game is all about customer acquisition, than marketing dollars, you need to just go hoard as much cash as you can.
Frank Bria: 19:44 Yeah, that’s really wise. You know, there really isn’t one. I’ll occasionally, get questions. Just yesterday got a question about raising capital and there’s just no one right answer for everybody. There’s a lot of different ways to do that. But leading with a metrics first approach like you recommended, I think that’s wise, that’s really smart. So, this group, you’ve curated itwhat are your growth plans for that? Are you going to add to this group? Are you going to start a new group, do you think later? Are you going to create cohorts and they stick together? Do you have any plans for that growth?
Damon D’Amore: 20:24 So my plan, so this group’s closed now that it began because they’re on a six month schedule and at the end of our next meeting they’ll all have a 12 week, 90 day cycle set of action items that they’re going to be accountable for. My goal is, I looked at my world of my business and I do public speaking and right now it’s probably about one sixth of my revenue stream. I’d love it to ultimately be a full quarter or a third, but that takes a lot more time and energy both creating content, testing it out and getting those gigs. So I can coach one on one with my corporate and VC, I can speak, I can create content. I’m trying to finish a book because you need some sort of authority out there and I could do my mastermind. Revenue wise, time wise, all that, my goal with the mastermind is by the time January rolls around and we have a solid three months of a case study; to go hardcore and really do some paid marketing this time and see based on my network and the extension of it, I think I can fill up two of these cohorts per six months every year so I can tolerate 4 a year. That’s my goal, and I really only work with two to three corporate clients a year and they’re on one year contracts and I try to work with no more than three startup clients and they’re on six month contracts because the cashflow might be, you know, so I’m hoping.
Frank Bria: 21:41 Nice. Yeah, that’s really solid. I think that three months in you, you should have some really great testimonials and that’s gonna really drive a lot of the marketing avenue. But again, this is one of the reasons why it’s so important all of the strategic pieces that you put up front, right? To have the right group, to make sure that there’s front-loaded, really solid milestones people are hitting so that they can create. You don’t have to wait until the end of the six months for them to be able to express what’s going on. You got great stories to tell and then you’re able to kind of put the next one in place. That sounds like a great plan.
Damon D’Amore: 22:21 And creating structure. Like a friend of mine runs a mastermind online, it’s a lower price point in one of these giant zooms with like hundreds of people and he’s like, “What do you do in a prep”? I’m like, “Oh, I built a shared Google sheet where they all do their updates, I built this, I built that, I built that”. He’s like, “Why are you doing all that”? I’m like, “I want to make it as easy as them to succeed and if they had a shit ton of money, they’d be hiring me as a coach and already to be funded. So their time is scarce just as their money is”. We need to create systems around you so that I already know for the next four weeks what blog post and podcast are getting listened to about, whether it’s time management, productivity, forming habits, raising money, whatever. I already know what’s going to go down. So it’s about doing all that pre-work for the last month and a half sitting in my house on a weekend watching college football with a notepad being like, what do I wish my mastermind could do if I could start all over?
Frank Bria: 23:11 Yup. I mean that effort about sort of designing the customer success in advance, that’s the critical success factor I think. And it’s funny, there are a lot of people who just don’t do it. Either because they don’t understand the importance of it or because they sort of expect the client to do all the work to get the success. “I Just show up, they have to do the work” and I just feel like there’s a balancing act there around making sure that your clients are set up for success, that you’ve got the structure in place and you’ve thought it through and you know what the path is to the next milestone. So good. Good for you.
Damon D’Amore: 23:56 I’m a big fan of therapy. I’ve been with my therapist like 12 years, but I prep my notes for next therapy session in a file every two weeks before I see her. I texted her the other day, I said, “I need you to watch the seven minute Toastmaster’s speech I did because it’s related to something” and she will because she’ll do the work. You need to be, yeah. You need to expect your clients to do the work, but you need to put them in a framework to do it because most of them, if they’re coming to a mastermind, they don’t know about accountability or time management or like what they should even be doing.
Frank Bria: 24:23 Right, right. Yeah, absolutely. No, that’s great. That’s good structure. You’re doing all this stuff that we teach people to do with that. So that’s great. That’s a great case study, do what Damon’s doing everyone. That’s cool. Hey, we are out of time, I really apologize. I’d love to continue the conversation, but I know you’re really busy and really grateful for the time you’ve taken today for this conversation. But one last question for you. So for folks who are listening and are intrigued by what you’re up to, want to connect with you, what’s a great way for them to do that?
Damon D’Amore: 24:55 So the mastermind website is www.legacymentormastermind.com so they can reach out there and there’s a contact form, it links to my bio and also to my full website. My website for corporate and venture backed clients is www.legacy.mentor.co. Somebody’s holding my “.com” domain hostage, which is crazy in this day and age. But so the mastermind is legacymentormaster.com and legacymentor.co. You can email me through both of those sites. I’m on LinkedIn, my profile is public if they want to reach out. Yeah.
Frank Bria: 25:26 Cool. And we’ve got the link to the mastermind here below the video. If you’re on the show notes page, it’ll be there. If you’re out and about listening to this audio, come on back to the show notes page and click on through. If you didn’t catch that URL and click on through to Damon and all the great stuff he’s doing. Damon, thanks so much for spending time with us. Really appreciate it.
Damon D’Amore: 25:46 Thanks. Really this was wonderful.
Frank Bria: 25:48 Yeah, absolutely. And thank you for being with us on this episode of the 6 to 7 Figures Show. I’ve been your host, Frank Bria. Take a look at the structure of what you’re doing and see if you’ve got all the structure there for customer success. It’s a really great lesson for me, really appreciate that. We’ll see you next time on our next episode. Take care, bye bye.