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Stepping Into your Leadership artwork

Be Different-er, How Everyday Leaders Build Legendary Brands

Stepping Into your Leadership · 2026-04-08 · 36 min

0:00--:--

Key moments - from our scoring

Substance score

53 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality10 / 20
Guest Caliber14 / 20
Specificity & Evidence9 / 20
Conversational Craft9 / 20

Mark DiMassimo, founder of DeMassimo Goldstein, a New York-based behavior change marketing agency, explores what separates legendary brand builders from the rest. With the firm approaching 30 years of independence, DiMassimo has shifted focus toward working with founder-led growth-stage companies and healthcare institutions, alongside his partnership with bestselling author Garry Maxwell on understanding what makes brands legendary. The core insight he shares is that success comes not from special advantages or blending in, but from the ability to be authentically different. Drawing on stories of visionaries like Steve Jobs (whom he prophetically identified as a future great during Apple's wilderness years), Doug Levine (who pivoted from Wall Street to comedy to create Crunch fitness), and others, DiMassimo argues that legendary brand builders start with no special advantages and actively seek ways to differentiate themselves. In a world where attention is now the rarest resource and thousands compete for single opportunities, DiMassimo positions personal branding as essential equity - whether you're a job applicant competing against 1,200 others or launching a company. The conversation explores how leaders can apply campaign thinking to their own positioning, the importance of admitting when others have better ideas, and why authenticity matters more than prestige.

Key takeaways

  • →Legendary brand builders succeed because they deliberately choose to be different and operate by their own rules, not because they have special advantages.
  • →In a world saturated with competition and attention scarcity, personal branding and authentic differentiation have become essential career equity, even for job applicants.
  • →The best strategic move is to apply campaign thinking to yourself - if you're better in conversation than on paper, send a video instead of submitting a standard application.
  • →The ability to recognize and defer to better ideas (even from outside your industry) is a key leadership skill that compounds competitive advantage.
  • →Building a legendary brand requires positioning yourself as a person with distinct values and ways of operating, not just mimicking competitors who blend in.

In this episode

  1. 1Introduction to Mark DiMassimo and His Agency Philosophy
  2. 2Building Dego: 30 Years of Positive Behavior Change Marketing
  3. 3Legendary Brand Builders: Stories of Steve Jobs, Oprah, and Doug Levine
  4. 4Strategic Pivot: Focusing on Healthcare and Growth-Stage Companies
  5. 5Partnership with Garry Maxwell and the Idea That Changes Everything
  6. 6The Power of Personal Branding and Standing Out in a Competitive World
  7. 7How to Build Your Brand as an Individual Leader

Mentioned

Mark DiMassimoChristine CourtneyDegoDeMassimo GoldsteinSteve JobsApplePixarOprahDoug LevineCrunchGarry MaxwellVistage

Guests

Mark DiMassimo

Topics in this episode

Steve JobsMemorial Sloan KetteringLiquid DeathDeMassimo GoldsteinPositive behavior change marketingDoug Levine and Crunch fitnessGarry Maxwell and Big Little LegendsNational Jewish HealthDartmouth HealthE-Myth worldwide

Questions this episode answers

What changed about Mark DiMassimo's agency strategy two years ago?

He fired $2.5 million in revenue from clients with delegated middle managers and misaligned values, then refocused DeMassimo Goldstein into two specialized practices: healthcare (academic medical centers like Memorial Sloan Kettering, National Jewish Health) and founder-led growth-stage companies that need brand building to reach the next level.

Why did Mark choose Steve Jobs as the face of his agency mission in 1996 when Jobs was considered a failure?

DiMassimo believed the number one skill predicting outsized impact is the ability to build legendary brands, and he saw that capability in Jobs even when Jobs was in the wilderness after being kicked out of Apple, before Pixar recognition or the iMac's success.

How does Mark advise job applicants competing against 1,200 others to stand out?

Instead of submitting standard applications, he recommends treating your job search as a marketing campaign - if you're stronger in conversation than on paper, send a video. This filters for employers who value you authentically and can create a compelling story that attracts future opportunities.

What is the relationship between Mark DiMassimo and Garry Maxwell?

Maxwell, a bestselling author of Big Little Legends and former Canadian broadcaster, researches what makes things legendary from the outside in (Mona Lisa to Savannah Bananas), while DiMassimo works alongside founders building legendary brands from the inside out - they complement each other's understanding.

Why does Mark emphasize being a person with a brand rather than just becoming a brand?

He distinguishes between authenticity and marketing gimmicks: you need something genuine in you that leads to a different way you show up in the world, creating authentic differentiation - not artificial persona-building that people can see through.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains some genuinely useful ideas - particularly the reframing of job applications as personal brand campaigns and the observation that 'difference beats better' in crowded markets. However, substantial portions are anecdotal storytelling (Steve Jobs, Crunch gym, Doug Levine) that illustrate concepts rather than teach novel principles. Much of the conversational fill is praise-trading, meandering narratives, and repetition of themes ('be different,' 'legendary brands') without dense, non-obvious claims per minute.

you don't do applications, you do a campaign
difference or beats better out there

Originality

10 / 20

The core ideas - differentiation through authenticity, brand as personal asset, attention as currency - are well-established in marketing and leadership discourse. While Mark frames them memorably through personal anecdotes and the 'legendary brands' lens, the underlying frameworks echo conventional wisdom about personal branding, positioning, and standing out. The Liquid Death reference is topical but not analytically deep. Little is presented as first-principles rethinking or genuinely contrarian.

you need a brand...there needs to be something authentic in you that leads to a different way that you show up
positive behavior change

Guest Caliber

14 / 20

Mark DiMassimo is a legitimate 30-year agency founder with real client relationships (McKinsey, Memorial Sloan Kettering, etc.) and has built measurable business (fired $2.5M in revenue to reshape culture). He is a practitioner, not a pure thought-leader or podcast circuit guest. However, he is primarily a creative/marketing executive rather than a founder of a scaled operating business, which slightly limits relevance for ops-heavy B2B operators. His work is adjacent to, not central to, core business leadership.

founder and creative director of Dego or DeMassimo Goldstein, a New York agency
I fired or resigned $2.5 million of revenue at the agency

Specificity & Evidence

9 / 20

The episode relies heavily on named examples (Steve Jobs, Doug Levine, Oprah, Crunch, Liquid Death) and specific client work (McKinsey, Sloan Kettering). However, these are mostly illustrative anecdotes without hard metrics, timelines, or dollar figures beyond the $2.5M revenue cut and vague references to 'billion dollars' potential. The Liquid Death example is mentioned but not analyzed with specifics. Most claims about 'legendary brand building' lack quantified outcomes or measurable proof of the strategies discussed.

I fired or resigned $2.5 million of revenue
you could approach a billion dollars

Conversational Craft

9 / 20

Christine asks warm, conversational questions but rarely pushes back or challenges Mark's claims. She mostly affirms, asks him to elaborate on stories, and provides soft prompts ('how can people listening do this?'). Mark dominates airtime with long, meandering narratives; Christine's role is largely facilitator and cheerleader rather than interrogator. There are no moments of productive disagreement, no hard follow-ups on vague claims ('positive behavior change,' 'legendary brands'), and the dynamic feels more like mutual admiration than rigorous inquiry.

I'm curious as to what you're doing now
I wrote down a ton

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

mark42christine35courtney32dimassimo31agency18first15back14today10york10build10brand10world10different10room9everybody9life9

Episode notes

What makes a person, company, or idea truly unforgettable? In this episode, Christine sits down with Mark DiMassimo, founder and creative director of DiMassimo Goldstein, to explore how everyday leaders can build legendary brands by standing out with purpose, personality, and courage. Drawing on decades of experience in positive behavior change marketing, Mark shares stories from his own journey, lessons from iconic founders, and practical insights on what it really takes to capture attention and create lasting impact. This conversation is full of energy, wisdom, and a powerful reminder that blending in is not the path to meaningful leadership.

Full transcript

36 min

Transcribed and scored by The B2B Podcast Index.

Christine Courtney: Hello everyone. Welcome to Stepping Into Your Leadership. I'm your host, Christine Courtney, and I'm excited today to have in the studio a good friend and a powerhouse of a thinker, and that is Mark DeMassimo. And Mark is the founder and creative director of Dego or DeMassimo Goldstein, a New York agency built around positive behavior change marketing.

He's a writer, ⁓ advertising commentator. He helps build brands that turn emotion ⁓ action in designing campaigns ⁓ customers. But ⁓ newest news, hot off the press, is that He is traveling the country talking to peer advisory groups of CEOs and senior executives about how everyday leaders become legendary brand builders and why that is one of the most powerful and positive changes people can make. So we are going to learn a lot about him, but I have to say something personally too.

Mark is a fantastic person to have in any room. Okay. He is part. what I would say like childlike, playful, mischievous of sorts, right?

And then he is also open that part of childlike, he's kind of open to the wonders of the world ⁓ or is happening. And then he's also ⁓ at same time, ⁓ part ⁓ strategist who like waits in a room of a lot of leaders when I see him, ⁓ Waits just the right moment. when all of his like childlike, strategy, sage, clever, parts come together and he says something that like, drop and people often in the room go, And that sound is, I think, the sound of what you talk about when you say, Mark, the idea that changes everything.

I am thrilled to have Mark DeMassimo in the house today to talk about a lot of what he brings to so many companies at a much higher rate than you pay for this podcast. So get whatever nuggets of wisdom you can get from him today because it's bound to be a fun time. So welcome Mark. Mark DiMassimo: Thank you so much, Christine.

Wow. ⁓ I appreciate you. I appreciate you so much and find you so enlivening, ⁓ you so to hear. See, here you say those things about me, they just mean more coming out of your mouth.

Often I'd be like, I dismiss, you know, I'd be like, oh, come on. But when something comes out of your mouth, I'm like, wow, all right, you know, that's good. Cause you know. Oh, yes we will.

Christine Courtney: Well, thank you. just give each other lots of compliments today. But anyway, I really want to talk about this new, because you obviously, well, let's start first with what you've done, what you guys have done for years. Let's just give the audience a little bit of background about your agency and what you've done for years.

And then we'll talk about where you're kind of going now. Is that fair? OK, so what is the bread and butter of what you guys have been doing? Mark DiMassimo: That sounds great.

All right. I'm going to go all the way back because we've got an anniversary coming up. We'll be 30 years independent advertising agency in New York City. 30 years Cinco de Mayo, May 5th, 2026.

So I'm going go all the way back to April of 1996. Christine Courtney: Okay. Mark DiMassimo: Bring yourself back there. song should be playing in the background?

Let's put a little Nirvana on because some of us weren't letting it go, right? Wonderwall. Wonderwall ⁓ up the radio. We're watching the movie fresh on our little ⁓ DVDs whatever they were back then.

And ⁓ I working in an agency, ⁓ Kersh ⁓ Bond Partners in New York City. Very cool agency. We've got like Snapple and I'm on Christine Courtney: Yes, or a wonder wall or something there. Mark DiMassimo: like Citibank Advantage card, it's a classic campaign and it's good, really good for me.

And Steve Jobs, ⁓ out in California, one of the things we worked on over there was the Apple card, okay? But Steve was out, was Apple without Steve and Steve himself at that moment, he thought of himself sort of as a failure. He had created, you know, he felt ashamed that he'd been kicked out of the company he started. He started next.

with a sort of a well-designed revenge fantasy and it just kind of went sideways. There were certain, you know, it was ahead of its time in various ways and certain tactical that were made and ⁓ so didn't feel like that was great. He was involved with Pixar but the world wasn't really giving him credit or recognition and you got to give him credit for not making himself the center of that story I guess but he really felt like he was sort of in the wilderness and at that very moment ⁓ I up a magazine.

I tore a picture of Steve Jobs out of it, I pasted it, taped it to the front of my computer. I wrote the line, we will exist to inspire greatness in courier type, which was the agency's first typeface. And I pasted it right next to it. And then I wrote an email with this picture I took of it.

I sent to everybody in the agency, they weren't pleased, saying I was gonna start an agency. to inspire greatness in legendary brand builders. So why would I pick failure, somebody who hadn't really yet ⁓ a success in business and might never be? Because believed then, and I believe even more strongly now, that the number one skill that predicts enormous outsized impact.

So talk about positive behavior change impact in the world. First and foremost, ability to drive change, positive ideally, and the ability to build enormous value. is the skill set of building legendary brands. And Steve Jobs had that, he had me.

So imagine the force. ⁓ of this person, they're in the wilderness and all the way on the other coast, this creative director in an ad agency in New York is making you their poster guy. So that's where I started the agency. my goal, my goal when I got into advertising, want, you know what, I was a musician.

So I was a performer, right? I was a musician. I was in the bands. I was acting.

I went to school. We were talking about this earlier. We know some people in come. I was at SUNY Purchase, you know, lot of my friends went on to be professional actors, fairly famous actors, and they'd always be like, Mark, you're always acting.

You're in these shows with us. Why don't you become an actor? And I had zero interest because I said, I want to play roles in real life. ⁓ Whatever meant, I wanted to like ⁓ play doctor.

⁓ Christine Courtney: I'm writing that down. Play rules. Mark DiMassimo: I couldn't be like a con man, my father worried I might be. But I wanted to play roles in real life that I thought that would be the most fun.

So I started this agency because I realized if you want to succeed as a creative person, go home to your family at night and sort of have some power to steer your own destiny that you need to be a great marketer. So that got me to agencies and me thinking about why people do what they do obsessively. So when I started the agency, it wasn't for the usual reasons. It wasn't because I wanted to win more awards and I'd never, I've never been a camp.

everybody goes every year. I'm too busy working back in New York or whatever. I did it because I wanted to earn a place at the table with people who are going to build legendary brands. I wanted to earn my place right next to that person so I could keep on learning how they do it.

So I also didn't get into it because I felt like it was my best skill or that I was, you know, destined to be great at it. I got into it because it was the thing I was most curious about and that challenged me the most. The things that were easier for me, found boring. so ⁓ was this is always going to be challenging the rest of my life.

I'm talking long, but I will. So I'm going to go back now that you have the background to focus on what it is we do. So I got that wish. First off, so I actually have several books, if I ever write them, of stories of people, some of whom you know, like Oprah.

I mean, everybody knows Oprah's story. My biggest challenge with Oprah's story is people think she's successful because she's rich, rather than she's rich because she's successful. So, ⁓ you know, but, Christine Courtney: ⁓ yeah. Mark DiMassimo: For every opera on my list, and of course there's only one opera, there are nine other visionaries.

⁓ who wore whatever hairstyle they wanted, even if it was terribly ill-advised, I could show you some pictures, and lived exactly they wanted, created exactly what they wanted, built the cultures they wanted to build, changed the lives of folks all around them. ⁓ when I about Doug Levine of Crunch, who, he was on Wall Street for a little while, talk about childlike. Then he was like, yeah, this is boring. I can do this, this is boring.

He became a stand-up. comedian. And then he's out there. He met all the comedians.

He's produced some of your favorite, ⁓ you know, comedy video, you know, series and stuff since then. But anyway, so he's like, you know, not making any money. So in a basement in the West Village, he starts a what was a craze then aerobics class. It was crunch.

And he names it crunch because he's a genius and he makes that crunch logo. Christine Courtney: really? Genius. Yes.

I joined crunch in the nineties. I'm sure I was there. Mark DiMassimo: And You and I were the target audience. It was professionals come to New York City and they work 10, 12 hour days.

And at the end of the day, and this is what Doug taught me, I wish I could take credit for all this brilliance, but I take credit for being there, paying attention and then earning my place. He said, look, this is who we're talking to. They're professionals that come from all over the country. They work long hours.

They want to make it in New York City. At the end of the day, they've got a choice. This is the 90s. Go home, sit on the couch, watch cable TV.

We will be there. They go to a bar. Oh, maybe I'll meet somebody, blah, blah, blah. A nightclub.

Yep, yep. That's how, yeah. There were an ass. Christine Courtney: because that's how we had to meet people, by the way.

There was no online. Mark DiMassimo: So we pioneered the first bathroom advertising. been very big in bathrooms for 30 years, but we pioneered the first in-bathroom advertising for Crunch because it was there, there, or go to the gym. So he said, we are an entertainment choice ⁓ with those other choices.

And they're not here, we want to be there, not telling them they're wrong. not talking about their muscles, but entertaining them so they remember, it might be fun to go to crunch. Genius. He years in, it was the biggest fitness brand and it was a media company and he sold it, he moved to Miami, he started a family ⁓ selling it.

He has big move properties down there. He's ⁓ founded and exited three or four other companies since he's produced all these comedy albums. He lives the life he wants. He operates by his rules.

He mentors entrepreneurs. He builds these cultures that are fun and different. So I could just not let you ask me a question and tell you about people like this this whole time. Christine Courtney: Thanks for spending time here on stepping into your leadership.

I'd like to give a special shout out ⁓ to our podcast producer, Richard Francisco. ⁓ Check out our notes for any and if you wanna get anything out of this, go to our YouTube channel and please subscribe to Leadership Lab TV. If you heard something today, of course, that resonated with you, do something with it. fascinated.

So it's good. And I do want to also get into because what's so great when you tell these stories and, know, it's I love storytelling too. So I love just sitting around the fire. I feel like we're sitting around the fire, ⁓ But I ⁓ also to eventually to like, how can everybody do this?

Right. How can people listening to this go, wait, what's my brand? How do I build this a little bit more? I think there's some great It's all about the choices that you make.

It's what you say in conversations, how you show up in a moment. Share this episode with someone who's maybe starting a new job or stepping into a new level of leadership try one idea because it just might create some pretty powerful leadership ripple effects. Until time, keep stepping in. ⁓ wisdom that you have, you know, that I've seen you give people in this live when you, when they meet you.

But, but before we get there, and we will get there folks, if you're listening and you want to know how to, how to, you know, take this stuff that these guys, Steve Jobs are, it David Levine? Who was it from Crunch? Doug Levine. ⁓ did.

And that how, you know, the way that Mark sees those ⁓ ⁓ I'm curious as to what you're doing now. ⁓ because the room changes when you do. Mark DiMassimo: Doug Levine, Doug Levine. Christine Courtney: ⁓ it is very exciting and it's very linked to all of this.

⁓ explain a little bit about what you're doing now when you're going around the country ⁓ and meeting different peer groups of CEOs and senior executives. Mark DiMassimo: So last year, made a... I got to a strategic juncture, two roads diverge in the wood and I had to choose which road to travel down. And the result of road I took is I fired or resigned $2.

5 million of revenue at the agency that had become sort of, you know, you get successful and then big clients hire you. And then some of them hire you, delegate you to middle manager. who want to tell you what to do and they want to do the right things, not inspiring things. you've got mouths to feed, right?

And so you're, so ⁓ you know, you're tempted to, you know, to keep taking the money, but that affects culture. That affects a sense of what are we really in business to do? Are we in business to just make money? And So I realized we needed a more focused strategy if we were going to once raise our standards on who gets in and who stays in.

And so the that we made was that ⁓ the agency has, in a sense, practices. ⁓ One is health And I'm not talking pharma crap. don't do that. God bless folks who do it and do it well.

We don't do that. I'm talking academic medical centers. We've got a lot of experience. We're Memorial Sloan Kettering, National Jewish Health, ⁓ Dartmouth Health, and on and on.

Christine Courtney: New York Animal Hospital. Mark DiMassimo: you're right. Yes, ⁓ animal Medical Center, the Schwarzman ⁓ Center in New York, a new client, the Center for Neural Wellness in New Jersey, ⁓ Keene, who will be very happy. I mentioned ⁓ name, Dr.

Christine Keene ⁓ our Vistage Group. What? ⁓ man. Where you are the center.

Christine Courtney: Yeah. Mark DiMassimo: Talk about the idea that changes everything. So healthcare, healthcare is sort of one leg because we feel good about what we're doing and we have smart clients who are caring. we a, we have a wonderful track record there where, you know, they need responsible, experienced folks, ⁓ but be able to get a high level of creativity with that, that's, that's, ⁓ our, niche But the other side of the business, which is the bigger, more anarchic, more creative.

Center of the fastest learning is ⁓ what I growth stage companies. They're generally founder-led. ⁓ we some startups, but I'm not talking startups. I'm talking owner-led businesses that have gotten as far as they can get ⁓ on market fit and sales, and they really need to build a brand in order to ⁓ get that next level.

like our friend Dan Rudenberg was with Spear, know, by anybody's measure, a fantastic success, but reaching that outer limit where he needed the rocket booster to get to the next level. Christine Courtney: Yeah. Mark DiMassimo: So that is the focus. I am, two years ago, Garry Maxwell, bestselling author of Big Little Legends, walks into our group, our Vistage group, he ⁓ plays his music and it gets quiet.

⁓ And he ⁓ meanwhile, back Paris. ⁓ What is the number one undisputed indubitable factor that drives demand? Is a secret formula? And on ⁓ on.

And ⁓ listening to guy, this Canadian ⁓ former broadcaster I realize he's written the playbook I've been learning my whole life. I'm working alongside, I'm focused on who builds them and how do they build them and what do I bring, what kind of creativity helps, right? That's what I'm focused on. He's...

from the outside in studying legends. So it's the what, what makes a legend? How do things become legends? He's starting with the Mona Lisa and working his way the Savannah bananas.

I'm with the Savannah bananas ⁓ and like, wow, the Mona Lisa, that's interesting. So I according him, I did the thing that... almost no marketing person the country did, even though he has spoken to over a thousand Vistage groups and is the number one ⁓ speaker. I said, you're fantastic.

I agree with everything you said. We must get to know each other. And he says, really? Because most marketing people either think they know better than I do or they feel threatened.

And You know, ⁓ strong ego that, you know, I do, ⁓ that needs, know, needs tending and all of that. But thing that has really driven my career is that, ⁓ is one, admiration for other people's The best idea wins for me. And I can quickly forget whether I had best idea if someone else has a better one. ⁓ So that's really driven my career.

And two, and I think it might be the frugal entrepreneur in me. I have a weakness for ⁓ low brilliance. Like, know, McKinsey was our client. McKinsey hired us seven times.

Christine Courtney: You Mark DiMassimo: Seven times, they're so strict with their non-competes, but you know what? Sorry, don't hire us again. We've moved on to other people. But McKinsey hired us seven times.

And so McKinsey's full of prestige, ⁓ you And they're hiring us and we're competing well with them as well too. But when Goldstein and I, Lee Goldstein, my partner at Dego, who will not mind my mentioning in his name, when we needed training, we E-Myth worldwide. The E-Myth. Because we didn't whether it was prestigious.

We didn't care about the price, although we liked that it was lower than the million we might have had ⁓ to pay. We admired the content. Christine Courtney: Yeah. Mark DiMassimo: And can I tell you, Judy Wade, my friend, who first hired us, the most senior woman at McKinsey at the time, who first hired us there, chose us over the two biggest agencies in the world at the time, even though we were in a small circle of chairs in a completely demolished office.

And I said, why? asked her why as we were sitting around in those chairs. And she said, you think I got where I am by not being able to pick the best team? I just want the smartest team.

I don't care about anything else. So learned that, I guess, from her as I've learned a lot of things from her. Christine Courtney: That's cool. when you're going around now, are you working with Gare?

Are you doing some of the stuff of the how behind ⁓ to build legendary ⁓ Like how people can do that? Is that the take on it that you do or just to inspire them to make a change? Mark DiMassimo: So ⁓ I think it was about two, years ago that Judy and I, she's out in San Francisco, but she and I were having a lunch. we only see each other every few years off of Zoom.

But we were having lunch in New York and she's like, you know what, take it for what it's worth, Mark. But what you have always been about, what you guys have always been about, and what you particularly have always been about is the idea that changes everything. That's what you bring. So that my head.

It hit at the right time. know, positive behavior change. I always felt like that's our mantra. Like ⁓ that expresses values.

I caution clients all the time. Don't make your mantra your advertising campaign or your tagline. But you know, you're busy working on clients. It's the cobbler's shoes.

So I put it out there in the world and some people were super attracted to it. Other people found it super vague. What do you mean? I said, I want to work on good habits.

That's what I mean. why don't you say that? Well, so because I'm figuring out what you should say. That's So ⁓ but ⁓ what but this focus.

I wanted to put positive behavior change in its rightful place ⁓ that mantra, that pillar of values, ⁓ in which positive behavior change are you helping people primarily? And this is actually building legendary brands and for whom we talked about it. yeah, ⁓ how and who are these people? And the truth is these are people who start with no special advantages, none.

It's actually hard if they start with too much money the first time, the first time. No special advantages. They realize they have no special advantages and therefore they seek of being different. If you were to start, just as a mental exercise, if were to, you know what, I want to go back to one thing because you said this earlier and I think.

Christine Courtney: That's funny. Mark DiMassimo: You know, I wish I had said this earlier, but ⁓ for those who are still with us, I'll say this now. You don't want to compete blending in in this world. You didn't want to do it 30 years ago when I started this agency.

This is a world that is disgorging itself of employees, that is creating freelancers ⁓ know, at an epical rate. I mean, ⁓ than ever. Where are thousands of people competing for each project, much less job. You don't want to go out there blending in.

So the things that maybe you don't want to create the next Liquid Death. I think it would be really fun if you did, but maybe you don't want to create the next Liquid Death. We'll talk about that. You still want to need to and I'm not saying become a brand, be a person.

Okay, I think there is a difference. Be a person, but you need a brand. Okay. You need there needs to be something authentic in you leads to a different way that you show up.

So you stand out. Christine Courtney: Okay, okay. Mark DiMassimo: So I spoke for an hour and half, and I think you're suspect now that that's not hard for me, to a college class yesterday. And after the class, some students stayed over on the Zoom.

And one young man said, I'm applying for jobs now. And there are like 1200 other applicants. And I feel like I know my strengths. And when I'm in the room and in the conversation, I'm really good.

But how do I get in the room? So I said, first off, you're way ahead of most people because you know your strengths, you know where you play well. Okay, so that's a strategic, that's a strategic asset that we're going to put on the table. We're not going to forget that.

how do you leverage it? The idea I would give you that I think will change everything is you don't do applications, you do a campaign. Christine Courtney: cool. Mark DiMassimo: You do a campaign.

You're a marketing student. You do a campaign for yourself. If you're better in the room, what's the closest? Send a video.

What if six out of 10 people don't like it, feel you broke the rules? You don't want to work for those people. In fact, next job out, when you're out in the marketplace with the great story about how your video got you a job, they'll want to be next in line, some of those people. There are people who don't want to be first in line for everything, anything.

They want to follow, right? So, but all you need, how many jobs do you need? Christine Courtney: to. Mark DiMassimo: So the things we're teaching now, this is a kind of power, a kind of equity you can build.

Benjamin Franklin said, empty your person to your head and you'll never go hungry, right? You'll never be broke. What do you need in your head in this world? You need the ability to have a brand.

Christine Courtney: Right? Mark DiMassimo: to express yourself as a brand, be different in the world, to capture attention in a world where... We talk about rare earths, We want, you know, we're trying to take over continents and we're fighting a global economic and cold war over rare earths because we need them. And there were the rarest things on earth.

No attention is the rarest thing on earth. It's the rarest thing. We're all competing on these global platforms with billions and billions of other people. So you were to start.

Christine Courtney: Yes. Yeah. Mark DiMassimo: a water brand right now, and you really believe ⁓ healthy, clean water, would you put it in a plastic bottle ⁓ in a screw top bottle of any kind and talk about how healthy it is and show healthy people drinking it? I would say don't do it.

If you have money, you'll lose it. If you take investment, you'll lose it. Why not instead? put it in a can that looks like your dream of a bad ⁓ beer or more liquor.

Why don't you never ⁓ show sipping it, but they're always guzzling it messily. Maybe sitting behind a Marshall stack and a bunch of too many drums, you know, on a stage with Christine Courtney: at a rock concert where I saw my kids drinking it and I was like, what are you drinking? Mark DiMassimo: at a rock concert with a sea of people in black and some ill-advised tattoos, run a commercial breaking the law as your song. Maybe if you did that, you could approach a billion dollars.

And what's in the can? People think, well, I'm different. I fundamentally bring a different product, right? My service is different.

I have a unique selling proposition. You can learn a lot from water because it's really the same stuff in there, right? It's yeah, I mean, you... And I'm not some, I believe in the character ethic.

right up there with Stephen Covey. I don't believe that personality is everything. But if you don't stand out in a way that resonates with your character. people will never notice you, they'll never engage with you, right?

So attention is the gate, you've got to get people through that gate. Then your show better be good. but difference or beats better out there. So this is what you can learn.

So I'm out there, I was with Gare ⁓ a multi Grammy and CMA award winning country music director, three men in an Airbnb for a week. should have video taped it for reality TV, it was fun. of us, all us, Christine, when I tell you that I am the least verbose ⁓ of three of us, I wish was, ⁓ I wish was exaggerating. ⁓ This the verbal bunch ever.

But the stories, the stories, the director, Christine Courtney: It's so funny. Mark DiMassimo: He knows Taylor Swift, he worked with her when she was 19. Stories of Dolly Parton, but we're all there together. Gare is coaching me generously and really intelligently.

He's coaches me so well that I'm like 4.9 on my first presentation and he's like, okay, now don't use the notes. Don't look at your phone, don't use the notes. I'm like, what?

It's three hours. Christine Courtney: you Mark DiMassimo: He hasn't yet. So he's like, look, it's a crutch. You got it.

You know what you got it. Yeah. So I do my next one. It's it.

The first half is like the like like the bumpy, like white knuckle flight. Like the tech's not working. I don't know what slide I'm on. People are like, does this guy know what he's doing?

And but. At the end of it, the guy who knew better than anybody who was also a marketer and all of that, he's sitting in the middle of a room next to me and weeping. He said, this is exactly what I need today. So, so the strengths overcame the weaknesses and there were significant weaknesses.

Christine Courtney: Wow. Yeah. Yeah, that's great. That's great.

Good for you. I love it. Well, you did it. I love it.

I can't wait to see this journey unfold before our eyes. A couple of questions, because you brought up that you were a musician. You did some acting. ⁓ that, you know, music background, you think create who you were?

Do you ever draw on that? I mean, I've seen you play piano pretty and pretty intensely. like what ⁓ do you think that? Works in your life today, you know, even professionally.

Mark DiMassimo: I'm so tempted to pull out my Tommy Hilfiger branded guitar, I really have. My wife was marketing director at Tommy Hilfiger back in the day and they sponsored a Rolling Stone concert and I got an SG guitar and SGs are my favorite. We had the Gibson guitar account, by the way, in the first few years of the agency. And you the licks that I've been working on.

You know, I'm... Christine Courtney: away. Mark DiMassimo: I think the thing about me is that I'm fundamentally an improviser and I like to be challenged. by sort of maximum difficulty on my feet, thinking quick, and yes, also stepping back and waiting for my moment and all of that.

I like that. I'm better at that. I'm bad at, and I, you know, I've gotten better, but I'm fundamentally pretty bad at filling out a form. I don't like doing things linearly.

I love washing dishes, ironically though. I like doing laundry and washing dishes. and that kind of stuff, so I'm useful around the house. But those things that require attention to just doing it right, I hate that stuff, but I love being on my feet.

So being with actors, writing while we're shooting it, if it was 1969, I'd ⁓ be a I would, I'd creating, but I'd be in the back, because I wouldn't want to be arrested, and I'm not that confrontational, I'm a people pleaser. but I would be back there saying, say this, hey, why don't you do this? That would be me. So you learn in a band that one guitarist that turns up their amplifier too loud and steps on everybody else is all it takes to ruin the vibe.

That's one thing you learn. So I've learned I learned that back when we all used to be in conference rooms, and especially now that we're all on Zooms, person who doesn't tune in to other people, who doesn't create space for to be heard. who lacks that self control or emotional intelligence or generosity or whatever it is, is all it takes to ruin the vibe, ⁓ make it impossible to create the experience you want to create. So ⁓ just one, that's just one.

⁓ Christine Courtney: I love that. That's just one thing, but I think that's so interesting what you learned from the arts, right? Just even what you said. And I think that's a really good tip for everybody out there.

Like that ability to tune in, To tune in, feel that vibe of that room and go, wait a minute, this is the time I need to step in. This is when I need to step out, which is what jazz musicians do, which is what, you know, any of an ensemble that's learning or improvising together. I always find it interesting, you know, in theater, in improv. I was always amazed that the best improvisers were the quieter ones, to a large degree because they listen.

And in improvisation, it's not about how funny you can be or how you can talk. The best laughs come from the person that's listening the most. Mark DiMassimo: yeah, yeah, it's, yes, pauses ⁓ underestimated, underestimated. I grew up with people who talked all the time, so I really got a lot of training in listening.

And I think it's the reason that when I get the opportunity, I wrote this email to you last night about much families want you to talk more and think everything that you say is brilliant, right? But it's growing with Italians who talked a lot and sort of being a kid who did a lot of listening growing up. ⁓ It's a wonderful skill actually to be able to off the need to attention, you know. by talking.

So yeah, you do, I think you learn so much in the arts. I won't mention her name, but have a woman at the agency, who by the way, you have got to get to know. The only reason I don't introduce you to, she, because she at Dego, she's one of the most valuable people we have there. I don't have to all my time worrying about.

the vibe at the agency, how people are feeling, whether they're feeling seen, whether their issues are being dealt with. Her emotional intelligence and skills in that sense ⁓ amazing. has like this, she designed education like RISD, know, but she worked in managing creative people and photographers and all of that, and in educating creative people. And I just, don't want you two to meet because I think if you met her that she would be working with you and you'd be standing around in the road in a second.

because a generous person, I don't want her to achieve what she's supposed to achieve in life. I want her to keep on working for me, you know, ⁓ doing I need her to do. ⁓ Christine Courtney: Maybe both can exist, Mark. Maybe both.

It doesn't have to be one or the other. Maybe both. Mark DiMassimo: I agree with you. We're on the same page, but I just, I learned so much.

It's a band, you know, it's a band. And it's what we... like the jazz bands or those sort of jam rock bands or jam funk bands where everybody does get their time in the sun, but everybody really earns their place by the way they support the other players. They really you gotta do that.

Christine Courtney: Thank you so much for coming today. We could talk forever and we will. We do every time we see each other. And I'm gonna have you back on after you've done, after we'll hear more of your stories because they're so great.

And there's so many nuggets that people can take away from today. I wrote down a ton. I wrote down blending in is not the currency of today, right? Be different-er.

I love that idea about not, you're not applying for jobs. You're creating a campaign for them. I loved what you said about. that you really like to do things that where you're the most curious about or you have the biggest challenges.

And I also cracked me up and I'm going to share this with my parents, you know, as a former actor myself, ⁓ you said, I want to play roles in real life. So because that's all I do. I feel like nowadays all I ⁓ do pretend I'm just playing roles now in real life. It's a different kind of acting, right?

So thank you so much, Mark. It's been a total pleasure this morning. I appreciate it. Mark DiMassimo: Ha ha ha!

Well, you're Academy Award level. ⁓ and tell everybody to buy and read big little legends, how everyday leaders build legendary brands. Christine Courtney: Yeah, it's great. It's great.

And I know that your voice adding to it is gonna make it even greater. All right. All right. Take care.

Bye bye. Mark DiMassimo: Ha ha!

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