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How you sell to a disrupting executive is very different from selling to the average executive. In this thought-provoking and inspiring conversation with Mark DiMassimo, chief of DiMassimo Goldstein, a leading New York agency representing clients like The Bronx Zoo/Wildlife Conservation Society, Jackson Hewitt, TradeStation, Online Trading Academy, National Jewish Health, Recovery Centers of America, and Sallie Mae, you’ll learn about what creates a mindset that keeps on disrupting.

Mark DiMassimo

Mark DiMassimo

Inspiring Action Hero | Chief at DiMassimo Goldstein

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Inspiring Disruptive Action: The New View on Media and Marketing

Mark DiMassimo

Click here to download the transcript PDF now.

Mark S A Smith: My guest today on the Selling Disruption Show is Mark DiMassimo, who is the head of DIGO brands in New York City. He is an extraordinary creator, an extraordinary thinker. You’ve seen him on TV. You’ve seen him on “The Pitch.” You’ve seen his advertising work, his teams work everywhere because he works with name brands such as Reader’s Digest, Weight Watchers, and many, many other brands. Welcome, Mark.

Mark DiMassimo: Hey, Mark. Great to talk to you again. Let’s inspire some action together. You’re my brother an inspiring action. I’m just looking forward to having this conversation. Let’s do it.

Mark S A Smith: Thinking back to the first time we met, which was in a United flight somewhere from New York out to Denver. We were sharing first-class seats and we introduced each other, and then, you realized you had one of my books on your bookshelf.

Mark DiMassimo: That is right.

Mark S A Smith: Then, you had pulled out your laptop to get some work done, and then, you said I can do this later but I’m not going to have a chance to talk to you for a while. I was really impressed by that move of yours because I’m always interested in talking to people. It’s where I get all my stuff. My inspiration comes from talking to smart people like you. I like having me not be the smartest person in the conversation. It’s always great and always inspiring.

Thank you for that respect that you showed me in that moment on that airplane, and of course, we’ve had lots and lots of conversations through the years, helping each other stay inspired. Thank you so much for being here. Let’s talk about what’s going on in the world of marketing. You do disruptive and innovative things with your clients. You’ve seen a lot of shifts in the world of marketing through the years. What are you observing now?

Mark DiMassimo: Agencies, marketers, we are living in a world of disruption. What happens when disruption is happening on multiple planes? There’s technology, market categories, media channels, media platforms, finance, everything is changing. What tends to happen is people can’t tell the signal from the noise.

Mark S A Smith: Boy, is that the truth.

Mark DiMassimo: They can’t tell … They don’t know what the true fundamental long-term disruption is, those trend lines that you could really follow to know what the future of the industry is and what the mere fads or micro trends are, which tend to be buzzwords, hot flashes that people get in the midst of the emergency.

Mark S A Smith: A really good example of that is the fidget spinner.

Mark DiMassimo: Right. Sure.

Mark S A Smith: These have been really the hot giveaway at trade shows and now you can pick them up for a dollar and a half.

Mark DiMassimo: Right. The brilliant idea for people with attention deficit disorder, a way to allow them to give everyone else in their immediate vicinity attention deficit disorder, right? It’s solved one person’s problem while it creates problems for everyone else in the room.

Mark S A Smith: That’s hilarious. It’s true. It makes ADD viral.

Mark DiMassimo: Yeah. By the way, that law of unintended consequences is another thing that happens in a world of disruption.

Mark S A Smith: Yes.

Mark DiMassimo: You designed to solve it, and then, you’re solve actually creates other problems, right?

Mark S A Smith: Always.

Mark DiMassimo: What’s changing is pretty much everything. The large advertising agencies are in a global recession right now. The big package goods marketers have backed off of traditional advertising.

Mark S A Smith: Yeah. Interesting.

Mark DiMassimo: They’re taking a lot of the money out of the global business. If you really want to look beyond the fads to the mega trends, I really view it as the direct revolution.

Mark S A Smith: Interesting.

Mark DiMassimo: My definition is marketers have to stop thinking about marketing as something that organizations do in order to sell stuff to people and start to think about marketing as something that people do, people go to market in order to get better, in order to make their lives better, in order to solve problems in their lives, but in order to become more who they want to be.

Mark S A Smith: Oh, that’s really good, Mark. Well, you nailed something really vital. All change comes out of shifts in identity.

Mark DiMassimo: Beautiful.

Mark S A Smith: The whole idea about marketing is to help identify people who want to shift their identity towards what you’re offering.

Mark DiMassimo: Amen. To me, one difference between a brand and a commodity is a brand becomes part of somebody else’s identity.

Mark S A Smith: That’s right.

Mark DiMassimo: If you don’t become part of somebody else’s identity you’re not a brand.

Mark S A Smith: That’s right.

Mark DiMassimo: You sell a commodity, sell commodity you’re not going to make any money, and you’re not going to be around. You have to think from the consumer on in, outside in, rather than inside out. If you think that way and you realize the problem that the person faces in trying to self-actualize, in trying to actualize their identity in the market, an overwhelming amount of information, an overwhelming amount of choice, and constant distraction in this world of multiple media channels, in this world we produce more information in one day than existed in the history of man before the year 2000.

Mark S A Smith: Yeah. That’s just insane.

Mark DiMassimo: Right? How do we help that person? If you can figure out how to help that person you’re going to be ahead of trends. One of my fundamental beliefs is that marketing today is inherently behavioral because I can persuade you of something cognitively. I can persuade you of something and two minutes later you will have experienced eight or nine distractions. You’re not even going to remember. If you don’t take action, if you don’t commit yourself, you don’t commit your identity.

Mark S A Smith: Absolutely true.

Mark DiMassimo: If you don’t commit your identity I’ve lost you, so today marketing is behavioral. We need to become behavioral marketing experts, all of us.

Mark S A Smith: Tell me more about that. That is to me is a brilliant and disruptive idea. Marketing must become behavioral. How do we do behavioral marketing?

Mark DiMassimo: Well, the good news is that there were pioneers. We’ve all heard of behavioral economics and people maybe have read for Freakonomics, Drunk Tank Think, some of these books that summarize the experiments of behavioral economists, but the truth is that there were behavioral economists 50 and 70 years ago. The early direct marketers go all the way back to Sears …

Mark S A Smith: That’s right. Kellogg’s.

Mark DiMassimo: He was able to sell a house through a catalog. Seriously.

Mark S A Smith: Right. The house and tractors. Yes.

Mark DiMassimo: Tractors. That whole field, right alongside the sales field by the way. Thousands of what we now call A/B splits, experiments, which works better if I put my call to action button at the bottom or if I put it at the top, if I include something about their identity in the headline or if I don’t? What works better?

These tests have been going on for let’s say, at least, 70 years, and then, now behavioral economists have brought educational institutions to the party and interactive marketers have brought their own learning in user experience design and all of that. By the way, there’s also clinical experts. For example, we work with the Partnership for Drug-Free Kids. They help families to help kids stay off drugs or get off drugs if they’re having problems.

There’s this whole field of clinical electronic innovations, mobile interventions to get people to take their medicine or to not take their medicine or to not have that extra drink before they get in the car or whatever to help them. All this information exists but unfortunately, it’s not integrated anywhere. One of my great missions is to try to integrate this behavioral marketing expertise from these various streams.

I’ve tried to do it in myself and in my own career but I want to now go beyond that and start to help identify all of the sources of this behavioral marketing information. The results of these A/B split tests and help people to learn faster about how to make changes in their own behavior and how to help other people make changes in their behavior. I believe that’s the future of marketing.

Mark S A Smith: I think you’re absolutely right. A realization that I’ve had recently is that marketing and sales has really changed management.

Mark DiMassimo: Absolutely.

Mark S A Smith: What we have to do is get people to change their state from where they are to the desired state. Sales is really about helping people change so that they can get what they want. Hopefully, for me, that’s really the reality of it. I’ve started to approach everything that I’m doing in the world of sales and marketing from a change management standpoint. Then, all of a sudden becomes a whole lot easier. How do we get people change?

Well, we help them identify the motivation to change. We help them identify what the other side of change looks like, feels like, smells like, what it means to their life, and then, we help them take the small steps that are required to make those changes day after day after day until they’re getting to the new state. That is what I see as being elevated marketing, elevated sales, and so, you and I, are in absolute alignment with that concept.

Mark DiMassimo: Absolutely. You know what’s interesting, Mark, when I talk to top academics about what they are learning through this slow process of diligent experimentation? They always say at the end of the conversation, the very principles that you’ve learned and that you spread in your books and that I’ve learned through what I’ve done are absolutely 100% confirmed by the experimental learning that they’re doing.

Right now, we are very far ahead because we have only had to learn what works in practice.

Mark S A Smith: That’s right.

Mark DiMassimo: We haven’t had to prove it to academic journals. We actually have this body of learning that we know works and we can show that it works, we can demonstrate it to our clients.

Mark S A Smith: Hey, we make money with it.

Mark DiMassimo: We make money with it and we actually help people move toward these identities that they want and these lives that they want for themselves. To me, selling is serving and it’s always about change. Change is always fundamentally about behavior change. I don’t believe you can change somebody’s state without their participation.

Mark S A Smith: Impossible, at least, not make it stick.

Mark DiMassimo: You can make it stick.

Mark S A Smith: We can hold a gun to their head but somebody’s got to be holding a gun to their head the whole time. That’s not sustainable. We’re scalable.

Mark DiMassimo: You’re exactly right. There’s no sustainable change without their participation. They have to behave.

Mark S A Smith: That’s right and they have to make some new choices in their behaviors along the way. I think you’re absolutely right, Mark. We are the leading edge for behavioral experimentation because first of all, you and I think about this stuff every day of our waking lives. What can we do to improve the state of our clients and our customers? The end result is that we’re experimenting all the time.

I know you’re always out there trying something new, you have zero fear in failure because that’s how we fail forward. For me, every speech has 10 or 15 minutes of new content nobody’s heard before, and if it bombs, nobody knows but me. If it works, I just added a whole new trick to my bag. We’re out there experimenting every day, not to academia rigor, but to reality rigor.

Mark DiMassimo: You’re exactly right. I was lucky, my grandparents lived on property that Thomas Edison first lit up with electric light bulbs and my dad was an engineer working on experiments with microchips and speed dial and that sort of stuff from a very early age. Probably, earlier than I even know. I absorbed this idea that I didn’t fail I successfully found 7000 ways that don’t work.

The joy of having a hypothesis and having it disproved because you learn something …

Mark S A Smith: Every time.

Mark DiMassimo: … you learn something. I went out in the world with that expectation like let’s go out there and be proven wrong. My self-worth and my self-image isn’t tied up in being right. I want to be right in the marketplace because we were wrong really effectively in a focus group or an experiment or in a conference room 500 times. We finally created the machine that just works incredibly well. It’s just so fun to be part of that inventive process. We’re talking like this and you would think the whole industry is going this way, right?

Mark S A Smith: Well, they can’t. As you pointed out their identity is tied up in being right. Your identity is not tied up in being right. I think what we’ve just uncovered there is the fundamental element of a disruptor.

Mark DiMassimo: That’s it.

Mark S A Smith: You cannot disrupt by insisting on being right because the disruption comes by challenging what’s right.

Mark S A Smith: Yes. That’s it. It’s funny, you can’t sell yourself to a disrupter in the same way you would sell yourself to an average executive. When you sell yourself to an average executive, you say, “I’m an expert. Here’s why you can rely on me to be right in these situations.” “Oh, good. I want somebody who’ll be right.” You sell yourself to a disruptor and what you want to say is, “Let me tell you what I want to learn. Let me tell you the experiments I want to do. Let me tell you about the productive failing I want to do so that we can find a new way to succeed in the world.”

I might say, “Tell me why you’re ready to do those experiments? Tell me why you feel you’re ready?” But the truth is if you know how to frame the experiment, if you know how to frame the question then you’re probably the right person to go and do that experiment.

Mark S A Smith: I can find a lot of really innovative thinkers out there on the leading edge that are willing to try something knowing it’ll fail most of the time, and those are the people we want to round up to create a disruptive edge. I have to say that out of our conversation that’s probably the most important idea that we’ve revealed, is this concept of, is your identity tied to being right or not? That concept is what blows open innovation, opportunity, disruption, and inspiration for that matter. It’s really beautiful. That you need to write down. That you need to put on a beautiful poster.

Mark DiMassimo: I’m going to write that down. I’m going to write the “right.”

Mark S A Smith: Listen, that comes out of a conversation Mark and I had pre-show about how quality is what makes quantity valuable.

Mark DiMassimo: Let me read this. This is a Mark S. A. Smith quote that I captured from our pre-conversation, which … It just unlocked something for me so maybe it will unlock something for you. This is what Mark said … Let me just say, you didn’t have this prepared, this just flowed right out of his mouth, free form. “It’s the quality that allows the quantity to be valuable.”

Because I had said, “Mark, I can see how hard you work to make sure that when you do a show like this and you edit it and you get it ready, the quality just shows in every way and I’m sure your audience values that and I certainly do as a listener.” He said it’s all about quality. I challenged him. I said, “But I know you, Mark. You also have quantity.” You have so many great ideas.

He said, “Yes. It’s the quality that allows the quantity to be valuable.” That just inspires me to choose a portion of my ideas to prioritize and to put the extra energy and care, it’s a craft to make sure that the quality comes through. By unlocking the quality in those efforts it’s going to unlock the value in all of the rest of those ideas.

Mark S A Smith: Beautiful idea. Thank you for sharing that and I’m delighted that you inspired that idea in me. I won’t take full credit. I’ll take co-creative credit in that particular idea.

Mark DiMassimo: Since I have the design team and the studio I am going to put your name after the quote, but then I will autograph the bottom of it and send it to you.

Mark S A Smith: Oh, that’s beautiful. Thank you, Mark.

Mark DiMassimo: There you go.

Mark S A Smith: What a beautiful thing. That whole idea though ties back to how do we disrupt. We disrupt by people being attracted to the quality of what we are creating and what we are producing. DIGO has been doing this for such a long time. You have won so many awards and not the stuff that people line up pay money to get awards for, but the industry awards where they truly recognize your ability to disrupt.

You’ve created this extraordinary culture within DIGO brands and I have to also point out to my listener that I have been using your mantra, your DIGO brand platform, your culture statement as an example of one of the best culture statements I have ever seen. I distribute it widely. You’ve been very kind to share with me a high-quality copy of that. With your permission, I’ll put it up on the show site that people can download.

It’s literally, folks, it’s a poster of the four elements of the DIGO brand. Mark and his team really spell out what it means to be part of the DIGO team. It’s beautiful.

Mark DiMassimo: Mark, thank you so much. I hope that’s useful for people. Since we wrote that we have had levels of revelation and epiphany about how important culture is. We didn’t even realize at the time we thought culture was important. We wrote that and it’s been supremely valuable. What we didn’t realize was that even then we were undervaluing culture. Culture is even more valuable than we thought it was. We have doubled and tripled down on our focus on culture.

I don’t want people to get the wrong idea. When you talked about identity and you talked about awards and recognition, I talked about Thomas Edison and all of that and I think people get the wrong idea. People think that because those are the signs of a successful disrupter that those are somehow the motivations or those are the path of a successful disrupter. They’re not. They come at the end of the road and when they’re worthwhile they come unbidden.

You’re right. They’re not the ones you pay. I have never been to the Cannes International Film Festival. I’ve never been. I don’t go to collect awards. I don’t go to try to lobby for them. I’m working. It’s not just me. When I went to Edison’s laboratory, he slept on the desk and he celebrated failure and just love to work. When I went to Picasso’s studio, I found out he was a success because he loved playing. I had no idea that he would produce sometimes 10, 15 things a day in all different media because he loved playing and experimenting. His failures littered the studio. Today, his failures are worth thousands and thousands of dollars.

When I started this place in 1996, Steve Jobs was a failure. He was a success and a failure. It was just before he went back to Apple for $1 a day as the interim CEO and one of the first things I said is we’re not starting this place to be heroes or icons or whatever, we are starting this place to serve great disruptors. I would rather have the kind of productive suffering that would be involved in working for a Steve Jobs as a client than I would having an easy life being an expert for some predictable high-paying lessor functionary. Steve Jobs would be my ideal client. I said that in ’96 before Steve Jobs really became what Steve Jobs became.

That’s really been the secret for us. We look for disruptors and we want to serve them. We want to be part of their teams. I wanted to learn from them. My first goal has always been, how do I get more of what they have? I’m not a Thomas Edison. I’m not this guy who if I went off alone into my studio and created my own civilization, it would be brilliant, and different, and disruptive. I need to be on the team other disruptors so I can learn that and bring that back to my own team.

What I’m going to do in exchange for those, I’m going to serve. I’m going to have the resilience and mental flexibility and willingness to be wrong and willingness to start over and be a blank slate that it takes to really work with a disrupter. Elan if you’re listening, we should be working together. We really should. Let’s change the world.

Mark S A Smith: Mark that is exactly the reason why your clients have been attracted to you. You’ve won massive companies away from huge agencies just because of your willingness to go out and experiment and to try something fresh and new. You’ve taken brands and revitalized them and grown them into from maybe an old crotchety brand to something that’s fresh and alive again. That all happens through that innovative approach. That disruptive, let’s try something, let’s experiment, let’s make every day a little bit different, let’s help the people that you can help improve their lives.

Mark DiMassimo: Mark DiMassimo and now the DiMassimo Goldstein, DIGO for short. We’re always in a rush. We call ourselves DIGO. That’s our nickname, Listen to what that got me and us, I got to work on the first social network before Myspace, before Facebook, Six Degrees.

Mark S A Smith: Oh, yeah.

Mark DiMassimo: The idea of a social network. I got to work on the first streaming entertainment service, Netflix. I got to work on the first auction site, eBay, the first direct delivery from the internet to your door,, the first direct groceries to your door, FreshDirect, the first milk delivery service, HelloFresh, and now we’re working with Sun Basket, which is fantastic, by the way. That’s a client. I need to disclose that.

I could go on and on. The first online banking, having worked with all these innovators, having built and scaled all these new categories, and learning so much. That’s the ultimate change management problem because people are doing things one way and now we’re saying, “Think differently. Act differently. Do it differently.” Much as you hear someone events a better mousetrap, the world beats a path to their door.

Mark S A Smith: Not anymore, baby.

Mark DiMassimo: No. No way. You actually need to design that path, but here’s the difference now because culture is so important, we’re focusing what we do in behavior change on fighting the opioid epidemic, working with recovery centers of America. The biggest fundraising round ever, helping kids who are opioid addicted and have other addictions recover. We’re working with the Partnership for Drug-Free Kids to help their parents help them.

We’re going after the obesity epidemic, working with Weight Watchers. One of the great tragedies in this country is the fact that we have whole generations who do not have money for retirement. In fact, the majority of Americans if they lost their job have about two weeks to figure out a new source of money. That’s how much money they have. The edge of failure, we’re working with Online Trading Academy and TradeStation, we want to help people to get financially literate so that they can take responsibility for their own finances because let me tell you, these government programs like the 401K they have become something that costs more than it’s worth.

That creates a false sense of security. Social Security, the 401K, false sense of security that people have so that they don’t have this identity of taking personal responsibility. We’re helping with that too. We think of it as healthy, wealthy, and wise.

Mark S A Smith: I like that. I can buy into that one.

Mark DiMassimo: Here I am right here helping you with wise.

Mark S A Smith: Yes. Helping our listener with wise. That’s such a great thing. Mark, I am so delighted to share your thoughts and insights and the outcome of our conversation. What do you have for our listeners? What would you like for them to do next?

Mark DiMassimo: Like all great agencies, we have a tagline. We call it inspiring action. Your question to me today, Mark, is what action do you want to inspire in my audience? Reach out and connect with me, Mark DiMassimo, on LinkedIn. I will accept your connection requests. I want to be connected with you. If this leads you into my content, I want to inspire you to inspire yourself, to change your behaviors in ways that help you reach your potential. I want to help you to do that through marketing, to help other people reach their potential as well.

I’m constantly sharing stuff and LinkedIn is a great place to connect with me. If I could ask you to do one other thing today, I would ask you to go and check out the Partnership for Drug-Free Kids. We’ve got an epidemic in this country today. It’s not just rich towns, it’s not just the inner-city, it cuts across this whole country, geography, class, economics. Kids are dying of opioid overdoses. Maybe they hurt their leg playing sports and they were prescribed a medicine and the medicine was super powerful and the next thing you know they’re buying it at school or they’re switching to heroin because heroin is cheaper.

Mark S A Smith: That’s really astounding and shocking. Thank you for sharing that. Let’s inspire some action. Thanks again.

Mark DiMassimo: Thank you, sir.

Inspiring Disruptive Action: The New View on Media and Marketing

Mark DiMassimo


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