How I Grew My Digital Marketing Agency From $0 to 7 Figures: Career Lessons From a Marketing Communications Manager

Ben Guttmann is a marketing communications manager and author of Simply Put: Why Clear Messages Win — and How to Design Them.

Previously, he co-founded Digital Natives Group, an award-winning agency that worked with the NFL, I Love NY, Comcast NBCUniversal, Hachette Book Group, The Nature Conservancy, and other major clients.

Currently, Ben teaches digital marketing at Baruch College in New York City, the largest business school in the US, and consults with a range of thought leaders, venture-backed startups, and other brands.

In this episode, Ben shares his marketing career story, how he grew his digital marketing agency to 7 figures, talks about his book, and answers questions surrounding marketing communications.

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How did you get into marketing communications?

I was very fortunate that my high school had a business department. Like many others, I didn’t know what I wanted to do at a young age, but I went into my first business class—sports marketing—and I was intrigued. I like sports—I’m a Yankees and Jets fan—and I loved the class.

It was about how to apply all the things you learn: psychology, sociology, and philosophy. 

At that point, I fell in love with marketing because it was the pure meaning of marketing. I was interested in connecting producers and consumers: the people who make the thing and the people who want and need it. 

Marketing is bridging these parties correctly to yield positive results and profits for society. There are ways to do that negatively, but I wanted to make sure that any work I’m doing is going to be in the positive direction. 

I was also in a club called DECA, a big international business club. This club made me learn more about marketing, and I found that it matched my skills and interests. 

In addition, I was the president of the student union government in my senior year. Now that I think of it, that was also marketing. You have to attend parties, market yourself, and win campaigns.

I believe that everything involves marketing. I have found that knowing those skills, understanding them, and using these tools makes everything else a little bit easier.

What digital marketing agency did you build?

I ran a marketing agency called Digital Natives Group for ten years. I started it with a couple of friends in an old professor’s basement. 

We drove my old car up there, we slapped our logo on the wall, and we said we were in business. And so, we worked with the local ice cream shop, local camera shop, and other local businesses. 

Bit by bit, we began doing slightly bigger work and got a couple of lucky breaks. Lo and behold—10 years later—we are working with the NFL, Comcast, ILoveNY, and other leading brands. 

We had an office in Queens and several employees back then. We grew the marketing agency to 7 figures in annual revenue, and then we sold it.

What was the creative process behind the I Love NY app?

I Love NY is one of the clients I’m proudest of because I’m a lifelong New Yorker. I Love NY is actually for the whole state, not just the city. We were a full-service digital marketing agency, and we built the app.

The idea was to design the best-in-market tool for travelers visiting New York State. 

Over the years, we tried to keep it fresh and fun because many tourism apps and websites just say, “We are a big directory. Here’s all the stuff. Go search for the hotel, museum, or restaurant you want.”

While this is fine, it doesn’t provide much utility for people. So, we decided to embrace the discovery component of this as much as we could.  We wanted our app to provide fun and functionality for users, which other tourism apps and websites were lacking.

There were 11,000 items in their database. How do we figure out how to do interesting stuff?

One of the tools we built was inspired by Tinder’s swiping feature. We used the same behavior for “things to do in New York State.” 

If you say I really like the Baseball Hall of Fame and the National History Museum, we built an algorithm that says, “You might actually like this other museum” or “You might like going to Yankee Stadium.”

We used that as a novel way to take that dataset and do interesting things with it. 

How do you ensure consistent messaging across different marketing channels?

Let me start with how important it is: A common mistake most marketers make is that you think of blogs, videos, social media, packaging, ecommerce transactional emails, etc., as different things. 

However, as a customer, if you buy a pair of shoes somewhere, it doesn’t matter what channel you got it from. It’s all the same voice. It’s the same way you don’t exist differently in emails or on social media.

So, you have to be—across all channels—cohesive. You can’t have a different tone of voice on different platforms because that creates dissonance, and your audience will ask, “Do they not talk to each other?”

Harmonizing all of this requires getting your direction right—making your verbal branding as cohesive, disciplined, and strong as possible.

We often think of a brand as a logo, color, or font. All of those represent brands, but they aren’t actually the brands.

A brand is a promise!

It’s that when I make choice X, I get result Y.

For instance, when I go to McDonald’s, I expect to get fast, tasty, hot, and convenient food. That’s the promise I’m getting from the brand.

Similarly, Disney’s brand is that I will get happy, family entertainment.

McDonald’s brand is not the arches and the red and yellow colors. Disney’s brand is not the script and Mickey Mouse. Those are representatives of the promise you’re getting.

So, if you can figure out what that promise is—your brand essence and positioning—that makes everything easier. 

You can get everyone on your team and say, “Our brand stands for XYZ. This is the promise. This is who it’s for, this is the problem they have and this is why we are the best at solving that problem.” It’s a positioning exercise.

The branding process can be hard, but once you understand the words that make up your brand’s promise, everything else will be easier.

A brand is not a logo, color, or font. Those represent a brand, but they aren’t actually the brand. A brand is a promise!
- Ben Guttmann, Marketing Communications Manager

Why should brands care about messaging? 

Messaging is everything—it is the entire ballgame. You have to know what message you’re trying to tell and whether it reaches the audience. 

If you’re building a business and need to attract customers, what story are you telling them about the product you’re selling? 

If you’re trying to attract employees, what story should you tell them to get them on your team? 

If you’re trying to get investors, what message are you telling them? 

If you’re trying to reach out to partners or suppliers, how do you make sure that you get heard and you get what you want?

However, people don’t take it seriously because they think it’s just “talk,” and they can do it regardless of not understanding the key points. The important question to note is, “Are we doing it in a way that’s most effective?”

What misconceptions do people have about marketing communications?

The biggest misconception is that marketing can be evil and advertising can be slimy—you’re trying to sell and separate people from their money. 

While there are people who use this skill for nefarious purposes, I like to argue that marketing can also be used for very positive purposes, and more often than not, it is.

I try to advocate to my students that you have to make choices in your life and career to do work that helps, not hurts, people. 

We are not doctors out there saving lives, but marketing does, in many ways, shape people’s fortunes in their lives and businesses, so you have a responsibility to do something good with it.

How did you generate leads for your 7 figure digital marketing agency that freelancers and agencies can emulate?

In the beginning, we were everywhere. We were reaching out and asking if anyone knew anyone in need of a website, logo, social media, etc.

We were trying to figure out a way to get some business. The truth is that once you get a little bit of business, it turns into more business. There are referrals, case studies, and testimonials.

The big thing is to do as many things as possible for as many people as you meet, on as many different projects as you have, and get good reviews or awards. 

It takes a lot of effort, but once we got it going—3 or 4 years in—it suddenly became much easier to get more businesses because people knew us and referred us.

For instance, we did a website for someone who was at a barbecue with a cousin. That cousin mentioned needing help with some stuff, and they referred us.

I know it’s not particularly novel, but we realized that every time we tried to do something else, like advertising or cold outreach, it was a lot of work, and the results were never what we wanted.

We did advertising for our clients but rarely did advertising for ourselves because we realized 90% of our business came from referrals. 

Make yourselves more referable, friendlier, and attentive, and try to meet more people. Try to be somebody that people want to refer business to. I’m not talking about paying a referral fee—although that can be a part of it—but it is “How do you become more referrable?” By giving quality service!

We did cold outreach every now and then. Sometimes, that turned into leads. Other times, we did PR, and that turned into attention. But the real, most important thing was making sure that we were visible and people had a good impression of us. 

What has your experience been: marketing agency life vs teaching marketing?

It’s been awesome. It’s my favorite hobby because I love meeting the kids, mentoring them, and seeing them in this transition phase where they’re about to become professionals. My class is for seniors—most of them are about to graduate—and I get to witness that firsthand. 

I try to prepare them as much as possible by bringing in outside experts, guest speakers, and judges to help build their network and give them a head start. I have them do real-world projects based on case studies and a real brand. 

I also feel selfish because teaching makes me better at what I do. There’s the old adage that if you want to learn something, teach it.

If I want to learn a specific area of marketing that I’m not an expert in, I challenge myself to make a lesson plan based on it. I reach out to some people, read, and experiment until I have a much better understanding than I did months ago.

How do you create a concise message that is also clear and useful?

I talked about this in my book, “Simply Put: Why Clear Messages Win―and How to Design Them.” The thesis behind this book is that we prefer things that are fluent.

According to cognitive scientists, fluency is how easy it is to get something in your head, make sense of it, and use that information. The easier that is, the less work it takes. The more you like something, the more you trust something, the more likely you’re likely to buy it.

The opposite is also true: if it takes a lot of work and mental cycles, you’re not going to like, trust, or buy it.

So, it’s important that we optimize for fluency. I argue that “simple” is something that is easily perceived, understood, and acted upon. The more your messaging follows that route, the more successful you will be in your marketing, branding, emails, messaging, and PRs.

The mistake is thinking that “minimal” is the fewest number of words, sentences, pages, or slides. 

Instead, it’s everything you need and the least amount of friction. When it takes more work to digest, it becomes less fluent, and we don’t like it. 

However, when a message is easier for us to digest—sometimes that means it’s more words or more pages—we’re going to be more predisposed to all the positive things associated with it.

How do we set marketing communication priorities when we know that everything will change in 5 or 10 years?

Everything changes about social media, phones, how we consume media, the biggest celebrities, the hottest brands, etc., but humans have remained the same for about 250,000 years. 

We have the same wiring that we had eons ago.

So, if you understand the psychology, sociology, cognitive science, and behavioral economics—those are pretty durable and don’t change when you go from an iPhone to a tablet to a computer to a VR—we are still the same humans using it.

If you can understand these foundational principles—psychology, cognitive science, and so on—you’ll be better suited for whatever comes next. 

What are the best non-marketing books that every marketer should read? 

Everybody should read “Influence” by Robert Cialdini. It is a marketing-adjacent book, but I based my book on it as much as I could because it’s largely about how to defend yourself from persuasion. It’s a lot of behavioral science about how we react to things in the world and how we are nudged into doing different things, such as buying, donating, and voting for people.

Another book in that same vein is “Thinking, Fast and Slow” by Daniel Kahneman. 

Daniel Kahneman and his old partner Amos Tversky were foundational figures in behavioral science and economics. Their research influenced some of the stuff in my book and my understanding of human behavior.

I also try to emphasize the importance of reading good novels. Read about plants, space, history, psychology, and baseball. Read things that are completely irrelevant to what you think would work.

For instance, there’s an insight I got from reading a biography of Jim Henson, who created the Muppets, that I wouldn’t have gotten if I dwelled solely on reading marketing books.

What marketing trend do you think is overrated, and which one is here to stay?

A lot of the NFT, crypto, and metaverse were overhyped, and a ton of people sprinting into that space were doing it as a PR stunt. When a company announces that it has a metaverse location, it does so because it wants the press release for it, not because it believes that it will be a real source of business for them.

Another thing that is currently overhyped is TikTok, reels, and YouTube shorts, which are classified as social media, but I think they’re fundamentally different from social media. Unlike Facebook, Twitter, and Instagram, which are filled mostly with people that you know in real life and are more interactive platforms. 

If a friend posts a photo on Instagram, Facebook, or Twitter, I can like and comment and send a DM back and forth. Owing to this, everyone posted and created content. People posted a status, a photo, shared a text update, and checked into a location. The bar for getting into creation was low.

However, video creation and the effort required have caused a drastic decrease in the number of creators compared to consumers. 

I think the social era is ending, but I don’t know if that’s underhyped or overhyped. We are in a really interesting moment where we have to ask ourselves, “Is social media something that is done, or is it something that is in a lull for the moment?”

The answer to this question will shape marketing and technology, including our culture, in many ways over the next five or ten years.

If you could give your younger self one advice, which would it be?

I would give this quote, “A ship in a harbour is safe but that is not what ships are built for.”

It’s very easy to do the easy things—stay at home, not ask for things, not compete and try for something, not put yourself out there and create stuff, not explore other places or relationships. It’s hard to do other things, but we are built to do hard things.

I don’t have any regrets, but it’s just a good reminder to keep trying for things. The easiest thing for me would have been not to write the book, but I wanted to try, and I did. The easiest path would have been not to start the marketing agency, but I started it.

I always try to remember that even though the easy things are appealing, you often want to do hard things whenever possible.

What tools do you use day-to-day as part of your workflow?

I know this is the Marketing Over Wine podcast, but one of the tools I use daily is a cup of tea. Depending on the climate, it could be hot or iced. 

The next tool I use is Webflow. It’s an interesting half-step between Squarespace and WordPress. I recommend WordPress for businesses that want a bigger site, but Webflow works best for marketing websites and designers.

I also recommend Carrd for a quick website setup. I tell my students to get out there, and everyone should have a website with their or something as close to that as possible. 

The website can simply contain their name, a photo, a link to their LinkedIn, and a description. I also tell clients working on a landing page for a new product to try it out. It costs only $19 a year.

Other tools would include my pen and paper and a notebook. In my career, I have found that every time I try out a fancy piece of software to solve my to-do list problems and task management, it doesn’t work. 

I also use Notion to create a checklist of my tasks. I don’t use any fancy design or outline because I have always believed that if the work of creating a task is a task, you’re not going to do it. 

Focusing on creating to-do lists and tasks rather than doing the main things you have to do will result in misplacing your energy.

Also, I try to keep my content production minimal and as high-leverage as possible. So, I write a blog and send an email every week. I also post a couple of times on LinkedIn. It’s easy to think that you have to be on every channel, but I like to keep it simple.

I use Sender for my Tuesday emails because it gives me just enough of the tools that I need without trying to weigh it down with a million things like other emailing software.

What is your favorite type of wine?

I had a good French Beaujolais not too long ago, and it was pretty good. I also like a lot of Spanish wines like Garnacha and Tempranillo.

If you could have a glass of wine with any marketing professional, past or present, who would it be and why?

The first person that comes to mind is David Ogilvy. I still have his book “Ogilvy on Advertising,” and I recommend it a lot as a good primer on customer behavior.

I often argue that if something is 20 years old or 50 or 100 years old and still applicable, then you should listen to it. It’s much more valuable than a book that comes out today on social media trends and whatnot.

Where can we go to find out more about you?

Ben Guttmann on LinkedIn

Visit Ben’s website and check out “Simply Put” book:

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