The Content Marketing Interview with Andy Crestodina

XX min
May 31, 2023

We sat down with Andy Crestodina, Cofounder and CEO at Orbit Media to discuss content marketing.


Andy, let’s start with how you got into the content game.

Sure, we were having lots of conversations. We actually started as an outsourced partner to agencies. We didn’t have any technical skills. My partner could program things and I could animate things or do a bit of UX. But when, when I realized, we’re not gonna control our own destiny until we can generate our own leads and service our own clients.

I landed on the idea that I need to be able to do marketing for our business and not just be a white-labeled service for somebody else. I realized I’ve had a ton of conversations. I’ve worked with a lot of people. I need a way to keep in touch with a lot of people efficiently, over long spans of time.

That was the problem to solve initially. I need to keep in touch, with these 400 people I’ve worked with over the years. This is like year four or five. I started this because you only need a website every four years or five years. So, how do I stay relevant to this buyer, this decision-maker?

So I thought, okay, I’m gonna write an article. I actually wrote three articles the first day. Hilarious how thin the content was back then. And I’m gonna send it to this list of people that I’d met over the years. It was about 300 names or something. So that was it.

What happened after that was content marketing began to evolve as a practice, and these other channels for promotion got mixed in.

And so now content marketing is broadly defined right as the ability to attract and retain a likely buyer you can entertain or inform with something helpful and practical and useful. And then promote it through search optimization, social media marketing, email marketing, influencer collaboration, and digital PR.

That’s what’s interesting and where it all began. Content marketing sort of was the convergence of a lot of things that were considered separate at the time.

So, what do we create? Articles, videos, you know, there’s all the formats that we use. White papers, how do we promote it? Search, social, email maybe influencer collaboration.

But really the impetus. That’s what started us down this path — to keep in touch.


You’re, you’re producing a ton of content on a daily and weekly basis. You also have responsibility for running the agency How do you blend both?

Well, there’s an inherent challenge with time, attention, and energy, and there’s an inherent advantage in that as I’m close to the audience. I’m close to my buyers.

I do a lot of sales and I do a lot of service, so by being on the front lines I know what the objections are. What’s happening? What are the trends are, what do people care about, what they’re afraid of, and what they’re hoping for.

Plus, I have the freedom of choosing my topics, so I can have a dozen articles baking in the background at any given time. So, it’s not as if I have to sit down with a blank page.

Usually, when I start writing it’s something that I’ve kind of had in the back burner for a while. Another advantage, I’ve written 500 articles.

My frequency has never been greater than once every two weeks. So every other week I can curate something, freshen it up, uh, put it out there as if it’s new.

I can update the research or the statistics or make a new image or diagram to go with it. Or update the headline. So there’s the efficiency of being able to repurpose and reuse things. Also, the fact that I’m in different formats is an advantage. I’m speaking. Sometimes I have presentations. I’m writing, sometimes I have articles. Those feed off each other. There’s a big advantage to, repurposing your materials it's quite natural if you're thinking about topics and information separately from formats. Our audiences all have information needs, but format preferences. We’re making something right now that’s super repurposable. This is a great format for repurposing. But you could take one thing, if you’re clever about it, if you’re strategic in the approach, you can repurpose that.
So there’s a couple of different ways in which you can do that. There are challenges, but also big advantages, for people that are just active listening, empathetic, for lots of forethought, you know, planning ahead strategy, working on ideas in the background, and then recycling things strategically.

Based on your expertise, and your experience what do people not understand about content marketing?

Yeah, I’ll, I’ll oversimplify it. The easiest way I think to define content marketing is to contrast it with advertising. So advertising is about renting an audience. Content marketing is about trying to own that audience or building it more from scratch.

With advertising the advantage is being very fast. I can have lots of visibility next week if I were to get the right placement.

Content. Marketing’s very slow. It takes a long time to build up the flywheel of results. Advertising is temporary. You stop paying, your message goes away. Content marketing is very durable. In fact, almost everything I’ve ever written is still online.

Many of my pieces are search optimized and being found and are being read right now. The things I wrote 5, 10 years ago are being read right now as we speak.

Advertising is about distraction. That person was actually trying to do something else when you interrupted.
Content marketing is about attraction. People subscribe to stuff. They want more of it. They search for things, they’re looking for help. They follow accounts because there’s useful stuff. They want it in their stream.

Jay Bear calls it the hype versus the help. Content marketing is helpful, useful content that helps people in their lives answer a question or get some advice, typically found through search, social, through email, and it has, the long-term ability to participate in that visitor’s buying decision earlier.

Andy, do too many marketers promise something via a headline, but once you get in, it’s like, hmm, there’s nothing here?

It’s the number one problem. What do we do? Is it differentiated? Is it say, you know, who could have written this? And I think AI’s fun here because that’s gonna disrupt. I mean, how do you differentiate now?

Especially now, right? So yes, it is the people who are the best at this. Are obsessed with quality. They don’t stop. They have an idea. They’ll continue to add more things to it. They don’t say that’s enough. Like, did I miss a question? I’m gonna answer that. Do I know, if I can find someone who can add to this?

I’m gonna reach out to them and get a quote on this topic. Or can I turn this complicated concept into a diagram? Can I record this piece? Can I put a video at the top and summarize this complicated thing? So formats and outreach and depth and detail.

I’ve tracked over the years with a blogging survey, uh, how long it takes people to write a blog post. The first year we did it was in 2014. The average answer was like two hours and 20 minutes to write a blog post. It’s now north of like four hours. Why?

For me, these things take me 10-plus hours to create. Why, because there is so much out there to differentiate yourself from, you just have to do something where you’re, I mean, this sincerely, 10x the expectations of the audience and what your competitors are doing.

And it doesn’t mean 10x is necessarily bigger or longer, you can try to make something 10x simpler. Make it more, much more concise. Turn that complicated thing into like a juicy soundbite. Like I just said a minute ago. Jay Baer calls it the hype versus the help. Wow, that’s so concise. It’s so clever.

Also, strong opinion, very differentiated. Most brands don’t have the guts to do it. It’s hard to do. I understand original research, is extremely differentiated. Takes more time, more initiative, and more resources. It’s harder to produce. So yeah, there are lots of ways everyone sort of knows what is different.

There’s just a minority of people who are willing to invest to put something out. Probably if they set aside frequency and just focus on quality, maybe make something great once a month they can get a ROI.

Talk to us a little bit about the landscape in your world, what that’s looking like, and how are you and your company, differentiating from others?

Yeah. Well one of the problems in our category is that the barrier to entry is too low. Anybody can start a web design company if they got a laptop. So that’s a problem. So, how do you differentiate?

One of the ways is simply, to be more human in your marketing. More personal. That’s ultimately what we’re doing here is helping people. So, put faces. Show the team be a personal brand. You’re the only company with you. So that’s a big advantage.

If you go to our team page, you start scrolling through, you see this must be a legitimate company. You see these people have been here for a while. You see, the median tenure here is like six years or longer.

That’s just very unusual in our category. So how does that work as a sales message? If nothing else, we’ve got clients that came back four or five years later and the whole team’s still here. So retention and culture and loyalty and love, these are differentiators.

You know, answering unasked questions can build a lot of confidence and differentiate you. The client feels like they’re learning and they’re grateful for that. You taught them something that they should be aware of and at the same time addressed, raised a concern, then addressed the concern.

If your competitors don’t do that, then you’ve got a slight edge.

What are the questions you ask to help out a client?

I’ll break it down into two actions. One, you can drive more traffic. And we can think of that as like the cheese. The other is you need to convert your visitors. That’s the mouse trap. I’m gonna make the case that we should fix the mouse trap before we make more cheese because if there’s something hurting the conversion rate on the website, there’s really no amount of traffic that will make a difference.

All the best cheese on a broken mouse trap doesn’t really catch mice. So I would first look at the main success factors for the website to convert. Starting at the end of the process, look at the contact page.

Anything confusing or weird or difficult. Or is there friction there? If you fix that and improve the conversion rate from the contact form, every visitor to that page forever after will have a higher conversion rate.

Next, I’m gonna go back through this chain of conversion. Next, the call to action that brings people to the contact page.

If the call to action has a low click-through rate, nothing else that you do in marketing will make that much of a difference because the click-through rate to your CTA is low. Could you change the call to action on your website to get a greater percentage of visitors to click it? That’s usually by making it more specific, more compelling, make it sound more valuable, or make it sound easier.

People click things because they’ve done a cost-benefit calculation, and the benefit exceeds the cost, right? So, to make a high click-rate call to action, you can make the cost seem low. Talk to an expert, or you can make the benefit seem high. Talk to a conversion rate expert or to an industry veteran, or chat with a founder. That sounds valuable.

So, these are ways to maximize the clickthrough rates in your call to action. Next, the page on which the call to action appears. Does that page fail to answer any questions? Did that page make a bunch of unsupported claims?

Could you add more evidence to that page? Could you pull, a statistic out of a case study and put it high on that page? Could your high-converting pages have three elements: answers, evidence, and calls to action? So a great page emulates its sales conversation like you’re talking to the top sales rep.

It also needs to address objections and answer questions and add evidence to support the answers. Just go look at any of your pages to see if you are making unsupported marketing claims. That’s conversion optimization, that’s conversion copywriting. Now I’m going backward through the chain for the sales pages.

I would also apply that same thinking to both the homepage and the About page. I have access to 500-plus analytics accounts. I’m in three to four analytics accounts every day. Rare, very rare for me to ever see an account where the About page wasn’t one of the top pages on the site.

Yeah, people kind of blow it off. There are About pages that don’t really tell the story. There are not many faces or people or humanity there. They don’t tell the origin story. There’s no video. They don’t have any, passion, right? Next is probably the just search for your brand.

Look at the Google search results page. Could that be polished? That’s like one of your home pages, right? That’s a very important page. If there are reputation problems there, you’re not even gonna get the visitor.

Once those are in place, then work on the cheese, refine your content strategy, work on your targeting, or pick your channels and your battles in your formats and your topics.

I have a lot of evidence to support the idea that the shortest path to greater demand and leads is to start optimizing from the very bottom of the funnel, the thank you page. So right before that, all those steps in that order you can almost help anybody make more money right away by polishing those things.

Since we started this interview, you’ve had a way of breaking down what could be very complicated to many of us in a way that’s absorbable. And a lot of your comments go back to the human side of things, and I think there’s a formula here.

You touched on what I think is maybe the best message of them all, which has come up a few times, about that personal human side of it.
What are we really doing here? You’re trying to connect with an individual. People always ask me, what about B2C or B2B? It’s really about the person. What do they need? What are they afraid of? What are they hoping for? What do they trust? What’s persuasive?

What would be disarmingly, straightforward to them? How can I be more forthright and direct and simple? So, yeah, I think those two things go together perfectly. Getting lost in the weeds, that’s getting lost in their mind, that’s getting lost with the person, the human, the brain you’re trying to interact with.


Andy, would you say that the biggest problem when clients come to you for a new site is they’re not human enough?

We should all just try to be more human and more personal. It’s kind of a common way to get better results.

Break down a typical day for you. Give us the morning routine. I mean, you’ve got a family. You’re running an agency; you’re producing a ton of content. How does the flywheel work?

Well, I’ve got a five-year-old and a seven-year-old. So I have to get up before they do or else it’s over.

I wake up, feed the cats, start the coffee, and start writing. I will write from usually 5:30 until 6:45. Every morning. One general principle is to do something important before you do something urgent.

Urgent stuff is gonna take over your day. As soon as you open your inbox, you’ve kind of lost a little bit of yourself in that moment. So, start by writing something or planning a piece of content or, thinking ahead. Sometimes I sketch diagrams, visuals are absolutely half the game in marketing.

I get here before nine, and then I’m immersed. I will do six to eight meetings a day. Those are often sales meetings or service meetings. There are internal meetings. And then I’m done.

I want to wrap up with your latest article on, AI. You did a survey and some proprietary research. That was interesting.

It’s quite interesting because, with 1,075 consumers, they basically want their service providers to use AI. There’s a comfort level. That’s the bottom line. There’s a comfort level in the marketplace about having service providers use AI to some extent, varying extents for various verticals, which you pointed out.

There’s also a tactic in here that AI cannot do which is AI can’t build relationships for you. That’s the humanity side again. So everybody says, oh yeah, AI could do all these things. Well, not that. So, influencer marketing, relationship building, you know, that’s the element we are safe from no matter what the robots can do because only we can build relationships with each other. Only we can use marketing as a networking tool.