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044: Why Content Marketing Should Sell… and More Lessons with Tyler Hakes (Optimist)

By December 29, 2021January 10th, 2022No Comments
Why Content Marketing Should Sell... and More Lessons with Tyler Hakes (Optimist)

Marketing agencies are a dime a dozen, but Tyler Hakes wanted to build Optimist differently. 

Tyler found himself often frustrated that companies and agencies often play a game of telephone, never actually speaking with the people who were creating content on their behalf.

That’s why Optimist functions as a collective of high-level freelancers of varying specialties, who come together to take content strategy for Optimist’s clients from end-to-end. 

In this episode, Tyler shared the lessons he’s learned over the past 5 years of running Optimist, and why he always thinks of content in terms of ROI-driving assets. 

Show Topics

  • A decentralized agency model 
  • Why strategy is more important than content
  • Don’t be scared to sell
  • Think of your content as assets

Show Links 

Listen to the podcast

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Key Takeaways

6:24 – Remove yourself from the center of your business 

As his agency has matured, Tyler has learned that he should focus more on growing and directing his team and less time emphasizing his skillset as the center of the agency’s universe.

“In terms of the business of Optimist, probably the biggest thing for me has been not making the business about myself. That’s a hard thing for a lot of entrepreneurs, myself included. And I think, especially in like the service business world, you come into it and you sort of have your level of expertise and you kind of build the agency around yourself and around your experience. Or at least that’s what I did, and possibly to my detriment, or definitely to my detriment. As we’ve grown, I’ve had to get a lot better about how do I sort of remove myself from that equation and how do I extract myself from the center of the agency where I’m sort of directing everything and everything lives in my head. And I am sort of direct steering all the different elements of the business to how do I think about it at a high level, and really think about the team and educating the team and helping them grow and helping them learn.”

10:23 – Move from content creation to strategy

Tyler started out as a freelance writer, but decided to found an agency when he realized that companies really needed a strategy to pair with their content. 

“The impetus for going from freelance to an agency model, or at least having a team, was sort of the scope of work question. A lot of times what would happen is I would get hired as a freelance writer and I would come in to work with an organization. And I was working either directly with the CEO or with a marketing leader or something like that. And it was very apparent that they didn’t really have any kind of strategy or anything else in place besides, Hey, we need content on our blocks that we’re going to hire a writer to write content. And hopefully that turns into something. What ended up happening is I continuously became a defacto content marketing consultant for all the clients that hired me to be a writer…and I joke, but they were sort of like wasting money, lighting money on fire. Hiring me to write content, but they had no strategy in place. They had no promotion built into it. There was no SEO component. So I really wanted to figure out how do we help companies take content and rather than it being an expense, turn it into an investment?”

12:34 – A decentralized agency model 

Tyler built Optimist as an “anti-agency” featuring a collective of talented freelancers of varying specialties. 

“The whole Optimist model is sort of the anti-agency. The whole premise of Optimist has always been that we wanted to be a collective of autonomous smart experts at the various roles. Building the team, there wasn’t sort of that, okay, we have to hire somebody now and it’s going to cost us X dollars a month. It was hey, we need to find smart people who can be writers or strategists or designers or whatever, and get them all talking and then start getting clients and start putting together the team for each individual client. From an operations perspective, it was literally like, I put out like a job post. I call it a job post for lack of a better term, but it was basically like, Hey, I’ve got this crazy idea for this sort of collective agency model. And I’m looking for people who have experience doing this. And if you are interested in doing this, you apply. And then I vetted people and we basically just built the team in Slack until we had some clients coming in.”

14:18 – Stay close to your clients 

Tyler was frustrated with the fact that in traditional agencies, the people who do the work are far removed from the client. That’s why he built Optimist to be different. 

“There were a lot of things that I hated about agencies. One of the big ones is that the people who talked to the clients were not the people who did the work. And there was always sort of like these layers of communication where I felt like things got lost in translation. A big part of the impetus behind Optimist and the reason why we built it in this way is to say, how do we get the people who are doing the work as close as possible to the actual clients, and the work that they’re doing, and the strategy? And how do we get kind of a shared understanding of the goal rather than hey, you’re a writer, just take this brief and make this article and you don’t have any other say.”

27:34 – The agency timing challenge 

One of the biggest struggles Tyler faces with Optimist is the ability to keep a steady flow of work that meets the needs of both his clients and team members. 

“One of the persistent challenges of any agency and maybe especially for us is timing and balance. It always seems like we won’t have any new leads for two months and then we have 10 leads. And then trying to sort through that and deal with that. And also then how do we balance that with everyone’s time? I’m certainly guilty of trying to do too much. So trying to find that balance and strike a good stable position, that’s always a challenge. That applies both to taking on new work, hiring people, all of that is always a challenge. I think we’re getting better and smarter about how we do that, and we try to do a better job of forecasting upcoming workloads. And an answer to pacing, like, okay, we’re going to take on one new client a month or whatever it is. But of course that’s not always feasible. If you’ve got five clients that want to work with you, they’re not going to wait five months to start.” 

34:10 – Strategy is more important than content

It may sound controversial, but incredible content is meaningless without a solid strategy to back it up. 

“In my opinion, the most important thing that companies get right in terms of content marketing is the right strategy, and targeting the right keywords, and doing all that stuff in and in the right proportions and in the right order. All that stuff is usually the missing piece of the equation, right? Like you can write really great content, but if you have the wrong strategy, it’s not gonna matter. And on the flip side, not that the quality of content is something that you should compromise on, but I think with the right strategy, you can win even with not the best content. Sometimes it doesn’t always have to be the best piece on the internet if you have the right strategy.”

42:58 – Find your agency’s niche

Tyler started out wanting his agency to be a jack of all trades, but as time passed he realized there is value in honing in on the right set of clients and services. 

“One big thing we’re really trying to do now with Optimist is really focused on which clients we serve best, and sort of where we’re best. We have traditionally been, as part of a quote-unquote “full service” agency, we’ve made a lot of concessions about what kinds of content we will do and what different strategies we will pursue for different kinds of clients. I think in the early days especially I thought that was a feature rather than a bug. We were sort of going to be the “everything” content marketing agency that could deliver results for all kinds of businesses. And now the more I think about it, the more I think that has forced us to compromise in a lot of ways, and not always for the better.”

48:42 – Don’t be scared to sell 

Some content professionals view content as art and education, but Tyler is firmly in the camp that content should have a direct impact on ROI in almost all cases. 

“I think there’s a lot of content purist people who are scared to sell, but I think content marketing should sell. I don’t think there should be any concessions about that. I don’t think it should be like, “oh, we’ll just build brand awareness with our content.” I think pretty much every piece of content, with a few exceptions, should be built to sell your product or service in some very specific way. Again, there’s obviously a nuance to that and depending on the specific use case and whatnot. But I think here’s still probably 50% of people who operate in the kind of space who view content as art rather than a business. And I definitely lean into the business side. And especially looking at the metrics and the numbers for clients and trying to figure out how do we justify the money that these people are paying us to do this work? You shift really quickly to okay, how do I show ROI? How do I show actual business value from this content?”

57:48 – There is no magic piece of content 

One piece of content will never hit all the buttons you need it to. Instead, tailor separate pieces of content to separate goals, such as viral, link-building, and keyword-focused content. 

“When I was working with startups and stuff earlier on, I think there was always this false notion that if you just made the right piece of content, it was going to do everything. It was going to rank and go viral and drive links and like do all this stuff. And I mean, every once in a while you hit on sort of a very specific piece that’s going to work on a bunch of different levels, but usually the best use of your time and resources is to say, no, no, no, no. We’re going to make one thing that’s gonna go viral. We’re gonna make one piece that’s gonna build links. We’re gonna make one piece that ranks for a keyword. And we’re going to put them together and that’s going to be the strategy, but it’s not going to be one piece that does everything.”

1:01:59 – Think of your content as assets 

You should not feel pressured to publish content on a regular schedule. Instead, a novel way to think about content creation is about generating assets. 

“That’s another thing that my thinking has shifted over the years on, is I think I still had some of that “publication” mindset where it’s like, one measure of success here is that we’re publishing new content constantly. And the more I think about that, the more I’m like, like no, this is a collection of assets. We’re grooming this collection of assets. We’re investing money in this. It makes way more sense to invest a marginal amount in refreshing or updating or expanding an existing piece of content to see 10x results than to throw another mark on the board by making a new piece. In most cases you’re going to see much better ROI by maintaining content, at least to some extent when you get to that point where you have a lot of existing assets, and really taking that asset-based approach.”

1:05:35 – The entrepreneur’s curse 

These days, Tyler is seeking a good work-life balance. It’s easy to get caught up on the treadmill of always growing and creating, but it can also be healthy to set boundaries. 

“For better or worse, I think many entrepreneurs have a hard time being happy with what you have. That’s sort of the curse of ambition, I guess. Which I hope I don’t sound like a huge douche by saying that. But when you’re trying to build stuff and you’re trying to make things and grow stuff, it can be hard to be like, okay, this is good now. We’re happy with this. This is where it’s at. And you can tell from what I was saying earlier, like logically I know that that is an okay outcome. And I want to be okay with that. But I think as an individual, that’s something that I constantly struggle with is that I will get bored, or I’m not making use of my time in a productive way. So I think that’s maybe a cop-out answer, but I think at the end of the day, I feel like I’m always chasing that ideal state of trying to find some kind of balance for myself.”


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Karissa Barcelo

Karissa is a Content Growth Marketer at Omniscient Digital. She enjoys producing and repurposing content with a killer marketing strategy behind it. She has a diverse background in video production, content strategy, and writing B2B blogs and customer success stories. Karissa has a passion for storytelling and turning complex ideas into relatable material. She lives in Las Vegas with her fiance, Sam.