Fully Managed EP 181 – Jason Berkowitz

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Last updated August 1, 2025

Fully Managed EP 181 – Jason Berkowitz

The Journey to an SEO Agency

Daniela: Hello, everybody. Welcome to the Fully Managed Podcast. This is the podcast where we discuss marketing and business tips to help assist you in your business journeys. I’m your host, Daniela, and I’m Penji’s Partnership Coordinator. I’m joined here today with a very special guest, Jason Berkowitz from Break the Web. Hi, Jason. How are you?

Jason Berkowitz: I’m doing great, Daniela. Thank you so much for having me. It’s great to be here.

Daniela: Thank you so much for being here on the podcast today. I’m very excited to talk to you. Now, to get started and kind of break the ice a little bit, can you tell us a little bit about yourself, who you are, what Break the Web is all about? Anything that we need to know about you, your favorite color, all of that.

Jason Berkowitz: My favorite color is blue, and it’s all over our branding because of that. With that, Break the Web, we’re an SEO agency that focuses on helping in-house marketing teams of B to C, D to C brands just make the annoyances of SEO, the nuances and the ambiguity of SEO just a lot less annoying and make it more manageable, measurable, and allow brands to see success. Me personally, I’ve been doing SEO since about 2010 and started as a freelancer. And over time, when you start delegating things out, you bring on people to help you with things. And before you know it, you have an agency. So I currently serve as both the founder and SEO director at Break the Web.

Daniela: That’s so cool. So can you tell me a little bit about how you actually held the journey to having your own agency kind of happened? I’m always curious to hear that because I think we hear a lot of people who work with agencies, but not a lot of people have the guts, I guess, to have their own. So I want to hear your story.

Jason Berkowitz: Yeah, I mean, this whole journey is just like anything you do as an entrepreneur. It’s kind of like an emotional roller coaster and something most people don’t. Some people don’t intend to sign up for. In my case, it wasn’t. I was just looking for kind of freedom. And I guess as a freelancer in SEO was looking to just delegate things out and it just made logical sense. I wanted to get out of this area of the work. I want to get out of this area and just started bringing on people so again having virtual assistants as the original start that’s when okay I need someone to help manage client relationships I need someone to help manage execution with link building with content I can’t do it I’m not a creative I’m a technical guy by nature so just getting the right people before you know it again you’re not you’re no longer just a freelancer you’re an agency.

Daniela: That’s amazing. So you kind of became a solopreneur at the beginning, right? From what I’m hearing, it was kind of like you were a man-man agency. At this time, are you still just doing it all yourself or have you looked into outsourcing with other people?

Jason Berkowitz: I was handling a lot myself. It started, I was working in a completely different field, a different career and wanted to do something from home. I just didn’t want to leave the house. I didn’t want to do much. And I stumbled upon SEO for my previous career. I was a personal trainer in New York City. I wanted to see how I can get inbound leads, have people come to me instead of me having to rely on the gym’s leads. And over the course of a few months, connected with the right people, took some training. I was able to learn, again, SEO was very, very different at the time, help bring in a website to the top for Personal Trainer NYC, which was getting traffic. But then I’m like, forget personal training. I’m going to lead into SEO and dive deeper into that journey. And oh, I did this for my website. I can do this for other websites, too. And then I just wanted I was doing it all myself just because of budgets being tight, wanting to make more money. And then start bringing in virtual assistants. Virtual assistants were kind of like the easy way to just help make things during the day to day a little bit easier once I had more revenue coming in and then start to get other experts in their field.

Understanding SEO as a Business Owner

Daniela: That’s incredible. I think really interesting. I think how much I think what you said also makes sense because I think people didn’t understand the Internet as much as they do now. That’s also my impression. Like, I feel like there are certain people that did. There are visionaries like you who kind of saw worth in it a future blah blah blah and then there are people who are kind of old school still who are like I don’t trust all of this and then nowadays it’s like the internet is you have to be online you cannot be online especially if you’re a business owner I think.

Jason Berkowitz: Absolutely agreed 100%.

Daniela: So I wanted to ask you because I think SEO can be very scary, even if you know we’ve been talking about how we all know about it. I think even if people are not necessarily super familiar with how to do it, everybody has like a vague concept of what it is. And even then, I think a lot of like small business owners, new business owners and up and coming business owners are afraid of SEO and when they hear search engine optimization, it can be a little bit terrifying on how to do it properly, how to make it work, how much to invest in all of this. How do you help people with that and sort of put it into a way that’s digestible for a person who’s already overwhelmed, I’m assuming, from a really big business that they’re already trying to handle?

Jason Berkowitz: Yeah, absolutely. The way we work, we typically work with in-house marketing teams. So there’s already kind of a jargon lingo level of understanding related to some of the things. But of course, there’s a lot of nuances and ambiguity with SEO. There’s also a lot to it. There’s like a million things going on in an SEO strategy. The way we work at it is first and foremost is try to understand our clients way of digesting information. How best do they get information? Is it us recording videos? Is it us giving different advisements? We aim to follow a specific framework of giving advisements so that it’s easy to digest. Also, that explains the outcome and the effort. Basically helping put weight to why someone should implement our recommendation. So it does get challenging. And then even just for new business owners, the complexities could even just be resources where SEO and website development, things that are taking place on your website and on-page SEO aspects, they’re two different areas of expertise. Like I’m not a developer. I know code just as a byproduct of what I do over the years, but most implementation of some real technical SEO recommendations tend to come in and go to developers or engineers of certain websites. So also making sure that any advisements or recommendations don’t step on toes or have conflicting interests with other people and other marketing departments.

Daniela: That happens so much when something that you want to do is sort of stepping on the toes of someone else’s work. Especially when I think, you know, if you don’t understand an engineer’s work, it’s really hard to not realize that you might be putting them in a lot of trouble when you’re like, fix this, right? Like I need you to optimize this. And then they’re like, what? I think that that’s very common. It’s probably one of the first things that I learned once I got out of like school and I started working was how much you have to have some kind of understanding of what other departments do, even if it’s not yours, because it can be really confusing for the other person to even understand what you want. And sometimes, you know, like the same way someone can ask you like, oh, do this. And it’s like a really complicated task and you have to be like, no.

Jason Berkowitz: Yeah, I mean, that’s you just nailed it. Because a you don’t want to throw someone under the bus for maybe they did something a little bit weird. And at the same time, there’s like, every department in a brand has their own set of egos. And they all kind of like butt heads because no, I need this or I need this. And kind of the mantra we adapt as we play well with others. So we also tell developers, engineers like, hey, SEO comes second to what you do. You’re doing. If your key focus and your KPIs are user experience, conversions, and we give you a recommendation that’s going to sacrifice that, then yeah, tell us. And it might be a discussion back and forth. We can weigh the pros and cons of not implementing a certain advisement. But absolutely, some people get very protective over their work.

AI, Social Media, and Marketing

Daniela: Yeah. I also wanted to ask you, and this may be a little bit of a change in topic, but AI, what are your thoughts on how much it’s increasing? The role of AI is increasing, I might as well say, and how much machine learning is happening with search marketing and how are you guys sort of adapting to that? I feel like obviously every industry is being affected by AI, but I want to talk specifically about the marketing industry.

Jason Berkowitz: Yeah. An outcome perspective, I think the impact that AI or LLMs are going to have directly on the world of SEO is still yet to be determined. We know that AI hallucinates a lot and it’s still nowhere near perfection. And I think even just user perception, like the average person, not us in the tech field, we have a very different perception of AI than your everyday person. But I think it’s also great for workflow productivity things. You can cut out a lot of time having new operators and agents do some of the things that would take you 30 minutes get done in like two minutes is a dream and also like using it as like a non-biased view of information is also really great because we tend to also get biased and things that we see quite frequently. So we use it internally really as just a workflow aid process aid in our way of doing it.

Daniela: Yeah, I use it. I use it internally as like, I think, I think I’ve said this in another podcast. It helps me get rid of the blank page. It helps me sort of have something to work from. I remember when I was in college, you know how you have to write college essays to get in. It was so hard to write a college essay for me. Like I remember it was like, because maybe I had a lot to say, but I hadn’t at the moment, I would just stare at this blank piece of paper and be like, I don’t know. I just want to get into this school, you know? And I think I really struggled a lot to like, try to get that written down and when I got into college, that was in 2015, 2016. AI like tragedy wasn’t a thing. So I had to sit down and write it myself and. I would have really appreciated to have, you know, some kind of thing that would have like I would just like write a college essay and obviously that’s not what I’m giving them, but it would have given me something to sort of work from and then, you know, get some ideas and then put something together. But I was just kind of staring at that blank piece of paper for so long and. From that, I think that in my job, it has helped me a lot, the same way that you said. If I’m struggling to write an email, if I’m writing some kind of article, if I’m doing something for work, if I’m writing in the description of a video that is going to be posted and I have to explain what the video is about, I have to sit down and think. A lot of times, if the ideas are not flowing, yes. AI is a really good way to help. I still think it’s not replacing humans because sometimes it’ll give you some wacky ideas, but it definitely helps with like getting the ball rolling.

Jason Berkowitz: I guess that’ll be like the tagline message of like helping, helping D students get into Ivy League schools. Can you imagine all of them giving the same essay that just was made by ChatGPT? And it usually starts with explore or discover, you know, the same exact words.

Daniela: Yeah. Yeah. It’s always like, I think you can still tell when something has been AI made. I don’t think generative AI is at a place right now where like it’s, it’s sophisticated enough where it’s like personalized and perfect. I think I can still tell when it’s been made with AI because it’s always super extra. Like when I’ve asked a Chajapiti to write emails for me, it’s like a long email and I’m like, this could have been like a paragraph. Like this was really not necessary. So like, do you remember like the whole TikTok ban thing happened and then it didn’t. And now it’s like, there’s a 90 day extension. I don’t know if it’s going to be banned by the time this comes out, but with all of that stuff sort of happening, what’s your take on that and marketing and business marketing in general?

Jason Berkowitz: Yeah, I have a few takes. On the personal side, I’m not a fan of social media myself. I like to have certain levels of privacy. The only one I’m really active on is LinkedIn, just because I like to stay up to date, connect with people, read other people’s interesting business-related, work-related posts. But when it comes to brands that are in the DTC market, will admit I do have the social profiles and I’m the biggest sucker for ads. I am an impulsive buyer and I’m the easiest person you throw a retargeting ad at me. I am going to buy and I’m going to convert and I think a lot of people are still like that if you’re able to define the proper traits and demographics people you’re trying to reach with social activity with ads organic reach via social I think it’s important. I think a lot of people and consumers like to do their due diligence before they make it. It all depends on like the price point, but the higher price point something is, the more due diligence a consumer is going to make. The more information you can share about your product, use cases. We do a lot in DTC. So the biggest win for our clients in DTC social is kind of like real person reviews of videos of people using their products. That’s the biggest thing, social proof for them. So social media, I think it’s important. It’s not what we do. I don’t offer it, but I think there’s value there. Absolutely. Same time, it’s also destroying people. So who knows?

Daniela: Do you think that it’s worth investing on every platform that is coming out? Not just social, but you know, I think there’s like different sort of waves that the internet is currently going through. I mean, people are using SEO for social media. I’ve seen they’re using SEO, like they’re targeting words and phrases and stuff in the videos that they’re making in the posts that they’re making in order to attract a certain kind of audience to those posts. So I think, is it worth invest or I guess dipping your toes in all of these kinds of new platforms that are coming out and then, you know, one’s going away, the other one’s coming back, blah, blah, blah, all these things that are sort of happening all the time?

Jason Berkowitz: Yeah, I think as marketers, you want to be data driven. So you could be the first one to throw tons of bucks at a new platform and share the data for other marketers, too. At the same time, it really depends. I would say for a new platform, it depends on audience size, engagement, the type of people also that are on there. I think every social platform would have a different. Well, first off, different types of people go to different platforms, but also different types of platforms are in different stages. You know, if someone’s on LinkedIn, it’s usually not at the same time they’re Browse Instagram at the same time. So it’s also capturing what mode they’re in, what mood they’re in, where they might be. People might be a bit more relaxed when they’re on meta-related platforms. People might be at their computer pretending to work, but not really working, and they’re on LinkedIn. So matching people where they’re at could be advantageous too. At the same time, also investing in new platforms, I imagine is probably really cheap to do some advertising. I’m assuming like also riding the wave of something, right? You want to be the first one there if it works. And if it doesn’t, if it’s cheap, I guess it’s a good investment. But I mean, that’s what marketing is. It’s like constant testing. So it’s normal for you to invest in something and it not work out. And then you, okay, this didn’t work for us, or maybe we didn’t do it the right way. But at this moment, we’re going to not go that route or not go to that platform.

Daniela: Yeah, totally. I think what’s what’s difficult with marketing is that even though it’s very data driven, there’s a lot of stuff that can’t be tracked data wise. I think about it.

Jason Berkowitz: Oh, yeah, exactly.

Daniela: No, because I think of it from the perspective of me as a consumer. I have sort of seen, for example, a restaurant down the street and I’ll think about like, oh, yeah, that place looks good. And that’s it. It’ll stay in my thoughts, in my head. And then about a week later, my friends is like, what should we eat? And I’m like, oh, let’s go to that one restaurant that looked really good because they had a really flashy ad or, you know, it was exciting. And then we go and then I guess the marketing worked on me. But the marketing team who worked on that will never know because it was all happening in my head.

Jason Berkowitz: Yeah. Yeah, there’s a lot of like attribution that can’t happen, especially when it’s, I mean, offline, offline attribution. You might be reliant when you go into like a doctor’s office. How did you hear about us? And people don’t know. They’ll say like online. And that’s still so ambiguous, even though the marketers behind the scenes want to ask, like, we’re online. What did you type in? What platform were you on? What did you browse the day before that allowed us to show up, you know? Attribution, yeah, is getting a lot more challenging. SEO, it’s really hard to tie in attribution due to, I mean, Google and most search engines want you to pay for ads to get that attribution. But yeah, offline attribution is extremely hard. With local SEO, you know, it gets even more challenging. You got to rely on stuff like conversions being clicks or email form submissions and aim to tie that in from there.

Daniela: Yeah, I think also because people just want efficiency more nowadays. So you’re also talking like thinking about someone who might have been a like interested, but just was too lazy to fill in that email application. And then you’ll just like never know that it worked.

Jason Berkowitz: Yeah, absolutely. I mean, once you have, though, like a baseline of where things were before you started certain activities, that can help. It may not be accurate in terms of numbers and what you’re actually getting true ROI. But as long as you trust the initial baseline before you start activities and things go up from there, then what you’re doing is working.

Rapid Fire Questions

Daniela: That’s great. Well, Jason, we’re almost out of time. But before we finish, I do have a game prepared for us. I do this with all my guests. It’s a 20 questions rapid fire. Is that is that scary for you? Are you good at that?

Jason Berkowitz: Let’s do it.

Daniela: So you have one minute and I want to put a little I always want to put pressure on people. Nobody has won. So if you can win, you’ll be the first winner of the fully managed podcast to actually do some like be able to get through 20 questions in this game. And if not, you will join my list of losers, which are all my guests.

Jason Berkowitz: Well, as long as you can ask fast enough, I’ll try.

Daniela: I’m joking, of course. But let’s see. We’ll start. And let me pull up the questions over here. And three, two, one. Coffee or tea?

Jason Berkowitz: Coffee.

Daniela: Early bird or night owl?

Jason Berkowitz: Early bird.

Daniela: Favorite social media platform?

Jason Berkowitz: LinkedIn.

Daniela: Go-to karaoke song?

Jason Berkowitz: Spice Girls. That’s my wife’s. That’s not mine. I don’t do karaoke.

Daniela: Yeah, sorry. Books or podcasts?

Jason Berkowitz: Podcasts.

Daniela: One word that describes you?

Jason Berkowitz: Resilient.

Daniela: Dream vacation destination?

Jason Berkowitz: Bora Bora.

Daniela: Most used app on your phone?

Jason Berkowitz: Alarm.

Daniela: Favorite emoji?

Jason Berkowitz: Cowboy.

Daniela: Hidden talent?

Jason Berkowitz: I skydive.

Daniela: Go-to comfort food?

Jason Berkowitz: Cheesecake.

Daniela: Superpower you’d want for a day.

Jason Berkowitz: Teleport.

Daniela: Who inspires you the most?

Jason Berkowitz: Other resilient people.

Daniela: Guilty pleasure.

Jason Berkowitz: I don’t stop until something’s completed.

Daniela: Time. So you got through 13, which is not bad. I think a minute’s not long enough.

Jason Berkowitz: Yeah, that you’re the first one who actually says that to me.

Daniela: I always say that to my guests and they’re always like no I was a bad guest like blah blah blah but I always think I think a minute is not long enough I mean in fairness to you I think it takes you longer to ask the questions than it does for someone to answer.

Jason Berkowitz: Yeah probably. Maybe I should add more time, but then everyone’s gonna win.

Daniela: Well, what we can do is take the transcript from this podcast throw in the chat gbt and ask How long does it take? Ask a single question compared to the answer on average.

Jason Berkowitz: Yeah, no, I will. Maybe. You have a good idea.

Daniela: Thank you so much.

Jason Berkowitz: Of course.

Daniela: Jason, it’s been great having you today. But before we finish today’s episode, I want to give you the space to plug anything that you want to plug, promote anything. If you’re looking for friends, employees, work, whatever it is, the floor is yours.

Jason Berkowitz: Yeah. We are Break the Web, the in-house marketing agency for in-house SEO teams, helping make SEO a lot less annoying. Feel free to check us out, breaktheweb.agency, or just go to Google, type in Break the Web.

Daniela: Awesome. Yeah, I will be adding the links to Break the Web on the description of this video so that people can click and go easily. And to you, Jason, thank you so much for doing this today.

Jason Berkowitz: Thank you for the time, Daniela. This was great.

Daniela: It was great. Everybody else, I will see you on the next episode. Bye.

https://www.linkedin.com/in/jasonberkowitzseo

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