From Personal Trainer to SEO Expert: Building a No-Contract Agency
Meet Jason Berkowitz, founder of Break the Web!
Hey, it's Alex!
This week, I'm chatting with Jason Berkowitz, founder and SEO Director of Break the Web, an SEO and content marketing agency that helps in-house marketing teams make SEO "a million times less annoying."
Jason went from personal trainer to SEO expert and is a perfect example of spotting an opportunity, developing a skill, and turning it into a thriving business.
From the challenges of managing a remote team to his unconventional no-contract business model that makes agency coaches cringe, Jason shares the real ups and downs of building a boutique agency, and what it really takes to stay adaptable in a constantly changing industry.
Dive in below!
Break The Web Quick Stats:
🤝 Business Model: SEO & SEO-driven content marketing agency
👥 Team Size: 10 full-time employees plus contractors and freelancers
💵 Average Monthly Retainer: $5,000
🧾 Active Clients: Around 20 at any given time
⏳ Time In Business: 8 years as Break the Web (since 2017)
📱 Top Marketing Channels: Referrals/network, SEO, niche communities
📍 Structure: 100% remote team across different countries
🔄 Client Results: 200-300% average increase in non-brand organic traffic
From personal trainer to SEO expert...
I'm the founder and SEO director of Break the Web. We're an SEO and SEO-driven content marketing agency that helps in-house marketing teams make SEO just a million times less annoying.
And I actually got into SEO by accident…
I was a personal trainer in New York City that was reliant on new gym memberships to generate leads for personal training. There's only so far I could get with that for my own personal income and revenue and client list.
You know, I'd be schmoozing around with the membership consultants and maybe giving them a commission like, "Hey, send the good leads my way, I'll give you a cut."
That was helpful, but I didn't want to be solely reliant on the gym.
I'm in Tribeca, New York, one of the wealthiest areas in the country — every apartment building out here has their own gym.
Why can't I just travel within the three, four block radius with my backpack, and just train people in their gyms?
That's what started it – questions like:
How do I branch out?
How do I market myself?
I learned people are probably googling "personal trainer NYC…”
How can I get to the top?
That's what first helped my personal training business, but then I thought, "Fuck personal training. I enjoy the aspect of SEO and the challenge and the puzzle behind it a little bit more."
So that was the transition.
Personal training is interesting because you can be the best personal trainer in the world, but if you suck at sales, you're not going to have a packed schedule.
You might be the most knowledgeable, but that doesn't matter.
It was eye-opening to see people at the gym who were kind of airheads, but very charismatic – and they're solidly booked. It didn't really matter as much about the actual training as it was being a good conversationalist.
That was one thing I had to learn as a trainer first – the sales aspect, and then also the difference between marketing and sales.
Building credibility and landing the first SEO clients...
There's the first five clients and then there's the first PAYING client, because I knew I needed social proof.
I couldn't just say "I'm good at SEO" without proof to show that outside of my own personal training website.
I went to brands that I thought could use SEO work and would be an awesome case study. I said, "I'll do your SEO for free if you let me publish a case study and we'll collaborate for six months."
SEO was very different back then too – there weren't a lot of hard costs to it, and it was more "click button, get results."
I was doing that while still personal training to help build up a portfolio.
I also built up a website that ranked – I think it's still ranking really well.
I haven't touched it in years, but SEOServicesNewYork.org and ranking for New York SEO terms. That was a really good start and good social proof – the SEO agency that actually can rank themselves against other SEOs was a good value prop.
I just did a lot of that to build case studies first.
Then clients came in, some from that website…
But my first paying client was actually on Elance, which is now Upwork.
The New York site was just an SEO play.
I created what's called Exact Match Domains (EMDs) – where you get a domain that's the keyword you want to target. So, in this case, SEOServicesNewYork.org.
Building that gave good social proof and helped me get clients.
I still have one of our oldest clients who's been with us over 10 years that came in from a lead gen form on that site.
Around 2014 a lot of penalties were going around, so a big part of my business was penalty recovery because Google got more advanced.
Behind the scenes legally we were called Hyper Web Marketing, which was also a bad name.
Both names were stupid…I was an SEO guy – I didn't know anything about branding and marketing. laughs
Navigating the challenges of being a business owner...
One of the biggest differences between being a business owner is when you’re an employee, you report based on a limited set of functions you’re responsible for, but in a small business, you're wearing many hats, a lot of which you’re not that great at…
Finance kills my brain…
I suck at math…
I still count on my fingers.
I hate everything related to finance, taxes, and at the same time you still need to be responsible for that area of the business, and finding a good CPA was challenging.
When it was just me, I knew I was making profit because this was how much my direct expenses were but as we got bigger, I started bringing on VAs to help me.
SEOServicesNewYork.org was advertised as a one-person show – "you're getting the expert" – but I had VAs helping me with the various execution aspects.
Then my VAs kept dropping off…
I was thinking, "What's wrong? Why are they not sticking around?" They were getting paid decently when you look at currency rates.
Then I realized I don't know anything about being a good manager.
My New York bluntness didn't go well in other areas, so I had to learn about how to be a better communicator to people you work with.
And I remember dealing with finances – the CPA told me what he needed: "All of your expenses from the last year need categorization."
He actually gave me a warning: "I'm sorry you have to do this. Go to your bank, export all the transactions, and try to categorize them into typical P&L buckets."
That took me about a week and a half to do, like full-time.
Since that moment, I realized I'm never going to do this again – it was exhausting.
I hated money. I hated every moment of it because you start realizing like, "Did I really just spend that money six months ago on that thing and do nothing with it?"
Ever since then, I’ve outsourced it.
That was my first delegation of a bigger priority item.
Adapting to the ever-changing SEO landscape...
I think the core value for success in SEO is being able to adapt, learn, and evolve.
There are a lot of people I knew 10 years ago doing SEO that aren't anymore.
People get stubborn and fail to adapt as times change...
In the world of SEO, there's always going to be something new to learn, someone new to learn from.
For us, being able to swiftly adapt has been key.
Our philosophy has been aligning with what Google has been transparent about over the years – what they were aiming for and where they wanted to go.
If we're able to blend what we think might be working now with what might continue to be a process in the future, we wouldn't be hit with an overnight "Oh shit, we got to start from the ground up and throw away all our SOPs."
It made the transition easier.
Then of course, just the network of people you surround yourself with – being able to bounce ideas, share data in private masterminds with very small groups where we can share what's working and what's not.
The helpful content update was a brutal one and wiped a lot of people out…and what was interesting about that was it wasn't live refreshes.
If you were proactive and tried to recover, you still wouldn't see the results of all that effort until the next helpful content refresh, which I think was like a year.
It used to be that way with Google's older algorithms like Panda or Penguin.
If you had an algorithmic penalty, you would have to wait until Google decided to release an update to see the impact of your work.
Now those algorithms are kind of real-time.
Educating clients who don't understand SEO...
I'm vibe checking potential clients from the very first few minutes of the call to see how open-minded they are or what they first know.
We might say, "SEO has been around a while and you're a seasoned marketer. How would you rate your knowledge of SEO on a scale of 1 to 10?"
That gives me insights...
Some people might say, "I know the basic concepts, probably a three or a four…"
Some people might say – which makes me laugh, it's one of my pet peeves – "I know enough to be dangerous."
People who say that, you can tell right off the bat it's like an ego thing.
We also have a very interesting value proposition, a very risky value proposition as an agency.
We don't work with contracts. Every single client has a 30-day out, which is not normal in the agency world, and definitely not normal in the SEO agency world.
Expectation setting is super important and starts from the very beginning.
There was something I got years ago by a guy named Johnathan Dane who owns an agency called Klient Boost based out of California. He talked about having the client sign along with their regular MSA an ‘expectations agreement.’
It blew my mind.
He had a video called the expectations video and also written documentation stating:
"You hired us because we're the experts…
We have the process, the framework to follow, and as long as we follow that and everything is moving along the timeline we laid out, these are the results you'll expect."
Level-setting is hugely important, so we're constantly managing expectations for clients, and frame it as: we're an extension of your existing team.
Building a business with no contracts...
That started because SEO historically has had weird stigmas behind it – people promising the world and delivering nothing.
I from the very beginning had to be different...
I didn't like the idea of having to lock in a client that's not happy with the service and them have to continue paying for it.
That's the philosophy. And it's risky – business coaches hate it.
My SEO agency mentor and my regular agency mentor all keep telling me to use contracts.
Sometimes I consider a three-month contract, but during the sales process, I get a verbal or head nod agreement that "we're going to be in this for six months until you really start noticing an impact."
If they're hesitant to give that, it tells me a lot – are they expecting quick results?
The expectations are off.
It's like a gentleman's agreement or handshake agreement.
It's on us to earn your business each and every month.
We also have a timeline of execution which lays out the 12-month roadmap of what we're going to do each and every month.
This is the timeline of expectations.
Standing out in a competitive, misunderstood industry...
There are two different types of agencies in the SEO world…
You have agencies that are really awesome at delivering kick-ass results, but they suck at communication.
Then on the flip side, you have agencies that are really good at experience, kick-ass communicators, but suck at SEO.
Our goal is to bridge that gap.
Internally, what we follow is kick-ass service and kick-ass experience with two different leaders - somebody to own the outcomes, then someone else owns how the client feels.
Our philosophy is having the client's back.
Our account manager is meant to be on the client side and advocate for them, even yell at us internally if needed.
We make things as easy to understand as possible. A lot of companies will give technical jargon that's confusing and annoying, and clients just don't know what to do with it.
Things don't get done.
Clients leave and the SEO agency says "we told them what to do and they didn't do it." They just didn't understand it.
We follow a framework based on SCQA (situation, complication, question, and answer).
We have our own take on it, but it's following that structure of: here's the issue, here's why it matters, and here's how to solve it.
What makes great SEO content today...
People are forgetting that content quality is very subjective.
Depending on who's reading it, people can have very different interpretations of a single article...
I think with SEO-driven marketing, that SEO is the end goal so they create these hugely bloated articles, but we actually want to create value for our clients audience.
It reminds me of online recipes...
You want a chicken parmesan recipe, you find link, and it says "here's why my chicken parmesan recipe, which has been passed down from generation to generation, is so great."
Nobody cares…
Just tell me what ingredients I need to buy, the measurements, how long I need to bake the chicken for – just get right to it.
Avoid the fluff – it would be better for everyone: users, Google, your sanity.
Managing remote teams and leadership challenges...
The biggest internal challenge is reminding our team our core value and giving them security.
We have unlimited PTO, which comes with its own set of pros and cons from the agency side...
And reminding the team that SEO is not dead, telling them not to ignore the noise because people who are making the most noise are trying to sell something different.
At the same time, helping manage their own work-life balance and their sanity.
I'm a big believer in work-life balance, which is why that is a hill I'll die on.
I can preach all day about the pros and cons of unlimited PTO…
But at the end of the day, if people are working more than you promised they would, bringing work home with them, or waking up stressed, it’s a bad signal.
This has been a challenge I've been trying to tackle for years.
Also, I'm happy now that I have another person on my leadership team because there's always a weird dynamic between the founder and everyone else.
I might think people are transparent with me, but they're still thinking, "Oh, he's the business owner…"
But now I have someone else on the leadership team who's an employee, saying the same things, and that helps.
I've had a lot of direct reports and I would always ask during one-on-ones, "What is something I can do to better support you?"
And it became a running joke because I would never get anything from anybody.
But then she starts doing these one-on-ones and gets all sorts of feedback about me, and how I could be a better leader.
And I'm not mad.
I can put my ego aside and know where I can improve.
It’s actually great, because it's a whole different feedback loop and set of insights.
That opened up a whole new world and reminded me people might not feel comfortable truly being transparent with me.
If they say they have a problem, they might fear "Am I going to get fired?" – which is not going to happen – but having someone else on their side to speak to has been helpful.
Effective lead generation for an SEO agency...
We're an SEO agency that does SEO for ourselves.
Just a month ago, we made Break the Web a client of Break the Web.
Our team had opened up some bandwidth, so now the leadership team is the client. We're seeing things from a whole new perspective...
Our own SEO rankings are mostly super top-of-the-funnel informational, but we do have some more bottom-of-the-funnel queries for specific services.
We get a lot of mixed leads in terms of quality.
I think referrals and our network still continues to be on top.
We connect with other agencies that have complementary services.
We only do SEO but we can partner with agencies and give 10% referral fees, which has been great.
And then even just asking clients if they know anybody that they feel like they can get a referral from.
If they're more budget-conscious, we might say, "For the next three months we can take 10% off of your budget if you happen to know anybody."
They'll look like the hero too – "Break the Web's giving us a 10% discount."
I do a lot of LinkedIn content, but my intention there is not lead gen…
It's thought leadership, social proof, or backing up when people are going to do their due diligence.
The value of mentorship and learning...
It's a shortcut really.
Especially for entrepreneurs.
From the very beginning I've had mentors.
When I started, I had no money for SEO education programs, so I reached out to people I thought would be awesome to work with.
I just emailed them and said, "I got no money for your training program or one-on-one, but I am a trainer. I know SEOs sit in front of the computer all day and it's hard with family balance. Would you be open to a value exchange? I can help get you healthy, maybe some people in your family, write out nutrition programs, things you can do at home, just for some time."
I read Influence, the Power of Persuasion as a teenager.
He talks about the power of reciprocation. So even when I didn't have money for a mentor, I would aim to reciprocate with value.
That's how I learned about SEO much quicker than if I'd done trial and error.
Every education course is different and might have conflicting information, but mentors help set a good standard. As I got older and priorities changed, my mindset shifted, and I started bringing in different mentors for different things.
I met my current agency mentor Frank Cowell through a HubSpot webinar years ago. He talked about the ups and downs, about having the full aspect of things as a leader.
Like it's not all sunshine and rainbows.
Shit gets hard.
Shit gets confusing.
There's going to be days where you're like, "Fuck it. I'm out. I'm going to get a full-time job."
I resonated with what he said, I hit him up, and he's still my coach today.
If starting over today...
I think I would delegate more earlier.
There's a lot of material out there about the art of delegation because it really is an art.
I'm pretty happy with the process I've followed but very early on, I would sit in Starbucks just hustling from open to close and I know I could have taken a break and gotten more done if I had delegated things sooner.
Moments of doubt and wanting to quit...
Last week! laughs
I mean, there's times I'm just trying to manage my own stress levels with work-life balance.
I'm thinking, "Why am I taking on so much responsibility?"
Then you also have the pressure of the team...
At the end of the day if you're the sole owner – can I match my income getting a full-time job?
I don't know if I can, but I definitely can't match my freedom.
So it's like the pro and con.
But there was a time years ago, around 2018, when one client was largely responsible for most of our revenue.
If that client leaves, then you're like, "Holy crap!"
Forget my employees – what about me?
I was living in New York at the time, so even just my own rent and cost of living – it was very existential.
I approached other full-service agencies in New York City, met with them in person, and just told them the situation I was in.
I said, "I'm really good at SEO. I know SEO is a small little line item. Is it worth opening a discussion about an acquisition?"
That was probably the low, low point. But battling through that was probably the best thing.
There are highs and lows in being an entrepreneur.
People only see the highs because thats all anyone shares, especially if they have something to sell.
But really, it's an emotional roller coaster.
The highs are so fucking awesome when things go great.
But then the lows are so low and dark.
And if you're a solo founder too, you might be the only one experiencing that low, which is even harder.
There have been low points, but it was just getting back to that entrepreneurial spirit.
People who are backed into a corner get their best shit done.
Sometimes over the years, these same moments keep coming where your best work comes out when you're in that corner and hustle mode activates.
I had to get more business, and dug deep, getting back into cold calling, which I hate.
But I created a script, approached it systematically and started again from the basics.
I'm a New Yorker, so I've had a job since I was 13. I know what hustle is like. I know what hard work is like.
And it's like, alright, it's time to hustle.
Perseverance is a big trait of a good entrepreneur.
That’s it for this issue!
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