Jason Berkowitz

I don’t allow anyone to be accountable for what happens with my work or in my agency except for myself. When I remind myself that I fully own the responsibility of internal growth, my mind switches into a different gear.


Since 2009, Jason has been an active leader in the New York City digital marketing community, founding two successful firms, Break The Web & SEO Services New York.

Since inception, Jason has managed marketing campaigns for some of the most significant brands in the world and carries a unique philosophy when it comes to campaign success.

On his spare time, Jason can be found falling from the sky as an amateur skydiver.

Where did the idea for your company come from?

Break The Web was formed from my own need to successfully market a business online.

Around 2009, I had a personal training company based out of NYC that lacked an online presence. I was exhausted from the hustle and was researching ways to get potential clients to come to me.

I stumbled across the odd acronym, SEO and spent several months researching, collecting data and networking to be able to run my own Search Engine Optimization campaign for my business.

Ultimately, an internal paradigm shift developed and I absolutely became obsessed with SEO and inbound marketing. I knew that if I could apply these methods to my own website, I could do it for other, leading me to become a freelancer, then eventually, a digital marketing agency owner.

Break The Web is the brainchild of my agency growth.

What does your typical day look like and how do you make it productive?

With my 5am wake-up call followed by a gym session, I’m at the computer by 7:30am sharp.

The first thing I do when I’m in “work-mode” is a combination of a daily (sometimes weekly) to-do lists paired with email checking, adding to the list as necessary.
This to-do list sets the standard for the whole day. Nothing is more enjoyable than physically striking-through an action item on a notepad.

With this, I find myself completed most tasks by 2pm, giving the rest of the day for random/minute tasks.

Aside from the list, the majority of my day consists of data review, connecting with new partners & clients, reading a business-related book, strategy development, and research & education.

How do you bring ideas to life?

If an idea is in the draft phase, I speak to my colleagues, collaborators and close partners. I do this to first, gauge if the idea is actually good or to determine if I’m actually a crazy mad scientist.

Sitting on an idea for at least a day is what works for me because I might make an early/impulsive decision. If, after a day goes by, the idea still resonates clearly to myself and collaborators, we work on executing the idea.

Many times my collaborators will love the idea and come up with suggestions to enhance it to a new level.

If the idea is realistic, it goes into a blueprint/mapping session to determine how to effectively make that idea a reality.

What’s one trend that excites you?

Every day the digital marketing world excites me. It’s definitely not a trend but with the plethora of news about the marketing industry being published every single day, there’s not a day that goes by where I’m not fascinated by something new or something that has been modified.

Right now, there’s a lot of discussions regarding Voice Search, and while that’s not a trend either, it’s going to be exciting to see what the future brings with opportunities in the Voice Search Optimization market.

What is one habit of yours that makes you more productive as an entrepreneur?

I don’t allow anyone to be accountable for what happens with my work or in my agency except for myself. When I remind myself that I fully own the responsibility of internal growth, my mind switches into a different gear.

If we need to hit certain targets that are delegated to me and I feel I might be slacking a bit or in a weird funk, my internal accountability reminder goes off, leading me to a pre-recorded video of myself discussing what needs to be done, how I’m accountable, our core values and a few more inspirational points.

The above, coupled with work breaks and dog walks helps to regain the thought process and ‘step-out’ of the task obsession.

What advice would you give your younger self?

Shiny objects in the marketing industry aren’t all they’re cracked up to be.

Unfortunately, years were wasted trying to follow the shiny marketing tactic of the month, instead of growing one tactic that could make us market disruptor.

It’s definitely a required learning lesson for any marketing entrepreneur but it was definitely an exhausting time.

Tell us something that’s true that almost nobody agrees with you on.

People give certain platforms, search engines, social sites a bit more credit than they deserve.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Map out your life.

Write down your goals, not just business goals but everything. Wealth, health, relationship, etc. goals all on separate pieces of paper, with the one thing it will take to get you one step closer to that goal.

If you have a goal that doesn’t have a next step to achieve, come back to it later but don’t forget it.

What is one strategy that has helped you grow your business?

My agency has always been about giving a personal touch with our service. One of our core values is transparency through Access, ensuring that the clients are in the know-how about all aspects of their marketing campaign, with the options to get access to us at any time for questions/comments.

We’ve also enhanced transparency by giving our clients access to our internal project management programs.

What is one failure you had as an entrepreneur, and how did you overcome it?

My first take at the agency life was a failure. Hyper Web Marketing was my first attempt at growth and from a business stand-point, nothing was done correctly from the start. Margins, leadership, accountability, deliverables, team members, the agency wasn’t set up for growth and a shift took place, leading to a complete revamp to become Break The Web.

What is one business idea that you’re willing to give away to our readers?

Men’s underwear that truly doesn’t ride up. It’s such a random concept but something I have yet to see the Calvin’s or the Tommie’s of the world successfully complete.

What is the best $100 you recently spent? What and why?

Just coming back from Kentucky, I bought myself a nice bottle of Woodford Reserve bourbon. Sometimes you have to treat yourself for a hard day’s work and if a day was productive, this will be my wind-down elixir (until it’s gone).

What is one piece of software or a web service that helps you be productive? How do you use it?

Our project management platform is primarily responsible for my team and I remaining productive. Aside from delegating tasks for projects, we can delegate tasks to ourselves in to-do formats, with deadlines and more.

I use my account for personal matters, as well.

What is the one book that you recommend our community should read and why?

I’m sure everyone is throwing out their favorite business book so I’ll go a different angle; What Doesn’t Kill Us by Scott Carney.

Read the journey of a man dedicated to learning how to control his body temperature and withstand the cold while climbing Mt. Kilimanjaro in nothing but shorts and a beanie.

What is your favorite quote?

“People will forget what you said, they’ll forget what you did, but they’ll never forget how you’ve made them feel.” – Maya Angelou

Key learnings:

• Have a daily/weekly to-do list that can be drawn through when completed.
• Wake up early, focus on your health, the rest will follow.
• Keep yourself accountable for everything that you’re involved with. There is no magic wand and you have to put in the work.
• Map out your life with goals and objectives to achieve those goals.
• Collaborate with individuals who will help grow your ideas.
• Failure is not the end. Keep pushing forward.