Lift Your Legacy: How business leaders find balance in the work and lives with Kean Graham and Jacob Rupp

There’s no reason for everyone to be in the office fifty weeks a year and forty hours a week. In fact, for some projects, team members can be much more productive outside of the office. This goes for leaders as well. Working from a whole new environment can be very refreshing. Kean Graham is the […]

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There’s no reason for everyone to be in the office fifty weeks a year and forty hours a week. In fact, for some projects, team members can be much more productive outside of the office. This goes for leaders as well. Working from a whole new environment can be very refreshing.

Kean Graham is the Founder & CEO of MonetizeMore. He started MonetizeMore in 2010 with the goal to build a bootstrap business that would dramatically increase ad revenues for publishers. Over the years, Kean has developed his strategy and increases ad revenues for hundreds of publisher networks in over 40 countries. Kean is an avid sports and traveling enthusiast. He lives his dream of traveling the world and growing MonetizeMore. .

Thank you so much for doing this with us! What is your “backstory”?

I originally fell in love with the online industry when working for a large online classified network. The job was an immense learning experience but once the recession hit, the company decided to lay off the marketing department. I lost the best job I ever had but I was determined to turn the bad into something great.

Five days later, I’m on a plane to South America to go on a life changing trip. Four months into my backpacking trip, I was on a four-day trek through the incredible Inca trail towards Machu Picchu. While sitting on the top of Wayna Picchu reflecting on my experiences throughout my trip, I have had the most fulfilling time of my life and reached a level of vision for my life.

I will work and travel when I want, where I want.

I have to start a digital business to enable this autonomous lifestyle. Seven months later, I started the digital business called MonetizeMore which offers this autonomous lifestyle to every member of our team. Since then, the company has grown to $16.7M in revenue, is a Google Certified Partner with 100+ full-time team members remotely based across the planet.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

A digital nomad friend and I were on a safari in Okavango, Botswana during our digital nomad trip about a week ago. We were lucky enough to come across a pride of mother lions and their cubs feasting on a water buffalo they killed the previous night. The driver brought us dangerously close to them. As we got close, the lions stared right at us and got into pouncing position. One even got up and starting pacing.

We knew if we made any sudden movements or sounds, we could become lion lunch. I had my phone in my pocket and I couldn’t remember if the ringer was off. I was one impromptu client call away from being the next kill for that pride. Luckily, I had no calls during those moments that felt like hours and we got away safely.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

Our largest bottleneck and challenge is we cannot build technology quick enough. We have a good foothold in our industry, a developer team of sixteen and we have strong growth each year but the tech we want to build is that X factor that can give us the infamous hockey stick growth. If we could find a way to accelerate the rate at which we build technology, we could go from over $15M+ last year to $50M+ this year.

To solve this, we have hired a technical director with a huge wealth of tech management experience. He initially audited our current tech, processes and systems and came up with many useful recommendations to improve the rate we build technology. We have hired him full-time to implement these recommendations, be a dev ops leader and be that coach that motivates each developer and instills a healthy culture.

We have implemented many other tech team improvements since that have increased the productivity and reliability of our technology. However, we still have a long way to go to fully realize the potential of our tech team. It is one of most difficult teams to optimize, however, the improvement of that team yields the greatest reward.

What does leadership mean to you and how do you best inspire others to lead?

True leadership is empowering your team to act as intrapreneurs within your company. The distinction between entrepreneur and intrapreneur are intrapreneurs act as entrepreneurs but as a team member within a company.

Actual leaders are able to inspire their followers to act as leaders themselves. To be a leader within a company is to act as an intrapreneur. Intrapreneurs view their role and responsibilities as their own business and take full ownership.

I get a lot of fulfillment seeing our team members act as intrapreneurs by exhibiting the below traits:

– Own Results: No matter the result, that team member will take responsibility for the result good or bad.
– Contagious Leadership: Intrapreneurs make the people around them better. They lead by example and encourage their team members to exhibit intrapreneur traits like leadership and accountability.
– Disruptive Innovation: Intrapreneurs tend to seek blue ocean opportunities that have not been realized where typical employees tend to take low risk conventional routes. We empower our team members to innovate with a drive towards disruption to realize blue ocean opportunities.

To see team members shift from conventional employee mentalities to empowered mentalities has been the most fulfilling part of running MonetizeMore.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I couldn’t say all my success came from the mentorship of just one person but rather many. My mother has been a huge inspiration in terms of raising me to be balanced, grounded, prepared and generous to those that deserve it. I can attribute my analytical skills and frugalness to my father.

I learned a lot of important business lessons early on from a business consultant involved in many self-employment seminars that I took. I still use some of the core business principles today that he taught me in the early days of my business.

I remember how shrewd he would be during the business planing phase. While it was tough at the time, looking back people can be quite vague and fluffy with their business plans, which leads to low quality execution. He would do a great job cutting through this and getting my attention which would lead me to make my business plan more executable.

Was it difficult to fit your life into your business/career and how did you do that?

This was actually the major driver for starting my business. I wanted to build a business that could drive my ideal lifestyle, which was to travel as much as I pleased. Since day one, I engineered a business and lifestyle that was ideal for me.

With that said, finding the ideal mix between my business and my personal wasn’t easy. The biggest obstacle from working from home was getting “cabin fever” from being inside in the same place for too long.

To overcome this, I make sure to break up my schedule. I start my work day by working 3–4 hours then do something active outside. I come back and work another 2–3 hours then do something social with friends outside of my home. After dinner, I’ll work another 3–4 hours. This gives me a variety of environments, fresh air and an active and social lifestyle on a daily basis.

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

There were definitely times in the business when we experienced significant growth, and I would have to work uncomfortably long hours. As a result, aspects of my personal life would suffer. I would get less exercise, my social life would suffer, and I would feel out of balance. Over time, I was less happy and the quality of my work decreased.

This happened when I started hiring for the first time and during a detrimental part of the company history in 2014. During those times, I had to tough through it and learn how to be more efficient, delegate better and make adjustments so I could work more optimal hours in the long-term. I was able to get through both periods. I was exhausted after each one but was able to recover and became a better leader from each experience.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

Ditch the Office: There’s no reason for everyone to be in the office 50 weeks a year and 40 hours a week. Team members can benefit from the additional lifestyle autonomy of location and schedule freedom. In fact, for some projects, they can be much more productive outside of the office. This goes for leaders as well. Working from a whole new environment can be very refreshing.

Seek Balance: Look for balance in each aspect of your life. Even if you have to work long hours, try to find time to be active with friends & family and the things that you love to do. You need to give your mind & body a break from work to replenish your creative juices.

Have Hobbies: Some business executives live workaholic lives which is unhealthy at so many levels. It puts you at risk of burning out and you will not be able to reach your potential just by focusing on one aspect of your life. You’ll be surprised the clarity you can gain from hobbies that you love. Some of the best ideas are bred from periods of enjoying activities people love to do.

Take a Vacation: You need to give yourself a chance to reset. Things can become more clear after completely stepping away for even just a week. The best timing for a vacation is when you feel like you’re always banging your head against a wall. Your creative juices will be replenished and you’ll be motivated to get back at it!

Have a Social Circle Outside of Work: It is not healthy to only hangout with the people that you work with. It’s impossible to get your mind off of work if you only hangout with people from your work. Social diversity is important to have a more interesting and enjoyable personal life but even having more weak connections help with getting more great opportunities via your network.

What gives you the greatest sense of accomplishment and pride.

I feel most accomplished by the fact that I’ve been able to grow MonetizeMore to 8-figures without an office while maintaining my dream lifestyle. I’ve also been able to grant each one of our 100+ full-time team location and schedule freedom. As a result, they have been able to take their lives back into their hands and engineer their ideal lifestyle.

Hearing each team member’s story of how joining MonetizeMore has changed their lives has been very fulfilling. Location and schedule freedom can mean very different things for various people. Some travel, some move to the town they always wanted to move to and some want to raise a family while staying career ambitious. Each lifestyle aspect is all possible with location and schedule freedom and I am truly proud I was able to empower each of our team members’ to live their ideal lifestyles.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

MonetizeMore is one of the pioneers of location independent businesses. We have proven that it is possible to run an effective business without any offices and over 100 full-time team members. Location and schedule freedom has shown to be competitive advantages for MonetizeMore in an industry where that is rarely offered. As a result, MonetizeMore has been able to acquire incredible talent, minimize turnover, out-innovate competitors and better tailor to international clients.

We can already see effect of the influence of location independent business pioneers like MonetizeMore has had on the technology industry. The trend of remote working has been trending as expectations for in-office work has decreased. I believe in the next ten years when someone mentions a new business, the next common question is: “Is that business location dependent or independent?

What is the best way for people to connect with you on social media?

Twitter: @monetizemore





Jacob Rupp is a rabbi, coach, speaker, and author that helps people live authentic lives.  Check out his website at 

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