Lift Your Legacy: Outsourcing your way to the top with John Jonas and Rabbi Jacob Rupp

I tend to gravitate away from popular business “mentors.” I’ve always tried to do the opposite of what everyone else was saying. I see so much generic advice out there that I almost never follow it unless 1. It makes sense to me and 2. I have the current capacity to implement it fully. John Jonas […]

Thrive invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive or its employees. More information on our Community guidelines is available here.

I tend to gravitate away from popular business “mentors.” I’ve always tried to do the opposite of what everyone else was saying. I see so much generic advice out there that I almost never follow it unless 1. It makes sense to me and 2. I have the current capacity to implement it fully.

John Jonas has earned a 6–7 figure income online since 2004 — all while working an average of 17 hours/week. His secret? John delegates much of his work to his talented team of 19 Filipino workers. In fact, they are the inspiration for his business model and concept.

John’s website,, is the largest online job board for finding and hiring Filipino virtual workers. In addition to creating a space where employers and Filipino virtual workers can connect, John has taught thousands of business owners how to outsource “the right way.”

He’s been married to his wife, Kim, for 17 years and they have 5 kids. Most of the time, you’ll find him hanging out with his wife, goofing off with his kids or working on his drive on the golf course.

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

The most interesting story I can share IS my backstory (a story my followers are familiar with). It’s about the fluke that started my business. It began with a simple fact: I suck at being an employee. I can’t stand it. I can’t handle someone else dictating my schedule, telling me how to do things, controlling my paycheck and only allowing me 10 vacation days a year. Plus, getting paid the same amount (salary) regardless of the quality of my work just doesn’t sit super well with me. So I started my own online business back in 2004.

Before I understood the real power of outsourcing, I hired 2 guys from the Philippines to help me with menial tasks. I was paying them each $250/month for full-time work (that was over a decade ago, now I suggest starting workers at the average wage in the Philippines as of 2018: $450/mo plus generous raises and bonuses). Back then, I had no idea that they were going to make me so successful.

They’d worked for me for about 18 months (I had spent lots of time training them) when my wife, Kim, was diagnosed with a potentially fatal condition. To complicate things further, she was pregnant with our third child. Out of sheer necessity, I handed the day-to-day operations of my online business over to my two Filipino employees.

My new job was “Mr. Mom.” I was chasing two toddlers, up to my elbows in bath times and Kraft macaroni while trying to juggle the household work and take care of Kim. I barely thought about my online business for three months.

After Kim’s recovery and the baby’s safe delivery, I returned to work, expecting to find a huge mess. I was more than surprised to find the opposite — my business was totally functional under the direction of my two Filipino employees.

I couldn’t believe it! I had worked maybe a grand total of 10 hours in three months, and my business was still functioning AND profitable. It didn’t take me long to realize that between my workers’ “self-starter” attitudes and all of the previous training I’d given them, they were able to pick up the slack while I was caring for my family.

I originally hired my virtual workers to do menial tasks and basic programming. I had NO idea they were competent enough to run my business. It was like being hit in the face with a baseball; I had totally underestimated and underutilized these guys. So I started looking for more online business opportunities, and I hired more Filipino workers…

I’d tried outsourcing before (through India, Pakistan, Upwork etc…), but never with such success. As my businesses continued to thrive, I witnessed a pattern: because of the work ethic and moral code, specific to FILIPINO culture, almost every Filipino worker I hired was adept and hard-working.

So I started yet another business — teaching thousands of business owners how to achieve success by outsourcing to the Philippines. And now my focus is primarily — a marketplace where business owners can find hard-working Filipino employees, and Filipinos can find great job opportunities.

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

Worrying about losing my wife and trying to fill her shoes while she was sick — that was the hardest thing I’ve had to do in my life. I learned it can be more difficult to reason with hungry toddlers than with stubborn corporate execs. But on a more serious note, I learned that the threat of loss forces you to come to terms with what’s important in life.

I was determined not to spend my life busting my butt at a nine-five, just to come home too exhausted and too broke to enjoy family life. I wanted time. I wanted freedom. And, crazily enough, the solution was presented within the problem!

Creating more time and more freedom is the principle that supports the entire framework of We help pair thousands of business owners with affordable workers, and it improves the quality of life for both parties. Outsourcing creates time and freedom for business owners to do what they love and cultivate personal relationships. It also creates opportunities for Filipinos in a third-world country where steady, good-paying work is not always readily available.

I golf with my son. I hike with my wife. The seven of us go on lots of fun vacations. I eat three meals a day with my family, working from home. I’m successful in business. And I know I’m making a difference in the lives of my workers. It’s the best of all worlds.

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

I’ve learned from experience with both my kids and my employees — I think the best way to inspire anyone is to care about them. Caring creates a bond of trust and endearment that can’t be faked on either side. That bond secures confidence, and confidence feeds growth. That’s my approach when I teach entrepreneurs how to manage outsourced employees, and I believe “caring” is what makes or breaks an outsourcing (or any functional) relationship. Caring also requires quality time; so I spend quality time providing feedback and training for my employees the same way I spend quality time with my kids.

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?

The greatest influencer in my life is my wife, Kim. I’ve already shared our story as relates to business, and we have countless crazy adventures as the parents of five creative, rambunctious kids. I consider myself one of the luckiest men in the world to have her.

There’s no way I would be where I am without my outstanding team of workers in the Philippines. They’re the reason we’ve been able to create tens of thousands of jobs for Filipinos while teaching entrepreneurs all over the globe how to run their businesses affordably through outsourcing.

I also have to hand it to my business partner, Dan Goggins. He’s the magic man behind the curtain at and an amazing friend.

Beyond that, I tend to gravitate away from popular business “mentors.” I’ve always tried to do the opposite of what everyone else was saying. I see so much generic advice out there that I almost never follow it unless 1. It makes sense to me and 2. I have the current capacity to implement it fully. That’s why traditional “mentors” have minimal appeal to me.

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

Honestly, no. I make work fit into my family life. Tim Ferris’s book, “The Four-Hour Workweek” taught me about that. Freedom is the entire value of outsourcing, and a huge part of why I teach/mediate the process for others.

The fact of the matter is: if you’re ambitious, you can’t do everything by yourself. There’s not enough sunlight in the day or late hours in the night. If you want to be successful and have a life outside of the office, you need to delegate to dependable, qualified workers. That’s what I do. As a result, I get to be at every hockey game, every dance recital, every Sunday dinner and every holiday celebration. I wouldn’t trade it.

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

Almost the opposite (though I know that’s not a typical response). Whenever I’m faced with a decision towards growth I always ask the same question: “Who has to do the work for this?” If it’s me, I pass. If I can teach one of my Filipino workers how to do it, then I might take it on as a project.

As I’ve worked to automate my business through my Filipino workers, I’ve created more time to focus on the personal aspects of my life. Professionally, I focus on the things I want to do — networking, increasing sales, creating new systems, and managing employees. When I’m done with those things (I average about 17 working hours/week), I focus on being a dad, husband, friend, wannabe golfer and a triathlete.

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

It may sound like a shameless plug, but I only have one piece of advice — Outsource. Delegate. Nothing can change your capacity to balance work and personal life like an extra pair of qualified hands and a capable mind. And it works, which is why continues to grow. Stop trading time for money. Stop selling a service that depends on you. Find ways to hire out the work you’re currently doing. Then care for your workers so they continue to do great work.

You just got hours back into your life. Don’t replace them with more busy work. Replace them with managing better people so the spiral upwards continues.

What gives you the greatest sense of accomplishment and pride.

Probably watching my family at church on Sundays. We have five kids, so the pew usually resembles a circus. But we’re together, and going to church represents us trying to become the best people we can become. Then watching my kids try and become contributing members of our community. Nothing gives me more pride than that.

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. 🙂

Dang…I imagine a world where every entrepreneur has a VA (or a team of VAs) from the Philippines working for them. We would cut the 95% business failure rate in half. The economy would boom. More jobs would be created locally as small businesses succeeded. People would spend more time with their families. And millions of Filipinos would have good paying, stable jobs, rather than what they’re faced with today.

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

Definitely Facebook. I’m not social media-inclined, but I have a team that helps me stay on top of and aware of my FB accounts and campaigns, so that’s the best place. But generally, if you contact me on any social media platform, my team will let me know.

    You might also like...


    “Why you should enrich your relationships.” With Charlie Katz & John Jonas

    by Charlie Katz

    2020 Life Is Stressful Enough Without Money and Job Woes

    by Samantha Lile

    Cameron Yarbrough On How We Need To Adjust To The Future Of Work

    by Karen Mangia
    We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.