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Success Equals to When You Want To, Not Have To; An Interview With Colton Bollinger of Jumper Media

Today we sat down with Colton Bollinger, an entrepreneur based in California who went from 3 to 800 employees in the Philippines in 6 Months, to find out what made him so successful.

How did the idea of scaling an Instagram marketing agency with 800 people in the Philippines come about, what were your motivations?

When I was a sophomore in high school, my family moved for the first time in my life. When I was cleaning out the garage with my dad, I had found a small blank notebook of my dad’s with only a few scribbled words on the first page — “success = when you want to, not have to.” He said he remembered jotting that down when he was about to leave his job and start his own company. So it always stuck with me. 

For 3 years, from 2016-2019, I scaled an Instagram growth company In California to 3500 clients and 80 employees… 2019 had lots of complications with Instagram changes and the overhead crushed us, between the office, employees, snacks, company culture…. I loved it all, but running a company for almost 5 years and pouring everything you have into scaling it, then having to watch as it comes crashing down card by card, whether it was your fault or not, is the leader of the company – it was your fault… and my back was up against the wall for 3 months doing everything I could to hold it together before we ran out of cash.

This is when those scribbled words would playback in my mind every day during those three months… I didn’t have to try to pick up the pieces and make it work, my co-founders were ready to plan our bankruptcy… but it wasn’t what I wanted. I *wanted* to find a product offering to keep Jumper Media alive, and you try and do some crazy things when you realize what you want most. We were a software company… when the software no longer worked, we tried to perform our actions manually on phones, just as a test.

No one thought it would scale… but when I realized it was our LAST resort, I put everything we had into it, and here we are… 800 team members in the Philippines later, perseverance paid off for all sides. We now have a product that is much more sustainable, performing better, and making 1500 clients happier than ever… you don’t realize what you can do until you are up against all odds sometimes with everything to lose, and everyone who trusted you to lead them to let down. That was my motivation.


What’s the biggest piece of business advice you would give to a new entrepreneur?

Do things, take risks, and give open-handedly to surround yourself and build relationships with likeminded people of different skill sets as early as you can in life. If you plan on building any business, you will never do it alone. There are always people you must lean on for support, whether they are partners, clients, friends, acquaintances… they will remember 


Can you outline a challenge or problem you faced in business and how you managed to turn around the situation?

Our entire business collapsed, which forced us to rebuild an entirely new service for Instagram growth with real people doing actions, which is proving to be very sustainable and paving the way for many more opportunities. 


What is the best business book you have ever read and what did you take from it?

The hard thing about hard things – Ben Horowitz 

So many things to take from this book, but I think I took away that I need to work on being the person someone in my circle would call to tell something good to, and also the person they call when something went wrong. Also, never quit.


Are there any entrepreneurs you look up to? if so, who, and how have they impacted what you do?

I’m not sure if there is anyone person who stands out to me, I tend to be moved and motivated by anyone that helps me to be more emotionally intelligent. I look up to particular decisions and examples of emotional intelligence in my daily life all around me. This happens day to day within any surrounding and any person, not necessarily other entrepreneurs, but possibly the guy making smoothies behind the counter of the local juice shop… there are times you see interaction with another customer or person in a store, and the employee/owner makes a particular decision or shows a level of emotional intelligence that I wouldn’t have, and I admire the hell out of it and take that opportunity to learn.

Sometimes I will wait around if I expect a situation to arise, just to see how the manager will handle it, etc hoping to learn something… because sometimes the smallest gestures or words, make the biggest differences in outcomes when it comes to our emotions. So similar to my music in the way I only like particular songs, not necessarily artists… I’m inspired and motivated by particular gestures and decisions others make around me that I learn from. Sometimes it’s a homeless man in the way he politely starts a conversation in a way I never would have thought to, or the way a business owner overcompensates a contractor on the first job working together with a personalized thank you note because he knows it will make the contractor put 200% more effort into his future projects together without additional compensation… it’s little things you don’t think to do until you see the effect they have.

I've always had a knack for storytelling! Hi there, I'm Chukwuma Agugbue. I'm a copywriter and, a blogger. I Interview individuals who've achieved some sort of success in their field- Actively building a knowledge base for Millenials

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