Jon Boles Is An Entrepreneurial Success Who Dreamed Of Business Before Most Of Us Even Knew What We Wanted To Do With Our Lives

Jon Boles grew up in an era where there were no entrepreneurs or visionaries being celebrated in the news or in social media. Back then, entrepreneurs were called “college drop-outs.” Jon knew that he was a little different growing up as a kid. He saw things differently and processed things more advanced than a lot of his classmates but unfortunately for him, it didn’t shine bright in school as a child.

“My parents told me a few years ago about a story that happened when I was 4 years old. They would take me to construction sites to look at the trucks and houses being built. From my car seat in the back, I’d point through the window and tell them I wanted to be the boss. They laughed and asked which one was the boss. I pointed to the guy with a different colored hard hat and clipboard in his hand directing the other people. They didn’t know at the time but now looking back, they say it all makes sense now,” Jon Explains.

Although he was very smart on subjects that he cared about, Jon was surrounded by people who did not believe in his dreams. From a young age, he dreamed of business and a future that would include the ability to live a life of financial freedom while making an impact in the process. If he was born in today’s day in age, he would be celebrated thinking that way as a child but he wasn’t. Instead of being encouraged, he was told he had his head in the clouds and his dreams would never come true.

“My teachers made fun of me growing up saying that my head was stuck in the clouds and I had to stop dreaming of the rich and fame because it would never happen. They told me that I would never amount to anything. That hits a kid really hard when they truly don’t know why they’re different and there was no one around to embrace the way that my brain worked and allow me to be great at a young age. Instead, I was made fun of and was lead to believe that I was a failure and stupid, which carried into my early adult life,” Jon explains.

After many years of being ridiculed, he proved the teachers right for a while. Jon got mixed up in the wrong crowd and left behind his dreams. He came to a crossroads where he realized that his life was headed in the wrong direction, and if he didn’t do something to change, he would never succeed in the way that he had always hoped. 

“I got mixed up with the wrong crowd in my later teens and went down a dark path. I hit beyond rock bottom and was going to either end up dead or in prison. After years of pain and misery, my parents saved my life. I did a complete 180 and got my life together. I had zero money and actually had to take a 6-month loan from my parents to even move and get an apartment in a whole new city to start life over,” Jon remarks.

Jon came back from those years with a chip on his shoulder that he wanted to prove everyone wrong that didn’t believe in him growing up and he did just that. After he cleaned his life up, he went back to college, got straight A’s, and was working three jobs to get back on his feet. He went to school from 7 am – 4 pm and then worked from 5 pm – 3 am. This type of work ethic is what led Jon to his path towards success. He knew he had much to prove to the world and to himself, but this is what made him who he is today.

“At the age of 21, I started my first company in the nightlight industry and generated a few million dollars for my clients. After endless days and nights of work, it seemed like my career just picked up one day and didn’t slow down. It really became like a tunnel vision and got hard to slow down. I soon quit college and went all-in on entrepreneurship and never looked back,” Jon mentions.

Most people in the spotlight in their 20’s aren’t prepared to live that type of lifestyle. Jon was so motivated by making up for lost time, proving his teachers wrong, and just wanting to succeed that he was soon working 100hrs per week and killing himself in the process. He realized quickly that he was living a life purely to prove to everyone else that he had become successful. He quickly became unhappy and kept living for the next dopamine hit. He soon realized that career and life weren’t for him.

“When you go from nearly homeless to throwing nightlife events for professional athletes, DJ’s and celebrities, it blinds you from what’s important in life. That’s when my ego came back out and tried to run the show. I was living a super flashy lifestyle, dating models, living in penthouses, and doing whatever I wanted. I didn’t like whom I was becoming back then and knew that I had to make a drastic change again,” Jon explains.

This taught Jon a very valuable lesson because he wanted everyone to pay attention to the young successful entrepreneur instead of the failure he had turned into. Now, a lot of new entrepreneurs share their highlight reel on social media but Jon is here to show the behind-the-scenes of what it’s really like through telling his journey of the ups and downs. His failures are what has led him to where he’s at today and it took him years to figure that out.

“Entrepreneurship isn’t easy. A lot of people like to show a highlight reel on social media and post up in front of a cool car. I was that guy in my younger 20’s and that’s not the message I want to get across. That just isn’t real life and it’s giving kids the wrong impression. By the time I was 28 years old, I had been hospitalized for shingles, acute pancreatitis, and stomach ulcers, which were all due to stress. I’ve hired and fired hundreds of people in my career, have made millions, have lost millions, and everything in-between. What I’ve learned through maturing over the years is that what it’s really about is enjoying your own personal journey and trying to impact as many people as possible. I still wake up every morning acting as if it’s day 1 and I have everything to prove to myself. That’s how I stay humble and hungry to continue. I stopped chasing revenue and started chasing impact years ago and it has served me well,” Jon states.

Jon turned his wake-up call into his passion and life’s mission. After launching 8 other businesses, he realized that his mission was to help other entrepreneurs and businesses get to the next level. Jon now owns an award-winning digital marketing agency that is incredibly successful. Jon even received the title of ‘Top Entrepreneur & Visionary’ from Entrepreneur Magazine. That little kid who was dreaming of this life finally saw his dreams come true.

Avintiv Media is a 20-time award-winning strategy and growth-focused digital marketing agency. We’re a group of seasoned entrepreneurs and strategists housed in a culture-focused agency. We’ve had the honor of working with some of the biggest brands in the country, along with countless small to medium-sized businesses. It’s a dream come true being able to work with so many amazing businesses across the country. Some of our clients in the energy, powerplant, manufacturing, cannabis, and medical industries are truly making a global impact. It’s so awesome witnessing our team building and growing so many brands that are truly making a difference in the world!” Jon states.

With so much going for him now, one would think that Jon would slow down, kick back and relax, but you would be wrong. He is continuing to do what he does best and perfect his business while finding more ways to impact the world in a way his future kids would be proud of.

“We’re in the talks of buying and acquiring a web design agency in Q3 of 2021. We are very excited about this as we have our eyes on two M&A deals this year that will truly put us in a whole new category next year. Acquiring other established companies allows us to strategically corner certain markets to where we are the go-to provider. With these acquisitions we should end 2021 around 25-27 in-house team members which is very exciting,” Jon says.

To find out more about Jon, follow him on Instagram here and check out his website here.