Lifestyle

From High School Dropout to 22-Year-Old Millionaire: The Caleb Boxx Success Story

Published

2 years ago

February 6, 2023

Many individuals grow up hearing the same things from their parents—you need to graduate high school, go to college and get a degree, and then you’ll land a nice, steady job that will support you and your family. There’s this belief ingrained in us all that our grades hold the key to our future. First to get into a good college, then to get a good job that makes our family proud.

The fact of the matter is a bit more bleak than the web our parents wove, however. Many study for years, take on thousands of dollars in debt, and then that degree they worked so hard for takes them to other places, or even nowhere. Or, they get the job and it isn’t anything like what they thought it would be. They’re miserable, they’re stuck, and they’re feeling hopeless.

Fortunately for some, like Caleb Boxx, founder of YouTube Automation and Automate Channels, they find out early on that the one-track plan for their future isn’t actually what they want. Boxx realized that there is more than just one road that can lead to success, and he started paving his own path at just 11 years old. Now, he’s a 22-year-old millionaire and he doesn’t have any regrets about the decisions he made to get where he is.

Starting Young

Entrepreneurship is a part of who Boxx is as a person. At 11 years old, instead of running around with his friends, Boxx created a website company. He would charge startups a fee to create their sites for them, though it’s probably safe to assume that none of them knew they had hired a child.

At 12 Boxx decided to take his wit and business savvy to YouTube, trying his hand as a gamer, though success didn’t strike right off the bat and he even quit the platform that his business now revolves around for a period of time.

“I started recording myself playing video games and nothing would ever happen,” said Boxx. “I was only earning $200 a month, so I quit the whole dream because it wasn’t working.”

At one point a friend of his went viral and amassed a million subscribers on YouTube. Boxx decided to once again chase his dreams, this time learning from someone who was already making that dream a reality. He turned into a livestream, donated the last $200 in his bank account, and asked for a quick call. He offered to edit his friend’s videos, write his scripts, and do a majority of his work all for free so he could gain admittance into his mastermind group.

This was the chance he needed and it wasn’t one he was going to waste. He wanted to be a professional so he started acting like one, gaining maturity and absorbing as much information about YouTube success as he could. He made vows with those in the mastermind group to focus solely on building their individual empires, setting a goal of reaching $1 million. Throughout this entire experience, he learned about more than just YouTube, he also learned about entrepreneurship.

Reaching Success

At just 16 Boxx used all the knowledge he had gained and created his first YouTube channel. A year later he made another one and immediately gained 80 thousand followers. After roughly six months with his channels, he was making around $20 thousand a month, a far cry from the $200 he started out with.

One thing led to another and he was giving 30% of his site revenue to one of his friends, helping them build their own successful channel. From there, revenue kept increasing and he was bringing in employees. At 18 he first started making seven figures, bought his dream car, moved to a new city, and started to study entrepreneurship more in depth.

It was at this point that people started to seek him out, asking if he could show them the ropes of YouTube and share the knowledge that helped him become successful on the platform. He created a business model and began to teach, allowing him to enter his 20s as a successful businessman. Now, Caleb offers a “done-for-you” mentorship program, where his company holds the hand of clients and manages all of their content.

The path Boxx chose wasn’t exactly orthodox or without challenges, but it was his own and something he wholeheartedly wanted. He went from a high school dropout to a 22-year-old millionaire, generating over $3 million from YouTube automations. Sometimes the path to success looks different than we thought it would, but with hard work and perseverance, anyone at any age can make their dreams a reality.

About Caleb Boxx

Caleb Boxx is a founder of YouTube Automation, a business model that allows people to automate their YouTube channels creating passive income. Boxx has helped hundreds of content creators. To learn more about Caleb Boxx, please visit https://www.automatechannels.com/

Lifestyle

Why Derik Fay Is Becoming a Case Study in Long-Haul Entrepreneurship

Published

22 hours ago

July 2, 2025

Michelle Langton

Entrepreneurship today is often framed in extremes — overnight exits or public flameouts. But a small cohort of operators is being studied for something far less viral: consistency. Among them, Derik Fay has quietly surfaced as a long-term figure whose name appears frequently across sectors, interviews, and editorial mentions — yet whose personal visibility remains relatively limited.

Fay’s career spans more than 20 years and includes work in private investment, business operations, and emerging entertainment ventures. Though many of his companies are not household names, the volume and duration of his activity have made him a subject of interest among business media outlets and founders who study entrepreneurial longevity over fame.

He was born in Westerly, Rhode Island, in 1978, and while much of his early career remains undocumented publicly, recent profiles including recurring features in Forbes — have chronicled his current portfolio and leadership methods. These accounts often emphasize his pattern of working behind the scenes, embedding within businesses rather than leading from a distance. His style is often described by peers as “operational first, media last.”

Fay has also become recognizable for his consistency in leadership approach: focus on internal systems, low public profile, and long-term strategy over short-term visibility. At 46 years old, his posture in business remains one of longevity rather than disruption a contrast to many of the more heavily publicized entrepreneurs of the post-2010 era.

While Fay has never publicly confirmed his net worth, independent analysis based on documented real estate holdings, corporate exits, and investment activity suggests a conservative floor of $100 million, with several credible indicators placing the figure at well over $250 million. The exact number may remain private but the scale is increasingly difficult to overlook.

He is also involved in creative sectors, including film and media, and maintains a presence on social platforms, though not at the scale or tone of many personal-brand-driven CEOs. He lives with his long-term partner, Shandra Phillips, and is the father of two daughters — both occasionally referenced in interviews, though rarely centered.

While not an outspoken figure, Fay’s work continues to gain media attention. The reason may lie in the contrast he presents: in a climate of rapid rises and equally rapid burnout, his profile reflects something less dramatic but increasingly valuable — steadiness.

There are no viral speeches. No Twitter threads drawing blueprints. Just a track record that’s building its own momentum over time.

Whether that style becomes the norm for the next wave of founders is unknown. But it does offer something more enduring than buzz: a model of entrepreneurship where attention isn’t the currency — results are.