The Greatest Showman

Chris George’s entrepreneurial journey

By Cal Abbo

After years spent building his SubSummit conference, Chris George and his partners, John Hajji and Paul Chambers, exited the business earlier this year in an eight-figure acquisition by Nineteen Group.

The trio launched SubSummit in 2016 as an annual weekend conference geared toward subscription-based businesses. It created a space where founders, operators, and innovators could connect, exchange ideas, and push the industry forward together.

Over the past decade, SubSummit has welcomed guests and sponsors from some of the biggest names in subscriptions and beyond. Google, Duolingo, Peacock, the NBA, CNBC, Meta, The Washington Post, DoorDash, Forbes, Netflix, Mastercard, Verizon, Netflix, and many other companies have sponsored or attended the event.

For much of his career, George has positioned himself as a branding guru, leveraging his expertise for his own business success and passing his wisdom along to anyone who comes for advice. George is notorious for turning down pitches and requests for investment, choosing instead to focus on one business venture at a time, and one which he controls fully.

George’s story begins at home, watching with intent how hard his father worked to provide and how his mother worked to raise the family. Like many Chaldean families, George’s father worked long hours in the store. “He played it safe,” George said, which he believes was the right thing for that time. “I’m more like this: I’ll risk everything to build something amazing.”

His first major hit was the Gentleman’s Box, a subscription-based service aimed at elevating men’s style. The curated packages often included GQ magazine, ties, dress socks, grooming products, watches, sunglasses, wallets, and other accessories. In just six years, George and his partners shipped more than 400,000 orders.

As the subscription economy expanded, George began looking for mentorship and connection in his growing industry of subscriptions, one that he believed would soon skyrocket as the digital age progressed. To his surprise, he found surprisingly little infrastructure. There were no conferences or trade organizations that would allow him to meet and learn from others in his field.

So he created one and invited all his favorite subscription services.

Great businesses fill a gap in the market and offer something new and inspiring. SubSummit was built from this idea, that coming together and working together would strengthen the subscription industry overall and help connect individual businesses with the lessons that others had learned in years past.

George decided, without really judging interest and validity for the business, to move forward. He was ready to risk it all for the industry that he knew and loved, and he was willing to fill that gap in the market, even though he had no experience planning events. In 2016, he started planning the first SubSummit in Detroit. Around 200 people attended the event.

“The venue asked for a $3,500 deposit,” George said. “I gave them a credit card. I sold a sponsorship for $5,000 before the credit card was due.”

Many great businesses are built on a knife’s edge. SubSummit was no exception. By 2019, the conference was well on its way. Its fourth annual event was hosted in New Orleans and had around 1,200 attendees. It had grown into a mature industry conference.

Then COVID-19 hit, bringing a massive paradigm shift to events everywhere. In a business centered on a one-weekend annual event, this was almost a certain death blow. But George and his partners wouldn’t have it. They were forced to move the 2020 event to a virtual format, even though it killed their sales and dampened the experience.

It was a defining moment.

George and his partners were determined to pull through. They stopped taking paychecks for themselves to keep the business afloat. They maxed credit cards to push forward to next year.

While it took some time, they slowly but surely built the business back up into its healthy form. Just two years later in Orlando, SubSummit hosted more than 1,500 attendees.

This growth continued, and yet more impressive partners came on board. George described one moment when he knew they had made it.

“It was 2023,” he said. “Netflix applied to speak at the conference. It wasn’t us chasing them to get them there or trying to sell a sponsorship. They wanted to be a speaker at our event.” That moment marked a turning point. SubSummit was no longer fighting for validation—it had become a sought-after stage.

SubSummit has continued to grow and prosper. George and his partners made the strategic decision to sell to a larger firm capable of scaling it further. Under the acquisition terms, George will remain involved during a standard two-year transition period.

While he sold his business and decade-long passion project, George is far from finished. Over the last few years, as he cemented himself as a business leader in the Chaldean community, philosophizing and meditating on business, entrepreneurship, and leadership. As a result, he has also taken on a mentorship role. Entrepreneurs seek him out to hear his sage advice on their newest ideas.

This is perhaps what George loves to do most nowadays. He takes time and care to understand each business pitch, or a specific difficulty they are dealing with, and articulates a plan to overcome it. This he does for free, as a way to give back and use what he sees is a natural gift from God. He often travels to different colleges to speak to students and offer his wisdom.

What makes a good entrepreneur? Quick decisions, according to George. Deal with the consequences after. No emotion; don’t feel bad for who you are and what you do and who you work with. Take care of your employees and lead by example. George uses the golden rule: Don’t ask anyone to do something you wouldn’t do yourself. Do whatever it takes. Surround yourself with people like those you want to become. And at all costs, don’t be lazy.

George is proud of the entrepreneurial strength within the Chaldean community, but he also offers critique. He believes comparison is one of the community’s biggest weaknesses—that constant benchmarking against others can breed jealousy, envy, and unnecessary displays of wealth.

George is humble with his money and possessions and generous with his employees. As a part of the sale of his business, he gave his employees a large bonus as a gesture of gratitude and good faith. George has experienced a spiritual renaissance in the last few years, which has informed a lot of his mentorship and perspective moving forward.

As all of this is happening, George has also lined up his next venture. He rolled out the Moonlight Academy, a tool that serves as a launching pad for young professionals to start their careers. At Moonlight, students will get real-world training, expert instructors, job placement support, portfolio projects, and personalized career coaching.

If SubSummit was about building an industry, Moonlight Academy appears to be about building people.

And while one chapter has closed with a successful eight-figure exit, few believe Chris George is slowing down. The Chaldean community and the broader entrepreneurial world will be watching closely to see what he builds next.