EXCLUSIVE: Fresh After Helping Grant Cardone's 10X, Chris Tsiolis Launches Proago Marketing Systems, Helping Business Owners Digitize, Promote, Scale

While the startup ecosystem maintained vigor since the COVID-19 pandemic, an underlying narrative forewarned challenges that may disrupt this momentum and threaten unprepared founders and operators.

In this context, Chris Tsiolis recently engaged with Benzinga for an hour-long interview. He shed light on cultivating relationships and navigating the complexities of 2024 through automation, offering examples from his recent collaborations with finance and influencer marketing figures, such as Grant Cardone.

Immigrant Roots And The American Dream

A Chicago native of Greek descent, Tsiolis’s problem-solving skills and confidence in business stem from his family's relentless pursuit of the American Dream.

“That immigrant idea that you must build yourself remains true,” he said, noting having engineers as parents, speaking multiple languages, and playing instruments like the cello “built new pathways” and fostered creativity. Armed with a degree in philosophy and creative writing, Tsiolis sought his place in the professional world by becoming an unpaid CEO understudy.

“Naturally, I thought advertising or writing would be the logical progression to finding a job. That’s when I explored opportunities in Chicago and discovered a chance to work for free at a mid-sized advertising agency. Collaborating closely with the agency's owner, I engaged in everything from media buying to copywriting, creative design, auditions, and shooting commercials.”

From there, Tsiolis’s journey unfolded unexpectedly, guiding him through radio promotion, journalism at the World Series of Poker and finance.

Picture: Chris Tsiolis, a 2023 Seminole Hard Rock Poker Open Event 11 Champion.

“My passion for probability games of skill led me to play poker professionally and the world of options,” he recalled. His run-in with options trader Andrew Keene at a poker game catapulted him into a career in financial marketing and working with CNBC’s Jon Najarian and Pete Najarian.

Playing pivotal roles at optionMONSTER and Market Rebellion, co-founded by the Najarians, Tsiolis landed partnerships and orchestrated events generating millions in sales. This success eventually caught the attention of Jarrod Glandt, president at Grant Cardone Enterprises, who scouted Tsiolis.

Pictured: Chris Tsiolis, left. Shark Tank’s Kevin O’Leary, middle. Jon Najarian, right.

Customer-Centrism And Proximity

Central to Tsiolis’s career moves and success is empathizing with the customer.

“I had immersed myself in Grant’s materials, absorbing every piece, and utilized the content and strategies to build up Market Rebellion into a $30 million per year subscription machine. When the opportunity arose to promote the Grant Cardone brand, I pursued it because it felt like the decision had chosen me. I was well-versed and believed wholeheartedly in the content — I was a customer and a believer in the message before I was an employee.”

Additionally, Tsiolis believed strongly in proximity and getting close to decision-makers who operate within structured processes and those driven by top-line revenue targets.

“Seeing the differences firsthand still guides my work. I can tap into those experiences on both spectrums and use that as a rule of thumb.”

Develop A Passion And Monetize It

Tsiolis encouraged aspiring entrepreneurs and recent graduates to pursue a passion or skill that brings fulfillment, citing his success as an example.

“The secret is being able to do something you love, like writing, repeatedly until it starts yielding results in the real world,” he said. “You don’t have to reinvent the wheel to solve problems and help people.”

Tsiolis also advocated iteration, having varied offerings, and building communities through newsletters, for example, for sales or feedback. It revolved around applying the scientific method and adopting what he termed a "neural network mindset" — whether in statistical analysis within the gambling realm, the iterative process of testing and refining as a marketer, or the utilization of machine learning algorithms. Tsiolis saw these approaches as connected and deviating from them represented “slipping backward.”

Moving Forward With Automation, AI

Despite interest rates and inflation concerns, Tsiolis asserted the American Dream was alive and well for entrepreneurs. Accordingly, he was betting on himself.

"I am embracing the wave of AI automation," he said in a discussion on how to hedge 2024 risks.

"I navigate life with the mentality of a gambler in search of the next winning hand, always anticipating the next possibility and embracing failure as part of the journey. With a wealth of experience and clout, I've navigated these challenges thousands of times, enabling me to iterate and adapt seamlessly—I am desensitized to setbacks."

Much like the revolutionary shift from manual bookkeeping to computer-based accounting, AI promises remarkable efficiency gains in marketing and communication. However, the challenge lies in the early stages, lacking widespread use cases.

With Proago Marketing Systems, Tsiolis wants to make AI accessible and practical for entrepreneurs and business owners with notable applications like automated messaging, customized sales qualification chatbots and social media analytics.

“All the strategies I've honed over the past decade — crafting diverse digital campaigns and advertisements tailored to various platforms to educate audiences — are now being systematized and expanded,” Tsiolis ended.

“At Proago, we can initiate this process with code integrated into your website, channeling your social traffic. This evolves into a dynamic marketing ecosystem, proving especially pertinent as advertising networks and social media platforms pivot away from first-party data.”

Photo: Courtesy Chris Tsiolis