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Ben Harvey

Meet The AI Entrepreneur Who Used LinkedIn To Raise $13.8 Million

Financing His Future: Dr. Benjamin Harvey, CEO of AI Squared, says he took out a $20,000 credit card... [+] Photo Courtesy Of AI Squared
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Benjamin Harvey, the CEO of AI Squared, says he’s added investors including former TIAA CEO Roger Ferguson. Harvey joined Forbes senior writer Jabari Young at the Nasdaq MarketSite to discuss the startup’s Series A raise.


Benjamin Harvey and his investors describe startup AI Squared as a washing machine for AI. After four years getting the software company off the ground, Harvey, the 38-year-old CEO, figured a businessman like Roger Ferguson, the former CEO of TIAA, would appreciate what his company could do.

Harvey was so confident, he made a direct pitch to LinkedIn.

“Dr. Ferguson,” Harvey wrote in February 2022, “‘Here’s some of the work that we’re doing in financial services. I would love to just have a 15-minute phone call with you.” Ferguson’s response: An invite to have breakfast at the Four Seasons in Washington, D.C.

“When I have a vision,” Harvey tells Forbes, “I’m relentless with trying to make it become a reality.”

AI Squared closed on a $13.8 million Series A raise in March, led by venture firm Ansa Capital with participation from Baltimore-based New Enterprise Associates (NEA) and Ferguson, the parties tell Forbes. Founded in 2019, Al Squared is a third-party software company that extracts data from AI models and machine learning and calculates real-time business outcomes. Since its founding, the startup has raised $20 million from investors.

AI Squared isn’t profitable. In 2024, however, Harvey estimates the company will surpass $10 million in revenue. It makes money by charging product licensing and data usage fees. AI Squared is based in Washington, D.C., employs 30 people, and has contracts with the U.S. Air Force, U.S. Navy, the National Security Agency (NSA), Nasdaq-traded cybersecurity company, Rapid7, and a Coca-Cola contractor in Florida.

“Over the past five years,” Harvey says, “organizations have been building a lot of these world-class [AI] models. But they haven’t been able to actually receive the full value of those models. We’re helping bring AI and machine learning to life.”

Inside The Washing Machine

To serve the consumer of the future, when people will interact with computers more intimately than ever, tech companies are racing to build superior AI infrastructure. In 2023, investors poured nearly $100 billion into more than 7,000 AI and machine learning (ML) companies, according to PitchBook.

AI Squared investor Greg Papadopoulos of NEA called AI “a hugely democratizing technology. It’s going to give individuals amplifiers for their creativity,” he tells Forbes.

Asked about the problem AI Squared will solve in a rapidly shifting AI atmosphere, Papadopoulos, a former engineer at HP and Honeywell, traced the issue to engineers and data analysts inside companies that are mainly focused on building AI models. The problem, Papadopoulos says, is that many of the companies aren’t deploying the tech. He called it “the last mile problem,” or the struggle to identify ways to get new products in the hands of customers and employees.

Papadopoulos compared the current environment to the process of washing clothes.

“That’s where things have been,” Papadopoulos tells Forbes. “The equivalent of, ‘Yeah, I washed all this (data), and then I dumped it on the floor.”’

He adds that AI Squared will not only be the ultimate washing machine, “but at the end, it dries, folds your clothes and stacks them up neatly rather than leaving them on the floor.”

Harvey agrees with the washing machine analogy. “That’s exactly what it is,” he says. “We pull together that data, put it inside a washing machine, and out comes this product you can now use to support your business operations.”

Raised in Jacksonville, Florida, one of seven children, Harvey credits his upbringing for developing his passion for computers. Harvey’s father was a church pastor and AT&T project manager who would often bring home broken computers, and over the years, a young Harvey learned to disassemble and repair the machines. Harvey majored in computer science at HBCU Mississippi Valley State University, where he attended on a football scholarship.

After graduating, Harvey received a master’s degree and a Ph.D. from Bowie State University, and, in 2009, he joined the NSA as chief of operations for its data science division. There, he conceptualized the idea behind AI Squared after discovering major lapses with providing real-time data and analytics to U.S. military personnel from NSA scientists. A decade later, he left the NSA and joined Databricks, a data and analytics company that Forbes values at $43 billion, as a solutions architect. At Databricks, he would pitch company co-founder Matei Zaharia on the potential of AI Squared.

“Reverse ETL for AI ML,” Harvey says Zaharia called it, meaning, “Extract, transform and load” data from AI and machine learning. “Databricks stops at building models,” Harvey says. “We need technologies that can support integrating those insights from those models into applications” that drive business outcomes.

Harvey says he maxed out a $20,000 credit card, then begged his wife to drain their $500,000 retirement account to fund AI Squared. In 2022, the company went through a $6 million seed round. Over the last two years, though, capital for startups has slowed partly due to higher interest rates. To attract funds, early stage startups should have at least $3 million to $5 million in annual recurring revenue, Harvey says.

Now braced with $13 million in fresh capital, Harvey says AI Squared plans to expand business operations to meet forecasted demand around AI-as-a-service software platforms. And for that, he can partly thank Ferguson, who joined the AI Squared board.

“We’ve grown that relationship off of a LinkedIn message,” says Harvey.

Capital Gains: Watch the video to hear more on how AI Squared attracted investors for its Series A raise. Also, CEO Benjamin Harvey goes deeper to explain the company’s growth plans.

Correction: This article has been updated to reflect the proper spelling of Greg Papadopoulos’ name.

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