Hupside, an AI startup developing tech to measure human creativity, closes $1.7M pre-seed

A Northern Virginia startup just landed $1.7 million in venture funding to build out its concept that AI can help show why humans matter. 

Hupside, a McLean firm founded in 2025, is building closed-source AI models that determine workers’ ability to use AI through evaluating originality. The startup today announced a pre-seed investment led by the DC firm Ruxton Ventures, and launched its “Hupchecker” product. 

That platform, its code not open to the public, tests people’s creativity through a series of questions (asking things like how you’d sell broccoli to kids, for example) and groups them into different archetypes, explained cofounder and CEO Jonathan Aberman. Those determinations can be used when building teams, he said. 

“In order to know how people are going to react to AI,” Aberman, who is a former partner at Ruxton Ventures, told Technical.ly, “you have to understand … their individual superpower for how they approach solving problems.”

That philosophy is embodied in the company name, he explained: Hupside came from combining “hu” for human, and “upside” for potential and promise. 

Aberman’s goal is for companies to use AI more effectively, he said, and show the tech should be used as an assistant — not a labor substitute. Hupside has design partners but no formal customers yet, spanning across industries like education, private equity firms and professional services companies. 

“The reason why we started this company was, we’re providing an actual way to show economically why and how human originality matters,” he said. 

Hupside has had conversations with potential customers in the public sector, per Aberman. Justin Fanelli, CTO for the US Department of the Navy, recently joined the startup’s advisory board. 

Hupchecker: Like a useful ‘drinking game’ that keeps humans in the loop 

The tool, which originated from Washington & Lee University and Georgetown, is a “game” of 25 questions. A lot of the prompts are unserious, and can even be used as a drinking game, Aberman said. 

Users’ responses are plotted in Hupside’s proprietary “idea space” that gives a determination of how original the answer is, he explained. Typical answers collect in the middle, and atypical ones are on the outside. That mapping is determined through comparisons to other people, the most customary AI response to a given question and to the most outlandish AI answer. Then, a composite score is calculated for the person’s creativity. 

Participants are allowed to use LLMs to answer questions, Aberman said. The tool won’t flag whether AI was used per se, but if a user copies a chatbot answer verbatim, it will be classified as unoriginal. If AI is used to strengthen a response, the person’s originality will be recognized, he said. 

“Ultimately, in an AI workforce, what we really care about is how well they’re using the tools to be original,” Aberman said, “or using the tools as an enhancement.”

Outside of the composite score, there are 10 possible archetype outcomes to determine how employees operate in the workplace. For example, a “connector” excels in integrating ideas in a project. 

Humans are kept in the loop completely, and can change scores as they see fit, per Aberman. 

“We’re not telling you whether the answers that they give are good or bad,” he said. “That’s ultimately for humans to decide.”

There’s a free version of this tool that includes five to seven prompts for less than 10 participants. Aberman plans to keep the free version available as the company grows. 

Aberman hopes people will use the tool more than once to track how people’s creativity shifts as AI is introduced in workplaces. 

“You can keep assessing people every quarter to make sure that the AI isn’t making them cognitively decline,” he said, “because if you see the originality scores decline, that means that they’re losing their edge. So then you can intervene. You can keep an eye on people.”

Moving beyond bootstrapping to bring the product to market  

Outside of being a former partner, Aberman and his fellow cofounders decided Ruxton was a strong investor because of the firm’s network, Aberman said. He is still an advisor to six portfolio companies. 

While Aberman was at Ruxton, he came across the Hupside technology, and was searching for a full-time CEO to join the company. But because of his experience, including leading the business school at Marymount for several years, he decided to join the startup. 

“The more that we looked at it, the more I realized that with my background in change management and my background in leading knowledge workers,” Aberman said, “and my overall passion about the project, that I was the best CEO for the company.”

The firm has a staff of 20, with five full-time positions and the remaining being contractors. Aberman noted Hupside will add product and sales roles, and plans to pursue more funding at the end of 2025 or early next year. 

Hupside is also planning to release a second product in the middle of next year that focuses on gauging the originality of individual pieces of content, differing from scoring people on their creativity. 

Aberman and the cofounders were bootstrapping the business before this pre-seed raise. They knew it was time to raise money to pool resources to bring the product to market, he said, “to get to the next metric of success.”

“There’s a difference between having a really cool technology.” Aberman said, “and having a really useful product.”