Gators back Gators in new artificial intelligence investment 

Pablo Casilimas, left, and Justis Mendez, right, meet with Will Passo, CEO of Rain AI, in Seattle in January 2024.
Pablo Casilimas, left, and Justis Mendez, right, meet with Will Passo, CEO of Rain AI, in Seattle in January 2024.
Courtesy of Pablo Casilimas

Former Gators Justis Mendez and Pablo Casilimas want to bring venture capital funding to startups sprouting at UF and their company, OneSixOne Ventures, has already hit its five- and 10-year goals set in 2020.  

OneSixOne Ventures has invested more than $2 million into 12 startups since February 2022. In February, the company announced a new $950,000 investment into Rain AI, a startup developing a computer chip designed for use by artificial intelligence. 

Casilimas said OneSixOne Ventures raised the funds within a month given Rain AI’s already significant backing. As reported by Wired, Sam Altman and OpenAI, the company behind ChatGPT, has already considered buying $51 million in Rain AI’s product that has yet to hit the market.  

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But Casilimas and Mendez wanted to invest even earlier when they met Rain AI’s founders in Gainesville. Before OneSixOne Ventures and any five- or 10-year goals.  

At the time, Casilimas said he and Mendez were both trying to start businesses while attending the university.  

“We realized that the smartest people we knew kept graduating from UF and leaving because, at the end of the day, Gainesville is a college town,” Casilimas said in an interview. 

Selfishly, Casilimas said they tried to keep the talent local through highly curated monthly meetups. He said the group soon included business leaders, commissioners, real estate agents and others. The duo started roundtables and workshops for startup founders, and then the COVID-19 pandemic hit. 

Casilimas and Mendez began discussing their goals. They aimed at starting an accelerator program within five years and launching a fund to invest in startups within 10 years.  

“Basically, the pandemic just sped everything up,” Casilimas said.  

The two began a virtual accelerator program soon after the pandemic. The accelerator program is a 10-week boot camp for startups to learn how to pitch products, pursue investors and find advisors. 

After running the boot camp for two years, Mendez and Casilimas had helped 40 companies raise over $13 million.  

“We got some really interesting companies that went through our program that we really wish we could have invested in, but we had no capital to,” Casilimas said. 

He said it was a frustrating experience. To solve the problem, Casilimas and Mendez asked some of the investment firms for a kickback or finder’s fee. The duo was connecting investors and startups but not getting financially cut into the deals.  

Casilimas said the majority of companies declined.  

“So, that kind of pissed us off, and we said, ‘alright, let’s just raise our own funds’,” Casilimas said. 

The teachers began to raise funds, using what they had taught more than 40 startups over the previous two years. Casilimas said UF alumni form the bulk of investors in OneSixOne Ventures’ fund. The company is also backed by the Cade family, behind the Cade Museum for Creativity and Invention, and other Florida-based venture capitalists.  

Casilimas points to two factors that differentiate OneSixOne Ventues—a focus on UF and their continued training events.  

Casilimas said no other venture capitalist firms are based in Gainesville. In contrast, he said Stanford University has more than 50 of these firms in a five-mile radius.  

But UF doesn’t lack luster.  

Casilimas points to the new Malachowsky Hall that just opened on campus with a $60 million donation from alumni Chris Malachowsky, cofounder of NVIDIA. Founded by another UF alumni, Vobile Inc. recently announced its return to the Gainesville area—prompted by the university’s talent.  

In addition, UF houses HiPerGator, the most powerful supercomputer owned by an American university. HiPerGator runs off processors built by NVIDIA.  

Rain AI is a Gator-led startup that could mirror NVIDIA or Vobile.  

Casilimas and Mendez met Jack Kendall, co-founder and chief technology officer for Rain AI, while at UF. Soon the startup caught the attention of national investors.    

Rain AI moved to San Fransisco and, before long, Casilimas said the startup had gone through a first and second round of investing in 2018 and 2021. Altman himself had invested $1 million in the company, Wired reported.  

Kendall gave a Tedx Talk at UF about the concepts around Rain AI in 2018. 

Casilimas said he and Mendez had no funds to invest at the time. In December, he and Mendez had a call with Kendall and an opportunity to invest finally happened.  

OneSixOne has invested in two other Gator-led startups. Casilimas said UF has the resources to keep building on its top six ranking by U.S. News & World Report along with the Wall Street Journal’s designation of the number one public university in the nation.  

UF has also pushed artificial intelligence learning throughout all its programs. OneSixOne, while not exclusive to AI, has invested in five AI companies.  

“We see a lot of opportunity [at UF], and we want to keep building that ecosystem,” Casilimas said. “But as a firm, we have to constantly be fundraising, too. So we’re also working different ecosystems.” 

Different ecosystems fit into OneSixOne Venture’s second differentiator. Casilimas said it’s the ability to host highly curated events with top talent and investors.  

The company hosted Seattle Venture Day in July, Gainesville Innovation Summit in October and Enterprise AI Roundtable in January. Casilimas said these events have featured top officials at Google, Nike, Oracle and more.  

Casilimas said the company hopes to host another Gainesville Innovation Summit this year. The two also get a peek at local talent as two judges for the Cade Museum’s Innovation Prize.  

Casilimas said support from the Cade family, and other UF connections, has helped grow OneSixOne Ventures in its two years of operation.  

“Building a venture capital firm from zero is not easy at all,” Casilimas said. “We’ve got to be able to get to the right people, and I think that having their backing really helps us with that.” 

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