Originally published: The Chronicle of Higher Education | By Goldie Blumenstyk | Apr 6, 2015

Paul Freedman’s last big venture in higher education did not end well. But apparently he rebounds fast.

Less than two years after being ordered by an accreditor to shutter the 2,500-student Ivy Bridge College at Tiffin University and then selling most of what was left of his Altius Education to another company, Mr. Freedman is back on the ed-tech scene with an unusual business approach designed to bridge the gap between what colleges actually need and what Silicon Valley-type companies are creating.

“The fundamental problem is a translation problem,” says Mr. Freedman. Increasingly, there are colleges “that really do want to innovate,” but they often don’t know what products or tools may exist to help them, he says. At the same time, many of the new ed-tech companies are creating products that don’t serve real needs of colleges and haven’t proven themselves to be effective. “I can be a translator,” he says.

Few who know him are surprised that he’s back in the ed-tech game so soon, even though he says he seriously considered careers outside of education. “My last experience was pretty heartbreaking,” he says. But for the not-yet-40-year-old Mr. Freedman, the son of academics who established his first company when he was still in college and believes technology has a key role in making higher education more effective and affordable, the allure was too great: “I couldn’t walk away.”

His new company, Entangled Ventures, is hard to categorize. Part incubator, part investment fund, part consultant, and part reseller of services, Entangled, which Mr. Freedman describes as “an educational-technology studio,” seeks out relationships with colleges to better understand their needs, while at the same time making connections with ed-tech companies to help them better understand higher education. (He chose the name for its association with notions of coordinated complexity and as an homage to his deceased father, a University of California at Berkeley physics professor, who did his dissertation on “quantum entanglement.”)

“To some extent what our partners want is our opinion,” says Mr. Freedman. In other cases, Entangled will actually create new companies based on what it hears from the colleges about their needs.

In Search of Solutions

With about $2.5-million in initial investment from friends and others, Entangled has already helped to create one such company, Handsfree Learning, a platform for students to learn and practice technical skills, such as tying off a suture. The idea emerged from conversations Mr. Freedman had with officials at Arizona State University, he says, and it became more fully formed when he remembered the expertise of Josh Salcman, the co-founder of an online-tutoring company called Virtual Nerd, who is now Handsfree’s chief executive.

Entangled Ventures also invested in and recruited new executives to Student Blueprint, a company that is developing technology that would help students at community colleges plan for careers and summer jobs, or transfer to four-year institutions. The new product is already being tested at several community colleges. Entangled has also invested in at least seven other companies.

Getting his companies involved early in pilot tests is a key part of Entangled’s model and philosophy, says Mr. Freedman, who has been critical of the general absence of testing around new ed-tech products. “There’s zero evidence that anything’s working,” he says. “Universities want solutions, they don’t want products.”

Mr. Freedman may well be the Kevin Bacon of the higher-education tech scene — if there are people he doesn’t know, he probably knows people who do — and the Entangled business model pretty much embodies his personal style. He has a penchant for making connections and identifying opportunities and a readiness to offer his opinions in a way that is polite but leaves little confusion as to what he thinks.

Entangled will get involved in companies at an early stage to help them meet colleges’ real needs. From Entangled’s conversations with colleges, “they’re learning about the pain points and the opportunities to solve problems,” says Mr. Salcman, who sold Virtual Nerd to Pearson in 2013.

Private-equity firms like Learn Capital and University Ventures also invest in young companies, but rarely at such an early stage and often with much larger financial stakes.

For colleges, Entangled will serve as an adviser, akin to the general contractor on a construction project, helping to identify appropriate companies for specific purposes.

If you’re an ed-tech company, says Mr. Freeman, “it’s really hard to get the ear of someone at a higher-education institution.” And most colleges don’t have the expertise or the infrastructure to evaluate the myriad companies now seeking to get in the door. “What we want to be is the trusted relationship,” he says.

Because Entangled may have investments and relationships with companies it recommends, the company may be seen as having vested interests. But because Entangled will recommend products that have already been vetted, or that will be tested as part of a pilot, the colleges will be protected, Mr. Freedman says. They’re also free to take or leave his advice.

But he says ventures like his could also be a counter to publishers and other organizations that he contends are now using their historic relationships with colleges to sell “shovelware” — a derogatory term for tech products of questionable quality. And given the hundreds of millions in investment capital flowing into the ed-tech sector and the growing interest on some campuses for innovation, he thinks the market is ripe: This model “wouldn’t have worked as well five years ago,” he says.

‘Authentic in the Field’

In the summer of 2013, Mr. Freedman, along with Tiffin, Altius, and four other people associated with Ivy Bridge, was notified by the U.S. Department of Justice that he was being investigated under the False Claims Act for matters related to Ivy Bridge’s recruiting and handling of millions in federal student-aid funds. Since then, there has been no public indication about whether the investigation is active or closed. It doesn’t seem to have deterred Mr. Freedman’s fans.

While Entangled has only a handful of formal relationships with colleges so far, college officials with whom Mr. Freedman has worked informally say the services could be valuable because of his connections with companies and with people in higher education.

“It’s a new kind of animal,” says Nick Ducoff, Northeastern University’s vice president for new ventures. In his position, he says, he gets “inundated with emails from people trying to hawk certain things.” He’d open emails from Mr. Freedman, says Mr. Ducoff, “because he’s authentic in the field.”

Bridget Burns, executive director of the University Innovation Alliance, a consortium of 11 public universities, says the approach Entangled promises would be a welcome change because there needs to be a “greater sense of partnership” between the companies and their college customers. “A solution lobbed over the fence to higher ed will not succeed,” she says.