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Ross Freedman: Entrepreneur and Mentor of the Year

By Linda Barrett

December 5, 2023

Ross Freedman

The Creative Destruction Lab (CDL) is a non-profit program designed to offer founders of new ventures excellence in mentorship. A carefully selected group of mentors share their advice and judgment on what the founders ought to achieve in a series of eight-week sessions. Some of the mentors have experienced similar struggles, having started and exited from their own startup enterprises. Others are venture capitalists, while an additional group are people who operate in or have significant expertise in the domain.

Ross Freedman (BBA, ‘97) fits those categories, most importantly as a successful technology startup founder and venture capitalist. Freedman and fellow Badger Brad Schneider (BBA, ’97) have been successful business partners since moving into the same residence hall at UW-Madison as freshmen. Their first venture was Wired Matrix, a systems integration consulting firm based in Chicago. Their second venture was digital consultancy Rightpoint, which made several strategic acquisitions and grew to more than 800 employees across 12 offices globally before it was acquired by a public company. After Rightpoint, they founded 367 Ventures, which is a Chicago-based venture firm focused on advising, mentoring, and investing in founders of early-stage companies. More recently they started Origin, a new-age consulting company that operates at the exciting intersection of data analytics, artificial intelligence, and automation.

In addition to being a mentor for CDL, Freedman has been a member of the Weinert Applied Ventures in Entrepreneurship (WAVE) Advisory Board at UW-Madison. Students enroll in the WAVE capstone class to work on their venture ideas and receive mentorship from entrepreneurs such as Freedman. Dan Olszewski, the Goldberg Family Director of the Weinert Center for Entrepreneurship, states, “I think so highly of Ross. He is an engaging mentor who really wants to help the students and others get better. His energy and involvement are incredibly inspirational and impactful for the next generation of Badgers.” Olszewski noted Freedman’s commitment and forwarded his name to the Creative Destruction Lab (CDL)-Wisconsin, while simultaneously sharing CDL’s information with Freedman, who immediately understood that working with CDL would complement his work with other venture incubators and accelerators.

Then-Director of CDL-Wisconsin, Shabaka Gibson, recalled his first phone call with Freedman: “We explained CDL and what the expectations were while gauging whether Ross would be a good fit for the role, add value to the companies participating, and add value to the other mentors. It was clear that Ross would do all three, and he was on board immediately.” Freedman has been all that, and more.

Freedman indicated that there are two ways that CDL is distinct from other accelerators. “The foundation of CDL’s process is far more structured and refined. There is a lot of thought placed on the value of time for both mentors and founders. The structure of process and productivity is ultimately what really sets CDL apart. Further, the quality of companies that CDL brings forth is extraordinary. Many of the companies I have worked with through CDL have founders who are coachable and have an idea that is a good product-market fit, and many of them have the raw materials to be successful,” he shared.

Generally using a three-pronged approach to guide his mentoring conversations, Freedman indicates that “founders are typically great practitioners in their field but need to gain experience in other key areas such as growing top-line revenue through the acquisition of new customers early in the company’s maturity. Another area I typically help with is understanding their cash flow needs and assisting with fundraising. Finally, I look for coachable founders that are seeking help to discover the skills, and often the roles, that their team should consider in order to be successful.” His goal is to mentor others in the life-changing ways that helped his ventures through their early days.  

Recognizing his contributions, Freedman was recently awarded Mentor of the Year for the quality and quantity of support he has offered to startup founders in the CDL-Risk Stream the past 2-plus years. Co-lead of CDL-Wisconsin and American Family Distinguished Chair in Risk and Insurance, Professor Joan Schmit, noted, “Ross was the natural choice for 2023 Mentor of the Year. He has consistently spent his positive energy with the program. The quality of his comments and enthusiasm were outstanding, and he offered to help more ventures than other mentors. We recognize the time he spends, and wisdom he shares, when mentoring others.”

Freedman’s gifts to the world do not stop with his mentorship. Following in her dad’s footsteps, Olivia is currently attending UW-Madison. “I am so proud of her. She is majoring in User Experience (UX) Design and will contribute to startups because they need to better understand this important multi-disciplinary field when developing new products and services.”

It is obvious that Freedman has had, and continues to make, an impact on those within his reach. Schmit could not say it better: “We all improve when Ross is involved. We are grateful for his intelligence, energy, and thoughtful approach to everything he undertakes.”