A Not-So-Retiring Retirement

By Andy Steiner ’90 / Photo by Heidi Kirin

After she sold TI Health, the predictive analytics company she founded in 2018, for more than $100 million, Erin DeRuggiero ’96 could have luxuriated on one of the Maine beaches near her home for the rest of her days. But while retirement has given her the ability to cut back on her exhausting work schedule and spend more time with her wife and kids, DeRuggiero, 49, is instead using her time to empower other entrepreneurs and share the expertise she built through her business career.

When she created TI Health, a predictive analytics and insights platform, DeRuggiero leaned into her background in sales and digital marketing—combined with her lifelong interest in medicine and health care.

The company, now part of Swoop, a precision health care targeting and data company, supports pharma with commercialization, says DeRuggiero, harnessing the Internet’s power to identify the issues medical professionals are focusing on and then deliver information on those topics to them.

Guiding a new generation of entrepreneurs

In retirement, DeRuggiero has been flexing her creative muscles with her podcast “Corporate Confessions.” DeRuggiero and co-host Andy Lesh offer humorous-but-helpful career advice on submitted listener questions about everything from how to respond to a treat-stealing boss to how to deal with a co-worker’s flatulence.

When she’s not dishing out advice, DeRuggiero is offering another form of support for up-and-coming entrepreneurs through Short Sherpa, a private-equity consulting LLC that, she explains, works with funds to “pick apart health technology and predictive analytics businesses to advise and guide them into the right investments.”

Short Sherpa’s latest project, Lumiinus, is a good match for DeRuggiero’s health-and-technology expertise. It’s an early cancer detection platform that monitors users for colon cancer. The software looks for hemoglobin using hyper-spectral light in our cell-phone cameras. It’s still early days, she cautions: The company is in “stealth” mode, setting up clinical trials for humans while exploring how the patented technology can be used immediately to support the animal- and pet-health market.

“I want to stay involved in the data and predictive analysis and early-cancer detection space but through a different angle,” DeRuggiero says. “I like working at the edge of an industry that still has multiple challenges to solve to meet consumer demand.”

From her years in the business world, DeRuggiero knows all too well that women and members of the GLBTQ+ community, especially women of color, receive a shockingly small percentage of all venture capital money, “something like 2 percent,” she says with a sigh.

“I want to be more of a guide, more of an advisor, an investor,” she says. “I want to help other women in particular who have startups that need coaching and support to raise money from VCs and private equity.”

“I could see myself there”

DeRuggiero grew up in New Jersey, the fourth of five siblings. When she was a junior in high school, she visited a number of colleges, but, after a fateful campus tour, decided Macalester was the place for her.

“It was the only school where I saw two women walking across campus holding hands,” DeRuggiero recalls. “So that was my criteria. Academics were important, of course, but I just loved that I could see myself there because I already knew I was gay.”

At Mac, DeRuggiero majored in English and minored in Spanish and educational studies. She reveled in the support and encouragement she received from faculty, who, she says, told her what she had to say was important and encouraged her to pursue her dreams.

A confident natural performer with a sly sense of humor, DeRuggerio particularly enjoyed acting in Black Box plays and being a member of the Sirens, Mac’s all-female a capella singing group. She also was inspired by Linnea A. Stenson, a visiting assistant English professor and out lesbian who, DeRuggiero recalls, once said at a Queer Union event, “Coming out is not something that you do once when you’re 17 and you never do it again. It is something you consciously decide to do over and over and over again.”

DeRuggiero, who has been partnered with wife Yvette Webster since 2008 and married since it became legal in 2013, has taken Stenson’s words to heart: She’s always been unapologetically out in her personal and professional lives.

“It’s something that I took with me to my corporate worlds from my quirky little Macalester world,” she says. “I wanted to make sure people felt comfortable being out at work, being who they were.”

After graduation, DeRuggiero worked for a time as a restaurant server and in customer service gigs before landing an ad-sales job at Utne Reader magazine in Minneapolis, where she cut her teeth in the digital sphere. That job led her to form a consultancy and land a job at Facebook. At 38, she founded Social Reality, a programmatic advertising and data marketing company that became the early building blocks of what would later transform into TI Health. All this led to the company’s sale and then to DeRuggiero’s unique kind of retirement.

Now, DeRuggiero has time to think about her future while reflecting on her past. She’ll always look back on her considerable business successes with pride, but she says that her greatest accomplishment is much more humble.

“I know it sounds corny,” DeRuggiero says, “but I’m proudest of being a mom.” And with an eight- and a twelve-year-old still at home, this particular startup won’t be going up for sale anytime soon. “Co-parenting,” DeRuggiero says with a laugh, “is not for the faint of heart. But we’re in it for the long haul.”

Andy Steiner ’90 is a Twin Cities-based writer and longtime Macalester Today contributor.