Taking our Sunday morning walk through a Rockridge neighborhood, my husband noticed several cultural masks displayed on the trunk of a curbside tree.

As we were snapping a photo, their curator, Kai Drekmeier, stepped out of his house to tell us that they were part of a collection belonging to his late parents, Charles Drekmeier, Stanford University professor emeritus of political science, and Margot Loungway Drekmeier, who taught history at Stanford and Mills College. Both were prominent civil rights and anti-war activists who loved art and music.
“I thought the masks (mostly bought at flea markets) would be an interesting public art display that people would enjoy,” Kai said. He and his wife, Sarah Drekmeier, have lived and raised their family in Rockridge since 2002. Daughter Emily, a UCLA senior, and Beatrice (Beebe), a sophomore at UC San Diego, graduated from Chabot Elementary, Claremont Middle School, and Oakland Tech.
A Love Affair With Rockridge
Although he grew up in Palo Alto, Kai said he fell in love with Rockridge when his brother, Peter Drekmeier (a former mayor of Palo Alto), was studying at UC Berkeley. “This is like a dream neighborhood,” Kai said. “I like the diversity and vibrancy, the people, the food, the homes. Rockridge is upscale, but it’s got a modesty to it. Everyone is tuned in and has community-based values.”
“I call him the mayor of Rockridge,” says Rockridge resident Patrick Pernice, who has known Kai since their daughters were in preschool together. “He’s the most outgoing and positive person I know. He loves people and animals.” Indeed, while walking his dog, a black Lab named Lily, “I’ll see 20 people I know,” Kai said. One of his two cats, Bean, often follows them on the walk. Coco is less outgoing.

Tutoring Centers to Coaching Organization
Kai recently retired as chief development director of InsideTrack, a national nonprofit coaching organization that he co-founded in 2001, primarily dedicated to student enrollment, retention, and completion at community and four-year colleges. “I thought I would get into teaching,” Kai said, but starting in eighth grade and throughout high school he had enjoyed peer counseling. “I had a rebel element, but I always liked helping out those who were disadvantaged.”
After earning a B.A. in psychology at UC Santa Cruz while working at a little bookstore-café in Palo Alto he had a chance over-the-counter conversation with a potential purchaser of the bookstore, educational entrepreneur Alan Tripp. That began a partnership that led to co-founding SCORE! Educational Centers.
“The bookstore became an after-school learning center, the first of more than 100 we would eventually open,” Kai said. The company was known for its use of computers and a one-on-three tutoring model, with locations throughout the country. In 1996, it was purchased by Kaplan.
“Alan and I connected again in 2000,” Kai said, when we opened InsideTrack. At its beginning, “We would stop individual students at Stanford’s White Plaza and Berkeley’s Sproul Plaza and offer them a free academic or career strategy session.” But over the past 15 years, four-year colleges and, in particular, community colleges, K-12 schools, employers, and workforce development organizations have paid to have InsideTrack’s trained staff provide coaching to their students and employees.
Kai oversaw the growth of InsideTrack from three employees to several hundred and managed key functions, including coaching method development, performance management, professional development, and recruiting. He was listed as one of the most innovative people in higher education by Washington Monthly in 2016. “We’ve provided counseling to close to two million students,” he said.
“It was totally an unmet need,” Kai said. “Students who needed support couldn’t pay for it. We could make a difference, particularly with first-generation, lower-income, and students of color.” A Stanford random sampling of 100 students found that InsideTrack’s personalized counseling had improved retention and credits earned toward graduation.
Walking the Talk in Rockridge
A year into retirement, Kai is turning his attention to Oakland. Drawing on his familiarity with community colleges, “I’m thinking of running for the board of the Peralta system.” The seven-member elected body is responsible for governing Berkeley City College, College of Alameda, Laney College, and Merritt College.
He’s already on the board of Health Career Connection (HCC), an Oakland-based national nonprofit that connects undergraduate students and recent graduates, mostly those from underrepresented or disadvantaged backgrounds, to careers in healthcare and public health. Locally, HCC collaborates with the Alameda Health System, Alameda County Public Health Department, and UCSF Benioff Children's Hospital.
Rockridge resident Steve Wiersema has known Kai for over 25 years. “In my book, he is one of the most unique people I’ve met,” Wiersema said. “He is fearless in public settings, able to make people laugh, and engages them quickly, while at the same time he can talk with depth and sincerity. Kai and his wife, Sarah, have always been involved with the community and the schools, hosting fundraising parties every year and donating to the causes. They walk the talk.”
If you have a Rockridge story to tell, please email judyberne@att.net.