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The Connector: Kiesha B. Free

A former tech star using her skills—and her voice—to connect the region’s Black community.

By Rachel Gallaher February 2, 2026

Kiesha B. Free, also known as The Connector, sits gracefully on the floor in a cream top and colorful patterned skirt with a long train, paired with striking red high heels against a plain white background.
Photo by Ronnisha Hunter

This article originally appeared in the January/February 2026 issue of Seattle magazine.

In 2021, Kiesha B. Free was at a crossroads in her life.

She had left her job at Microsoft to pursue public speaking and was finding her way as a mother after a divorce—all while navigating a world emerging from the COVID-19 pandemic. “I was nowhere near my family,” says Free, who grew up in Oakdale, Louisiana. “A lot of my friends had left [the area] because they wanted to be closer to their families in other places. There was this huge turnover in my whole social and professional life. And so, I was like, if I have to rebuild my life from scratch right now, what would I dream up?”

For Free, the biggest thing missing was a deep sense of community. Since arriving in Bellevue in 2013, she had built much of her social life through tech networks, but after stepping away from Microsoft, she started exploring different pockets of Seattle and its vibrant Black community. The more people she met and businesses she explored, the more she realized that she wasn’t the only one looking to connect.

“I feel a bit like an emotional urban planner—planting seeds towards my ideas of what would be healthier, more human, and sustainable in this world.”

“I thought, if I’m going through this process for me, I can probably do this for a whole bunch of other people using what I know about building discovery tools, because that’s a lot of what I had been doing in tech,” says Free, who worked in publishing in New York before pivoting industries.

In February 2024, after collecting 200 entities—businesses, restaurants, bars, salons, boutiques—she thought “Black people who live here should know about,” Free launched Hey, Black Seattle!, which she describes as a “digital hub for Black life in the Pacific Northwest.” While there is a directory component, Free says that the website isn’t just another Black business list. “Our lives are more than just businesses,” she says, stressing that there is a rich array of connection points and information, including an events calendar, a job opportunities board, a community board, and a blog. Last year, Free launched a membership program with perks including discounts at local businesses and free tickets for cultural events.

Hey, Black Seattle! is mostly volunteer-run, and in the coming year, Free is looking to expand its reach with more opportunities for people to connect offline in low-cost, low-pressure environments. “We are building out the plans for this in collaboration with Wa Na Wari,” she reveals.

In addition to running Hey, Black Seattle! Free is an emcee, comedian, poet, and host of the YOU Better! podcast. “I joke about how multi-faceted my story is,” she says. “But I see the unifying element across it all as my desire to heal culture in ways that leave people taking better care of themselves and each other. I feel a bit like an emotional urban planner—planting seeds towards my ideas of what would be healthier, more human, and sustainable in this world.”

About Most Influential

Every year, Seattle magazine’s Most Influential list takes a close look at the people shaping the city right now. The 2025 cohort spans politics, philanthropy, arts, hospitality, business, and community work, highlighting leaders whose influence shows up in tangible ways across the city. Some are longtime fixtures. Others are newer voices. What connects them is impact—and the ability to move ideas, systems, and conversations forward as the city heads into 2026.

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