How This Startup is Making It Easier for You to Support Women-Owned Businesses

BOSSY Chicago: How This Startup is Making It Easier for You to Support Women-Owned Businesses

In traditional small business loans, only $1 out of every $23 in financing goes to women-owned businesses. They comprise 36 percent of all businesses, but only receive 12 percent of the revenue. With strong interests in empowering women, Sam Letscher and Isabel Benatar saw this as a problem that they could help fix with their startup, BOSSY — a blog and directory that celebrates female business owners by sharing their stories and directing consumers to their businesses.

“Internal biases cause us to take women less seriously, and banks trust women less with money, seeing them as less smart of an investment even through the research shows they are succeeding at a faster rate than other businesses,” says Letscher. “Their biggest problem is access to capital, and as consumers we can choose to support them.”

But the startup, like many of the businesses they’ve interviewed, has had its own story of obstacles and celebrations. Beginning as roommates in an Entrepreneurship 225 class at Northwestern University, the rising seniors were inspired to look at their own passions and problems and start their own organization.

In February 2017, the pair became residents at The Garage, a hub of innovation that spawns 60 student startups per quarter in an 11,000-square-foot space in the North Campus Parking Garage. With staff, entrepreneurs-in-residence, classes, workshops and other events, the space helps students bring their ideas to fruition, especially with the help of the twice-a-year Wildfire pre-accelerator program.

After applying and being accepted to Wildfire at the recommendation of Letscher’s professor Neal Sales-Griffin, the team had a strong start, but the startup faced many problems. They knew they wanted to support women-owned business, but what was the best platform? How do they get people to act on good intentions? What name would best suit their mission as an organization?

“Young girls who show leadership are called bossy in a negative way, but there’s no word for young boys who are in charge. We wanted to celebrate these qualities rather than see them as negative,” says Benatar. “The women we interview are literally the bosses, and we want to celebrate how empowered they are. We’re reclaiming the word.”

Wildfire then provided grants, mentors and resources to the 12 teams chosen for the summer program, and allowed BOSSY to flourish as a full-time endeavor. Deciding on storytelling as a primary platform, Letscher and Benatar have gone out and interviewed women in the Chicagoland area to share their stories on the website, and have started an interactive map directory showing consumers where women-owned businesses are located.

Just this summer, the website has published 15 stories to their blog, grown from 50 to 180 women-owned businesses in their directory since the site’s launch on July 13, started a newsletter with more than 120 subscribers, and has had more than 4,000 views on the page. BOSSY is growing every day, receiving submissions from the community to put more names on the map.

“We’ve been surprised by how incredibly generous and helpful all the women are,” says Benatar. “Everyone wants to help us get connected and give us any resources they can. We’ve had such a great time meeting them and being inspired by business owners.”

“Especially in the beginning with just two of us writing the blog with a few followers that were our friends and moms, [the women] were still so willing to talk to us even though it wasn’t necessarily giving them the biggest boost in visibility,” adds Letscher. “Their excitement is what gets other people more excited about the resource.”

With school beginning again soon, the team looks to add more hands to the project to sustain the growth of BOSSY. They hope to motivate consumers to become loyal customers of women-owned businesses, and realize the purchasing power they have to uplift the community. Rather than going for convenience — 2-day Amazon Prime shipping, the CVS around the corner, or the cheapest option — BOSSY wants to show that supporting these women is important, valuable and easy to do.

“Everyone we meet seems interested, but we’re all about turning words into actions,” says Letscher. “Everyone says they want to support women, but we want people to actually do it. Go out and find one woman to support.”

To learn more, visit, submit to their directory, and visit their Instagram, Facebook and blog.


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Manon Blackman is a Make It Better intern and rising senior at Northwestern University, pursuing a dual-degree in journalism and vocal performance. When she’s not in class, you can find her running, experimenting with vegan cooking, and drinking lots of coffee.