An openly queer founder who never thought she'd have a place in tech explains what startups can do to reach a more diverse audience


Rebekah Monson of WhereBy.Us

  • Rebekah Monson is the cofounder and COO of WhereBy.Us.
  • Monson realized she was queer in college, where she found herself debating gay marriage in the classroom and writing the first story on a trans student for her campus newspaper.
  • Now, as a media entrepreneur, she sees diversity and inclusivity as “core values” of her company.
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I never planned to be an entrepreneur.

I was a nerdy kid from rural Alabama, but not an outstanding one. I wasn’t the smartest, or most ambitious, or really the best of anything in my class of 100 students. But even back then, I was fascinated with — and passionate about — stories, about using technology to tell them, and about the communities those stories affect.

In college, I realized that I was queer right around the time I got obsessed with working for the student newspaper. Just after I came out, we debated gay marriage in a political science seminar. As I very consciously quelled my emotions to recall policies and court cases, I thought, “This will never happen in my lifetime.” A little later, I wrote the first story on a trans person for the campus paper. I was astonished and outraged at how hard it was for him to simply use the bathroom on campus.

Throughout my career — from restaurant gigs, to internships, to management, to eventually starting my own company — I have grappled with being a queer woman at work. A steady drip of fear, doubt, and responsibility niggles away at everyone who’s ever been “the other.” What should I do about my manager using a slur? How can I be most fair with this politician who deeply opposes my relationship? How can I help everyone who works here perform their very best? How can I get the power to make decisions and set priorities?

If you had asked me back at 18 to predict what the world would look like for LGBTQ people 20 years later, I would have landed far short of where we actually are. But people kept coming out. They kept fighting in court, protesting, lobbying, talking to their neighbors, challenging every little thing to try to change the one big thing: equality. And the tides are turning faster than I imagined. We still have a long way to go, but the progress when we work consciously and constantly to improve is obvious.

It’s still difficult for LGBTQ employees to navigate the workplace

All that social and cultural success hasn’t necessarily been as apparent in our work lives. LGBTQ people still face discrimination, are underrepresented in many companies and industries, and often lack employment protections. We can change this. As entrepreneurs, founders, and leaders, we have a mandate to disrupt broken systems and build a better way forward for our businesses. Diversity and inclusion efforts are often framed as a part of building company culture, but prioritizing diversity is also an essential business strategy.

You’ve probably read that diverse teams are more innovative, make better products, and make more money. But the benefits of consciously working on diversity stretches beyond internal initiatives. Inclusion is more important than ever in industries like media and tech, which aim to rapidly grow very large audiences of very different people, all while facing radical disruption and a crisis of mistrust with their users. 

WhereBy.Us, the startup I co-founded, is not perfect at this by any measure. But embedding diversity and inclusion into our work helps us to punch above our weight in the highly competitive market for attention. Our teams collect and analyze dozens of feedback reports and metrics each day to understand who we may be missing in our work, to learn more about the needs of our customers, and to find new ways for us to grow. 

We ask a lot of direct questions to our users: What are you curious about? What should we know about your work, your neighborhood, your community, your passions? What can we do better? These questions regularly turn into stories or sales leads, but they’re also sending a strong, steady signal of inclusion. We are listening to you. We want to learn from you. We work for you and with you.

Active outreach is key to cultivating a diverse audience and staff

Our teams are constantly working to strengthen relationships in the cities we serve, particularly among communities that are unfamiliar to us. Outreach builds networks that help us grow, find better stories, understand different user needs, and identify new sales and partnership opportunities. Ultimately, investing in stronger, deeper relationships helps us compete against far bigger teams with far bigger budgets.

When diversity and inclusion are deeply rooted in our work as a core value and a strength — rather than viewed as a lofty cultural aspiration — we create a continuing cycle for culture efforts. Extensive community outreach helps us get more highly qualified, diverse candidates in the applicant pool for every job we post. In turn, more diverse teams guide more diverse coverage, welcoming new audiences and helping our work serve more people more effectively. 

It’s hard not to be proud of how far LGBTQ communities have come during the time my career has unfolded. Yet we still have a lot more work to do. This requires extending equality at every step to every other “other.” As entrepreneurs, we have even more opportunity to do that work through solving problems, disrupting broken systems, and building better businesses. 

Rebekah Monson is cofounder and COO of WhereBy.Us, a platform for local media in growing cities, with a focus on delightful email newsletters and experiences for communities of local explorers, makers, and leaders. WhereBy.Us owns and operates The New Tropic in Miami, The Evergrey in Seattle, Bridgeliner in Portland, Pulptown in Orlando and The Incline in Pittsburgh.


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