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Emma Hinchliffe, Joseph Abrams

Why the League's founder sold to Match Group

(Credit: Courtesy of The League)

Good morning, Broadsheet readers! Former Supreme Court Justice Sandra Day O'Connor dies at 93, Target taps women-led brands for its nonalcoholic spirits section, and a dating app founder tackled her own risk aversion—by selling her startup. Have a productive Monday!

- Match made. Almost 10 years ago, Amanda Bradford founded the dating app the League. The app branded itself as an invite-only, exclusive place to date. It emphasized quality over quantity, was early to the paid space, and became known as a dating app for the "elite."

Bradford was a solo founder, and over the app's existence she only raised $2.2 million in seed funding. Much of her net worth was tied up in the company, and as time passed she felt herself becoming more risk-averse with the business. "I didn't necessarily want to swing for the fences and make a mistake," she said on a recent visit to the Fortune offices. "I saw myself taking less and less risks."

So, she realized, it was time to sell. Last year, she sold the League to online dating giant Match Group for a reported $29.9 million. Over the past year-and-a-half, she's found a level of freedom that comes with running a business she no longer owns.

"I could afford to look at it like an employee instead of owning it," she explains. "I'm not nervous about spending every dollar perfectly."

The League founder and CEO Amanda Bradford

As she considered potential sources of capital, Bradford decided to avoid further venture funding or a private equity acquirer. She'd heard "horror stories" from friends who were forced out of their companies. And she most wanted a backer that understood the dating space and knew how to scale a dating app. Match's track record growing Hinge—it first took a stake in the relationship-focused app in 2018 before fully acquiring it a year later—impressed her too.

The League is now one of the smallest brands in the Match portfolio, which includes Tinder and OkCupid. Bradford says the small team has remained "pretty autonomous" within the $3 billion-in-revenue company.

She hopes to use Match's resources to scale as a hybrid online-offline dating platform. For instance, she envisions building maps that help users identify where singles are hanging out as they decide which bar to go to, enabling in-person connections.

And while the League was a well-known brand among millennials, the startup completely paused all marketing during the pandemic. That's left it with an entire new generation of Gen Z daters who haven't even heard of the app. With a new marketing budget, Bradford hopes that changes. "I really want us to be the most innovative brand in the Match portfolio," she says.

Emma Hinchliffe
emma.hinchliffe@fortune.com
@_emmahinchliffe

The Broadsheet is Fortune's newsletter for and about the world's most powerful women. Today's edition was curated by Joseph Abrams. Subscribe here.

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