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The League founder Amanda Bradford became more ‘risk-averse’ as her dating app grew. That’s why she sold it to Match Group for $30 million

By
Emma Hinchliffe
and
Joey Abrams
Joey Abrams
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December 4, 2023, 8:21 AM ET
The League founder and CEO Amanda Bradford.
The League founder and CEO Amanda Bradford.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.”

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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.
Courtesy of The League

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.

ALSO IN THE HEADLINES

- Remembering the first.Sandra Day O’Connor, who served as the first female Supreme Court Justice in U.S. history from 1981 to 2006, died last week at the age of 93. One of O'Connor's most memorable decisions came in Planned Parenthood v. Casey in 1992, which upheld federal abortion rights. O'Connor reaffirmed the constitutional right to abortion in the 5-4 ruling, despite personally finding abortion "abhorrent." New Yorker

- Stocking up.Target is teaming up with Sèchey, a woman-led retailer of nonalcoholic drink brands, to stock shelves with increasingly popular dry cocktails and other spirits during the holiday season. Kin Euphorics and De Soi, the nonalcoholic lines cofounded by Bella Hadid and Katy Perry, respectively, are among those hitting stores. CNN

- Old money, new life.Lyda Hill’s grandfather made a fortune off of the oil and gas hub he built in Dallas, Texas. Now Lyda’s taking that money to pivot the city into America’s next biotech capital. After the federal government chose one of Hill’s office campuses in Dallas as its new health research headquarters, biotech startups have lined up to use the space for projects like reviving the long-extinct Wooly Mammoth and Tasmanian tiger.Bloomberg

- Stacks of cash.The great-granddaughter of Lego founder Kirk Kristiansen sold around 6.32 billion kroner (USD $930 million) worth of stock in the company last week. Fourth-generation heir Sofie Kirk Kristiansen now plans to use the proceeds to fund nature and preservation initiatives.Fortune

- Take it to the limit. Supporters of the temporary New York Adult Survivors Act says that it should be extended to give more victims time to pursue justice. An extension of the act, which removed the statute of limitations on civil sexual assault lawsuits, likely would also be time-limited.The 19th

MOVERS AND SHAKERS: Carrot Fertility promoted Brooke Quinn from chief customer officer to COO.

ON MY RADAR

How TikTokers and Swifties became political power brokers in Guatemala Washington Post

A play about Black women’s experiences, met with violence New York Times

Cami Téllez's underwear startup Parade went bust, and employees blame her. Is it OK to write about it? Business Insider

PARTING WORDS

"Aging is not that terrifying. We’re all doing it. I wish someone had told me earlier, ‘Just relax. It is what it is. Don’t pay attention to the obstacles.'" 

—Meg Ryan, star and director of the recently released romantic comedy What Happens Later, on loving the aging process

This is the web version of The Broadsheet, a daily newsletter for and about the world’s most powerful women. Sign up to get it delivered free to your inbox.

About the Authors
Emma Hinchliffe
By Emma HinchliffeMost Powerful Women Editor
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Emma Hinchliffe is Fortune’s Most Powerful Women editor, overseeing editorial for the longstanding franchise. As a senior writer at Fortune, Emma has covered women in business and gender-lens news across business, politics, and culture. She is the lead author of the Most Powerful Women Daily newsletter (formerly the Broadsheet), Fortune’s daily missive for and about the women leading the business world.

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Joey Abrams
By Joey AbramsAssociate Production Editor

Joey Abrams is the associate production editor at Fortune.

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