• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock

2

OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation

3

‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion

1

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock

2

OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation

3

‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
MPWMost Powerful Women

How Lena Dunham’s Budding Empire Breaks Every Rule of Business

By
Gwen Moran
Gwen Moran
Down Arrow Button Icon
By
Gwen Moran
Gwen Moran
Down Arrow Button Icon
June 22, 2016, 9:30 AM ET
Late Night with Seth Meyers - Season 3
LATE NIGHT WITH SETH MEYERS -- Episode 352 -- Pictured: (l-r) Actress Lena Dunham, producer Jenni Konner during an interview with host Seth Meyers on April 6, 2016 -- (Photo by: Lloyd Bishop/NBC/NBCU Photo Bank via Getty Images)NBC NBCU Photo Bank via Getty Images
Add Fortune on Google for similar content.

They got Hillary Clinton to own the f-word (feminist) and Jennifer Lawrence to discuss her personal wage gap. Alicia Keys opened up to them about not wearing makeup. Oh, and they also sell cute tote bags.

While most people now know Lena Dunham and Jenni Konner as the creative team behind controversial HBO series GIRLS, the pair are now making a name for themselves as emerging media moguls. Their Lenny brand, which began as simple email newsletter, has been quietly growing into major force, with a growing presence in digital media, podcasting, online retail, and book publishing.

Their success so far has been fast-paced—the first Lenny newsletter went out in September of last year—and much of it has been achieved by completely flouting conventional business wisdom. Fortune talked to Dunham and Konner about the evolution of Lenny—and how they’ve rewritten the rules of building a budding media empire.

Revised Rule #1: Talk about sex and politics

During the 2014 book tour for her New York Times bestselling essay collection, Not That Kind of Girl, Dunham spent time talking with members of her audience. The more she did so, the more she realized that there was a big audience out there that wanted more of the feminist, progressive ideas and frank discussion of sex, friendships and relationships that GIRLS—and Dunham herself—are know for.

“The same lady can be obsessed with the presidential race and super-concerned about how to handle a zit and both those interests are valid and deserve airtime,” Dunham said in an email interview.

Sign up: Click here to subscribe to the Broadsheet, Fortune’s daily newsletter on the world’s most powerful women.

She and Konner soon began toying with ideas for a business that would provide those women with the content they crave. When they began zeroing in on a plan, they reached out to Benjamin Cooley, who, in addition to being Konner’s ex-husband and father of their two children, has an extensive background in entertainment management. He would ultimately become Lenny’s CEO.

Revised Rule #2: Don’t be afraid to go old school

While sites like Gwyneth Paltrow’s Goop and Zoey Deschanel’s HelloGiggles were thriving, the Lenny team wanted a more intimate and direct way to reach their readers, Cooley says. What they landed on was a decidedly old-school format, at least in digital media: The email newsletter.

 

From the beginning, the Lenny newsletter and its accompanying website buck the conventional format, which relies on short “listicles,” blurbs, and links. Instead, Lenny Letter specializes in long-form stories, essays, and Q&As. The first issue featured an in-depth interview with Hillary Clinton (Dunham is a vocal supporter). Konner says each issue mirrors what she and Dunham would be discussing with each other on any given day.

“It stems from the dialogue we are always in about work, feminism, politics, fashion, health and where it intersects. Part of what connects us is a bottomless appetite for information and dialogue. We see that same hunger from our readers,” she said in an email interview. Dunham says she knew they hit a nerve after Jennifer Lawrence’s essay about being paid less than her male co-stars started a viral conversation about wage inequality.

Revised Rule #3: Work with disparate partners

Since its launch, Lenny Letter’s subscriber list, which initially included the founders’ own network of media pros, academics, celebrities, and politicians, has skyrocketed to more than 445,000. Much of that growth has been driven by a deal stuck a couple months after the launch, which gave Hearst Media the rights to distribute and monetize the newsletter.

Hearst sells advertising and branded content, and promotes the Lenny brand across properties like Elle, Cosmopolitan, and Marie Claire. Konner and Dunham say they’re very involved with editorial planning and that they consult with the Hearst ad sales team on setting prices, developing advertorial, and working with advertisers.

From there, the opportunities came quickly. Konner and Dunham were already partners in their production company, A Casual Romance. They teamed up with IMZY, a community platform that uses paid moderators to help cut down on trolls, to create message boards to serve as a gathering place for their online community. And Random House, which published Dunham’s collection of essays, approached them to partner on a Lenny imprint, which will publish its first two books in 2017. (Hearst and Random House declined to discuss specifics about revenue shares.)

Working with disparate partners doesn’t worry Cooley. Instead, he points out that partnering with various specialists—book publishers, digital publishing giants, and the like—makes each part of the business stronger.

Revised Rule #4: Don’t worry about scaling

While Lenny is definitely designed to be profitable, says Cooley, the idea was never to grow Lenny into a huge brand. He points to the newsletter as a prime example of the company’s strategy.

“Hardcore readers who will want to sign up for a newsletter that comes in their inbox and will reliably open it—that’s not tens of millions of people. That’s 2 million people. That’s 3 million people,” he says. It’s not a billion-dollar business, but it is one that can hold its own—and grow—especially if it branches out into different ventures like podcasting and sells media across each of them, he says.

Revised Rule #5: Expect the haters

Of course, strong women’s voices—especially when they’re discussing issues like abortion and equal rights—are going to attract detractors. Dunham especially has been a favorite target of trolls ever since she broke into the mainstream with Tiny Furniture back in 2010. Since then, she’s been criticized over everything from the content of her book to the lack of racial and ethnic diversity in GIRLS.

But Lenny’s strategy of eschewing mass-market, please-love-me branding and its insistence on being bold, even when people don’t like it, has been a smart way to build a loyal following, says Syracuse University media professor Robert Thompson, who studies pop culture. Instead of adapting the voice to appeal to the greatest possible audience, the voice comes first, attracting the people with whom it resonates.

“In the case of this type of brand, in a fragmented world, to get to the ones who really love you, you’re going to have to have the collateral damage of people who really hate you,” he says.

Revised Rule #5: Work with friends and exes

Another way in which the Lenny team bucks conventional business rules is in the management mix itself. Blending friends, exes, and business could be a recipe for disaster, but it seems to work for Lenny’s leadership team. They insist that the key to the combo is putting people before work.

Dunham says she considers Konner “family” and that they tend to agree most of the time. Konner says their biggest disagreements happen when Dunham wants to get a new pet. (“I tell her what a bad idea it is and that she’s going to cause us all strife,” Konner says.) Cooley, meanwhile, notes that negotiating compensation with “a woman who also sends me a monthly child-support check is really interesting.” But the three agree that such complex business and personal dynamics force them to be honest with each other, deal with their issues, and move on.

“They key is that when we disagree, we really hear the other one out and agree that there is a more elegant solution than one of us ‘winning,’” Konner says.

Revised Rule #6: No plan is a fine plan

It would be easy to claim that Lenny’s success is the result of a well-planned and well-executed business plan, but Cooley says that’s not the case. The company doesn’t have a comprehensive growth plan. Rather, Dunham, Konner, and Cooley just follow their noses, branching off into whatever interests them.

They’re also open to experimenting with new business models. In May, Dunham took a page from the music industry, which has been increasingly relying on “surprise drops,” releasing a self-published and previously unannounced book, comprised of her old diary entries. Is It Evil Not to Be Sure? had a limited run of 2,000. At $25.00 each, the book quickly sold out, with all proceeds benefitting Girls Write Now, a writing mentoring program for young women. It’s now available as an ebook.

With GIRLS now in production on its sixth and final season, the team has been working on a variety new projects. Dunham and Konner produced Suited, a documentary about a Brooklyn tailor that caters to the LGBTQ community, which will air on HBO on June 20. Dunham says she wants to make more movies. Cooley says the team is looking at opportunities to bring video and possibly a podcast network to Lenny, playing on the success of Dunham’s “Women of the Hour” series, which she hosted for BuzzFeed in 2015.

“Our interests are pretty boundless, as is our appetite for new creative experiences,” says Konner. “We just want to be sure that what we’re creating is pushing the ball forward for women and diversity in media.”

About the Author
By Gwen Moran
See full bioRight Arrow Button Icon
Add Fortune on Google for similar content.

Latest in MPW

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • TikTok icon
  • YouTube icon

Latest in MPW

Anthea Hartig, Director of the National Museum of American History, looks to her left at a House Committee.
PoliticsWhite House
Smithsonian director derides a White House report branding the museum as ‘woke’
By The Associated Press and Steven SloanJuly 21, 2026
16 hours ago
Cleveland’s WNBA team doesn’t play until 2028 but Progressive just scored jersey sponsorship
SuccessSports
Cleveland’s WNBA team doesn’t play until 2028 but Progressive just scored jersey sponsorship
By Joe Reedy and The Associated PressJuly 21, 2026
16 hours ago
jd
PoliticsWhite House
JD Vance becomes first sitting vice president to welcome a child in office in over 150 years
By Darlene Superville and The Associated PressJuly 20, 2026
2 days ago
Backed by Daymond John and Post Malone, this Afghan-born founder built a $150M brand. Her real mission: the women back home
Successfemale founders
Backed by Daymond John and Post Malone, this Afghan-born founder built a $150M brand. Her real mission: the women back home
By Sydney LakeJuly 20, 2026
2 days ago
t
PoliticsWhite House
Analysis: Trump approves 80% of GOP disaster aid — and 60% for Democrats
By David A. Lieb, M.K. Wildeman and The Associated PressJuly 16, 2026
6 days ago
ruemmler
PoliticsCongress
House Epstein probe calls ‘Uncle Jeffrey’ email author Kathryn Ruemmler, former Obama White House counsel and Goldman Sachs banker
By Joey Cappelletti and The Associated PressJuly 15, 2026
7 days ago

Most Popular

Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock
Success
Mark Cuban says he has the solution to growing income inequality, and it's to reward every employee—from CEO to janitor—with company stock
By Sasha RogelbergJuly 20, 2026
2 days ago
OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation
Cybersecurity
OpenAI says its AI models secretly broke out of a secure test environment and hacked into AI company Hugging Face in order to cheat on an evaluation
By Jeremy Kahn and Emily ForliniJuly 21, 2026
18 hours ago
‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
Success
‘I want to die broke’: Billionaire philanthropist Denny Sanford dies after giving away $4 billion
By Sydney LakeJuly 20, 2026
2 days ago
Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
AI
Mathematicians grapple with a ‘very rapid and very unsettling change’ as AI cracks yet another century-old problem
By Eva RoytburgJuly 21, 2026
21 hours ago
Despite a $156 million contract, Knicks star Jalen Brunson still calls his parents for financial advice any time he makes a big purchase
Success
Despite a $156 million contract, Knicks star Jalen Brunson still calls his parents for financial advice any time he makes a big purchase
By Emma BurleighJuly 21, 2026
22 hours ago
'Dr. Doom' Nouriel Roubini says we're headed for universal basic income or 'some form of socialism' as AI revolutionizes work—He calls that optimistic
AI
'Dr. Doom' Nouriel Roubini says we're headed for universal basic income or 'some form of socialism' as AI revolutionizes work—He calls that optimistic
By Jason MaJuly 18, 2026
4 days ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.