How Lena Dunham and Jenni Konner Became Best Friends and Business Owners


*Presented by Cole Haan*

We spend a lot of time together. Like, a whole lot. When we’re not working, we’re chilling, and when we’re not chilling, we’re texting. (It’s not for everyone; Lena sometimes wonders if it’s even for Jenni. The invention of the text message was not good for Lena’s clinically diagnosed OCD. _”Hello? Hello? Answer me!! Are you SAFE?!”_ ) But it’s an inextricable part of how we run our business and our lives.

Deep personal engagement + nonstop commentary on the happenings of planet Earth x putting writing first = Lena & Jenni’s proprietary mix for professional success.

So when the idea of interviewing each other about starting a business with your best friend emerged, we wondered how much there was to say that we hadn’t shared already. After all, keeping our creative relationship fresh is a big part of the reason we pursued the side hustle known as Lenny.

But it turns out that when the audio recorder came out, with it came some hot new info. For example, Lena was surprised and inspired by Jenni’s take on the “having it all” dilemma, while Jenni didn’t know about Lena’s long-held dream to be a drama teacher for tweens (that’s in the outtakes, where Lena also wonders if “bed tester” is a job).

Our biggest hope is that when you read this, you don’t take it like a line-for-line blueprint for your business endeavors. Rather, we want to be an example, letting you know that the passion — and shared connection — of two women is an unstoppable force. In the last seven and a half years, we have been through a stunning array of work disasters, family breakdowns, personal faltering, health crises, and even moments where we didn’t quite know how best to hold the other up, or whether we had the strength. But the love and power that sparks when two women see the world through the same pair of glasses? Well, that’s incredible, and it keeps you coming back, with more power than you knew you had. LYLAS.

**Lena Dunham:** You’re a busy woman, a working mother. When you said, “We should have a web presence” and we came up with the idea for Lenny, what made you go, “Yes, that’s a good idea, that’s how I should be spending my precious time”?

**Jenni Konner:** I just felt like you needed a platform — we both did, but you especially — that was more than 140 characters. _Girls_ could speak for itself, but at the end of the day, you needed to be Lena Dunham and not Hannah Horvath. You have such a strong political voice and a fierce feminist agenda; we didn’t have the time to wait for books to come out or your mayoral campaign. We just had to get in there.

> We need to understand why it’s as amazing to survive a miscarriage, or start a small business with your friend, as it is to go out and do this wild empire-building.

**LD:** People talk a lot about side hustles. At this point it’s confusing: what is our front hustle and what is our side hustle? I think our main mission will always be to do what we started with _Girls,_ which is to make really strong narrative content. Lenny and our other projects support that. I wonder how you think about the concept of a side hustle in your life and how you decide what to center for yourself. How do you split your time?

**JK:** I think you’re right when you said it’s hard for us to figure out what is a side hustle and what is just a hustle, because it just depends on the day.

**LD:** One of the big fears that a lot of people, particularly women, have when starting something like a side hustle is: How am I going to do this and continue to be engaged with my day-to-day work, and continue to be a parent, and continue to be a partner? How do you talk to those women who had a big dream, but also a fear around that dream?

**JK:** Whenever someone says, “How do you balance it? How do you give as much love to motherhood as you do to work?,” I just think that, for me, as I grow older, what I’m trying to do rather than balance it, is come to terms with the fact that there is no balance. When I’m at work, there’s a good chance that I’m not doing my best mothering. When I’m doing my mothering, I’m probably not doing my best job at work. For me, the best thing is just to try to accept that and not feel so much guilt and shame around it.

**LD:** You and I have an interesting story, which is that we became business partners as we became best friends because we were introduced through work. A lot of people share their primary passions with their closest friends but also feel afraid to begin an endeavor with them because they’re afraid that differences in managerial styles will create a riff. At the same time, who better to start a business with than your best friend, because presumably you guys have similar dreams and agendas. What would your advice be to a woman who wanted to begin something like what we’ve done with the woman who’s closest to them in their life?

**JK:** I don’t see any downside to starting a business with a friend, because the most important thing in the way we work is our communication with each other. We had already honed how to get through a drama or a crisis or a little decision or a big decision.

**LD:** I think the biggest thing when people ask me about working with my best friend, they ask, “How do you and Jenni keep it going on a day-to-day basis?” The most important thing is rigorous honesty. That honesty doesn’t have to be unkind. Honesty can just be a commitment to keeping it real every day.

**JK:** Part of that is, we both have to indulge each other’s desires and meet somewhere in the middle. That way, we both get what we want or we both compromise.

**LD:** When you think about our audience of women, how would you define what is extraordinary about them? How would you discuss that everyday remarkable that we’re reaching for with Lenny?

**JK:** When we started Lenny, we always said we wanted to push the ball forward for women. I think our writers are extraordinary for sharing their stories. But it is also about creating a community of women.

**LD:** People talk a lot about Lenny’s being political, that we interview lots of female politicians, and we talk about the right to choose, and we talk about real, quantifiable political change in this country. To me, one of the most political things Lenny does — and one of the most political things that you can do in general — is that it centers women’s stories in a way that is giving them the same essential importance that we’ve always given to men’s stories. The fact is, we give a lot of time and space to men’s stories of war, for example, but the things that women experience every single day, the small plights and challenges that come with being female, need to be centered too. We need to understand why it’s as amazing to survive a miscarriage, or start a small business with your friend, or notice a need for a library in your neighborhood, as it is to go out and do this wild empire-building. We need to understand how impactful these small shifts can be, too.

_This interview has been condensed and edited._

_Jenni Konner thinks she may have invented the term “front hustle.”_

_Lena Dunham added in “back hustle,” but it’s not as good._