How 2 roommates got shot down by hundreds of startup investors and racked up credit card debt — but built a newsletter empire anyway

The Skimm founders CEO Carly Zakin Danielle Weisberg

Carly Zakin and Danielle Weisberg cofounded theSkimm, an email newsletter sent to 5 million subscribers every day at 6 a.m.

TheSkimm picks the most important new stories of the day and tells readers what they need to know in a conversational tone that’s full of millennial lingo. Loyal subscribers include Oprah and Hillary Clinton’s former campaign manager, John Podesta.

The business was far from easy to build. Zakin and Weisberg quit jobs at NBC only to get turned down by “hundreds” of venture capitalists, who saw no value in creating an email company. Together, the pair went into credit-card debt, which they say they finally paid off just last year.

We sat down with Zakin and Weisberg to talk about their battle stories, how they eventually got investors on board, and how theSkimm took off, all on this episode of “Success! How I Did It,” a Business Insider podcast hosted US editor in chief Alyson Shontell that explores the career paths of today’s most accomplished and inspiring people.

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The following transcript of the interview has been edited for clarity and length.

Alyson Shontell: Carly Zakin and Danielle Weisberg launched theSkimm, a morning email newsletter, in July 2012. Business Insider wrote the first article about it back then, and today the newsletter has over 5 million subscribers, including Oprah and Hillary Clinton’s campaign manager, John Podesta, as we learned last year after WikiLeaks’ publication of Clinton’s hacked emails.

To start, I wanted to go back to 2012 and even a little before that. You met as students studying abroad in Rome. You both worked at NBC and then quit to start a newsletter. Tell me about that process.

Danielle Weisberg: Thanks for having us — it’s exciting to be back here. You wrote the first article about us, so it’s a lot of déjà vu. Carly and I met studying abroad in Italy. We had a great time and didn’t think about what we were going to do later on. We had really similar backgrounds. We’re both storytellers, we love journalism, we love news. It was our passion.

We started interning for NBC news as soon as we could and we grew up in that world. NBC was our universe — we always wanted to work there. We worked our way up the ladder from intern to full time, and then we were producers, and between the two of us, we worked in pretty much every news division they had.

We were roommates in an apartment in New York, and we would come home to each other every day and talk about two things.

One, as clichéd as it sounds, we were very much having a quarter-life crisis. Being 25 and 26 and loving what we were doing but wanting to move up and not wanting to hear that you have to get in line and wait 10 years for a position that might open. That was really frustrating as two people who loved what they were doing and wanted to do more of it.

The second thing was our friends who were smart and had great jobs and knew everything about their industries would come home and ask us what was going on in the world. That was our job. That’s what we did for a living. We read all day long, and we reported on the news and our friends didn’t do that. They had other things to fill their time with. It wasn’t a matter of intelligence, and it wasn’t a matter of interest; that’s not what they were being paid to do.

So we wanted to create a news source that actually brought this audience that was exemplified by our friends, female millennials, who are smart and leading in so many ways, but didn’t have a news source that they loved, and we knew that we could create that.

So the newsletter was never the be-all and end-all. It was the beginning to a very big empire that we knew we could create in harnessing the power of female millennials, and being their go-to source for information that really matters and can drive the big decisions that they’re making in their lives.

Shontell: When you did this in 2012, it felt like newsletters had been there, done that. Daily Candy had been acquired for a ton of money; Thrillist, a popular guy newsletter, had been around for a few years. What made you think that newsletters were where it’s at?

oprah TheSkimmCarly Zakin: It wasn’t newsletters that we thought about; it was email. There was a beauty in how naïve we were. We didn’t have a tech background. We didn’t have a business background. It helped us not overthink things. We just thought — what’s the best way to get in front of our friends? We went back and forth. Should we text them?

We were like,”No, the very first thing you do in the morning is you turn off your alarm, it’s on your phone, you grab your phone, and you literally open your email to be like, Did someone die? Am I getting fired? or Is my boss yelling at me? and What did my friends send me? And we knew we had to be in that moment. One of our friends worked in finance, and she left for the office at 5:50 in the morning every morning. So we were like, we gotta get it out to her on that commute. So we chose 6 a.m.

A lot of the hallmarks of what theSkimm is about, that one-eye-open routine, we call it. Being in that moment and being there at 6 a.m. happened because we were just thinking about our friends’ daily experiences. We weren’t overthinking it. We weren’t like, let’s A/B test this. We didn’t even know what A/B testing was.

When we started theSkimm, we started meeting with investors, industry experts, and everyone was like, email is dead — this is a really bad idea. But they would email that to us.

And we would just laugh at it because we’re like, you’re saying email is dead, but you’re emailing that to us. And we both still read email every single morning. Obviously, since then, we’ve seen a resurgence of email newsletters, and a lot of that, we’ve been told, is credited to what we’ve done.

But for us, I think we’ve talked so much about all the things we didn’t know. We haven’t spent a lot of time talking about what we did know. And what we did know is that we knew how to talk to this audience, who they were, and we also knew that we were not starting an email newsletter company. We knew email was a marketing tool.

‘We made a list of all of the investors, angels, and seed funds, and we would turn anyone who said ‘no’ red — then the whole list was completely red’

Danielle Weisberg and Carly Zakin, The Skimm

Shontell: Talk about quitting your jobs at NBC. Because you did that and bootstrapped for a bit, right? You said just now there wasn’t a ton of investor interest, you were first-time founders with no technical background. That’s everything that makes a venture capitalist run away.

Zakin: Yeah, everything that would make you not think “This is a good idea.”

Weisberg: It’s funny when people ask that, because they’re like, “Oh, you decided to bootstrap it.” And we’re like, “We didn’t ‘decide.'”

Zakin: “Bootstrap” is such a generous term because it makes it seem like we had money to bootstrap. We worked in media in mid-level jobs. We had just over $4,000 between the two of us. We lived in a rent-stabilized apartment downtown and agreed to go into credit card-debt together.

‘Bootstrap’ is a generous term. It seems like we had money to bootstrap. We worked in media in mid-level jobs. We had just over $4,000 between the two of us. We lived in a rent-stabilized apartment and together agreed to go into credit-card debt.

We just both paid off our credit-card debt in the last year or so, and it was a huge sacrifice, that even looking back now I’m like, “I can’t believe I made those choices.” Because it sounds so unlike myself, it sounds so unlike Danielle.

Weisberg: The other part, too, is people hear our story now and they think about it as two women decide to quit their jobs and start their own company. Quitting our jobs, it was the scariest day of our life. That was not easy. And those first months … every point of this company has been hard. That’s the case anytime you’re building something. But those first months, we only got through it because we didn’t have a backup plan. We didn’t have a safety net financially or emotionally. This was everything.

That was our saving grace, because there was no plan B. There was only, “We’re on our couch, we can’t afford cable, we’ve maxed out our credit cards, our parents are giving us hugs.” But that was the support. Carly’s parents made us a lot of dinner. That was it. There was nowhere else to go.

So when everyone was saying no, and we made a list of all of the people — all of the investors, angels, seed funds — and we would turn anyone who said “no” red. And then the whole list, which was a lot of names, was completely red. I remember a day in our kitchen, we had just gotten off a pitch that again ended with “Thanks so much, not interested,” and we just had to make a decision. Are we going to go for this or are we going to go try to get jobs freelancing for the 2012 election?

It wasn’t really even a decision — it was just a half-second to reevaluate where we were, change our pitch a bit, and that was it. That was the closest we’ve ever come to a crisis of confidence in this company. If you let those things get to you early on, then you don’t know what else is coming. There are going to be a lot more challenges.

Shontell: Had you launched the first newsletter at that point? Why quit your job if you’re launching a newsletter to begin with? You can do that while keeping your 9-to-5.

Zakin: Well, two things. One is we had both weird schedules. I worked daytime and Danielle worked nights. So we couldn’t do that. One of us would have had to change our schedule.

Second, we took a Skillshare class while we were employed, and it was ironic because the class we signed up for was “How to Find Your Business Partner” and that was the only thing we knew how to do. But the person who taught it, Alex Taub [an entrepreneur and investor], became a mentor to us, and he was one of the first people to tell us, “If you’re going to start something, you need to be all in. How can you ask anyone to even think about giving you money if you have not made sacrifices to prioritize the effort yourself?'”

When people come to us and ask for advice on starting a business and are like, “I can’t afford to quit,” I still have mixed feelings about what to tell them. Who am I to tell someone what financial decisions they should make? But for us, we were asking people to believe in us, and we had to show that we believed in us so much that we were willing to take a huge risk ourselves, quit our jobs, have no financial security, and give it a shot.

So we took that approach. That’s not for everybody. I don’t know if it could have worked out differently. But there was actually a third reason.

A lot of people ask us, “Why didn’t you just bring this to NBC? Why didn’t you get this in front of Steve Burke?” There is no way that NBC would have allowed two associate producers to not only run the editorial but to run the business side of what we were doing. There was just no way. We knew that in our gut.

Weisberg: That would have ruined the company in a lot of ways in starting off, because the authenticity of having this idea came so much from our friends, and it was developed around routines of this target audience. It couldn’t then have had a successful launch if it had then been led by people who had been doing this for 30 years and thought about the same strategy that had worked for all of these other companies and startups. That’s not what we’re building.

4 days after launch, theSkimm got a shout-out from Hoda Kotb on the ‘Today’ show, and it changed everything

Jeff Zucker Hoda Kotb Kathie Lee Natalie Morales

Shontell: Tell me about launching your first Skimm. Who did you get to subscribe?

Zakin: We didn’t add anyone to the list. We sent an email to everyone in our address book. When we say everyone in our address book, at that point you could download your Facebook friends’ email addresses, so we literally took every email address that we had in our possession.

Meaning like, my grandma is on chain letters, chain mail that she forwards. We took those people. So we had, between the two of us, 5,500 names. We sent an email and were like, “Hey, we quit our jobs and we’re starting this. Can you please sign up?”

That first day, almost 800 people signed up. But we didn’t add anyone to the list. I think the first email had our closest friends and family on it, and it was not a lot of people on it.

Shontell: So 800 pity subscribers?

Zakin: Eight hundred people who were like, “I’ll take a look.”

Weisberg: The first went out to our family and friends. And then there were two press articles that came out on the first day, and Business Insider was the first to cover us. Thank you! And we got the traction from that.

It all happened very quickly, because we had also emailed every news anchor out there, truly. We didn’t know most of them, but we were like, “We’re former NBC-ers, thought you would love this, thought you would appreciate the need that we’re solving.” Most of them didn’t respond. Hoda Kotb responded, and she said, “I’ll check it out!” We did not know her. We followed up with her two more times, but got no response. Day four of us in business, she said we were one of her favorite things — on air — and it totally changed our life.

So we went from, at that point, let’s say under 1,000 users to thousands. All of a sudden, we had geographic diversity. And all of a sudden, we had huge pockets of the country paying attention to what we were doing.

Shontell: Wow. What does a Hoda bump do to your newsletter subscribers?

Zakin: It crashed our site. It crashed our email inbox. We got a few thousand people from it. It was so funny, we were actually back visiting our old bosses at 30 Rock. We were in Starbucks and I tried to load my email and it wouldn’t load. Then someone wrote on our Facebook wall: “Just saw you on the ‘Today’ show.” And we thought we were caught walking on the plaza in the background, and we were like, “Oh, how embarrassing — what were we doing?” Then someone had posted what she had done. So it was life-changing.

Shontell: How did you create the voice for theSkimm? It’s really something that resonates, and sometimes people will say, “Are they dumbing it down too much?” Or “Do women need their own news source?” But the voice did set you apart, so how did you create theSkimm’s tone?

Weisberg: It was the easiest part of building this company. The voice comes from how people speak and how we talk to our friends. We spent a lot of time thinking about, “How do we launch this? What are we doing? What’s the ultimate vision?”

We literally sat down in separate parts of our apartment and went to write what would become the Daily Skimm. We came back together, and we hadn’t really talked about what the voice would sound like, aside from knowing that it would be how we actually speak to our friends. And we came up with the exact same voice. Since then, we have put a lot of time into explaining the voice to our team and putting a brand guidebook together, and talking about how well we know theSkimm girl, our character inside and out.

Anyone on our team can tell you what her favorite drink is, what she’s going to order at Sunday brunch, and it’s a living, breathing document — what she likes and where she is in life changes. That is something that everyone in our company knows because they’re all telling the story of theSkimm and this character is who the brand is.

So when we put the voice together, it’s not for everyone. I think that when we hear criticism like that, that the voice is condescending, we hear it all the time, it’s nothing new. I don’t think that there should be a one-size-fits-all approach to news. Just because someone doesn’t like it, that doesn’t mean it’s for them.

Shontell: You have coined terms like Mitt Romney was “Mittens” and Hillary Clinton is “Hillz.” Business Insider has found the same, that there’s something to a conversational nature. That doesn’t mean you’re dumbing it down; it means you’re explaining it so that everyone, the really smart people — because you’ve got incredibly smart people like John Podesta on your email list — and the people who aren’t heavy in politics can understand it.

Weisberg: I think it also goes back to what we were creating, which is it’s not something for experts. It’s not something for just people who love politics or who love business. That was a huge thing t
Source: http://www.thisisinsider.com/how-carly-zakin-danielle-weisberg-founded-theskimm-podcast-interview-2017-4

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