You Don’t Need To Understand Software, Just Learn The Art Of Openness

For the founders of the enormously popular email newsletter theSkimm, humility was the key to succeeding at something new.

You Don’t Need To Understand Software, Just Learn The Art Of Openness
[Image: Flickr user JayD Photography]

When Danielle Weisberg and Carly Zakin started news-curating startup theSkimm back in 2012, these wide-eyed young news junkies had the odds stacked against them. They had no tech experience, no business savvy, and–perhaps most dubious of all–they were roommates.


And yet, at barely a year old, theSkimm raised $1.1 million with major contributions from the firm Homebrew and Fast Company‘s own Most Creative People designee Troy Carter last November. Now running a steady business boasting an email open rate just shy of 50%–on average for media and publishing, the rate is 16.4%–Zakin and Weisberg at 27 years old are at the helm of an exponentially growing venture, no longer just a pet project.

In January of this year, they moved headquarters from their small New York apartment into an office space with a full team in tow. And the news summaries, which were initially viewed as female-oriented, now include a 30% male readership. We asked the founders to give us some perspective on their earlier days.

Validation–By Accident

What’s incredible about theSkimm is not its technology–after all it’s just an email newsletter–but how they verified their concept before writing a single line in English or in HTML. Rather than keep their idea secret, as many entrepreneurs are wont to do, they naively asked the advice of everyone they respected in the media industry. Here’s what happened next.

For the uninitiated, theSkimm is a -style email newsletter that gives you the rundown on the day’s top news stories–mainstream, general-interest digests about situations like the ouster of the Ukrainian president. (Think The Week, but in daily email form.)

“Carly and I had a big challenge in not only that we were first time entrepreneurs, but [we lacked] a traditional tech or business background,” says Weisburg. But they did know the media business; prior to founding theSkimm, Weisberg and Zakin were producers at NBC News who met while studying abroad in Rome in college. While working in media, they saw a hole in the news market as friends and coworkers would often complain that there was not enough time to know and understand everything that was happening in the news.


So with no formal training and a looming idea, the pair decided to do the one thing they knew best: They networked. Unknowingly, they were validating their idea, as engineering types like to say. They began talking to people about media business models, asking questions about “what were innovative media businesses that were coming up, and looking at how they were developing and their growth,” Weisberg says.

“We really took a meeting with literally anyone who would talk to us,” Zakin says. The group decided early on that they would work with people within various companies to get a deeper understanding of what allows any company to grow and what makes them curdle. They tapped anyone they could, from lawyers to a real estate agents, feeling like they could learn something from anyone who had built a business.

Finding Partners

After attending an ironically titled SkillShare class, “How to Find Your Business Partner,” they met Alex Taub, former biz dev guy for Aviary and now a founder at SocialRank. He agreed to meet Zakin and Weisberg afterwards for coffee, which was the beginning of a pivotal friendship and more importantly, the beginning of their digital baby, theSkimm. Taub told them: “The only way that you’ll ever fail is by not trying.”

How Lack Of Experience Was A Blessing

Taking up Taub’s advice, Zakin and Weisberg created the newsletter themselves, working feverishly through the night to get it delivered to readers’ inboxes every morning. The newsletter aggregated the news in a cohesive, succinct, and friendly manner that appealed to a wide variety of people. But once the newsletter was a functioning entity, theSkimm was in dire need of external capital.

“Naivete was a blessing in certain ways,” Weisberg says. “Fundraising is a really challenging, scary thing, and I think if we knew how challenging it would be, I don’t know if we would have pursued this so aggressively.”


Zakin says that their lack of knowledge helped them power through. There wasn’t enough time or energy to be wasted on anxiety over whether or not the project would succeed, “because we really didn’t know what was to come,” she says.

Everyone Makes Mistakes

“Every day we pinch ourselves that this is really coming true,” Zakin says. “We have worked so hard, we knock on wood every day because we are very superstitious but I think we are two people that came from media that get how to pitch things for press.” They have never spent a dime on PR or marketing, but have received their fair share of media attention, attributing a lot of their “organic growth” as they call it, to word of mouth.

A recent post on their blog opened by saying “People make mistakes. New entrepreneurs make mistakes all f’ing day long. We’ve made a LOT…” They went on to explain four scenarios in which they have screwed up, including an intern they totally forgot to take advantage of and the time they forgot to show up for an important meeting with a successful cofounder of a big brand. After summarizing the mistakes made in theSkimm format, they outline lessons learned.

In it, Zakin and Weisberg candidly admit that they have been wrong, especially in the situation where they aimed too high financially, which abruptly ended negotiations afterward. Consequently, theSkimm lost out on potential capital and a future mentor. Yet, they also validly point out that mentors should take time to use scenarios like that as a learning tool, rather than to destroy morale.

When the entrepreneurs forgot to schedule and attend an important meeting with a top-tier cofounder, Zakin and Weisberg avoided dwelling on the incident. After writing two apology letters and sending flowers, this specific cofounder was relentless in being unforgiving. The lesson Zakin and Weisberg instill is to be mindful not to waste anyone’s time.


In addition, a pivotal takeaway Zakin and Weisberg learned was after vacillating too much with a potential investor. Because of the long wait time, the women lost out on a golden opportunity with the investor. They discovered that you should always be determined to go after what you want. A window of opportunity is not always open, therefore you need to take advantage of every chance you get, while you have it.

Zakin and Weisberg explain one more occasion where they forgot to fully utilize an employee. The lesson they learned was to identify particular areas where assistance is needed to maximize the company and your employee’s potential. By merely having an additional, but untapped employee for the sake of having “help” is a waste of time and energy on both ends.

Zakin thinks the blog post is an example of showing that “they are not too big for their britches.”

“People make mistakes, we are learning,” Zakin says. “Anytime we talk to a big company, we say that we’re figuring out how we do things. And that it works sometimes and sometimes it doesn’t. But it is really important for us from a branding perspective to be very honest.”

Learning From Those Mistakes

One of the key lessons Weisberg and Zakin have learned from is “knowing the fine line between not asking enough and asking way too much.” Weisberg goes on to say that “if you’re not going to ask for what your business needs, you’re not just going to get it. That was something that seems intuitive but actually putting it into practice was something learned.” This came in handy when they were putting together the company’s budget, negotiating, and finding backing.


“We don’t think of things in terms of boundaries,” Weisberg says. And as the company flourishes the cofounders try and make their vision become a reality under this billboarded idea. “It’s our first time doing this, so we’re going to think big,” she says.