Interview with Jennifer McFadden, Associate Director of Entrepreneurship at SOM


On Tuesday, April 14th, I sat down with Jennifer McFadden, Assistant Director of Entrepreneurship at the School of Management, to talk about her career, inside and outside of the classroom.

How has your career arc—with its focus on women, media and tech—led to Skillcrush and your role at SOM?

Actually, it all started at Yale. While I was a student, I helped launch the Yale Entrepreneurial Institute (YEI) with Jim Boyle, Rich Madonna and a handful of students from Yale College who were running YES, including Brad Hargreaves, Sean Mehra, and Jeff Reitman. I worked part-time at YEI during my second semester as an SOM student, and then helped run the summer program during that first year. It was 2007.

The summer program was structured slightly differently at that point. We had 50 speakers visit during the program, each spending at least half a day with the students. Out of those 50 speakers, maybe 5-7 were women. There was only one female student, Emily Yudofsky, out of the 15 summer fellows who made up that inaugural class. Throughout that first summer, she and I were often the only women in the room. It was pretty glaring and it stuck with me.

After graduating from SOM in 2008, I then went to work at the New York Times as a Product Marketing Manager. I spent the next 6 years working on innovation in the news space both as a consultant and as a researcher and Adjunct Professor at the Tow Knight Center for Entrepreneurial Journalism at the City University of New York. During that period, I also spent some time trying to build up my technical skills via online coursework.

In the Fall of 2011, I spent some time researching the online education space. I had taken a few classes and was interested in learning more about the space, particularly given my involvement with CUNY. So I started doing research and thought there was room to create an online accelerator similar to what we had done with YEI, but with a twist. I began putting together a plan (yes, a plan) to create a site that was focused on increasing the number of women in tech and entrepreneurship via a suite of classes.

Fast forward to January 2012, when I had a fortuitous conversation with Adda Birnir, MC ’07, who was one of my students at CUNY.

What came out of that meeting with Adda?

By that time, I had spent a considerable amount of time researching my idea and talking to potential users. But I lacked one thing—the technical skills to execute.

As part of her coursework at CUNY, Adda was required to work on a venture over the course of the semester. She had entered the program with a different product completely, a publishing platform that would allow news organizations to easily create mobile applications. After conducting customer interviews, she realized that it was time to pivot. We were sitting at Dean & DeLuca brainstorming different ideas that she could work on over the course of the semester. Prior to starting the CUNY program, Adda had launched and successfully run a client services company with her partner, Kate McGee, where they build web and mobile applications for clients in the news space. So she had the technical skills necessary to build products and had, in fact, taught herself how to code usng online tools. As a side project, she had launched Digital Divas, a simple website that allowed people to purchase  “playing cards” with really fun technical terms like “What’s HTML?” The cards were fun, well designed, and explained technical terms in a clear, simple, irreverent way.

When I saw this, I began to share what I had found through my research. After a long conversation, we decided to join forces. Kate joined as the third co-founder.

So what is Skillcrush?

Skillcrush is an interactive online learning community for creatives, thinkers, and makers. Our goal is to demystify technology and create an opportunity for women (and men) to learn how to code in a fun, collaborative environment.

The initial goal was to be the first place that women go online when they want to learn new digital skills. Many of the existing sites that were focused on teaching technical skills were either masculine in tone, look and feel, or were less than accessible to a beginner student due to the presumed level of knowledge that was required before even beginning a class.  Many students were overwhelmed by the language barriers inherent in learning new technical skills and were often confused about where they should even start or why they should learn technology A vs. technology B.

We were all really passionate, in particular, about increasing the number of women with technical skills. We had all come from the news space where there had been a lot of layoffs, and had seen that the people with deepest technical skills were the ones who were most likely to keep their jobs in the face of these layoffs. The goal was to create something that was aimed at women very explicitly from the beginning, where women would feel excited to learn new digital skills.

After a lot of early conversations around tone and vibe, we decided to target women who were 25-35 and were working in tech adjacent roles in organizations like advertising agencies, news sites, and startups. We wanted to reach the women who were touched by technology but weren’t necessarily doing the actual coding of a site on a daily basis.

In April 2012, we launched a stand-alone email newsletter that highlighted a single technical term every day, with a fun and funny tone. We launched our first paid product later in December 2012, a course on HTML and CSS.

Was the initial funding hard to find, for a website aimed and geared at women?

We were not interested in pursuing the traditional VC route. We certainly talked to some VC’s, and that question—“why are you focusing only on women”—definitely came up. But we were not willing to move away from that. It was and is core to the mission. We were also very on the fence about raising VC money to begin with, as we thought that we could bootstrap the venture to profitability. That being said, we did decide join Brooklyn Beta Summer Camp, a new accelerator that was launched by the founders at Fictive Kin, and received 25K from Brooklyn Beta, as well as another 50K from Collaborative Fund.

How much does the current website reflect how it was when you were still involved in the day-to-day running of Skillcrush? 

We started our first classes in December and had 10K in sales that first month. Shortly after, I stepped out of a full-time role. It was not an easy decision, but it was the only decision that I could make at the time. I had spent the majority of 2012 travelling 3 hours each way in and out of the city, couch surfing and working on the venture. I had made a commitment to my co-founders that I would either move to NYC by January 2013 or would step aside. Given that we decided not to raise venture, there was not enough money to support a salary that could justify a move to the city—particularly given the fact that it would mean uprooting my husband and two kids. So I stepped aside from the day-to-day operations and took on an advisory role.

When we launched our paid product (classes) we had 7,000 people on our email list. We did a bunch of outreach that first summer. Adda and I presented at New York Tech Meetup. We met with a number of amazing women who are part of the tech scene in New York. Our initial blog posts and daily newsletter provided easy-to-digest, fun technical terms that included “Cocktail Party Facts” that could be shared with your friends and that provided an easy way for people to show off their growing technical knowledge. By making technical terms accessible to a broad audience early on, we were able to get lots of people to sign up. People got great utility out of having one simple thing to talk about with their friends.

A lot has chanced since that first year! We now have close to 45,000 people on our mailing list. The design has evolved and become much more sophisticated. There is a ton more content and several new courses have been launched. The pricing model and packaging of the courses has evolved. There are many more interactive elements embedded in the courses. We have a number of fun cheat sheets that users can download to make learning more accessible and host webinars around different topics, including web design, career opportunities in the digital space, and more technical things. And, most critically, the community has grown to be this amazing resource for students. We also went from 3 co-founders to 11 full-time and part-time employees. I couldn’t be more proud of what Adda, Emily (our developer), Leslie (our head of sales and marketing), and the rest of the Skillcrush team has been able to accomplish!

Two things have remained the same: the mission and the overall tone of the site. Adda was in a comedy troupe while at Yale and that definitely comes through in the cheeky way in which the content is presented. The ability to make learning new technical skills both fun and accessible is HARD. And this is really where Adda and the team excel.

How have you seen the environment for women in tech change over the past few years?

There has been a lot of conversation about women in tech over the past three years, and I think we’ve been a part of that. This is such a big issue and many of the major employers in the sector are actively working on initiatives to spur change. We have been lucky because these changes have enabled us to reach a new audience.

However, there is still a long way to go. Looking at the courses at Yale and SOM, you still see some fairly significant gender imbalance. This is particularly the case at SOM, where the percentage of women to men is already skewed.

That being said, we are working on a bunch of initiatives to bring more women into tech and entrepreneurship. Kyle Jensen, the Director of Entrepreneurial Programs, is a total feminist and he spends a great deal of time working to generate interest among the female students at SOM, as well as on the undergraduate level—particularly in the Computer Science department. I have spent a great deal of time reaching out and speaking to female students in an effort to bring more women into our entrepreneurship and technology courses. YEI is also working to reach more women to get them involved in the programs that they manage. It is a goal for all of us to engage more women in entrepreneurship.

What would you say is the defining trait of a Yale entrepreneur?

Across Yale, many founders are focusing on launching ventures that will not just have a potential positive impact on their personal finances, but will also have the maximum impact on people’s lives. I think that that is really special and is one thing that makes us unique. We will likely never match Stanford or MIT in terms of number of new purely technical ventures that launch each year—we just don’t have as many students. But we can win at creating ventures where there is a focus on building bridges between different disciplines or where there is a societal benefit (of course, not to the exclusion of profits!). We can win at creative problem solving, collaboration, teamwork, and just being really thoughtful about impact that we are having on the world.

What advice would you give to students interested in pursuing entrepreneurship?

Go find the thing that you’re super passionate about. I am most interested in the consumer web. I’m also super passionate about online education, the news space, and the process of building brands and communities online. Don’t be afraid to jump in and do a deep dive on a particular subject or industry. Follow the rabbit holes that you find on the web. Insatiable curiosity can sometimes be a great way to find that next new idea to work on.

There’s a perception that Yale is behind other schools in how it fosters an entrepreneurship community. Is that true?

That may have been the case in 2005, but I think that a lot has changed over the past 10 years. And, the University continues to dedicate more resources to entrepreneurship and engineering, that will certainly move the needle even more in the years to come. Since 2007, YEI, CBIT and CEID all launched. Our program launched. The university is very interested in providing the resources to both faculty and students to continue to grow these programs. I can tell you that it is a much different place than when I was here in 2008, which is fantastic.

I think there is also a rising interest in general around entrepreneurship. And it is not just startups. Everyone has to be somewhat more entrepreneurial now—you’re not going to find yourself in a job for ten or fifteen years like our parents did. The whole nature of work is changing. Technology is impacting so many different industries. So Yale’s continued focus on these areas will help not only those students who are interested in launching new ventures, but all students who will be part of the modern workforce.

Do you see a way for undergraduate students to benefit or be involved with entrepreneurship?

Absolutely. We introduced 8 new classes at SOM this year, the majority of which are open not only to SOM students, but also to undergrads and students from other graduate schools. These new courses explore topics such as lean startup, venture capital, coding, and technology management.  One of the most popular new classes is MGT656: Managing Software Development and Teams, where students are taught front end web development (HTML/CSS, Javascript) and are exposed to some back-end technologies, as well as the tools that many developers use to manage agile projects.

I would encourage every single person at Yale to attain some base level understanding of how to code, even if it’s just front-end web development. Technology is touching every single industry and if you don’t understand the basics, you’re going be left behind. Period. Whether that means venturing up to SOM to take MGT656, taking the new CS50 class that will be introduced in the Fall, or taking a course with HackYale or Float Yale. Just do it. That’s why you’re here—to learn something new. Not only will you have the skills to kill it when you enter the workforce, but you will also have the ability to sit down and build something on your own. And that is an extraordinarily powerful skill to have.

Getting undergrads to interact with students from all of the graduate programs is a big goal of ours. You end up with this amazing mix of people who are all incredibly smart, bringing different skills to the table. And that’s closer to what you’ll experience when you’re out in the real world. We look forward to creating more opportunities for this cross-pollination of people and ideas in our second year!

Anna Lipin

Anna is a Freshman in Ezra Stiles College. She's a New York Ciry native, and has spent her first year at Yale exploring New Haven, writing entirely too much for Directed Studies and the Yale Herald. She's not sure what her major is yet, but engineering is definitely out.

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