Season 01, Episode 07

S.01 / E.07

Jennifer McFadden

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Over the last nine years, Jennifer McFadden has played an integral part in developing and fostering an entrepreneurial culture across Yale University.

On the show, we dive into the net of who is an entrepreneur and who has the opportunity to become one. Jennifer explains why she feels that we all have a responsibility to think wisely about our organizations, why we're building them, who we include, how we reward them, and why she’s optimistic that these changes are coming. We also zoom in on the role of design and design research and how Jennifer advises that new founders approach it when preparing to launch their new business.

Jennifer serves as an advisor to the Yale Landscape Lab on Yale’s West Campus, which supports synergistic projects in health science, entrepreneurship, and more, and connects over 20 professional schools, departments, organizations, and student groups across Yale. She also launched the Women Entrepreneurs at Yale (WE @Yale) Initiative and is a co-founder and advisor at Skillcrush, an online education company that focuses on teaching women technical skills. Prior to joining Yale SOM, Jennifer worked in media and tech. She was an adjunct professor at the Tow-Knight Center for Entrepreneurial Journalism at the City University of New York, where she also conducted research at the intersection of media, tech, and entrepreneurship and worked with start-ups in the news space.

“It's equally as important to pull people through the process of just exploring what it's like to find a problem, to find people who have that problem, to talk to them, to figure out how you can solve that problem and to put something out into the world.”
Jennifer McFadden : Associate Director of Entrepreneurship & Lecturer in the Practice of Management / Yale University

References & Socials


Wilma Lam,


Hi everyone, and welcome to this episode of Optimistic Design, a speaker series where we take a practical positive look at the future of design, ethical innovation, and technology. I'm your host, Wilma Lam, Director of Strategy here at Substantial.

Today, I'm excited to be speaking with Jennifer McFadden, Associate Director of entrepreneurial programs and lecturer at the Yale School of Management.

Over the last decade, she has played an integral part in developing and fostering entrepreneurial culture, both at Yale and in the broader industry.

She has mentored and advised founders across a wide range of experiences, industries, and stages of development along the way. Jen is also co-founder of Skillcrush, an online education company she founded in 2012, which focuses on teaching women technical skills.

Hi, Jen! Thank you for joining me today.

Jennifer McFadden

Hi, Wilma! I'm so glad to be here.

Wilma Lam,


We're so excited to have you with us. Well, I always enjoy talking to you just personally, generally.

Jennifer McFadden

You're still one of my favorite former students, Wilma.

Wilma Lam,


Awesome. Thank you.

Jennifer McFadden

You carry that mantle on.

Wilma Lam,


I appreciate that. So, you co-founded Skillcrush in 2012, and you are now teaching and mentoring upcoming entrepreneurs in your current role at Yale. I love to just hear a little bit more about what drew you to entrepreneurship.

Jennifer McFadden

Sure. I mean, I think it's a little bit in my blood. My dad was an engineer. He worked at NASA when he was at Virginia Tech, spent a lot of his early career around technology. He worked at IBM for about ten years and then went off and founded his own company when I was still pretty young.

He ran that company for about 30 years. He did large-scale projects with manufacturers across New England, helping them automate. So, I grew up both around a lot of technology, probably more so than the average individual, and then also around somebody who was going through the daily ins and outs and struggles and positive sides of running their own company.

And so, I think it just was part of who I am and what I grew up with. I also think as the daughter of an engineer, you have instilled in you at a very early age this kind of idea of questioning everything. Why is it that way? Why should it be that way? Why shouldn't it be some way else? How can it be improved?

Those are kind of part of that mentality. I think that a lot of what you see in entrepreneurs is curious nature and questioning why things are there.

Wilma Lam,


And so, when you became a founder, like starting Skillcrush, who are the most kind of influential mentors and advisors for you?

Jennifer McFadden

Yeah. I mean, this is such a funny thing. I would say I had everything from the kind of standard former faculty members. I had Barry Nalebuff there, who I would go and pester with questions post-graduation.

I'd reach out to two colleagues that I'd worked within the news industry. I'd worked at the New York Times and then was at the time working for Jeff Jarvis, who runs the digital program over at the City University of New York's Graduate School of Journalism.

Jeremy Kaplan is there as well. Both of them were former news folks who were really interested in the application of entrepreneurship to the news industry, which, you know, this is back in 2009 to 2014.

When I worked with them, clearly, there was a lot going on, as there was a transition more to the digital side of the news industry and margins were being hammered, and it's really wonderful to have kind of both of them in my corner.

My co-founder herself, Adda, who I still reach out to all the time whenever I have ideas that I want to bounce off of her or questions that I have with former students.

And then, we went through formal accelerator programs, things like Brooklyn beta, which I think we were the only cohort to go through it. It was called Summer Camp. It was a one-and-done type thing, but we did meet a lot of incredible people through that.

So, like, Liz Danzico was someone who we chatted with early on. And just them being part of the ecosystem in New York in that early period of time when everybody was really getting up to speed.

You have people like Brad Hargreaves and the crew that was starting general assembly at the time where Charlie O'Donnell was running a lot of events and bringing people together. As a good citizen for those sorts of ecosystems, you try to give as much as you can get. And so, my perspective on all that is, regardless of the industry in which someone operates, they always have something to offer, and you always have a problem that you're facing that needs to be solved.

And so, being kind to people and being available when other people reach out to you, I think, allows you to find people who are both. Well, I reach out to you occasionally with questions or have you come in to speak in my class. I've former students now who are there as mentors and advisors to people who are 20 years my senior. So, wide net. Half wide net is my advice on that.

Wilma Lam,


Yeah. Over time from when you founded Skillcrush to today, you've definitely shifted in this direction of being more of a mentor, an advisor to a lot of new founders. So, how do you think about your role today when you're working with founders?

Jennifer McFadden

Yeah. I mean, I think the biggest thing that you're trying to do is to help founders see what they can't see on their own. In my role now, both in the work that I do within Yale and outside of Yale, for the students that I work with, I work with everything from students who are founding semiconductor materials, companies to autonomous robots to pure-play non-profits, and there's no way that any single person can have a deep understanding of every industry in which the standards are operating.

And honestly, even if you're in the exact same industry, so much of the context is different from startup to startup, so you're bringing your own personal perspective to it, you're bringing your own set of resources. So, whether that's a background and understanding that someone may not have, whether that's capital and access to capital or access to people who have capital, there's just so much that is different from startup to startup.

And then, there are things that are commonalities that you can see. I would say the biggest thing is to really listen to the founders to hear what they have to say. I try to approach it as, "What problem are you facing right now? Why do you think you're facing this problem? How do you approach solving that particular problem?

What do you think your options are, and listening to that, so that you really understand the context in which they're operating with the understanding that there's absolutely no way that you will ever know as much as that individual knows at that particular point in time about their business and what's going on?

I think where you see some issues with mentorship is where sometimes when mentors come in with what they perceive to be an asymmetric set of experiences, and they might view themselves more as the expert in a particular field, and they may be an incredible expert. But that level of expertise does not give you the right or the responsibility to tell that entrepreneur what to do.

I think what you should be doing is exploring with them a set of possibilities. And then from that saying, "Okay, for that particular problem, here's what I've seen in this particular case." I've now worked with hundreds and hundreds of entrepreneurs. So, in this instance, I saw this person had the same problem. They went down this particular way down that path, they made this particular choice, and this was the outcome. Here were the circumstances as I saw them in which they were operating. These pays may be different to you, etc.

Here's another example of somebody who kind of faced the same decision point. Here's a couple of articles that you can read about other people who face these issues. And here's a couple of people that you might want to talk to. So, like a good for instance on this is, I had a student this semester, who was wrestling with somebody who was coming in who had deep experience in the field, who had already sold a company in the space, who was looking to come on as an advisor, but also kind of, I would say an advisor plus, and so was looking for non-standard equity grant for the role that the person was trying to play in this business.

The student was proposing what I would say was an outsized amount of equity at the start. And so, you sit there, and you have a conversation about what are the consequences if you make that choice? What are the expectations if you're giving away that much equity relative to the role that the person is playing? How might an investor in the future rejigger your cap table because of it?

There are all these different ways in which you can approach it. I think approaching it with empathy and then with actual examples and materials to read and people to talk to is kind of the best thing you can do. I think entrepreneurs should shy away from any mentor that says you need to do X, Y, or Z because it's not that mentor's choice, ultimately.

Wilma Lam,


Now, that makes a lot of sense and is really helpful. So, tying into what you just shared of the number of founders with which you work, I'm curious, what are the biggest kind of common challenges that you feel new founders face?

Jennifer McFadden

Oh, my gosh. This semester had more founders facing the issue of naming than I've ever had before. I think, as you see, particularly in the DTC (direct to consumer) space, because there's so much available for people who are interested in launching direct-to-consumer brands that so many more brands are launching, and therefore, so many more names are taken. Naming is incredibly difficult for people to do.

Prioritizing your time. You will always have a list of a thousand things that need to get done, and the best entrepreneurs figure out, "All right. What are the things that I need to be doing now? Sequentially, why does that make sense because Action A may lead to Action B? And if you don't do Action A first, you may have missed the opportunity to do Action B correctly."

So, really understanding what those dependencies are and then prioritizing their time based upon it. And then recognizing, "Okay, well, you've spent enough time on that. It is good enough that the 80% rule really is right. You've got enough information to make a decision. Stop spending your time spinning your wheels, trying to come to the perfect answer, because there is no perfect answer when you're trying to get something up and off the ground."

And then, how do you delegate those things that you can't do yourself? So, what's most core to the business that you need to be focusing on that you need to understand that you need to own at the earliest stage?

And if you don't have this set of skills to help you execute on that, how are you going to find them? How are you going to spend your time reasonably trying to find them? And at what point do you need to bring someone else in to help you out? I think it is the biggest thing as well.

Wilma Lam,


Are there any sets of skills that you feel new founders often underestimate the need for when they're first getting started?

Jennifer McFadden

Gosh, so many. I mean, you really are just doing everything. And therefore, you've got this situation because you're doing everything where you have to figure out which things are you going to do at 100%, which things you're going to do at 50% basically.

I think if you are starting a digital company or you're starting a web application or mobile application, something that is more than a digital product is core, and you don't have product development experience. I think that doesn't preclude you from being able to be a good product developer, but you do have to do a little bit more work just to kind of get there.

I would say for you, your background in architecture. Although I wouldn't necessarily say that's a perfect background for our product person, the reality is that you had to figure out how a system of things worked and then design a process that would create an experience for the people who are moving through the space that you were building, and therefore that is very much of a product experience.

I'm working with another former student right now who has a background in real estate. One might say, "Okay, well, you worked for that real estate company that was very much of a kind of experiential consumer-facing real estate, but you don't have any digital product management. And so, how do you think you're going to be able to be the person who's coming up with the best product here?

The reality is that she spent a lot of time creating experiences for those users. And ultimately, that is what you're doing when you're building a web application or a mobile application. You're trying to figure out how this technology is impacting the user. How is it getting them to do whatever we want them to do?

And so, I don't necessarily think that's the case, but I do think that when I have students who don't have those skills, I will point them to some resources that will kind of help them get up to speed.

Wilma Lam,


No, that makes a lot of sense. I mean, I think from what I recall and have experienced, it becomes very much about understanding the skills that you have and then learning how to take that skillset from the problems you used to solve to a new set of problems that you're now engaging, and really understanding where your strengths are, where the gaps are.

Jennifer McFadden

I think if you're looking at it within the context of the majority of the entrepreneurs that I'm working with who aren't necessarily friends who reached out to me to talk to me about their ideas, or former students who are reaching out to me, the majority of them are actually currently students. And so, I will direct them to classes.

If you are at the School of Management and you are planning to launch a web application or software-based application, you should take Kyle's Managing Software Development in Teams. And even though you probably won't be the person who day in and day out is building the backend of a website, you will at least understand the vocabulary to be able to operate. And to be able to manage those people who are with more empathy and understanding than you might otherwise be able to.

Same thing with the databases class that he's teaching. Same thing if someone doesn't have any design background. Go take a class at the art school. There are ways in which you can get enough information so that you can better understand when you are hiring or whether it's a consultant or a full-time employee when you're hiring them and bringing them on what are those realistic expectations that you can set for them and hold them accountable for? And what's unrealistic? How long should something take? How much should it cost?

Without having that understanding, it becomes very difficult, I think, to be able to make those decisions. I think again, that's another place where if you don't necessarily have access to a school that has many classes on many things, you can find those correct mentors who can kind of give you some guidance.

Wilma Lam,


I'm also curious. I mean, having been with the School of Management, and in this kind of advisor/mentor role for the last decade, are there trends in the kinds of problems that founders are trying to solve today versus when you first started in this kind of advisor/mentor role?

Jennifer McFadden

Yeah. I started specifically at the City University of New York's Graduate School of Journalism. So, the majority of the companies that were coming through that were more kind of pure-play news sites.

Looking at the set of people coming through the School of Management over the past seven years, as I said, there's just a much greater set of low code, no code technologies now that allow you to build certain types of ventures more quickly. And therefore, you see students gravitating towards those. You see a lot of students who are interested in launching some sort of DTC brand because they want something that's not out there in the market.

It's, frankly, easier to get something and launched in that space, much more difficult because of that, because there's a greater supply of products coming online every day to kind of breakthrough the noise. But you can spin something up fairly quickly, whether it's a beverage company or whether it's a clothing company with not a huge amount of capital, and test it out in a way that I don't think was possible even five years ago. They were seeing more of a shift to that.

I think I've seen in the past year some students who are trying to tackle some of the big problems. I'm not sure the year of COVID that we saw is much of that, as we probably will going into next year. I think the reason for that is that a lot of those solutions to some of the bigger hairier problems really do come at those intersections of management and the environment or management and the Econ department.

I've seen a couple of students who are trying to deal with income and equality, which I think is one of the largest issues that we have to deal with our non-period right now. I suspect when we're back on campus, and we're all interacting with each other in person, again, you'll see more of that. Because world-class school environment, we do tend to see across Yale, not just within our narrow scope at the School of Management students who are trying to build ventures that have some sort of positive environmental benefit. And I think we will continue to see that.

Our program is still fairly young. We launched in 2014. So, you're starting to see things like wild type, which is a sustainable food company that's come up. We have Seth Goldman, who's there who's done Beyond Meat and is now involved in several plant-based ventures. As you see more of that publicized writ large across the University, we just by that nature, then attract those types of students who are interested in those sorts of ventures.

So, I think things related to climate change, particularly given the focus on that within the Biden administration and the subsequent funding that will come through the federal government because of it, we'll start to see more of that over the next couple of years. Definitely.

Wilma Lam,


A lot of these are really big complex problems. I think in a typical year, you'd be spending a lot of time with these founders engaging in conversation in person on campus. So, I'm curious. Over last year, year and a half, as you are kind of teaching and working with founders remotely, what is changed in your thoughts on teaching and mentorship? And do you approach it differently now that we're in kind of more of a virtual environment?

Jennifer McFadden

I would say there definitely have been positives and negatives. The negative I would definitely say is that lack of just the casual interactions, the water cooler talk, per se. I really do think that that impacts founders in a very specific way.

You went through the program, you know the benefit of being in a cohort of people who are facing the same pain and suffering that you are, whether it's at that particular moment or whether it was a month prior, or whether you're experiencing and sharing it. They just had such fewer opportunities to hear that. You can set up something that's a virtual conversation, but everybody was very much zoomed out by the end of this semester. Really, really zoomed out.

I think you missed out. I think you missed the, you know, I have an office, as you know, that has the floor to ceiling glass. And when people see me in there, they knock on the door. So, they miss knowing when I'm available and not available.

I think one of the things that I did notice this year, and we'll see if this changes when we're back in person again next year, is people seem more hesitant to look around them and make the asks that they should be asking. So, pinging me and asking me if I have 15 minutes, or when I've got somebody who's coming into the classroom, being bold enough to ask a question, and then to follow up, and then to set up a follow-up call.

All those things are so incredibly important. Again, back to that idea of building that kind of cloud of people around you who can answer all of those various questions that are going to come up at some point or another.

I don't know if that's a generational shift that we're seeing or if it's just something from COVID. I think COVID caused people to shut down a little bit more than maybe they typically would. And so, hopefully, that's a behavioral change that's tied to COVID itself and not necessarily to a generational shift and how they approach interacting with people and networking, etcetera.

I would say I have fewer questions and fewer students who are standing in line five in a row to talk to the speaker post-class. And again, those people who are a little bit more introverted, who may not want to ask that question in front of 22 other students, probably didn't follow up with that person afterward, versus having an in-person experience with a speaker where they are casually. Then in our space as the School of Management, and you can kind of catch them and have a side conversation.

I think that piece, hopefully, again, will change in the fall. I would say from a positive perspective because we are in New Haven, I think it's very difficult to get somebody from the west coast unless they're on the East Coast already to commit to them coming to New Haven to speak in class.

And so, I had some incredible speakers this year who just simply wouldn't have been able to come in the past. So, I think going into the fall next year, we'll probably continue to do some of that remote side of it. Maybe not necessarily in class, but in separate workshops during the fall, so that students have the ability to hear these stories or do a deep dive on a particular sector from somebody who really is an expert who wouldn't traditionally be able to come to campus.

I think just in general, people are tired. I think people are starting to come out of it now. But everyone's facing the same issue of this being this weird. I don't know how it is on the west coast right now, but things are certainly opening up here if you've been in your kind of circle of either family, or it's just closed quarters for so long, reentry is interesting and difficult, and I think exhausting in and of itself. So, I think it's going to take a couple of months before we start to see things coming back to normal.

Wilma Lam,


I think that makes a lot of sense. I'm also curious kind of on a theme of connection and networking. I knew in 2018 you were involved in launching, Gay or Women Entrepreneurs and Innovators Initiative, We@Yale. So, I'd like to ask a little bit about what prompted that initiative and what your goals are for We@Yale going forward?

Jennifer McFadden

I mean, I think what prompted that was exactly what you're seeing now. And honestly, over the past three years, you've seen such incredible progress. I feel like in some regards, and then if you look at the data, I think there's a lot more that's being said about it now.

The data is still lagging on whether or not some of it is being solved, but you have these statistics that everybody knows around the number of women who are in investing roles in venture capital, the number of women who are founders, the number of female founders, and in particular, female founders from backgrounds that are non-traditional founder backgrounds.

Women of color, in particular, face just these unreasonable hurdles in getting funding. They are oftentimes some of the most hardcore and gritty, I would say, entrepreneurs because they've had to prove so much for so long in every aspect of their lives. When they take that to entrepreneurship, it's just incredible to see.

"What we were trying to do with that was to begin to try to build out a network across the University of founders, and then also mentors and advisors who were really interested in supporting female and female-identifying entrepreneurs and innovators. I think part of our approach there was redefining what it means to start something."

We are on the academic side of the house at Yale. We really do not do a lot of extracurricular work. We leave that to our colleagues. There are almost 20 innovation centers across the University. A good number of them do wholly extracurricular activities. And in particular, you have the Tsai Center for Innovative Thinking, which is a massive program at the University that crosses every school and every center.

And so, we tend to kind of leave that extracurricular side to the other people, but what we can do is, say, in one of our classes, we are going to provide you with the experience of launching something. We don't define that as you need to launch a semiconductor materials company.

We are super excited to help those students who have those aspirations and have the skills and knowledge to do that and have the technical expertise to be able to do it, but I do think it's equally as important to pull people through the process of just exploring what it's like to find a problem, to find people who have that problem, to talk to them, to figure out how you can solve that problem and to put something out into the world.

"It's about putting something out into the world and pressing 'go' that I think is often the biggest hurdle for people."

And so, that could be something as simple as, "Okay, I want to start a podcast." The process of starting that podcast and putting something out into the world and gathering an audience is still, in my mind, a very useful exercise.

This is a long-winded answer to your question. We don't measure our success by here's the number of ventures that we have that have received X amount of funding that has gone on to exit for Y amount of dollars, right? That is not our metric of success.

"Our metric of success is exposing as many people to the process of entrepreneurship and to lowering the barriers to do so."

And to help them acquire, again, what do you know, what do you not know. So, if somebody wants to build a web application and I've never been exposed to coding before, you're here, you're a student, go take a computer science class. When you get a C, nobody's going to care. Your parents might but probably not because they shouldn't be seeing your grades post-high school anyways. So, go take that risk to acquire a set of skills.

And that person who goes through that process then is more able to then go and become a technical product manager. And from becoming a technical product manager, they then may have the capacity to become Employee #12345, where they have the potential to acquire more equity than they would going into a traditional product management role at, say, Google.

And then, they're building out that wealth that they then can turn around and invest in other founders or can act as an advisor to other founders, and kind of start to build up that set of skills over a period of time that then collectively, we'll change that ecosystem for non-traditional entrepreneurs to see other people and to have access to other people who are like them.

That's kind of was the longer-term goal. I think it'll take 5-10 years for that to change. Some of the stats that were released this year indicate that I think we went forward, and now we're going back a little bit more. I suspect it's going to be a little bit like that for a long time. It's still for those venture-backed companies. There still are a lot of barriers to entry. But there's a lot of research around "You can't be what you can't see."

Wilma Lam,


I mean, it's an initiative that I was really excited to see when it got started. I tried to attend what I could. One of the things I thought was interesting about the answer you just gave was you also talked about the kind of process, right? It's learning skills in the process. You talked a little bit about technical skills.

The other thing I'm interested in, I think, maybe given the nature of this series, is when you're working with early-stage ventures, how do you think about the role of design and design research? How do you talk about that with new founders?

Jennifer McFadden

Yeah. I mean, I think we tend to go to the same materials that a lot of people use. So, obviously, a lot of us have a sudden lean startup methodology.

And before we get off of, We@Yale, I should acknowledge the fact that I am no longer running that, that we have Abby from Tsai City and Trish from my group are leading the charge there and doing all of the hard work and heavy lifting to make sure that program continues to succeed in the future. I just want to give them a little shout-out.

I think we use the same lean startup methodology that most people do. We rely on things from IDEO, that are kind of the earliest customer discovery type frameworks that you can refer to.

"It's all about, for us, getting students to understand that the most important thing they can do in the earliest days is getting out and talking to customers and getting your feedback and really understanding not just what are the demographics of your particular user persona, but what are the psychographics?"

What's motivating that person? Why are they doing something the way that they're doing it now? What are the biggest problems in their lives that keep them from doing whatever it is you're trying to help them do? And so, it's critically important. So, that's kind of the product side of it.

I would say, from the branding side of it, we're lucky this semester to have a guy in the class who was a former creative director from the big agency in New York. His lens and the way that he looks at early-stage startups is just so different than the typical, I would say, School of Management students.

So, again, to the best degree that we can. I think, ideally, next year when we're all in person, he'll still be here because he's a first-year student finding those people across campus that have those skills that you don't have, and again, interacting with them and understanding what their process is when they're thinking about developing the brand side of it.

From the earliest stages, I used the standard of Talking to Humans, testing with humans. I think that's the most digestible thing for students to read early on. The Runway Case is always really good. Warby Parker Case is always really good because it really talks about the process that those founders went through at the earliest stages to gather information from potential customers and then incorporate it into their product or their service.

Wilma Lam,


I mean, Talking to Humans is definitely highly influential for me. I think you're the one that told me to read that book.

Jennifer McFadden

It's just the easiest couple of dollars you could spend.

Wilma Lam,


Yeah. I do definitely feel like there is a big learning curve when you're starting to get really comfortable with speaking to strangers or speaking to people that don't know you and being really comfortable with the fact that they might not like anything that you're putting out there. What do you advise to founders like those first few times when they're going through that process, and they're nervous when they've gotten their first set of just truly terrible feedback?

Jennifer McFadden

Yeah. I mean, the standard set of things. I've done that before. I know how incredibly awkward it is. All I say to them is, "It becomes less awkward the more you do it. It's just like anything else."

The first couple of times you do it, and you go walk up to a random stranger in a grocery store because you're launching a food brand, and you want to know why they're buying X versus Y. That is super awkward. And you're going to get a lot of people who just say, "No, I don't want to talk to you. Get away from me. Why are you approaching me at the whole foods and dairy? No."

My dad has a phrase that's commonly said in our house as well, which is kind of get over it because you're going to get over it. But you won't get over it if you don't actually do it. So, just go do it and give yourself some time.

"Get over it because you're going to get over it. You won't get over it if you don't actually do it. So, just go do it and give yourself some time."

And then, the biggest thing is trying to put that journalist hat on. So, be objective in the way that you're collecting that information. Try not to influence what that person is saying to you. Make sure you go outside of your circle of friends because they will be kind to you, but that's really not what you need at that particular time. And to develop a thick skin. You're going to get a lot of no, and you're going to get a lot of information that might say like, "Okay, every indication as of this point that I have a really stupid idea."

"I think that it's still really valid to have to go through that process of collecting that information because that's something likely you've never done before. You will be so much more prepared when that good idea does come up to actually do that."

And then, gather the information that's positive that says, "All right. Great. I'm on to something. There are so many people who think the way that I'm thinking about this particular problem and approach solving it. Or think that the way that I'm looking to solve it is a reasonable way to solve it."

I try to approach things with a sense of humor, with empathy, but also with high expectations. So, yes. It might be painful, but that doesn't mean you shouldn't do it. Go do it. And then, come tell me the stories about how painful it was, and we can laugh at it together. And the next time you go do it, it's not going to be as painful.

Wilma Lam,


I feel like that's definitely an accurate representation of your approach and my experience of your approach. We've touched upon a lot of what you've seen change with founders and sort of with the industry at large. One of the things I'm curious about also is, has your own approach to advising founders and working with them evolved over the last ten years? Or, how does the industry think about teaching entrepreneurship? And how has that evolved over the last decade?

Jennifer McFadden

I think it has. The School of Management itself is unique, and that it's smaller than other schools. I think if you look at Stanford or MIT, those schools both have 4,500 students who are in engineering. We have roughly 5,000 undergraduates across every degree.

We just have a different set of students that come to Yale. I think because of that, we've tried a couple of different things along the way and have been very experimental in our approach as well. So, with my class, I think you were there for one of the classes when I was specifically incorporating a traditional curriculum into the class.

To give you a sense of what it is, because other people don't know, we essentially have a speaker who comes in once a week. Traditionally, that's in person. They then stay for the afternoon. They mentor students in the afternoon or meet with them. There are four of us who are associated with the class. We meet with student teams once a week and kind of help them work through those problems. That approach is, what have you done? What are you looking to do? How can I help?

A couple of years ago, we tried to incorporate more of a curriculum into that class that was along the lines of the standard that you would see in any other business school. And what we found was essentially, what students most need is they need mentorship and support. They need space in their calendar to be able to apply the things that they're learning in other classes to their particular venture at this particular point in time.

Students can take the class multiple semesters in a row. So, it becomes difficult to have a curriculum in there because people are coming in at very different stages, very different types of companies. We have non-profits in there. We have for-profits in there. We have high-tech, high-growth ventures. We have what would traditionally be called a lifestyle business. Because of that, it becomes difficult to incorporate that particular curriculum in there.

I think what I have tried to do, and again, this just comes from having done it for a longer period of time, is really get that right mix of understanding how to ask the right questions to get the information out of the entrepreneur at that particular point in time to help them make the decisions that they need to make that are most critical at that moment. And so, that just comes with more experience. I would say that's evolved quite a bit.

In terms of entrepreneurship in general at universities writ large, you see so much more now than you saw when I was a graduate student at the School of Management back in 2006. We launched the Yale Entrepreneurial Institute, which was really one of the first university-based programs for student founders that were roughly based on Y Combinator and TechStars traditional accelerators as a summer program. And now, if a university doesn't have that, it's just surprising.

So, there are hundreds of these programs across the United States and across the world. They all have roughly the same approach. Some have more of a focus on technology, some have less, but you're giving that same level of support mentorship education to students. I think just the scale of that is substantially different than it was ten years ago.

And then, I think in general, the ecosystem itself is just so much larger. So, outside of that, when you're looking again at venture-backed startups, you have so many seed funds right now that have popped up, and so many different types of accelerators, and so many different types of programs for all different stripes of founders.

And so, I just think the level of support is much more substantial than it was when I started ten years ago or longer than that—13 years ago now, 14, 15. Wow. I've been doing this a long time. Fifteen, that's scary. Wilma, thank you for making me feel old.

Wilma Lam,


I appreciate that. Give us specific numbers. So, I'm curious. Having reflected back on kind of what's happened with entrepreneurship as an industry and how it's taught, I would love to hear what you are optimistic about as you think about the future of entrepreneurship, both as an industry and also how it's taught?

Jennifer McFadden

I'll start with what I'm maybe pessimistic about, which is really the antithesis of this podcast.

"I still think there's so much work to do around diversity and inclusion in this space. I think there's a mindset shift that is less about ME, and what benefits ME, and how does it benefit ME to more of how does this benefit US collectively and society at large."

And so, I am optimistic that there are enough people that are either at the earlier stages of their careers and are really focusing on this in a substantial way or at the later stages of their careers and may be operated very much in that me versus we mentality for so long but have realized that that's not a sustainable path for us from a societal perspective. I think that will start to shift hopefully over the next five to 10 years.

I think, again, with some government support coming in, and I don't know if you saw the comments by Janet Yellen. Love or hate her based upon her history, but I think there is going to be more of an emphasis around how is government funding going to go back to the traditional levels that it has been at in the past that has allowed us as a nation to compete both from an infrastructure perspective, from an education perspective, from a technological advance perspective.

And so, I'm hopeful that, again, with that funding will come this focus on the WE. I'm not trying to sound like a socialist, but I do think Silicon Valley over the past ten years has become very focused on the ME. I'm optimistic that there are enough people now who are starting to say that's not great for all of us that hopefully going forward, I'm optimistic that that will change.

Wilma Lam,


Yeah. No, I really appreciate that answer. I think embedded in that is also this understanding that as we've sort of brought in the net of who is an entrepreneur and who has the opportunity to become an entrepreneur, it also changes just the nature of what the industry itself has shaped around because we've allowed more people to be a part of that process.

Jennifer McFadden

And the values that come from someone else's lived experience, who maybe did not grow up with as much access to everything as you did. And they do now have some access and are very motivated to do something positive with that access.

I think the issue is if you have, and this is a case with women, it would be great to say women should go out and go down the exact same path as a substantial number of male founders, say PayPal mafia folks have.

To me, that's not an optimal outcome. That's kind of women following a similar path that is very much excluding an entire set of people. And as a society, it's going to have a significant net negative impact over the long run.

"We have a responsibility to think differently about the types of organizations that we're building, why we're building them, and who we're including in that process, and how we're rewarding them."

So, I'm optimistic that's going to happen.

Wilma Lam,


Jen, thank you so much for joining me in all this incredible and deep conversation around these topics.

Jennifer McFadden

So happy to be here. So glad to see you on the West Coast. I look forward to having you back in class. Always.

Wilma Lam,


Yeah, hopefully soon.

Thank you, everyone out there, for tuning in. To follow along and hear the most recent releases, head to And join us again soon as we continue to take a future-focused look at design, ethical innovation, and technology.

I'm Wilma Lam, and I look forward to talking with you again soon.

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