Jenny Lefcourt on Dropping Out of Stanford Before It Was Cool (Part 2)

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Jenny Lefcourt is currently a partner at Freestyle Capital, a venture capital (VC) company with $216 million in funds and investments in over 89 companies to date. She graduated from the University of Pennsylvania Wharton School of Business in 1991 and started working for a big company in New York City before becoming “disillusioned with corporate life.” After a year of backpacking around the world, she moved to Palo Alto and have since been “hooked on the Valley way — combine big ideas, smart people, hard work, and a little bit of luck and great things will ensue.” Her adventures include dropping out of Stanford to co-found her first company, WeddingChannel.com, a gift-registry aggregator; starting another named Bella Pictures; and attending the Circus Center in San Francisco for contortionism.

Stories worth noting:

Path of Least Resistance

One thing you said earlier really stuck out to me: You chose the path of least resistance and that ended up not working well for you. That's something a lot of people here can take note of. People do it because they aren't well informed about what else is out there and/or what they want to do.

What's your advice on how students can learn earlier? What do you wish you did as an undergrad to get a more informed idea of what you want to do before you graduate?

It's a great question that I actually don't know the answer to. I never looked back and said, "I wish I had done something else during my college years."

It was more about when it happened, recognizing it and then making sure that I managed my way out of it because I didn't want to wake up in eight years and still be there, knowing the whole time that it was not my passion.

So, there's a few things. One is whatever anyone does, they should be really conscious about the choices that they're making. If you want to work on Wall Street or you want to be a management consultant, know what it is exactly that you’ll be doing and why you're doing it. You should go find out more about that thing you need to understand to make the right decision. There's so much that can be found online: readings, internships, speakers. There's so much access.

So when people are doing analyses of what their move should be, it should never be, “I don't know enough about blank even though I'm so interested and so I'll go take a different route.” That's just wasted time. There's nothing wrong with saying that I think one day I want to be an entrepreneur or blank. But right now, since I don't have the skills or the idea or the network yet, I'm going to go do this other thing because I'm going to learn a lot and I'm excited about that. That is okay.

That makes sense. For me, the deliberate decisions were driven by my experiences on a trip to explore the San Francisco tech industry, organized by Wharton, where I first met you. It really helped me and others on the trek understand what else is out there in the tech world that we wouldn't have understood from going to a bunch of info sessions at Penn, especially at Wharton, where they are more finance and consulting focused. Those were incredibly instrumental for me and I bet there's a lot of other resources out there that I just haven't come across yet.

Editors Note: Treks, like the one I met Jenny on, that I recommend are Wharton SF Tech, Wharton LA Media & Entertainment, Wharton NYC Tech, and Penn Tech Trek.

They are there. You just need to dig. There are so many great intern programs. Freestyle has one. We are a $60 million fund and we took in six college students and placed them in our portfolio companies. I definitely recommend you do an internship in this other world if you’re remotely interested. It’s a wonderful way to get exposure.

I wish I had heard this earlier because I had plenty of summers in which I could have done something unique. Everyone has competitive, pre-professional mindsets, thinking, "If I think I want to do X full time, then I have to get a junior year internship in that industry so that I can prove I can do it full time, and so I have to get a sophomore year internship in that industry so that I can prove I do it junior year." And people keep pushing it back to where now even freshmen are concerned about their summer, that they can't get that internship which will then provide some kind of domino effect to a full-time opportunity.

Totally, totally. Once again, it's just so easy. Those firms come, they make you great offers, and all your friends are doing it. I get it and it's fine for a lot of people.

But if you are interested in this other world or you don't even know if you are, but you want to know if you are, then you should absolutely try that because the traditional jobs will always be there.

Venture Capital

So you mentioned Freestyle. Let's talk more about your VC life. You started off in entrepreneurship, which is more operational work. Now as a VC, it’s all investing. What was your motivation behind the switch?

My advice is if you think one day you want to be a VC — and this is super biased — you should learn how to operate. If you can be a founder, be a founder. If you can join a young startup and learn how to operate, do that. There's nothing like living it to then be on the other side and know what to look for in investing. You’ll be a good coach, having been there and done that. You can add more value with empathy and insight than you can if you just looking at it through the ivory tower.

Jenny with her co-partners of Freestyle VC.

I had done a few startups and now I am married and have three kids. Startup life is really hard for good balance. I get so much joy out of working with entrepreneurs and being the person behind the scenes that helps them be successful.

For young people, do things that are harder to do when you're older. Being an entrepreneur while you're young is just a hell of a lot easier to do than when you have a family and children and whatnot.

I definitely agree. I always thought that one of the most powerful things about being young and fresh out of college is that you have this energy and enthusiasm and passion to go out and solve a lot of things. Obviously, this is coming from a very grandiose mindset that I have as a 21-year-old right now, but this energy matters. Many different places I’ve worked at didn't push me creatively or to think outside of the box. Personally I call it "feeling like an adult." That's my metaphor for it.

But I will say I'm 40 years old and have a ton of energy and passion and excitement. When I was 28 and working on my first company, I didn't need balance. It was so easy to completely indulge in that and I loved indulging in my career. It wasn't hard. I mean, it was hard but it was fun. It was exactly what I wanted to be doing. I would never do that at this point in my life with a family. I would miss out on too much. So it's not that I don't have the energy, I just have too much other responsibilities and opportunities that I don't want to miss.

I find that really admirable, just having that same energy now. Some older friends of mine who are still in their twenties feel burnt out already from what they're doing. How did you manage not to burn out? Was it something in your job or was it a life habit or philosophy?

Workplace balance is one of those things that gets thrown around and I don't really see that as goal. I see happiness as the goal. And so every person is different. If you're an introvert or an extrovert, you should recognize where your natural energy is. Your job is to make sure that you take care of yourself to have the energy to not get burnt out.

So I didn't mind giving up a lot of social action during those years because I loved my work and we were having fun and building stuff together. I saw my husband plenty, I didn't have kids, and so I just made sure that I slept well, I ate well, and did yoga. Other than that, I could give everything to the company. Some people need more than that. Some need less.

Just make sure that you have the stamina to keep on going. It's not a sprint, it's a marathon.

Editor’s Note: I first met Jenny on the Wharton San Francisco trip in January in which she told us her story, along with several other alums. Not only had she thrived in the male-dominated entrepreneurship scene, she is currently tackling the venture capital industry as part of the eight percent of VC partners that are women. I met her again at a Wharton Entrepreneurship lunch and learn in which we talked about how female entrepreneurs only get two percent of all VC funding and personal advice she had for students. I’m proud to call her a strong role-model of mine and hope her story can inspire many more students to keep hustling despite societal pressures.