Andrew Yang on Throwing Parties and Re-discovering Creativity

by Will Yoo

Editor's Three Key Takeaways

Andrew is the CEO and founder of Venture For America. After graduating from Brown University, Andrew pursued his J.D. at Columbia Law School before working at a variety of startups. He eventually landed at Manhattan Prep, becoming the CEO before Manhattan Prep was eventually acquired by Kaplan in 2009.***

Editor: I stumbled across Andrew's writings on the future of work in a technologically charged society. Andrew's work at Venture for America, a fellowship program that connects recent graduates with jobs at startups, is trying to imagine a future where work is generative, meaningful, and inclusive.

On Getting Started

Tell us about your journey from Phillips Exeter Academy to Brown University for undergrad and then your law degree at Columbia Law School?

I graduated from Brown with an economics degree and was not sure what to do so I took the LSAT and went to law school. After law school at Columbia, I became a corporate attorney at Davis Polk & Wardwell.

I was being paid for doing detail-intensive work and I felt like I was going to become a different sort of person over time if I stayed. I looked around me and saw that there weren't other people there whose lives and careers I wanted for myself.

So I thought, you're definitely going to leave this place eventually, and it's only going to get harder, not easier, to leave over time. So with those things given I thought logically, I should leave immediately.

I left after five months to start a company called Stargiving.com with a colleague and I did not know much about starting a business at that time. I hustled for seed money, eventually raised some and then we built a web site and launched. But then the bubble was bursting at this time and no one cared about my little company after a while. So we shut the company down after about a year and a half.

At this point I was a failed entrepreneur with education loans of over a hundred thousand dollars that I had taken out for law school. But at this point I'd been bitten by the bug and I said, "Wow, trying to start a company was much much more genuine and challenging and invigorating than being in a law firm."

And so the question I faced then was the question that many people who are graduating from Penn are thinking about: how to move in an entrepreneurial direction. I'm guessing most Penn students do not think they're situated such that they could start a company today and that's probably right. So the way I tried to develop was I worked for more experienced entrepreneurs, first at a mobile software company that did not work out. And then at a healthcare software company where I learned a lot, then I eventually became the CEO of Manhattan Prep. That was the fourth or fifth startup I worked at and then that company grew and grew and I had a great run with that company for the next five and a half years.

So I can relate to many of the anxieties and issues that Penn students are facing. You're some of the best students in the country and get heavily recruited by name-brand banking, consulting, and tech firms, and it seems like a no brainer to compete for those offers and take them.

On the flip side though some of you have spent summers at these firms and have not enjoyed it. Or you have friends who are at these firms and tell you horror stories about how they don't enjoy it and have very little time outside of work. And so you think: Wow, is this really what success is like? Am I supposed to take one of these jobs and compete because I'm supposed to? And is there is there something else I could or should be doing? But the other alternatives don't come to Penn and recruit you. So it's a really challenging landscape. And people who go to graduate programs in my experience end up deferring those issues for several years and then face them eventually anyway.

If you were back in college would you study something other than economics or law?

I would either be technical or creative if I could do it over again. I think because we are in a world where if you are technical you can create opportunities for yourself more easily. But I think that creativity is at a premium now today too. And it's interesting how little creativity finds its way into many corporate contexts.

And what do you mean by being creative?

The way I see creativity is being in touch with something that you originate and feel strongly enough where you want to bring it into the world. When most people hear creative they think artist, musician, or writer. And those are manifestations of creativity. But to me creativity can mean starting an organization that you think solves a problem, rounding up people to do something that you care about, or building a business. And I think the act of putting out into the world something you believe in and trying to get people to pay attention to it or rally to it is creativity.

And would you say creativity is a skill that can be taught or can be deliberately developed?

We all start out creative. We are then trained away from it. That was my experience when I was an economics major. And so in my case I think I re-discovered my creativity almost a decade later.

I was named one of the 100 most creative people by Fast Company a few days ago. I was really surprised by it. I don't even consider myself a creative. I've broadened my sense of creativity to include starting organizations and other things. By now I'm a bigger fan of pushing people in those directions.

So if you you're a student at Penn and you're an economics major, it's not necessarily like go take a painting or art class. Instead, reflect on the things that animate you, and understand it doesn't need to be profound. It could just be that your dorm really needs a book club or a basketball club or a potluck. And to make things happen — that's being creative.

While I was struggling in the startup world in my twenties, I started throwing parties. And the business training from throwing parties is insane. It is some of the the best business training.

But if you think about it, you have to have the vision to get people behind it, you have to organize a team, gather resources, and pay attention to key variables. You also have to be disciplined enough to not care what others think and to a degree also care that they think. So there are things like that that I would advise people to to pursue that you don't think of as creative or business training. But I found them to be very applicable.

Venture for America

Does Venture For America (VFA) become more or less relevant as many jobs and opportunities are taken by machines?

I inventoried all of the companies we work with. And I could not find virtually any that are geared towards dislocating jobs. A lot of this is because of the cities we operate in and the problems they are trying to solve. The vast, vast majority of our companies are what I call generative — if they succeed it's just going to be a win. We're as or more relevant than ever in trying to broaden the growth of businesses and entrepreneurship to more regions because with the increased pace of automation we're going to need more and more vitality and opportunity in places that are not New York or San Francisco.

Do you think initiatives like V.F.A and opportunity zones can keep up with the pace of automation?

I think that Penn students are going to see many dramatic things occur in their careers and lifetimes.

Now I'm not worried at all about Penn students because you all are the cream of the crop and there will always be incredible demand for smart people that can help guide organizations and really light the path of innovation. You guys should not be concerned about your own prospects. The dynamics of this economy actually advantage people with your skills and attributes.

That said I think that right now there are many worrying trends in American life that will affect many other people. That will require a very robust set of responses that we're not really realistically initiating right now. And that needs to change. And that's one of the things I'm most driven by.

What can students can do to assist those in parts of society where there have been large displacements of jobs and opportunities?

Maintain a degree of empathy and perspective. When you're young it's very easy to say, "Hey, my career is uncertain. I've got a struggle ahead of me and I need to focus on that."

The single biggest thing is to know that you all are some of the most gifted and sought after young people in the country. So number one maintain empathy. I remember when I was young how anxious I was and it was very hard for me to imagine that no matter what happened, things were going to be fine.

But I'm here to tell you that no matter what, things are going to be fine. Take it from someone who was part of several failed companies and is just fine! I'm a part of several failed companies, I owed $100,000 and in law school debt, and I'm still fine. My parents were concerned about it for a little while but now you know they love it and brag about me all the time.

The first thing is to know that you're going to be fine. The second thing is to try and make your work generative and part of a solution.

Now that's a very, very high bar because many of the opportunities that are naturally going to come to Penn students are not going to be generative truthfully. They're going to be market-driven and the market is going to be unkind to many workers in the years to come. So if you can find an organization that if they succeed will end up being a positive force in terms of making opportunities possible for broader numbers of people, that's ideal. If every Penn student were to do that we would actually be in much greater shape because you guys are one of the great collections of human and intellectual capital in the country. So if there were enough Penn students working on generative businesses and companies that would be awesome.

Finding Meaning in a Changing World

Imagine a scenario where smart and ambitious students work on non-generative solutions that are unkind and market driven. These solutions will drive many into a form of economic uselessness. In that kind of world, where will both students who are working on these unkind market driven solutions and the workers who are continually losing opportunities derive meaning?

You just summarized two ends of a really profound fundamental generational challenge. The issues you described are really going to be the great project of this era — which is what do millions of people that don't have an economic purpose in the workforce do to forge purpose in their community. And to me there are many possibilities in that direction and we're going to have to meaningfully invest in and explore them.

On the other side if you have a lot of people working on advancing market-based solutions that have neutral or possibly even negative effects for others that may be — and I don't want to let anyone off the hook — but that might be fine if the benefits of that progress are being distributed in ways that make everyone happy.

For example, trucks driving themselves ought to be a good thing. We can't shy away from it. It's just that this is a very important question as to what that means for real people and real families that currently rely upon driving trucks for a living.

And does a universal basic income fix everything?

To me a universal basic income is a very important part of a set of solutions that we have to consider. Because if you do hit the fast forward button far enough you wind up with a very short list of realistic means of distributing economic value to enough of the population where society continues to advance. It's something that I believe is going to become more and more front and center in the months to come.

You've said if there's anything that you learned in the last six years in building VFA it was that all things remain possible if you pursue ideals. What is the story of how you developed your ideals?

I really don't want people to feel this pressure to have a sense of their ideals. When I was a senior in college I had pretty much one priority and that was trying to be cool, whatever cool meant. I was just trying to get a date. Or trying get this person to pay attention to me. In my case values got built over time based upon the people you work with and the things you experience and the organizations you're part of.

So it's not unusual for people to still be grappling with how to articulate their values and how to live those values for years or even decades. It's not unusual. In my case I started to believe that our flow of talent was driving problems for both the people involved in our economy and society and I wanted to change that.

And I've been situated such that I believe I could change this problem, which is not a realistic ambition for a lot of people.

And what's funny is I kind of knew that I was part of a moderately narrow group that could have a positive impact if I busted my back for a number of years. So I felt like I needed to do it because if I didn't I'd be failing to live up to my potential.

So don't sweat it if you're still figuring out what it is that you're most motivated by or which you care mostly deeply about. The key is that when the time does come — and it will come — where the universe does speak to you and realize this may be your chance to do something important then you have to take that first big step. The first big step is the hardest. After you take the first big step the other steps just start following.

But you have to maintain a sensitivity to what opportunities come your way and what chances you get to work on the things you care about. One piece of advice I would leave you with is that you should write down the things you want for yourself, the things you care about, and the things you want to work on. I did that.

And then when the opportunities arose to work on those things I said: "Well, I wrote it down." So I was either lying or I need to do this. Writing it down to helps make it real. I was talking to one guy who moved to Ohio and co-founded a venture capital firm there to help the region. He told me he'd written down a list of things he'd like to do in his life. One of them was create thousands of jobs for people that wouldn't have them otherwise. And so he said when the governor of Ohio called him and said, "Hey, come to Ohio and become my economic development leader?" And he replied, "That's on my list!"

And the same thing happened to me when I had a list of things that I wanted to do. And so when I thought I could try and accomplish some of them with Venture for America I did it. So if you write down what you want to do and what you care about it will prove immensely valuable over time.