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Entrepreneurship roundtable Q&A: Poshmark CEO, FreeWill co-founder, Pear VC partner on unbridled optimism

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The Stanford Daily sat down with three keynote speakers who headlined the 2020-21 ASES Global Entrepreneurship Summit to discuss their startup experiences, mindsets and insights gained after years of startup leadership. Manish Chandra, the CEO of Poshmark, founded the company in 2011 and has since expanded the social-shopping platform to over 60 million users. Jenny Xia Spradling MBA ’18 co-founded FreeWill, an online estate planning software that has raised over $252 million for nonprofits, landing her on the 2019 Forbes 30 Under 30 Social Entrepreneur list. Ian Taylor MBA ’19 is a partner at venture capital group Pear VC and works with student entrepreneurs and founders.  

The Stanford Daily [TSD]: How long did it take you to make it to where you are now, and what key takeaways did you gain along the way?

Manish Chandra [MC]: [First], the foundation of any company is the team that starts it and the people that come along the way. Many times people get caught up with just the idea, but having a core team is really critical. Second, looking for disruption that is happening allows you to find big opportunities. For example, when Poshmark was beginning, the world of social sustainability and mobile platforms were opening up in 2010-11. This led us to create something big by betting on mobile early. The third thing that is key for all entrepreneurs is persistence. On one side there’s persistence, and the other side is being flexible and learning frequently from real-life customer feedback. Put your vision in the hands of the users and iterate fast along with them. 

Jenny Xia Spradling [JXS]: My co-founder Patrick Schmitt MBA ’18 and I started FreeWill in early 2017, so it’s been a full four years! Stanford’s access to every sort of expertise is wild. We were at this weird intersection of [financial tech] and legal tech and nonprofit software, and everyone we needed for all of those pieces were on campus. Do not be afraid to go into a challenging class or situation where you know nothing about it and figure out if you are the type of person who needs to be motivated by the impact. Another thing is that your co-founder matters more than the idea. Patrick and I spent a ton of time at the beginning not on our business model, but on values, culture and what we want out of a startup experience. That foundation has continued to carry us so far, and we continue to work on that relationship today. 

TSD: What advice would you give to Stanford undergrad students, and what pathways and fields should students check out before graduation to prepare them for cutting-edge social technologies? 

JXS: The thing that I took for granted during undergrad was that it wasn’t only the ideas in class, but also the relationships that I was forming and understanding who I worked well with and why. The other thing that I didn’t take advantage of during my undergrad was the professors. In reality, they are superhuman. They really love following their students’ progress and have done incredible things that they would love to impart and have a lot of great networks. 

Ian Taylor [IT]: In your early twenties or late teens, you’re always exploring, trying to collect more information to decide what you want to be and what you want to do. I think I have learned that you just have to dive right in. Pick something you really love rather than something that seems like the thing to do. Something that actually makes you excited. Surround yourself with people who you really admire to inspire you. 

TSD: What are your thoughts on the general entrepreneurship culture, especially at Stanford?

MC: Stanford has a rich and deep entrepreneurship tradition. It’s a really positive environment to learn. My only advice is “go slow to go fast.” Don’t be in a hurry as a Stanford kid, [thinking] that you have to start a company right away. Even though the culture may foster that, a little bit of patience is key. When we think about where the world is going, there is not only one definition of entrepreneurship. As young students, you can really think of how you can impact the world not just in a classical Silicon Valley kind of entrepreneurship but applying the principles to impact the world in multiple dimensions.

JXS: Having come from the East Coast, I feel that it is such a great vibe with so much energy here. There’s something about entrepreneurship that is just like unbridled optimism: the belief you will be able to change the world or solve this big problem and knowing that despite many billions of people surviving in a certain system for millions of years, they never solved it but you can. I think that attitude is probably the thing that feels the most special at Stanford. I also think that there are some weaknesses as well. There are so many ways to make a big impact and yet the single glorification of a Venture Capital-funded rocket ship is a little bit unhealthy and limits the optionality that people really have to make the change they want to see. 

TSD: If you were to hire college students, what are the top qualities, talents and features you would consider most significant? 

MC: Intellectual curiosity and collaboration, the ability to talk with people and work with them. This goes hand-in-hand with humility. Knowing that there is so much to give but also so much to absorb is powerful. These three things are really important for anybody we want to hire, but especially for amazing young, bright kids coming out of college. 

JXS: The biggest one is definitely grit, as when faced with a challenge, they will not stop until they find a creative solution around it. It doesn’t matter what you study, but more so your creativity and determination. Another one is kindness. We look for really high emotional intelligence and self-awareness, low ego kind of people. We really care about diversity, equity, and inclusion. I just don’t think that you can have an inclusive environment if you don’t have people who are truly willing to listen and put their egos aside in situations. 

IT: It’s really unlikely the first idea you have, the first problem-solution statement you have, is then going to work out. I want to understand what drives people or why they want to work on that problem. Someone who has a growth mindset and can realize they don’t know everything is important, along with a thirst to learn. Another one is clarity of thought. Someone who is structured in their ideas, can solve problems more efficiently and can draw on broader resources to help.

TSD: What are ways you destress when days get hectic — what makes you smile when you go to work each day? 

MC: Just seeing new people that have joined us since COVID started and my colleagues that I have known for a long time makes me feel so happy. I think I cried happy tears three times during a meeting in my office, because at the end of the day it’s people who give us happiness. The people we work with, serve and interact with. I’m lucky to have a few very close friends that I have known for a long time and [we] can share a lot with each other. Very early on, I was introduced to meditation, which is now a key tool for me to manage my psychology and stress. It’s something that I have practiced since I was 13. Another thing is that I like to do word puzzles, like solving many different types of crosswords. 

IT: This is a little thing that a friend told me to do once. Look up at the sky, and you just suddenly realize how small and insignificant all your worries are. I think this feeling is very relieving. I find the same feeling when I’m in nature. What also really makes me happy in this job is the success of all our founders. And secondly, pure knowledge—just learning every day. 

This interview has been condensed and lightly edited for clarity.

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Vol. 260 Academics Desk Editor
Tom Quach '24 serves as the Academics Desk Editor for Vol. 260 and previously covered startups for The Daily's SciTech section. Tom also serves as Account Manager for The Daily's Marketing Team. He's from San Francisco, CA, and enjoys biking, building LEGOs and watching Stars Wars on his spare time. Contact him at tquach 'at' stanforddaily.com.