2084: A Interview with Zach DeWitt

A part of my upcoming article for the Yale Daily News

I’m writing an article for the YDN on entrepreneurship for the WKND desk, and I had to do a bunch of interviews for it. Yale, as part of all its modernization projects, has in the last few years decided to become a part of this new space. The biggest symbol of this is the still fairly new Tsai City, which sits behind the CEID, a 12500 square foot building dedicated to entrepreneurship.

So since this took up a lot of time, for my post today, I’ll post my super super first draft of the interview with Mr. Zach DeWitt of Wing VC. I will edit it down in the final version.

Zach DeWitt, a Yale alum ‘09 and VC partner at Wing Ventures, who started a few successful businesses after Yale, Drop and Firefly, said  he started his first company when he was at Yale in 2008. “It was before social media, and I started a business with some friends, where we'd be hired for parties or, you know, sorority parties, fraternity parties, birthday parties, and we'll just go and take some photos of the event, and then post them online to a kind of secure site where people could from the party could log in and access them”. It was a success, and with that experience he went on to start another company in his senior year which matched student grades.

“I think Yale should make it a lot more flexible to let people take time off, if they're starting a company as an undergrad. I think Yale should connect a lot more with their successful former founders, like Max Rhodes, who is was my classmate and friend from Yale, he started Faire, which is, you know, a $12 billion startup right now, which is doing extremely well. Yale should bring him back to speak on campus and should really get him involved as much as he's willing to do and give back in terms of his time and mentorship. I think when I was at Yale, they brought a lot of journalists and politicians and, and that's, you know, that's interesting and important. But I also think they should bring an even number of founders and you know, both successful and unsuccessful ones and see the full spectrum and hear the stories and the ups and downs and and just and just starting to get more exposure, get people excited. You know, let people know that failure is okay. And and they should be taking risks when when they're in their 20s”. He also criticized the communication of Yale, and said that the current set up still seemed to be too siloed, and that the cross department communication could be improved. 

However, beyond the initiatives, the strength of Yale is still in its alumni. “You know, use that student email address@yale.edu. And reach out to alumni, you know, and find someone that you look up to, that maybe is an entrepreneur in a sector, you're excited about, right? If you're excited about, you know, fashion, you know, reach out to a Yale fashion founder, or reach out to one of the Rent the Runway founders or glossier founders and see if they will mentor you and help you and, and that's the first place to start once you have someone that is believes in you and is willing to kind of give some time to help you out. That's really enough confidence that you should take the leap and start exploring areas and you know what I would say don't rush it. If you don't have a great idea right now. You're young still and just go work for a company that's in that space. “, said Mr. DeWitt.  

Especially given the growth in venture capital. “I think the biggest mistake I made was not starting multiple companies full time. In my 20s. I think that it is such a golden era for startups right now, in that, you know, failure is accepted and actually encouraged. You know, if you, if you have a startup that fails, you're likely going to be able to raise money from your same investor for the second one, like, that's very rare. In where we are in the world, and where we are in the history of time, like, that's a very unique property. And on top of that, you know, the cost of starting companies has gone down with AWS, and, you know, so many other kinds of core infrastructures as a service. It's just, it's much more modular and easy. And, and, you know, the outcomes are just getting bigger and bigger, too. So, in hindsight, I would have started, you know, five companies in my 20s, and, you know, really stepped on the gas and just done it over and over and over.” 

Stay tuned for the better version!