Jessai Flores

“[At the SOM] we have a fantastic set of classes related to entrepreneurship that are taught by clinical faculty who either study entrepreneurship as scholars or have themselves been entrepreneurs. The classes are open to, largely speaking, the systems of the university and that’s wonderful,” said Professor Kyle Jensen. “So it’s different than other universities for sure. It’s better than most and different than others.” 

There’s also Tsai City, Yale’s flagship entrepreneurial hub. They have a variety of programs like Startup Yale — application date 20 March 2023 — which provides funding for Yale startups up to $25k if they get selected and LaunchPad a startup incubator,which helps to take early-stage founders to the next level with their ventures.  They also offer drop-in office hours for everyone interested in becoming an entrepreneur. Yale as a whole, too, has invested more and more lately into entrepreneurship.

But there’s still a lot of uncertainty about becoming an entrepreneur. After all, the industries of finance and consulting are so much more stable, and it’s hard to say no to a $600k paycheck.  Yalies also tend to do a lot of different things. Therefore, I’ve decided to look at entrepreneurship at Yale and after Yale, profiling both a Yale alumnus and a Yale student.

Yale Alumnus Zach DeWitt

Zach DeWitt  ’09 is currently a VC partner at Wing. He’s a serial entrepreneur who started the company Drop Inc and who launched two apps Drop Messages and Firefly after leaving Yale. 

Drop Messages was a location-based messaging app which won the TechCrunch Boston Pitchoff, and Firefly was a location sharing app. They were both acquired by Snapchat for an undisclosed amount in 2017. 

DeWitt also writes about the proliferation of product-led growth, highlighting the best public and private PLG companies in his weekly newsletter, Notorious PLG, and hosts the podcast Innovalters. 

He’s always been a tinkerer, but 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 from the party could log in and access them,” he explained.

It was a success, and with that experience he went on to start another company in his senior year which predicted a student’s grade in a class based on other students’ grades. That project, too, blew up across campus.

After that he worked for a few years at Goldman Sachs and TPG Capital and then went to Harvard Business School. While he was at TPG, he started his business Drop Inc on the side. 

“It was a way to leave digital content and physical locations,” he said. “So like, I could leave you a drop like a social network, I can leave you a drop at Yale dining hall, or the New Haven airport, or your favorite restaurant. And when you get there, whether it’s tonight, tomorrow or in a year, that’s when your phone buzzes and you receive that content.” 

DeWitt decided to drop out of the MBA program and work on it full-time. 

“We ended up winning this big TechCrunch pitch off and had a term sheet the next day, and ended up raising venture funding from Spark capital and accomplished ventures, and two years later it was acquired by Snapchat,” he said. 

After that experience, he started work at Wing Ventures. 

His only regret however is not starting earlier with going full-time and founding multiple companies in his twenties. In the current atmosphere, it’s a golden era for startups, he says, even if you fail.  

“Failure is accepted and actually encouraged,” he said. “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, which is very rare where we are in the world, and where we are in the history of time, like, that’s a very unique property.” 

In addition, the cost of starting a company has gone down so much with the advent of modular services like AWS, along with the expanding outcomes of acquisitions or mergers. So, there’s really no reason not to start a company.

 “I would encourage anyone who’s thinking about entrepreneurship at Yale, to lean into it and start companies, you know, right after their first job, or even right after college,” he said.

Yale was a definite help for him when it came to entrepreneurship, but DeWitt still feels like there are things that the University could stand to improve upon. He said that the current set up still seemed to be too siloed, and that the cross department communication could be improved. 

“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,” he said. “I think Yale should connect a lot more with their successful former founders, like Max Rhodes, who 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 that’s interesting and important. But I also think they should bring an even number of founders, both successful and unsuccessful ones, and see the full spectrum and hear the stories and the ups and downs. Just starting to get more exposure, and get people excited. You know, let people know that failure is okay. And that they should be taking risks when they’re in their 20s.”

He suggested that current Yale students who want to become entrepreneurs look for mentors in Yale alumni.

“You know, use that student email address @yale.edu,” he said. “And reach out to alumni 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 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. That’s the first place to start once you have someone that believes in you and is willing to 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. Just go work for a company that’s in that space. “

Profile of Braden Wong

Braden Wong ‘24 is a junior studying Ethics, Politics and Economics with a certificate in Computer Science. He’s from Southern California. 

He’s built a series of apps for Yale students, from the Yale Buttery Book, which lets you look up the menus for the various butteries, and which ones are open, to Meal Match, which lets you match with other students on campus so you can grab a meal together. He also built Janktable, which lets you easily see which course reviews are good  and which ones are not. Currently he’s trying to get all the various buttery apps on the same page so that they can agree on a protocol to share, which he plans  to release after Winter Break.

Wong first got into code during the COVID-19 pandemic.

 “I locked myself in my room and I started coding a lot more,” he said. “I didn’t know almost any coding in terms of how to build something until basically my first year of college. And so it’s crazy how fast you can learn stuff just based of YouTube and a few tutorials. That was basically the main website for everything.”

He says his most important skill, and the one that he says is indispensable for an entrepreneur or builder, is “the skill of trying to get whatever ideas you have into a reality as fast as possible.”

For the Yale Buttery book, the idea came on Halloween, and he spent the entire night of Halloween just coding it up.

 “My suitemate biked through the rain and got soaked to bring me my laptop so I could continue coding,” he said.

JankTable took a bit longer. The idea came when he was just walking around.  “I got kind of obsessed with the idea of ‘I really wish I could browse reviews much quicker and just figure out which courses even had good reviews that were written.” 

So during the October recess, when he was on a road trip with his friends down the East Coast, he started reverse engineering the API requests that were on Yale. 

“I just was glued to my computer, my friends were like, ‘You should put away your laptop, just relax a bit and enjoy October recess,’” he said.

Despite his successful projects, he still considers himself more of a builder than an entrepreneur.

“I shy away a little bit from the label,” he said. “I think that sometimes being called an entrepreneur, just in itself, can be a little cringe, because ideally, if you’re a good entrepreneur, you call yourself founder of X or founder of Y, something you actually built up that has a name, right? There’s a lot of noise, with the people who label themselves as entrepreneurs, because there’s a lot of people who build a bunch of stuff, but none of it sticks.,”

He says that if he didn’t have to worry about money, he would dedicate his life to just building Legos and other projects every day.

 “That’s not always what I’m able to do, because the world is not a perfect place, but at the very least, when I’m here on campus, I can build a few tools that other people might find useful,” he said.

He sees the apps as also helpful tools for students rather than direct gains. “A lot of students at Yale hopefully are going to have pretty impactful lives. And so, even the ability to help influence or make their lives even just a little easier, even maybe 20 people’s lives a little bit easier… I think that is a very big success. Or they take a course that’s a little different, and then their life trajectory changes.

He also says that “the best thing to do is just to start building as soon as possible. The best time you could have done that was yesterday. You should do it today. It’s the second best time.”

He sees himself in the short term at least as sticking with software engineering, but in the future, he plans to work in policy.

 “A lot of code generation tools and AI will make people more productive,” he said. “I think in general it will only become easier for people who want to build something or who want to code, but don’t yet know how to.”