Q&A with Contrary Capital and Cardinal Ventures' Tina Jiang

Tina Jiang is managing partner at Contrary Capital and managing director at Cardinal Ventures, based in the San Francisco Bay Area. She is a junior at Stanford University studying Symbolic Systems.

What attracted you to venture capital and working with startups?

My interest started when I was pretty young. My parents own a restaurant, and I probably spent more time there then I did at home. It was such an important part of growing up, learning what it meant to run a small business. Of course, it’s different from a startup, but some of the fundamental mechanics are similar.

I decided to learn more about startups and venture before I went to Stanford. I cold emailed startups in New York, hoping someone would take a chance on a high school senior with no work experience. I ended up getting a few replies and actually worked at two companies before I started college.

The first company I joined was called PaperFree. It was a really small team, pre-product market fit. This first experience was really interesting because the startup was at the ideation stage and still figuring out the business. Afterwards I worked for Ringly, a fashion wearables company backed by funds like Andreessen Horowitz. That experience really shed a light on the early stage and what marketing and digital strategy looked like for Series A startups.

Once I got to Stanford, I reached out to Cardinal Ventures, Stanford’s accelerator for student-run companies. With my prior startup experience, CV ended up being a great fit and I joined the team. I managed external relationships with our mentors, speakers, partners, and sponsors. Freshman spring, I also worked at Highland Capital Partners as a fellow. It was fascinating to see the investing process firsthand. These two roles really immersed me into the Stanford venture and startup ecosystem. I became confident talking with founders and figuring out how to grow their passion into a viable company.

What led you to Cardinal Ventures?

When I thought about the opportunities at Stanford, I wanted to be at a place where I could have the most impact and influence. There are entrepreneurship clubs that focus on inspiring people to be entrepreneurs. We have programs sponsored by VCs and the university. StartX, a non-profit startup accelerator affiliated with Stanford, is one of the longest standing organizations.

I considered all of these programs but knew that I was ultimately drawn to students helping students. Starting a company when you’re at college is very challenging; it takes someone who understands that struggle to help you and tailor a program specific to that (in terms of scheduling and programming). Student founders aren’t just faced with logistical and business-oriented obstacles, they face an existential one. They wonder whether they should keep building their company and drop out, or just quit. A lot of the time is spent discussing this inflection point and where to go next.

Now as the managing director of Cardinal Ventures, I’m exploring ways to elevate our programming. I want to be thoughtful about who we bring on as mentors and speakers, how we oversee operations, and the application process from start to end. My goal is to tangibly help startups instead of just doing diligence. CV’s approach to be involved in the full picture really drew me in.

In addition to Cardinal Ventures, you’re also involved with Contrary Capital as a managing partner. How did you get involved and how would you describe Contrary’s unique value proposition versus some other college-centric accelerator/venture programs?

During my sophomore year, I got email from Contrary Capital’s prior managing partner, wanting to know about Stanford ecosystem. I jumped on call with him. I initially didn’t really have the intention of joining, but by the end of the call I was energized by Contrary’s mission: giving young founders everywhere equal access to capital. That’s a mission worth contributing to. I decided to join as the first partner at Stanford. I’ve now grown the team here to four students. And it’s been wonderful to see the impact already - of our 14 investments last year, Contrary funded 3 Stanford startups.

Contrary is younger than the other university focused things out there. We’ve been around since 2016. Eric started Contrary by road tripping around the country; now we are trying to become the dominant student-run VC in the university ecosystem.

Alternative players in the university VC space often cut much smaller checks than Contrary (eg. $20,000). That money can help in beginning but it’s not super substantial runway. We give you more than that - anywhere from $50k to 200k - of meaningful capital. And it doesn’t end there. We are part fund and part accelerator. We host a summer program that brings all our founders for that year to San Francisco. They meet mentors from Andrew Chen from Andreessen Horowitz and Uber to the founders of WePay. Contrary’s LPs include founding members of Facebook and Tesla. The network is very powerful, and makes a meaningful difference for many entrepreneurs.

Broadly, there’s a lot of support through Contrary with a focus on value beyond capital. We certainly have some limitations, but I think it leads us to push the edge on what we can do to engage student sand entrepreneurs.

Given your focus on student-run companies, are there any trends you’ve noticed and spaces you’re interested in?

There are a couple of spaces I’m very interested in like consumer tech and retail. I worked at Casper, a direct-to-consumer mattress company, on their marketing team. That was really hands-on. I was primarily analyzing metrics around marketing campaigns on podcasts, videos, subway ads, print, and television. It was an interesting shift from the startups I’d worked at before. People undervalue offline marketing and Casper is famous for doing that differently.

When I think about the future of commerce, it seems there’s a lot to be unraveled in the backend. There are ways to create better platforms for improved retail experiences, and that means reconfiguring logistics, supply chains, etc. There are lots of opportunities for technology to help here. People primarily look at the branding side of consumer startups - your Caspers, Aways, Warby Parkers - but I see the billion-dollar ideas in the backend.

Of course, healthcare is another opportunity area. I started looking at CRISPR - gene-based editing to help people with serious diseases - while researching at NYU some years ago. I think the future of health is in genomics and adjacent applications. Healthcare has been very resistant to innovation, and for good reason too when there are lives on the line. But it’s changing and I see ways to positively shock the system. Drug discovery is a perfect example of this. Do you need to test experimental drugs on humans or can you replicate that in a software? How do you collect accurate, replicable data with the best test subjects? And there are huge legacy questions for electronic medical records. Consumer experiences in healthcare have been so terrible and there are some small fixes that could actually make a huge improvement.

The last space I’m exploring is future of transportation. Autonomous is bound to happen, but we face technological barriers on the path. There’s a great opportunity to be the first successful mover, but what happens after that? How do can we rethink the ways cities are structured and even how cars are structured? It’s made for people to drive. Once that isn’t the case, there will be a huge opening for infrastructure-based innovation. What happens to freed up space when cars don’t need to be parked anymore? What does a car look like if there’s no driver? These are unanswered questions I’m thinking about.

Have you faced any challenges as an undergraduate in venture? I imagine it takes extra work to get in front of other investors and startups.

Definitely. You hit it right on the mark with being young. Sure, Silicon Valley is better about people being young but there’s still an expectation in the community that you need years of experience to be a really effective investor. Even when you talk to startups, when I reach out and say I’m a junior in college, that’s so different from the typical VC-startup relationship. The investor is usually more experienced (and older).

It’s been great building the investor mindset and skills in student-focused venture organizations. But there’s still a level of surprise, a raised eyebrow, when they realize that I’m young and in college. The way I deal with it is pushing forward and being confident. Honestly part of it involves faking it - even in times where you aren’t confident, you need to put your best foot forward and be sure of yourself. I do that by knowing different spaces and industries. That’s proven effective for me because people don’t think I know anything about scaling a company, product-market fit, or fundraising. If you can show something of value, people will care regardless of age.

And it is fun to surprise people. It really comes down to learning, reading, listening to podcasts, and knowing spaces to help people that I meet with.

What plans do you have after graduation? Do you see yourself staying in venture, going to a startup, or something else?

It’s up in the air but I definitely want to be involved with venture at some point. I’m not sure if that means directly out of college though I’m open to it. I’m broadly interested in operational roles, including product. I study Symbolic Systems, an interdisciplinary major that bundles together computer science, linguistics, philosophy, and psychology. It’s an amazing way to blend business with a technical background.

One goal of mine is to start a company. I’ve always been excited by the idea of building from the ground up - it's why I decided to join Contrary and Cardinal instead of more obvious, present choices. So, yes, I definitely want to do venture but I see myself coming back to it after other things. The best VCs are mentors to their startups and that’s want I’m aiming for in the future.

What advice do you have for young women who want to enter VC - on the investing, operations, or platform side?

Do it. Lots of women don’t think they are perfectly qualified for venture. They question this and that and feel like they should prepare a little more. They feel like they’re not ready yet. It’s not true at all. Once you find something you’re interested in, whether that’s venture or something else, pursue it. Literally just say to yourself that you’re going to do it and then make it happen.

Also realize that at the end of the day, no one completely knows what they’re doing. You don’t need to know it yourself. Just put yourself out there. When you look at the opportunities I’ve had throughout Stanford and before that, most of them came from sending a cold email. There’s nothing wrong with asking and putting yourself out there. Even if they say no, it’s fine! People don’t do it enough and it can differentiate you.

Go for it. Believe in yourself. And definitely stay persistent.