Q&A with Cross Culture's Jennifer Richard

Updated: Sep 2, 2018

Jennifer Richard is a senior associate at Cross Culture Ventures, based in Los Angeles. She is also a MBA candidate at UC Berkeley - Haas School for Business. Prior to CCV, she worked in supply chain for three early stage startups.

What attracted you to venture capital and working with startups?

I started my career in media and entertainment. While I was working at talent agency CAA, I came up with an idea for a startup with my best friend. When we started pitching to investors, it became clear we were missing a critical piece: neither of us had tech experience. Since our startup centered on a mobile application, we knew that one of us needed to acquire technical skills. I didn’t want to stay in entertainment long-term, so it made the most sense for me to pivot. I found a job in user experience at a startup, Prizeo. That company was sold, and when the founders created their new company, I helped them start the venture.

One of the 3 founders left that second company to start his passion project. I joined him as employee number 2 at Pop & Suki, a direct-to-consumer accessories company. I was on the ground floor with all of these startups. From that experience, I realized I didn’t want to start my own company anymore, but I did know the ingredients that made a business successful. The second company I worked at was acquired; Pop & Suki was continuously growing before I left for business school. I loved working at startups and became passionate about building a company from the very beginning.

In terms of venture capital, I was typically one of the few women working at these companies. I was often the only woman of color. I realized that being on the other side of the table and influencing who receives investment would allow me to make the biggest impact. I could play a direct role in shaping the face of tech. That really gave me a sense of purpose and guided my decision to become an investor.

Why Cross Culture Ventures?

I’m currently an MBA student at UC Berkeley Haas School of Business. At Berkeley, I was lucky enough to become a fellow with InSITE (a competitive startup consulting program). Cross Culture’s founders, Marlon Nichols and Troy Carter, are affiliated with InSITE. Someone within the program’s national leadership circulated the opening at CCV and I applied. From the very beginning, I knew I didn’t want to work for just any firm. Culture and diversity are hugely important to me - I knew I’d find those values in Cross Culture’s leadership.

I didn't meet Marlon until the interview process, but Troy had actually invested in one of the startups where I had previously worked. It was very full circle. Troy knew people who could speak directly to my experience and credibility. During the interviews, I showed ways that I aligned with Cross Culture’s investment theses. Understanding Marlon’s purpose-driven approach to recruiting and investing also made me keen to join as a summer associate.

Now when I return to school, I will continue working remotely and helping the team with sourcing, diligence, and operations. The goal is to come back full-time after I’ve graduated from Berkeley.

You were a summer associate who has been brought on full-time. Congratulations! What are some characteristics that the CCV team saw in you that helped earn a senior associate position?

When you’re normally recruiting, you try to come in with an excited attitude and follow up with thank you emails. This was the first job where I thought to myself: I have to get this role - it’s perfect for me. That was definitely communicated throughout my interview process from intern to senior associate. I made sure to clearly articulate the ways I could contribute. I tied my background and skills to Cross Culture’s portfolio in a genuine way. Marlon and Troy could tell just how serious I was about working with them. Especially when you’re recruiting for a small company, it was important to show Marlon and Troy that I was a passionate and driven executer.

Having a startup background has also been a huge asset. I can identify teams that work. I know what it looks like to have early traction. It’s difficult for founders and early stage companies to BS me because I’ve been there in the trenches. I know what things look like when the business is healthy and heading towards growth and profit.

I’m cognizant that this is my first time working in vc. I went in having a lot of humility, knowing that I was starting at the bottom and had to hustle. I put in more than the expected hours. I leaned on Marlon, partner Suzy Ryoo, and Chief of Staff Danny Brown as assets. I wanted to learn as much as I could from them. And they were able to see how much I was absorbing in a small amount of time. If you work at a small company, you need to respect your colleagues and they need to both like and trust you. That’s something that I stand for. If I ever said to Marlon and Suzy that I was going to do something, I followed through. If I didn’t know how, I’d always ask and figure it out.

Lastly, in this industry, being a people person is really important. I don’t love networking. I’m kind of introverted. But I love vc and startups, and I used that to force myself out of my comfort zone. As a summer associate, I talked to as many people as I could. Marlon knows that networking isn’t something that comes naturally to me but that I pushed myself because I care deeply about this job and this company. I showed that I was a team player by having heart and doing things that are uncomfortable because they’re valuable for Cross Culture’s success. Making it bigger than yourself is key.

I think that last part is really important. People don’t realize how much time investors spend going to events, conferences, demo days…

You really are going out a lot. When I was working at startups, my hours were longer but my nights were free. I had more balance in the sense that I could make dinner plans with friends or have more nights to myself. In venture, you’re always doing something work-related. You have to love startups and venture to willingly sacrifice your time. It makes you decide whether vc investing is something that’s worth it to you.

What skills did you bring to this position from previous roles at CAA and startups like Prizeo and Pop & Suki?

First and foremost, you need to have some quantitative skills. Though it may not be evident from my resume, I happen to be pretty good at Excel. I don’t think my internship at Cross Culture would have been as successful without prior Excel experience.

In terms of being able to support founders… I have a really strong product and operations background. In the day-to-day, I can help with customer acquisition and growth strategy. While it’s harder for me to address an engineering challenge, I can look at a website and product to provide UX feedback. I might be advising anything from layout changes to and editing copy for customer retention.

My experience in talent and entertainment also helps with connecting people. At our fund, all of the partners have strong networks. That helps us link founders to relevant partners and mentors in their space.

The biggest thing is being able to relate with founders. Working so closely with entrepreneurs in my prior roles, I have empathy for them and know how to champion their success.

Cross Culture Ventures is based in Los Angeles. What are your thoughts on LA’s ecosystem in comparison to Silicon Valley?

Honestly, I don’t see a big difference between LA and Bay Area startups. LA is a little earlier stage and consumer focused than the software and hardware companies in Silicon Valley. But in general, they’re pretty similar and Cross Culture looks at companies in both places.

What does an average day look like in your role?

A huge part of my day is taken up by sourcing. Many founders contact the fund via email and I spend time going through and assessing pitches. If they pass that initial evaluation, they will be invited to pitch in front of the team. I also support diligence by researching companies; interviewing people who work at those startups; and creating financial models and projections to evaluate potential outcomes.

Otherwise, I’m attending events during the day. Sometimes that event might be open office hours for founders. It could also be a lunch for vcs in LA and the Bay Area to discuss startups and compare notes. Writing is another component. On Medium, I consistently put out content to share what Cross Culture is thinking about.

Going into your last year of business school, do you have any plans to leverage Berkeley’s startup ecosystem for Cross Culture?

I’ve had some involvement in Berkeley’s startup community as an InSITE fellow, but I was mostly working with startups in the city. This year I will definitely have more involvement in Berkeley’s incubators and accelerators. We’ve got quite a few on campus like SkyDeck (a joint partnership between Haas, the College of Engineering, and the Vice Chancellor’s office to bridge university research with a traditional accelerator) and The House (a fund dedicated to accelerating the development of Berkeley’s entrepreneurs).

In terms of cross-pollination, at Cross Culture we tend to invest in LA startups because of proximity. But we also have several investments in the Bay, Chicago, and Boston as well as Nairobi, Kenya. We are not hard set on location for the startups we invest in. So it’s great that I will be in the Bay Area as a set of eyes and ears to scope great companies. Berkeley and surrounding institutions have huge potential as a source of investment opportunity for Cross Culture.

Cross Culture is sector agnostic, but do you see areas where you’d like to become a domain expert?

Since I’m early in my career, I’m not committed to a specific vertical. I am generally interested in companies with social impact. We have a couple of investments that I really love like SoLo, a micro-financing platform for emerging markets. Users can get small loans on their phones with credit determined by a SoLo score rather than a FICO rating determined by a bank and creditors. This allows people access to financing without it being predatory. Users can borrow and lend money on the app; usually lenders are people with disposable income who would donate to a Kickstarter fund but choose to loan that money instead. The person who borrows can pay back a tip but the value proposition is that SoLo users don’t pay any interest. There are so many people in this country who have a bill out of nowhere - a SoLo loan can be the difference between paying rent and putting food on the table or financial strife. I really love human-centered companies like this.

Another company we’ve invested in this summer allows individuals to access primary care via telemedicine. A major pain point in healthcare is the inability to get to a doctor. Telemedicine allows people to access healthcare at any time through their insurance. These are companies expanding access and helping normal people… they validate why I moved into vc.

What are some challenges you face as an investor and woman in vc?

The lack of diversity is a huge challenge in the tech space. Coming to venture and being new to the community meant I had to develop a network quickly. I’ve been lucky to have a supportive team that has enabled that process. I didn’t feel like I had to do it on my own. Naturally, when you’re a minority (whether that’s based in gender, race, or sexual orientation), it might be harder for you to build connections because you don’t look or sound like or act like the typical male in tech. This is an obstacle you can overcome. It requires working hard and getting people – who are (a) in the majority and (b) already established – to take you seriously.

Being able to adapt and stay on top of the industry can also be difficult. You have to know everyone’s names and all the funds and who focuses on what type of tech. There’s a steep learning curve. You should know this information before you have conversations, so you demonstrate your knowledge. It doesn’t come immediately but it gets easier over time.

Any advice for young women who want to enter venture capital - on the investing, operations, or platform side?

My biggest piece of advice is to go for it! There are several studies that say women apply for jobs that they feel they are 100% qualified for while men apply even with 40% of the qualification. I’ve noticed that’s totally true. Don’t undersell or undervalue yourself. As long as this is something within your wheelhouse, just take the leap.

In venture, people are very open and willing to help you. I’ve reached out to people I didn’t know without a referral or introduction and they’ve gotten back to me. When someone messages me on LinkedIn, I get back to them. In particular, if you are a young woman or minority, don’t be afraid to reach out and ask people for their time. They’ll be happy to chat with you - especially if it’s someone who looks like them. So reach out to anyone you admire in the venture community; you might just hear back and create a great connection.