Bethany Crystal - General Manager @ Union Square Ventures

“One threadline throughout my life is that I have always been a storyteller. Even from a young age, I was obsessed with writing.”

After majoring in Journalism at Northwestern University, Bethany Crystal honed her skills as a writer before delving into sales and marketing jobs at top tech company, Stack Overflow. Today, Bethany is a General Manager at Union Square Ventures (USV), an early stage venture firm in New York City. USV invests in technology companies throughout North America and Europe, and has 70+ active portfolio investments. We sat down with Bethany to chat about breaking into venture, fostering workplace diversity, and the importance of building and maintaining strong networks.


How did you make the transition from journalism to marketing and sales for a technical product and then to platform and community at USV?

I did not study journalism because I wanted to be a journalist. I pursued journalism because I liked three things: writing, traveling and talking to people. Journalism seemed to be the most natural fit. In fact, all of my jobs have touched on those things.

I joined Stack Overflow as one of the first 10 employees on the sales team, which eventually grew to a 100-person sales org at a 300-person company. I moved from sales to marketing, and became familiar with how companies grow, change, and pivot in a lot of different ways. I kept getting asked to do things that were new. And that was challenging. But, we were part of a portfolio network, so each time I was asked to do something new (eg. the PR for our fundraise, or figure out something new about our customers), I reached out to the USV portfolio network and found people at other companies like Foursquare, Meetup, or SoundCloud, who were doing similar things. I learned a lot of how to do my own job in marketing from these peers.

As you moved between all of those roles how did you get up to speed quickly?

As a high achiever I didn't feel comfortable just wildly experimenting so I wanted to approach things in a pragmatic way. I started to look at what companies were doing and how the person at different companies was thinking about that function. 

Rather than seek out a ton of one-to-one mentorship who will help me in every path of my career, at different points I've noticed I have questions that certain people around me are more equipped than others to help with.

I have an “advisory board” of people who have more experience, that can give me different pointers.

You now manage the entire USV portfolio network. Can you tell us about your role?

USV is an early stage VC. One of the things that our portfolio companies have in common, is our thesis on investing, which relates to the idea of defensibility in network effects. When we think about network effects in the businesses that we invest in, we are referring to services that increase in value for every participant as more information is added. When you look in our portfolio you see network effects across a wide variety of verticals - from education, healthcare, fintech and even decentralized networks on the blockchain. We're not just working with 75 companies that are growing and building businesses but we're working with 75 companies that are all thinking about networks, communities and user groups. My role as the general manager of our network is to bring these companies together so they can learn from each other in a similar way.

If we're doing our jobs right as a VC that means every time we make a new investment, the experience of working at one of our companies gets better for everyone.

What is one of the biggest lessons that you have learned while working with these tech leaders?

It's interesting having been on the other side for so many years because I feel like I have a lot of empathy for what it is like to work at a company that's changing, outgrowing itself, and growing in ways that aren't always comfortable. One of the things I have realized is that there's a lot of emotion in business building. You think about VC as finance or technical driven. But the fact is that when you are a founder, this is your baby, this is your family, and this is your passion project. So when things go right, it is amazing, and when things go wrong, it could be the worst feeling in the world.

Moving to diversity and inclusion- while at Stack Overflow, you worked with other USV portfolio companies to develop a “Diversity Summit.”  What prompted you to start an initiative like this?

While at Stack Overflow, we had a lot of conversations about branding and inclusion. I was noticing that there were a lot more questions than answers during this time (2014-2016). I thought it would be helpful to hear from a lot of our USV portfolio companies, how they're approaching diversity, inclusion and belonging, how they’re attracting talent.

I teamed up with USV and Kickstarter (another portfolio company), and we put our heads together to come up with a list of questions that we were interested in discussing with others. We had a diversity summit where people from a lot of different areas of the organization joined us and we had some really interesting case studies shared.

We now host two a year, one in SF and one in NYC. We also facilitate monthly D&I roundtable discussions where companies across our network share best practices and case studies with each other.

What are some of the best practices you have learned through these summits in addressing inclusion and diversity in the workplace?

The most important thing is that these initiatives and ideas come from the leader of your organization. There needs to be buy-in, support and advocacy from the CEO or founder of your organization to make this happen. It is not good enough to tell your head of engineering or your head of HR and ask them to just make it happen. It really needs to be something that is permeating the entire organization.

Research has shown that when viewing a job description, women tend to only apply for roles if they feel that they meet ten out of ten criteria. Whereas men will apply if they feel they meet six out of ten criteria. This means that women may be opting out of even applying, and some of our companies have found that changing just the wording of a job can help a lot. For example, Kickstarter had a job description for what they called a “Trust and Safety Officer.” They were getting a lot of men applying for the role and decided to change the title of the job to “Integrity Specialist.” The word integrity had such a broader reach that they ended up completely switching the demographic of who applied and they got so many more women applicants.

One small tweak can make such a big impact. It's not about reinventing your entire culture but just paying attention to moments that can quickly change the perception from someone else's viewpoint.


You are in a male dominated industry. How have you found your seat at the table and what tips do you have for other females working in male dominated industries?

This is definitely something that I have found challenging and intimidating. Looking back I’ve now been working at USV for almost two years and it's pretty clear that a lot of my early trepidation has been self-imposed and in my own head.

I've been trying to make myself more comfortable being uncomfortable.

Coming from a middle manager role, as just another cog in a 7,000+ person portfolio network, to being thrust into this really visible position surrounded by a group of probably some of the smartest people I will ever work with, in a completely different expertise area than me, it was definitely intimidating. I spent a lot of that first year at USV trying to build internal social capital, and recognize where everyone stood on issues, in order to gain collective buy-in.

Given the role is more focused on the network, I look at my job as running a small business unit, in a pretty oddly structured company. In that way, the partners are less of a typical manager relationship, and more of a collective board.

Do you see any differences between female and male founders and operators that you work with?

Among our 75 portfolio companies, only 8 of the CEOs are women. I can’t make sweeping generalizations, but one thing that all these women have in common is that they are the minority. I think with that comes the feeling of being an outsider. It's a feeling that I feel a little bit working in this industry, and one I've heard that is very common among female founders as well. I think it is too soon for us to really answer that question until we have a lot more female founded companies being funded.


Fire Round:

What is one industry trend that you are most excited about?

Organizational Learning and Development.

What is one of the favorite / most interesting articles you have read recently?

It’s actually a TedX talk from one of our female founders, "Borders are within us,” Karoli Hindriks, Founder and CEO of Jobbatical.


Who is one female entrepreneur or investor that you would most like to meet and chat with?

J.K. Rowling, on how she built the Harry Potter empire and wrote books under the pressure of the entire world.


What is your spirit animal?

An ocelot - they are quiet animals that are wild cats and can pack a punch!


What is the best piece of advice you have ever received?

Done is better than perfect.


Want more from Bethany? Check her out on Twitter.

Samantha Kaminsky