Gabby Contro

“People have to trust you, both other investors that you're working with as well as founders. If they don't trust you then you're in trouble.”

Meet Gabby. Growing up in Colorado, Gabby traded in her accounting career for venture capital, working at early stage, tech- focused Crosslink Capital. We sat down with Gabby to chat about breaking into VC, the importance of mentors, and being a junior woman in a male-dominated workplace.


You were able to build a fantastic reputation as an investor - what did it take to do this early on in VC?

A few things.

You need to find mentors immediately and ask them for help. There is no playbook on how to succeed in VC so you need to have someone who's been in the industry, who you can trust, and who will tell you like it is. As an early stage investor, the feedback cycle is long - subsequent funding rounds and exits can take months to years - therefore it’s hard to tell if you're a good investor right off the bat. Finding mentors helps to hold you accountable and make sure you do the best at your job.

People have to trust you, both other investors that you're working with as well as founders. If they don't trust you then you're in trouble.

The final thing is you need to make venture investing your life. It can't just be your job. You need to be able to integrate these founders with other investors, treat them like your friends and your family. You should be ready and willing to pick the phone up in the middle of the night if a founder needs something or has a question. Facades don't work and founders will see straight through them. You really have to make it part of your life.


Did you have any female mentors?

Yes, it was extremely helpful and I sought it out very early on. It is incredibly valuable to have a person you can talk to about different things happening within your firm and in the industry. It is also really helpful to be able to co-invest with them. I think it was very critical in my career and personal life to have that person to talk to on a weekly basis about different things.

I was proactive about finding a mentor. I sought out an investor who worked at a friendly VC and asked for fifteen minutes of her time which then led to a monthly meeting which then led to investing together.


How did being female in a predominantly male environment impact the work?

From a sourcing perspective, you have a unique female lens and I think that serves as an advantage. The ability to show an investment to my colleagues from a female perspective allowed us to look at certain industries in a different way.

I like the idea of having a multitude of perspectives for an investing team.


The proportion of women in VC has been flat for many years. Why do you think that is? Why do you think there's a barrier for women?

There are a lot of women who are associates or VPs, but the numbers of management and partners is actually declining. It’s a double edged sword. Women who are associates at VC firms don't have role models in partners, so it's really hard to see any upward mobility. It’s hard to imagine your career trajectory, it’s a self-fulfilling prophecy. You think that there's no room for you at the top and so a lot of times women will leave after a couple of years. It's a hard problem to solve. I think it has to do a lot with culture.


So what can be done?

I think there are things to be done, but first and foremost, I think it is helpful for women VCs to discuss these concerns that they have instead of letting them build up. I think there needs to be an independent network of females to be able to talk about these issues. I think firms are being more open to having women rise to the top. It's just a very very slow process.


What areas are really exciting to you?

I enjoy earlier stage investing for a few reasons. You get your hands dirtier at earlier stages. I got to experience investing and building a very raw company from the ground up. You have opportunities to help operate the company at an earlier stage and entrepreneurs are open to advice.

It's people centric at the early stage, so you have to spend a lot of time with entrepreneurs and understand whether they are a personality fit with your fund and model. It’s almost like dating, whereas later stage investing can sometimes be largely metrics driven. Early stage investing suits my personality in that I have more opportunities to sit down and spend a lot of time with entrepreneurs and really get to know them.

In terms of sectors, I get excited about disruptive business models that will impact traditionally slow-moving, inefficient verticals such as logistics, construction, and healthcare.


Fire round

What is one theme you are most excited about



Is there a female entrepreneur or investor that you'd like to meet and chat with

Joanne Wilson. We've had a couple portfolio companies in common but I'd love to meet her. I think she is a phenomenal angel investor and adds a lot of value to her companies. I would also love to hear her perspective on how you navigate your own path, while being married to a venture capitalist. She has been very successful in carving out her own very unique thesis within investing independent of her husband.


What is your spirit animal



Best piece of advice you have received

"Stop worrying about things that will never happen to you."

I think it's really powerful both from a personal perspective and from an investing perspective. I think it speaks to calculated risk taking but also to not wasting time on what may not happen.

Samantha Kaminsky